JP6939746B2 - Polymerizable composition - Google Patents
Polymerizable composition Download PDFInfo
- Publication number
- JP6939746B2 JP6939746B2 JP2018187957A JP2018187957A JP6939746B2 JP 6939746 B2 JP6939746 B2 JP 6939746B2 JP 2018187957 A JP2018187957 A JP 2018187957A JP 2018187957 A JP2018187957 A JP 2018187957A JP 6939746 B2 JP6939746 B2 JP 6939746B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acid
- acrylate
- compound
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 142
- 229920000642 polymer Polymers 0.000 claims description 95
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 23
- 239000003504 photosensitizing agent Substances 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000003638 chemical reducing agent Substances 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 3
- 230000031700 light absorption Effects 0.000 claims description 3
- -1 acrylate compound Chemical class 0.000 description 150
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 99
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 51
- 239000002253 acid Substances 0.000 description 46
- 239000000463 material Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 20
- 238000000576 coating method Methods 0.000 description 19
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 229920000742 Cotton Polymers 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000178 monomer Substances 0.000 description 17
- 229920005862 polyol Polymers 0.000 description 17
- 229920000139 polyethylene terephthalate Polymers 0.000 description 16
- 239000005020 polyethylene terephthalate Substances 0.000 description 16
- 150000003077 polyols Chemical class 0.000 description 16
- 238000001723 curing Methods 0.000 description 15
- 125000004122 cyclic group Chemical group 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- 229920000728 polyester Polymers 0.000 description 14
- 239000005056 polyisocyanate Substances 0.000 description 14
- 229920001228 polyisocyanate Polymers 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000012860 organic pigment Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 12
- 230000006872 improvement Effects 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 230000001678 irradiating effect Effects 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000004040 coloring Methods 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 238000010526 radical polymerization reaction Methods 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 150000003926 acrylamides Chemical class 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 230000001476 alcoholic effect Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical class O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 239000011976 maleic acid Substances 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 6
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 229960002143 fluorescein Drugs 0.000 description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000007519 polyprotic acids Polymers 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 125000005396 acrylic acid ester group Chemical group 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N hexylene glycol Natural products CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 125000006353 oxyethylene group Chemical group 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 3
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical compound C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 description 3
- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical class C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
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- 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
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- 125000002252 acyl group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
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- 235000015278 beef Nutrition 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 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
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- 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
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
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- 229920000098 polyolefin Polymers 0.000 description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
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- 239000000243 solution Substances 0.000 description 3
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- 125000001302 tertiary amino group Chemical group 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- 150000003732 xanthenes Chemical class 0.000 description 3
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Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Description
本発明は、重合性組成物およびその重合物に関する。 The present invention relates to a polymerizable composition and a polymer thereof.
(メタ)アクリレート化合物等の反応性化合物を含む組成物は、開始剤から発生した活性種により容易にラジカル重合を起こし、硬化物を形成することが知られている。これらの組成物は様々な分野で使用されており、例えば、印刷インキ、オーバーコートワニス、塗料、接着剤、フォトレジスト、3D造形物等を挙げることができる。 It is known that a composition containing a reactive compound such as a (meth) acrylate compound easily undergoes radical polymerization by an active species generated from an initiator to form a cured product. These compositions are used in various fields, and examples thereof include printing inks, overcoat varnishes, paints, adhesives, photoresists, and 3D shaped objects.
近年、反応性化合物を含む組成物は歯科用途や、医療品および食料品のパッケージ用途等にも使用されつつある。組成物中における、ラジカル重合を引き起こす活性種を発生する光重合開始剤は低分子化合物であるため、ラジカル重合に関与しなかったものは硬化物中に取り残されてしまう。硬化物中に残留する光重合開始剤は、硬化物表面への滲み出しによる臭気、内容物中への浸透による内容物の汚染、品質劣化の懸念がある。よって、組成物に含まれる材料の中でも、とりわけ光重合開始剤は可能な限り使用量を減らすか、臭気や内容物の汚染、品質劣化の問題を引き起こさない材料を使うことが求められている。 In recent years, compositions containing reactive compounds are also being used for dental applications, packaging applications for medical products and food products, and the like. Since the photopolymerization initiator that generates an active species that causes radical polymerization in the composition is a low molecular weight compound, those that are not involved in radical polymerization are left behind in the cured product. The photopolymerization initiator remaining in the cured product may have an odor due to exudation to the surface of the cured product, contamination of the content due to penetration into the content, and deterioration of quality. Therefore, among the materials contained in the composition, it is required to reduce the amount of the photopolymerization initiator used as much as possible, or to use a material that does not cause problems of odor, contamination of contents, and quality deterioration.
一方、ラジカル重合において、酸素による硬化阻害は積年の課題である。酸素が存在する環境下でラジカル重合反応を行う場合、光重合開始剤から発生したラジカル重合を引き起こす活性種と酸素とが先に反応してしまい、低活性なラジカルが生成し、硬化不良等の問題の原因となる。この酸素阻害を改善する為に、窒素などの不活性雰囲気下で重合反応を行うか、光重合開始剤の使用量を増やすかの対応となり、コストや安全面で大きな課題がある。 On the other hand, in radical polymerization, inhibition of curing by oxygen has been a long-standing problem. When a radical polymerization reaction is carried out in an environment where oxygen is present, the active species that causes radical polymerization generated from the photopolymerization initiator reacts first with oxygen, and low-activity radicals are generated, resulting in poor curing, etc. Causes problems. In order to improve this oxygen inhibition, it is necessary to carry out the polymerization reaction in an inert atmosphere such as nitrogen or to increase the amount of the photopolymerization initiator used, which poses a big problem in terms of cost and safety.
近年、硬化阻害の最大の要因である酸素を活用した、重合又は硬化反応の研究が行われている。例えば、ローズベンガルに光照射する事で発生した一重項酸素と特定の共役ジエン構造との反応を用いた光硬化型接着剤が提案されている。(特許文献1)。しかしながら、フラン環のような特定の共役ジエン構造を有したもの以外、硬化反応は進行せず、非常に用途が限定されている。 In recent years, studies on polymerization or curing reactions utilizing oxygen, which is the largest factor of curing inhibition, have been conducted. For example, a photocurable adhesive using the reaction between singlet oxygen generated by irradiating rose bengal with light and a specific conjugated diene structure has been proposed. (Patent Document 1). However, the curing reaction does not proceed except for those having a specific conjugated diene structure such as a furan ring, and the use is very limited.
更に、同じくローズベンガルに光照射する事で発生した一重項酸素を、有機還元剤であるアスコルビン酸を用いて過酸化水素に変換し、更にアスコルビン酸により過酸化水素からラジカル重合開始可能な活性種であるヒドロキシラジカルを生成し、反応性化合物であるアクリレート化合物をラジカル重合した報告がある(非特許文献1)。しかしながら、重合に要する時間が非常に長時間であり、作業時間やコストに大きな課題がある。 Furthermore, singlet oxygen generated by irradiating rosebengal with light is converted to hydrogen peroxide using ascorbic acid, which is an organic reducing agent, and an active species capable of initiating radical polymerization from hydrogen peroxide by ascorbic acid. There is a report of radically polymerizing an acrylate compound, which is a reactive compound, by generating hydroxyl radicals (Non-Patent Document 1). However, the time required for polymerization is very long, and there is a big problem in working time and cost.
したがって、硬化物中に残留し、硬化物表面への滲み出しによる臭気、内容物中への浸透による内容物の汚染、品質劣化の懸念がある従来の光重合開始剤を使用することなく、ラジカル重合性(転換率)が高いラジカル重合を引き起こすラジカル重合性組成物は未だないのが現状である。 Therefore, radicals remain in the cured product without using conventional photopolymerization initiators, which may cause odor due to exudation to the surface of the cured product, contamination of the contents due to penetration into the contents, and deterioration of quality. At present, there is no radically polymerizable composition that causes radical polymerization having high polymerizable property (conversion rate).
本発明が解決しようとする課題は、臭気やマイグレーションの原因となり得る光重合開始剤や熱重合開始剤を使用しなくてもラジカル重合性(転換率)が高く、硬化性の良好な重合性組成物を提供することである。 The problem to be solved by the present invention is a polymerizable composition having high radical polymerizable (conversion rate) and good curability without using a photopolymerization initiator or a thermal polymerization initiator which can cause odor and migration. To provide things.
本発明者は上記課題を解決すべく鋭意検討を重ねた結果、本発明を完成するに至った。すなわち本発明は、光増感剤(A)と、二重結合を有する化合物(B)と、酸化還元触媒(C)と、有機還元剤(D)とを含んでなる重合性組成物に関する。 As a result of diligent studies to solve the above problems, the present inventor has completed the present invention. That is, the present invention relates to a polymerizable composition comprising a photosensitizer (A), a compound (B) having a double bond, a redox catalyst (C), and an organic reducing agent (D).
また、本発明は、光増感剤(A)が、200〜900nm領域の光吸収性を有する上記重合性組成物に関する。 The present invention also relates to the above-mentioned polymerizable composition in which the photosensitizer (A) has light absorption in the 200 to 900 nm region.
また、本発明は、二重結合を有する化合物(B)が、アクリロイル基および/またはメタアクリロイル基を有する化合物を含む上記重合性組成物に関する。 The present invention also relates to the above-mentioned polymerizable composition in which the compound (B) having a double bond contains a compound having an acryloyl group and / or a metaacryloyl group.
さらに、本発明は、上記重合性組成物の重合物に関する。 Furthermore, the present invention relates to a polymer of the above polymerizable composition.
本発明により、重合物中に残留し、重合物表面への滲み出しによる臭気、内容物中への浸透による内容物の汚染、品質劣化の懸念がある重合開始剤を使用することなく、ラジカル重合性(転換率)が高い重合性組成物を提供することが出来た。 According to the present invention, radical polymerization is carried out without using a polymerization initiator which remains in the polymer and may cause odor due to exudation to the surface of the polymer, contamination of the contents due to penetration into the contents, and deterioration of quality. It was possible to provide a polymerizable composition having a high property (conversion rate).
以下、本発明の実施形態を詳細に説明する。
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。
Hereinafter, embodiments of the present invention will be described in detail.
In addition, in this 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."
<光増感剤(A)>
本発明において、光増感剤(A)とは、活性エネルギー線を吸収して励起し、励起エネルギーを酸素に与え得るものを指す。詳細には、活性エネルギー線を吸収することにより励起し、その励起三重項エネルギーが酸素分子へエネルギー移動することにより、一重項酸素を発生させ得るものを指す。光増感剤(A)は、紫外(200nm)〜近赤外(900nm)領域に光吸収性を有するものが好ましく、三重項エネルギーレベルが100kJ/mol以上あるものが好ましく、励起一重項から励起三重項への項間交差効率が0.01以上であるものが好ましい。
<Photosensitizer (A)>
In the present invention, the photosensitizer (A) refers to an agent that can absorb and excite active energy rays and give excitation energy to oxygen. More specifically, it refers to a substance capable of generating singlet oxygen by being excited by absorbing active energy rays and transferring the excited triplet energy to an oxygen molecule. The photosensitizer (A) preferably has light absorption in the ultraviolet (200 nm) to near infrared (900 nm) region, preferably has a triplet energy level of 100 kJ / mol or more, and is excited from the excited singlet. It is preferable that the intersystem crossing efficiency to the triplet is 0.01 or more.
光増感剤(A)としては、ナフタレン誘導体、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、ナフタセン誘導体、ペリレン誘導体、ペンタセン誘導体等の縮合多環芳香族誘導体、アクリドン誘導体、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類、ベンジルやカンファーキノン等に代表される1,2−ジケトン誘導体、ベンゾフェノン誘導体、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、フルオレセイン誘導体、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、オキソノール誘導体等のポリメチン色素、ベンゾチアゾール誘導体、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、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、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、フェノチアジン誘導体、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、アゾ化合物、金属アレーン錯体、有機ルテニウム錯体、C60フラーレン等が挙げられ、その他更に具体的には大河原信ら編、「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)に記載の色素及び増感剤等が挙げられるが、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る。これらは必要に応じて任意の比率で二種以上用いても構わない。 Examples of the photosensitizer (A) include condensed polycyclic aromatic derivatives such as naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, naphthacene derivatives, perylene derivatives and pentacene derivatives, acridone derivatives, chalcone derivatives and dibenzalacetones. Unsaturated ketones typified by, 1,2-diketone derivatives typified by benzyl, camphorquinone, etc., benzophenone derivatives, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xantone derivatives, Polymethine pigments such as fluorescein derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives, benzothiazole derivatives, acrydin derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indolin derivatives, azulene derivatives, azulenium derivatives, Squalylium derivative, porphyrin derivative, tetraphenylporphyrin derivative, triarylmethane derivative, tetrabenzoporphyrin derivative, tetrapyrazinoporphyrazine derivative, tetraazaporphyrazine derivative, tetraquinoxalyloporphyrazine derivative, naphthalocyanine derivative, subphthalocyanine derivative, Phtalocyanin derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphyllin derivatives, anurene derivatives, phenothiazine derivatives, spiropyrane derivatives, spiroxazine derivatives, thiospiropyrane derivatives, azo compounds, metal arene complexes, organic ruthenium complexes, C60 fullerene, etc. Specifically, the dyes and sensitizers described in "Chemicals of Functional Dyes" (1981, CMC) edited by Nobu Okawara et al., Edited by Chuzaburo Ikemori et al., "Special Functional Materials" (1986, CMC). However, the present invention is not limited to these, and other examples include dyes and sensitizers that absorb light from the ultraviolet to the near infrared region. If necessary, two or more of these may be used in any ratio.
好適に用いられる光増感剤(A)としては、入手のし易さ、一重項酸素の発生量能から、例えば、ルブレン等のナフタセン誘導体、パープリン等のアントラキノン誘導体、アクリジン等のアクリジン誘導体、プロトポルフィリンIX等のポルフィリン誘導体、エオシンY、ローズベンガル等のキサンテン誘導体、テトラフェニルポルフィリン等のテトラフェニルポルフィリン誘導体、メチレンブルー等のフェノチアジン誘導体、3−ケトクマリン等のケトクマリン誘導体、C60フラーレン等が挙げられる。 Preferably used photosensitizer (A) is, for example, a naphthacene derivative such as rubrene, an anthraquinone derivative such as purpurin, an acridin derivative such as acrydin, or a proto because of its availability and ability to generate single-term oxygen. Examples thereof include porphyrin derivatives such as porphyrin IX, xanthene derivatives such as eosin Y and rosebengal, tetraphenylporphyrin derivatives such as tetraphenylporphyrin, phenothiazine derivatives such as methylene blue, ketocoumarin derivatives such as 3-ketocoumarin, and C60 fullerene.
本発明において特に好適に用いられる光増感剤(A)としては、キサンテン誘導体が挙げられ、入手のし易さ、一重項酸素の発生量能に加えて、化合物(B)との相溶性等の点から、下記一般式(1)および/または一般式(2)で表されるフルオレセイン骨格を有する化合物が挙げられる。 Examples of the photosensitizer (A) particularly preferably used in the present invention include xanthene derivatives, which are easily available, have the ability to generate singlet oxygen, and have compatibility with compound (B). From this point of view, a compound having a fluorescein skeleton represented by the following general formula (1) and / or general formula (2) can be mentioned.
(式中、R1〜R10は、それぞれ独立に、水素原子、塩素原子、臭素原子、ヨウ素原子、ニトロ基、アミノ基を表す。) (In the formula, R 1 to R 10 independently represent a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group, and an amino group.)
(式中、R11〜R20は、それぞれ独立に、水素原子、塩素原子、臭素原子、ヨウ素原子、ニトロ基、アミノ基を表す。式中L+は、任意のカチオンを表す。) (In the formula, R 11 to R 20 independently represent a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group, and an amino group. In the formula, L + represents an arbitrary cation.)
一般式(1)および一般式(2)におけるR1〜R20は、それぞれ独立に、水素原子、塩素原子、臭素原子、ヨウ素原子、ニトロ基、アミノ基を表し、入手のし易さ、一重項酸素の発生量から、R1〜R4、R11〜R14が塩素原子、臭素原子、ヨウ素原子、またはニトロ基でかつ、R7〜R10、R17〜R20が水素原子または塩素原子が好ましい。 R 1 to R 20 in the general formula (1) and the general formula (2) independently represent a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group, and an amino group, and are easily available and single. From the amount of oxygen generated, R 1 to R 4 , R 11 to R 14 are chlorine atoms, bromine atoms, iodine atoms, or nitro groups, and R 7 to R 10 , R 17 to R 20 are hydrogen atoms or chlorine. Atoms are preferred.
一般式(2)中のL+は、任意のカチオンを表し、入手のし易さ等からナトリウムカチオン、カリウムカチオン、トリエチルアンモニウム塩等のアンモニウム塩、1−ヘキサデシルピリジニウムカチオンが好ましい。 L + in the general formula (2) represents an arbitrary cation, and an ammonium salt such as a sodium cation, a potassium cation, or a triethylammonium salt, or a 1-hexadecylpyridinium cation is preferable from the viewpoint of easy availability.
光増感剤(A)の具体例を以下に示すが、これらに限定されるものではない。
2’,4’,5’,7’−テトラブロモ‐フルオロセイン(Solvent Red43)、2’,4’,5’,7’−テトラブロモ−フルオロセイン−ナトリウム塩(エオシンY、Acid Red87)、4’,5’−ジブロモ−2’,7’−ジニトロ−フルオロセイン−ナトリウム塩(エオシンB、Acid Red91)、2’,7’−ジクロロ−フルオロセイン、2’,7’−ジクロロ−フルオロセイン−ナトリウム塩、4’,5’−ジブロモ−フルオロセイン(Solvent Red72)、4’,5’−ジブロモ−フルオロセイン−ナトリウム塩、2’,7’−ジブロモ−フルオロセイン、2’,7’−ジブロモ−フルオロセイン−ナトリウム塩、4’,5’−ジクロロ−フルオロセイン、4’,5’−ジクロロ−フルオロセイン−ナトリウム塩、4’,5’−ジヨード−フルオロセイン(Solvent Red73)、4’,5’−ジヨード−フルオロセイン−ナトリウム塩、2’,7’−ジヨード−フルオロセイン、2’,7’−ジヨード−フルオロセイン−ナトリウム塩、トリブロモ−フルオロセイン、トリブロモ−フルオロセイン−ナトリウム塩、2’,4’,5’,7’−テトラクロロ−フルオロセイン、2’,4’,5’,7’−テトラクロロ−フルオロセイン−ナトリウム塩、2’,4’,5’,7’−テトラヨード−フルオロセイン、2’,4’,5’,7’−テトラヨード−フルオロセイン‐ナトリウム塩(エリスロシンB、Acid Red51)、フルオロセイン(Solvent Yellow94)、フルオロセイン−ナトリウム塩、4−アミノフルオロセイン、5−アミノフルオロセイン、3,4,5,6−テトラクロロ−フルオロセイン、3,4,5,6−テトラクロロ−フルオロセイン−ナトリウム塩、エオシン−1−ヘキサデシルピリジニウム塩、2’,4’,5’,7’−テトラブロモ−3,4,5,6−テトラクロロ−フルオロセイン−ナトリウム塩(フロキシンB、Acid Red92)、2’,4’,5’,7’−テトラヨード−3,4,5,6−テトラクロロ−フルオロセイン−ナトリウム塩(ローズベンガル、Acid Red94)、2’,4’,5’,7’−テトラヨード−3,4,5,6−テトラクロロ−フルオロセイン−ビス(トリエチルアンモニウム)塩。
Specific examples of the photosensitizer (A) are shown below, but the present invention is not limited thereto.
2', 4', 5', 7'-tetrabromo-fluorescein (Fluorescein Red43), 2', 4', 5', 7'-tetrabromo-fluoroscein-sodium salt (Eosin Y, Acid Red87), 4' , 5'-dibromo-2', 7'-dinitro-fluoroscein-sodium salt (eosin B, Acid Red91), 2', 7'-dichloro-fluoroscein, 2', 7'-dichloro-fluoroscein-sodium Salt, 4', 5'-dibromo-fluorescein (Fluorescein), 4', 5'-dibromo-fluoroscein-sodium salt, 2', 7'-dibromo-fluoroscein, 2', 7'-dibromo- Fluorescein-sodium salt, 4', 5'-dichloro-fluorosane, 4', 5'-dichloro-fluoroscein-sodium salt, 4', 5'-diiodo-fluoroscein (Solvent Red73), 4', 5 '-Diode-Fluorescein-Sodium Salt, 2', 7'-Diode-Fluorescein, 2', 7'-Diode-Fluorescein-Sodium Salt, Tribromo-Fluorescein, Tribromo-Fluorescein-Sodium Salt, 2' , 4', 5', 7'-tetrachloro-fluoroscein, 2', 4', 5', 7'-tetrachloro-fluoroscein-sodium salt, 2', 4', 5', 7'-tetraiodo -Fluorescein, 2', 4', 5', 7'-Tetraiodo-fluorosane-sodium salt (erythrosin B, Acid Red51), fluorescein (Fluorescein (Solvent Yellow94), fluorosane-sodium salt, 4-aminofluorosane, 5-Aminofluoroscein, 3,4,5,6-tetrachloro-fluoroscein, 3,4,5,6-tetrachloro-fluoroscein-sodium salt, eosin-1-hexadecylpyridinium salt, 2', 4 ', 5', 7'-Tetrabromo-3,4,5,6-Tetrachloro-fluoroscein-sodium salt (Fluorescein B, AcidRed92), 2', 4', 5', 7'-Tetraiode-3, 4,5,6-Tetrachloro-fluoroscein-sodium salt (Rose Bengal, Acid Red94), 2', 4', 5', 7'-tetraiodo-3,4,5,6-tetrachloro-fluoroscein- Bis (triethylammonium) salt.
本発明では、光増感剤(A)として、上記の光増感剤を単独で、または2種類以上組み合わせて使用することが出来る。光増感剤(A)の配合量は、後述する化合物(B)100質量部に対して、0.001〜20質量部であることが好ましく、0.01〜10質量部であることがより好ましい。0.001質量部以上であると、活性エネルギー線照射時に発生する一重項酸素の量が十分であり、所望のラジカル重合性(転換率)を得る事が出来、十分な硬度の重合物を得る事が出来たり、未反応モノマーの重合物中に残留量を抑制する事で、臭気やマイグレーションの問題改善に繋がる。また、20質量部以下であると、塗膜内部に十分活性エネルギー線が透過する為、未反応モノマーの重合物中での残留量が抑制されることで、臭気やマイグレーションの問題改善に繋がる。 In the present invention, as the photosensitizer (A), the above photosensitizers can be used alone or in combination of two or more. The blending amount of the photosensitizer (A) is preferably 0.001 to 20 parts by mass and more preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the compound (B) described later. preferable. When it is 0.001 part by mass or more, the amount of singlet oxygen generated during irradiation with active energy rays is sufficient, a desired radical polymerizable property (conversion rate) can be obtained, and a polymer having sufficient hardness can be obtained. By being able to do this and suppressing the residual amount in the polymer of unreacted monomers, it leads to improvement of odor and migration problems. Further, when the amount is 20 parts by mass or less, the active energy rays sufficiently permeate the inside of the coating film, so that the residual amount of the unreacted monomer in the polymer is suppressed, which leads to improvement of odor and migration problems.
<二重結合を有する化合物(B)>
本発明において、二重結合を有する化合物(B)(以下「化合物(B)」と略記することがある)は、分子内に少なくとも1個の炭素−炭素二重結合を有する化合物である。化合物(B)は、そのものが本発明の重合性組成物に活性エネルギー線を照射した際に発生した活性種によって重合・架橋する。
<Compound (B) having a double bond>
In the present invention, the compound (B) having a double bond (hereinafter, may be abbreviated as "compound (B)") is a compound having at least one carbon-carbon double bond in the molecule. Compound (B) is polymerized and crosslinked by the active species generated when the polymerizable composition of the present invention is irradiated with active energy rays.
化合物(B)は、水酸基を有さず−[O(CH2)2]2−を有する化合物(b1)(以下「化合物(b1)と略記することがある」)と、水酸基を有する化合物または−[O(CH2)2]2−を有さない化合物(b2)(以下「化合物(b2)と略記することがある」)と、化合物(b1)および化合物(b2)以外の二重結合を有する化合物(b2−3)とに大別できる。上記の化合物(b2)は、水酸基を有する化合物(b2−1)(以下「化合物(b2−1)と略記することがある」)と、水酸基を有さず環状構造を有する化合物(b2−2)(以下「化合物(b2−2)と略記することがある」)とに大別できる。更に、化合物(b2−1)は、環状構造を有さず水酸基を有する化合物(b2−1−1)(以下「化合物(b2−1−1)と略記することがある」)と、環状構造および水酸基を有する化合物(b2−1−2)(以下「化合物(b2−1−2)と略記することがある」)とに大別できる。また、化合物(b2−2)は、水酸基を有さず環員原子としてヘテロ原子を含まない環状構造を有する化合物(b2−2−1)(以下「化合物(b2−2−1)と略記することがある」)と、水酸基を有さず環員原子としてヘテロ原子を含む環状構造を有する化合物(b2−2−2)(以下「化合物(b2−2−2)と略記することがある」)とに大別できる。化合物(B)は、アクリロイル基および/またはメタアクリロイル基を有する化合物を含むことが好ましい。 The compound (B) includes a compound (b1) having no hydroxyl group and having − [O (CH 2 ) 2 ] 2 − (hereinafter, may be abbreviated as compound (b1)) and a compound having a hydroxyl group or a compound having a hydroxyl group. -[O (CH 2 ) 2 ] 2- Double bonds other than compound (b2) (hereinafter sometimes abbreviated as compound (b2)) and compound (b1) and compound (b2). It can be roughly classified into the compound (b2-3) having. The above-mentioned compound (b2) includes a compound having a hydroxyl group (b2-1) (hereinafter, may be abbreviated as “compound (b2-1)”) and a compound having no hydroxyl group and having a cyclic structure (b2-2). ) (Hereinafter, it may be abbreviated as "compound (b2-2)"). Further, the compound (b2-1) has a cyclic structure with a compound (b2-1-1) having a hydroxyl group and having no cyclic structure (hereinafter, may be abbreviated as “compound (b2-1-1)”). It can be roughly classified into a compound having a hydroxyl group (b2-1-2) (hereinafter, may be abbreviated as “compound (b2-1-2)”). Further, the compound (b2-2) is a compound (b2-2-1) having a cyclic structure that does not have a hydroxyl group and does not contain a hetero atom as a ring member atom (hereinafter, abbreviated as “compound (b2-2-1)”. "Sometimes") and a compound (b2-2-2) having a cyclic structure that does not have a hydroxyl group and contains a hetero atom as a ring member atom (hereinafter, may be abbreviated as "compound (b2-2-2)". " ) Can be roughly divided into. Compound (B) preferably contains a compound having an acryloyl group and / or a metaacryloyl group.
化合物(B)は、分子内に少なくとも1個の炭素−炭素二重結合を有する化合物であれば、特に制限はなく使用できるが、化合物(b1)を用いる事が、増感剤(A)との相溶性、重合物とした際に架橋密度が高くなり過ぎるのを抑制すると共に、−[O(CH2)2]2−基が架橋密度の高くなった重合物の剛性を緩和させるため、重合物とした際に硬度を維持しつつ柔軟性を付与することが出来る。 The compound (B) can be used without particular limitation as long as it is a compound having at least one carbon-carbon double bond in the molecule, but the compound (b1) can be used together with the sensitizer (A). In order to prevent the crosslink density from becoming too high when the polymer is formed, and to relax the rigidity of the polymer in which the − [O (CH 2 ) 2 ] 2 − group has a high crosslink density. When made into a polymer, flexibility can be imparted while maintaining hardness.
また、化合物(b1)を用いて、活性エネルギー線で重合硬化させて硬化物を得ようとした際、その硬化速度が向上する。その原因は解明中ではあるが、−[O(CH2)2]2−基同士の相互作用によって、化合物(b1)同士の距離が近接する事による硬化速度の向上、または光増感剤(A)に活性エネルギー線を照射する事で発生した一重項酸素に対して、−[O(CH2)2]2−基から水素を供給する事で過酸化水素の生成、活性種の発生を推進する事による硬化速度の向上に繋がるものと推察される。 Further, when the compound (b1) is polymerized and cured with active energy rays to obtain a cured product, the curing rate is improved. The cause is still being elucidated, but the interaction between the-[O (CH 2 ) 2 ] 2 -groups improves the curing rate due to the close distance between the compounds (b1), or the photosensitizer (photosensitizer). Hydrogen peroxide is generated and active species are generated by supplying hydrogen from − [O (CH 2 ) 2 ] 2 − groups to singlet oxygen generated by irradiating A) with active energy rays. It is presumed that the promotion will lead to an improvement in the curing speed.
また、化合物(B)として、化合物(b2)を用いても良い。化合物(b2)を使用することによって、重合物のガラス転移点(Tg)を向上させて高凝集力を発現させたり、耐熱性や耐水性等の耐性の良好な重合物を形成することが可能となる。 Moreover, you may use compound (b2) as compound (B). By using the compound (b2), it is possible to improve the glass transition point (Tg) of the polymer to develop a high cohesive force, or to form a polymer having good resistance such as heat resistance and water resistance. It becomes.
特に、化合物(b2−1)を用いる事が硬化速度の向上や重合硬化収縮の抑制の点で好ましい。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ものと推察される。 In particular, it is preferable to use the compound (b2-1) in terms of improving the curing rate and suppressing polymerization curing shrinkage. It is presumed that having a hydroxyl group has a great effect on reducing the curing shrinkage associated with 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、化合物(b2−2)を用いることが好ましい。更に、化合物(b2−3)も用いることができる。 Further, it is preferable to use the compound (b2-2) in terms of improving durability such as heat resistance and moisture heat resistance. Furthermore, compound (b2-3) can also be used.
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 not particularly limited, examples of the compound that can be used as the compound (B) include the following.
化合物(b1)は、水酸基を有さず−[O(CH2)2]2−および二重結合を有する化合物であれば特に制限はないが、例えば、アルコールやフェノールの水酸基を有する化合物を用いてエチレンオキシドを開環重合させて得られる反応生成物の水酸基と(メタ)アクリル酸のような二重結合を有するカルボン酸等とエステル化して製造することができる。
例えば、(メタ)アクリル酸メトキシジエチレングリコール、(メタ)アクリル酸エトキシジエチレングリコール、(メタ)アクリル酸エトキシポリエチレングリコール、ジ(メタ)アクリル酸ジエチレングリコール、ジ(メタ)アクリル酸トリエチレングリコール、ジ(メタ)アクリル酸テトラエチレングリコール、ジ(メタ)アクリル酸ポリエチレングリコール等の脂肪族(メタ)アクリル酸エステル類;
The compound (b1) is not particularly limited as long as it does not have a hydroxyl group- [O (CH 2 ) 2 ] 2- and has a double bond, but for example, a compound having a hydroxyl group of alcohol or phenol is used. It can be produced by esterifying a hydroxyl group of a reaction product obtained by ring-opening polymerization of ethylene oxide with a carboxylic acid having a double bond such as (meth) acrylic acid.
For example, (meth) methoxydiethylene glycol acrylate, (meth) ethoxydiethylene glycol acrylate, (meth) ethoxypolyethylene glycol acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, di (meth) acrylic. Aliphatic (meth) acrylic acid esters such as tetraethylene glycol acid acid and polyethylene glycol di (meth) acrylic acid;
例えば、(メタ)アクリル酸フェノキシジエチレングリコール、(メタ)アクリル酸フェノキシジエチレングリコール、ビスフェノールAのエチレンオキシド(EO)付加物ジアクリレート等の芳香族(メタ)アクリル酸エステル類; For example, aromatic (meth) acrylic acid esters such as (meth) phenoxydiethylene glycol (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, and ethylene oxide (EO) adduct diacrylate of bisphenol A;
例えば、テトラ(オキシエチレン)ビニルブチルエーテル、テトラ(オキシエチレン)ビニルフェニルエーテル、ポリ(オキシエチレン)ビニルフェニルエーテル、ビニルエーテル系単量体類; For example, tetra (oxyethylene) vinyl butyl ether, tetra (oxyethylene) vinyl phenyl ether, poly (oxyethylene) vinyl phenyl ether, vinyl ether-based monomers;
例えば、コハク酸ビニルフェニルポリ(オキシエチレン)、ヘキサヒドロフタル酸ビニルフェニルメチルポリ(オキシエチレン)等のポリオキシエチレン基部位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, vinyl benzoic acid ester-based or isopropenyl benzoic acid ester-based monomers having a polyoxyethylene group moiety such as vinyl phenylpoly succinate (oxyethylene) and vinyl phenylmethyl poly hexahydrophthalate (oxyethylene);
化合物(b1)の市販品としては、例えば以下が挙げられるが、これらに限定されるものではない。
ブレンマーADE−200、ブレンマーADE−300、ブレンマーADE−400A、ブレンマーADE−600、ブレンマーPME−100、ブレンマーPME−200、ブレンマーPME−400、ブレンマーPME−1000、ブレンマーPE−200、ブレンマーPE−350、ブレンマー50POEP−800B、ブレンマーPLE−200、ブレンマーPSE−1300、ブレンマーPDE−100、ブレンマーPDE−150、ブレンマーPDE−200、ブレンマーPDE−400、ブレンマーPDE−600、ブレンマーPDBE−200A、ブレンマーPDBE−450A、ブレンマーALE−200、ブレンマーAME−400、ブレンマーAAE−300 (以上、日油化学社製)、ニューフロンティアPE−200、ニューフロンティアPE−300、ニューフロンティアPE−400、ニューフロンティアPE−600、ニューフロンティアBPE−4、ニューフロンティアBPE−10、ニューフロンティアBPE−20、ニューフロンティアTMP−3、ニューフロンティアTMP−15、ニューフロンティアGE3A、ニューフロンティアNP−4、ニューフロンティアN−177E、ニューフロンティアME−3、ニューフロンティアME−4S、ニューフロンティアMPE−600、ニューフロンティアHBPE−4、ニューフロンティアTMP−3、ニューフロンティアPETA−4、ニューフロンティアMPEM−400、ニューフロンティアMPEM−1000、ニューフロンティアPEM−1000、ニューフロンティアBPEM−4、ニューフロンティアBPEM−10、ニューフロンティアHBPEM−10(第一工業製薬社製)、SR−101、SR−150、SR−210、SR−230、SR−252、SR−256、SR−259、SR−272、SR−415、SR−480、SR−494、SR−504、SR−540、SR−550、SR−602、SR−610、SR−9035、SR−344、SR−349、SR−454、SR−499、SR−502、SR−601、SR−9038(サートマー社製)、アロニックスM−260、アロニックスM−102、アロニックスM−113、アロニックスM−114、アロニックスM−210、アロニックスM−240、アロニックスM−350、アロニックスM−360、アロニックスM−370、(東亞合成社製)、NKエステルAM−30G、NKエステルAM−90G、NKエステルAM−130G、NKエステルAM−230G、NKエステルAMP−20GY、NKエステルA−200、NKエステルA−400、NKエステルA−600、NKエステルA−1000、NKエステルA−1206PE、NKエステルA−0612PE、NKエステルA−0412PE、NKエステルA−1000PER、NKエステルA−3000PER、NKエステル A−BPE−4、NKエステルA−BPE−10、NKエステルA−BPE−20、NKエステルA−BPE−30、NKエステル ABE−300、NKエステルA−B1206PE、NKエステルA−TMPT−3EO、NKエステルA−TMPT−9EO、NKエステルAT−20E、NKエステルAT−30E、NKエステルA−GLY−3E、NKエステルA−GLY−6E、NKエステルA−GLY−9E、NKエステルA−GLY−20E、NKエステルATM−4EL、NKエステルATM−8EL、NKエステルATM−4E、NKエステルATM−35E、NKエステルAD−TMP−4E、NKエステルA−DPH−12E、NKエコノマーA−PG5027E、NKエコノマーA−PG5054E、NKエステルM−40G、NKエステルM−90G、NKエステルM−130G、NKエステルM−230G、NKエステルS−20E、NKエステルS−12E、NKエステルEH−4E、NKエステルB−20G、NKエステル9G、NKエステル14G、NKエステル23G、NKエコノマー1000PER、NKエステルBPE−200、NKエステルBPE−300、NKエステルBPE−500、NKエステルBPE−900、NKエステルBPE−1300N、NKエステルGLY−3E、NKエステルGLY−6E、NKエステルGLY−9E、NKエステルGLY−20E、NKエステルTMPT−3EO、NKエステルTMPT−9EO、NKエステルTM−4EL、NKエステルTM−4E、NKエステルTM−35E、NKエステルD−TMP−4E、NKエステルM−DPH−6E、NKエステルM−DPH−12E、NKエコノマーM−PG5027E、NKエコノマーM−PG5054E、NKエステルATM−120E、NKエステルA−DPH−48E、NKエステルA−DPH−96E (以上、新中村化学社製)、Miramer M142、Miramer M144、Miramer M164、Miramer M166、Miramer M170、Miramer M232、Miramer M2100、Miramer M2200、Miramer M2300、Miramer M280、Miramer M282、Miramer M284、Miramer M286、Miramer M290、Miramer M2040、Miramer M3160、Miramer M3190、Miramer M3150、Miramer M4004、Miramer M193、Miramer M241、Miramer M2101、Miramer M2301(MIWON社製)、ライトアクリレートEC−A、ライトアクリレートMTG−A、ライトアクリレートEHDG−AT、ライトアクリレート130A、ライトアクリレートP2H−A、ライトアクリレートP−200A、ライトアクリレートBP−4EAL、ライトアクリレート3EG−A、ライトアクリレート4EG−A、ライトアクリレート9EG−A、ライトアクリレート14EG−A、ライトアクリレートTMP−6EO−3A (以上共栄社化学社製)、ビスコート190、ビスコート360、ビスコート700HV、ビスマーMPE400A、ビスマーMPE550A(以上大阪有機化学社製)、ネオマーPM201(三洋化成工業社製)、EBECRYL110、PEG400DA−D、EBECRYL11(以上ダイセルオルネクス社製)。
Examples of commercially available products of compound (b1) include, but are not limited to, the following.
Blemmer ADE-200, Blemmer ADE-300, Blemmer ADE-400A, Blemmer ADE-600, Blemmer PME-100, Blemmer PME-200, Blemmer PME-400, Blemmer PME-1000, Blemmer PE-200, Blemmer PE-350, Blemmer 50 POEP-800B, Blemmer PLE-200, Blemmer PSE-1300, Blemmer PDE-100, Blemmer PDE-150, Blemmer PDE-200, Blemmer PDE-400, Blemmer PDE-600, Blemmer PDBE-200A, Blemmer PDBE-450A, Blemmer ALE-200, Blemmer AME-400, Blemmer AAE-300 (manufactured by NOF CORPORATION), New Frontier PE-200, New Frontier PE-300, New Frontier PE-400, New Frontier PE-600, New Frontier BPE-4, New Frontier BPE-10, New Frontier BPE-20, New Frontier TMP-3, New Frontier TMP-15, New Frontier GE3A, New Frontier NP-4, New Frontier N-177E, New Frontier ME-3, New Frontier ME-4S, New Frontier MPE-600, New Frontier HBPE-4, New Frontier TMP-3, New Frontier PETA-4, New Frontier MPEM-400, New Frontier MPEM-1000, New Frontier PEM-1000, New Frontier BPEM-4, New Frontier BPEM-10, New Frontier HBPEM-10 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), SR-101, SR-150, SR-210, SR-230, SR-252, SR-256, SR- 259, SR-272, SR-415, SR-480, SR-494, SR-504, SR-540, SR-550, SR-602, SR-610, SR-9035, SR-344, SR-349, SR-454, SR-499, SR-502, SR-601, SR-9038 (manufactured by Sartmer), Aronix M-260, Aronix M-102, Aronix M-113, Aronix M-114, Aronix M-210, Aronix M-240, Aronix M-350, Aronix M-360, Aronix M-37 0, (manufactured by Toa Synthetic Co., Ltd.), NK Ester AM-30G, NK Ester AM-90G, NK Ester AM-130G, NK Ester AM-230G, NK Ester AMP-20GY, NK Ester A-200, NK Ester A-400 , NK Ester A-600, NK Ester A-1000, NK Ester A-1206PE, NK Ester A-0612PE, NK Ester A-0412PE, NK Ester A-1000PER, NK Ester A-3000PER, NK Ester A-BPE-4 , NK Ester A-BPE-10, NK Ester A-BPE-20, NK Ester A-BPE-30, NK Ester ABE-300, NK Ester A-B1206PE, NK Ester A-TMPT-3EO, NK Ester A-TMPT -9EO, NK Ester AT-20E, NK Ester AT-30E, NK Ester A-GLY-3E, NK Ester A-GLY-6E, NK Ester A-GLY-9E, NK Ester A-GLY-20E, NK Ester ATM -4EL, NK Ester ATM-8EL, NK Ester ATM-4E, NK Ester ATM-35E, NK Ester AD-TMP-4E, NK Ester A-DPH-12E, NK Economer A-PG5027E, NK Economer A-PG5054E, NK Ester M-40G, NK Ester M-90G, NK Ester M-130G, NK Ester M-230G, NK Ester S-20E, NK Ester S-12E, NK Ester EH-4E, NK Ester B-20G, NK Ester 9G , NK Ester 14G, NK Ester 23G, NK Ester 1000PER, NK Ester BPE-200, NK Ester BPE-300, NK Ester BPE-500, NK Ester BPE-900, NK Ester BPE-1300N, NK Ester GLY-3E, NK Ester GLY-6E, NK Ester GLY-9E, NK Ester GLY-20E, NK Ester TMPT-3EO, NK Ester TMPT-9EO, NK Ester TM-4EL, NK Ester TM-4E, NK Ester TM-35E, NK Ester D -TMP-4E, NK Ester M-DPH-6E, NK Ester M-DPH-12E, NK Economer M-PG5027E, NK Economer M-PG5054E, NK Ester ATM-120E, NK Ester A-DPH-48E, NK Ester A -DPH-96E (The above is manufactured by Shin-Nakamura Kagaku Co., Ltd.), Miramer M142, Miramer M144, Miramer M164, Miramer M166, Miramer M170, Miramer M232, Miramer M2100, Miramer M2200, MiramerM2200, MiramerM2200, Miramer28 M290, Miramer M2040, Miramer M3160, Miramer M3190, Miramer M3150, Miramer M4004, Miramer M193, Miramer M241, Miramer M2101, Miramer M2101, Miramer M2101, Miramer M2101, Miramer M2301 AT, Light Acrylate 130A, Light Acrylate P2H-A, Light Acrylate P-200A, Light Acrylate BP-4EAL, Light Acrylate 3EG-A, Light Acrylate 4EG-A, Light Acrylate 9EG-A, Light Acrylate 14EG-A, Light Acrylate TMP-6EO-3A (manufactured by Kyoeisha Chemical Co., Ltd.), Viscort 190, Viscort 360, Viscort 700HV, Bismer MPE400A, Bismer MPE550A (manufactured by Osaka Organic Chemical Co., Ltd.), Neomer PM201 (manufactured by Sanyo Kasei Kogyo Co., Ltd.), EBECRYL110, PEG400DA- D, EBECRYL11 (all manufactured by Daicel Ornex).
化合物(b1)は、上記の具体例に限定されるものではない。また、これらは1種だけを用いても良いし、あるいは、複数種を併用しても良い。 Compound (b1) is not limited to the above specific examples. Further, only one of these may be used, or a plurality of types may be used in combination.
以下、化合物(b2)について説明する。化合物(b2)のうち、化合物(b2−1−1)は、水酸基および二重結合を有するが、環状構造を有しないものであれば、特に制限はない。 Hereinafter, compound (b2) will be described. Of the compound (b2), the compound (b2-1-1) has a hydroxyl group and a double bond, but is not particularly limited as long as it does not have a cyclic structure.
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、(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二重結合基含有化合物に対してε−カプロ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、ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート等の水酸基含有の脂肪族(メタ)アクリル酸エステル類; For example, 2-hydroxyethyl (meth) acrylate, 1-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 1-hydroxy (meth) acrylate. Butyl, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxy (meth) acrylate Octyl, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate, ethyl-α- (hydroxymethyl) (meth) acrylate, glycerol monofunctional (meth) acrylate, or (meth) acrylic Fatty acid ester-based (meth) acrylic acid ester such as acid glycidyl lauric acid ester, (meth) acrylic acid glycidyl oleic acid ester, (meth) acrylic acid glycidyl stearic acid ester, or 2- (acryloyloxy) ethyl 6-hydroxyhexa (Meta) acrylic acid ester, pentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) having a hydroxyl group at the terminal by ring-open addition of ε-caprolactone to the hydroxyl group-containing double-bonding group-containing compound such as nonate. ) Hydroxid-containing aliphatic (meth) acrylic acid esters such as acrylate and dipentaerythritol penta (meth) acrylate;
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等の水酸基含有の脂肪族ビニルエーテル類;
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;
例えば、プロペンジオール等の複数の水酸基を有する二重結合基含有化合物類;
For example, hydroxyl group-containing aliphatic vinyl ethers such as hydroxyethyl vinyl ether and hydroxypropyl vinyl ether;
For example, hydroxyl group-containing aliphatic (meth) allyl alcohols such as (meth) allyl alcohol and isopropenyl alcohol, or (meth) allyl ethers;
For example, double bond group-containing compounds having a plurality of hydroxyl groups such as propenediol;
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, it contains hydroxyl groups such as N-hydroxyethyl (meth) acrylamide, N-hydroxypropyl (meth) acrylamide, N-hydroxybutyl (meth) acrylamide, N-hydroxyhexyl (meth) acrylamide, and N-hydroxyoctyl (meth) acrylamide. (Meta) acrylamides;
化合物(b2−1−1)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、ペンタエリスリトールトリ(メタ)アクリレート等水酸基含有の脂肪族(メタ)アクリル酸エステル類が好ましい。 Examples of the compound (b2-1-1) include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate in terms of adhesion to the substrate. , Ε-Caprolactone 1-2 mol-added (meth) acrylate 2-hydroxyethyl, pentaerythritol tri (meth) acrylate and other hydroxyl group-containing aliphatic (meth) acrylic acid esters are preferable.
化合物(b2)のうち、化合物(b2−1−2)は、二重結合、水酸基および環状構造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(b2−1−2)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。
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;
Of the compound (b2), the compound (b2-1-2) can be used without particular limitation as long as it has a double bond, a hydroxyl group and a cyclic structure. Since the compound (b2-1-2) has one or more ring structures in the molecule, it has durability such as heat resistance and moisture heat resistance even if it has a hydroxyl group, and also has aspects such as water resistance. Is preferable.
For example, (meth) acrylic acid 1,2-cyclohexanedimethanol, (meth) acrylic acid 1,3-cyclohexanedimethanol, (meth) acrylic acid 1,4-cyclohexanedimethanol, (meth) acrylic acid 2-hydroxy- 3-Phenoxymethyl, 2-hydroxy-3-phenoxyethyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2-hydroxy-3-phenoxybutyl (meth) acrylate, (meth) 2-Hydroxy-3-phenoxydecyl acrylate, 2-hydroxy-3-phenoxyoctadecyl (meth) acrylate, monohydroxyethylphthalate (meth) acrylate, 2- (4-benzoyl-3-hydroxy) (meth) acrylate Phenoxy) (meth) acrylic acid esters having a cyclic structure other than a hydroxyl group such as ethyl and a heterocycle;
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、2,2'−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;
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、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, hydroxyl group-containing benzophenone-based (meth) acrylics such as 2-hydroxy-4- {2- (meth) acryloyloxy} ethoxybenzophenone, 2,2'-dihydroxy-4- {2- (meth) acryloyloxy} ethoxybenzophenone. Acid esters;
For example, hydroxyl group-containing benzotriazole-based (meth) acrylic acid esters such as 2- (2'-hydroxy-5'-(meth) acryloyloxyethylphenyl) -2H-benzotriazole;
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- Examples thereof include hydroxyl group-containing triazine-based (meth) acrylic acid esters such as hydroxy-4- {2- (meth) acryloyloxyethoxy}] -S-triazine, and only one of these may be used. Alternatively, a plurality of types may be used in combination.
化合物(b2−1−2)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が好ましい。 As the compound (b2-1-2), acrylic acid 1,2-cyclohexanedimethanol, acrylic acid 1,3-cyclohexanedimethanol, acrylic acid 1,4- (Meta) acrylic acid esters having a cyclic structure other than a hydroxyl group and a heterocycle such as cyclohexanedimethanol and 2-hydroxy-3-phenoxypropyl acrylate are preferable.
化合物(b2)のうち、化合物(b2−2−1)と化合物(b2−2−2)に大別できるが、耐熱黄変性の点で、(b2−2−1)が好ましい。 The compound (b2) can be roughly classified into a compound (b2-2-1) and a compound (b2-2-2), but (b2-2-1) is preferable in terms of heat-resistant yellowing.
化合物(b2−2−1)としては、水酸基を有さず環員原子としてヘテロ原子を含まない環状構造および二重結合を有する化合物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、ジ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テニル、(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 (b2-2-1) is not particularly limited as long as it has a cyclic structure and a double bond that does not have a hydroxyl group and does not contain a hetero atom as a ring member atom. For example, cyclohexyl (meth) acrylate. , (Meta) 1-methyl-1-cyclopentyl acrylate, (meth) 1-ethyl-1-cyclopentyl acrylate, (meth) 1-isopropyl-1-cyclopentyl acrylate, 1-methyl-1 (meth) acrylate -Cyclohexyl, 1-ethyl-1-cyclohexyl (meth) acrylate, 1-isopropyl-1-cyclohexyl (meth) acrylate, 1-ethyl-1-cyclooctyl (meth) acrylate, benzyl (meth) acrylate, Iso-bornyl (meth) acrylate, phenyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, 2-oxo-1,2-phenylethyl (meth) acrylate, 2-oxo (meth) acrylate -1,2-Diphenylethyl, 1-naphthyl (meth) acrylate, 2-naphthyl (meth) acrylate, 1-naphthylmethyl (meth) acrylate, 1-anthryl (meth) acrylate, (meth) acrylate 2-Anthryl, 9-anthryl (meth) acrylate, 9-anthrylmethyl (meth) acrylate, 2-methyladamantyl-2-yl (meth) acrylate, dicyclopentanyl (meth) acrylate, (meth) ) Dicyclopentenyl acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl dicyclopentanyl, dicyclopentenyl diacrylate, 2-ethyladamantyl-2-yl (meth) acrylate, (meth) acrylic acid 2-n-propyl adamantyl-2-yl, (meth) acrylate 2-isopropyl adamantyl-2-yl, (meth) acrylate 1- (adamantan-1-yl) -1-methylethyl, (meth) acrylic acid 1- (adamantan-1-yl) -1-ethylethyl, 1- (meth) acrylate 1- (adamantan-1-yl) -1-methylpropyl, (meth) acrylate 1- (adamantan-1-yl) -1 -Ethylpropyl, (meth) acrylic acid-5-oxo-4-oxa-tricyclo [4.2.1.0 3,7 ] nona-2-yl, (meth) acrylic acid-5-oxo-4-oxa -Tricyclo [5.2.1.0 3,8 ] deca-2-yl, dihydro-α-terpinyl (meth) acrylate, -6-oxo-7-oxa- (meth) acrylate Bicyclo [3.2.1] octa-2-yl, (meth) acrylic acid-7-oxo-8-oxa-bicyclo [3.3.1] octa-2-yl, 2- (meth) acryloyloxyethyl Phtalate, 2- (meth) acryloyloxypropylphthalate, 2- (meth) acryloyloxybutylphthalate, 2- (meth) acryloyloxyhexylphthalate, 2- (meth) acryloyloxyoctylphthalate, 2- (meth) acryloyloxydecyl Phtalate, 2- (meth) acryloyloxyethyl hexahydrophthalate, (meth) acrylic acid (3,4-epoxycyclohexyl) methyl, (meth) acrylic acid-o-2-propenylphenyl, (meth) acrylic acid cyclohexylglycidyl ether , (Meta) acrylic acid cyclic esters such as (meth) acrylic acid phenylglycidyl ether;
例えば、N−(4−カルバモイルフェニル)(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
例えば、(メタ)アクリル酸スルホフェノキシエチ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;
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;
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)ノルボルナン等のアルケニル基含有の環状化合物類;
例えば、スチレン、2−メチルスチレン等の芳香族ビニル系単量体類;
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等の環状ビニルエーテル類;
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等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, (meth) acrylamides containing a cyclic structure such as N- (4-carbamoylphenyl) (meth) acrylamide, for example, (meth) acrylic acid cyclic esters containing a sulfonyl group such as sulfophenoxyethyl (meth) acrylate;
For example, metal salts and ammonium salts of (meth) acrylic acid cyclic esters containing a sulfonyl group such as (meth) acryloyloxyethyl dimethylbenzylammonium-p-toluenesulfonate;
Cyclic compounds containing alkenyl groups such as 5-vinylbicyclo [2.2.1] hepta-2-ene, 2,5-bis (allyloxy) norbornane;
For example, aromatic vinyl-based monomers such as styrene and 2-methylstyrene;
For example, cyclic vinyl ethers such as cyclohexyl vinyl ether and cycloxyl methyl vinyl ether;
For example, aromatic vinyl ether-based monomers having a long-chain alkyl group such as vinyl phenyl pentyl ether and vinyl phenyl hexyl 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等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;
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等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;
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等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;
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等のアルケニル基含有環状スルホン酸類;
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等のスチレンスルホン酸の金属塩類等が挙げられる。
For example, vinyl benzoic acid ester-based or isopropenyl benzoic acid ester-based monomers having a long-chain alkyl group such as 4-vinylbenzoate hexyl and 4-vinylbenzoate octyl;
For example, isopropenylphenyl-based monomers having a long-chain alkyl group such as isopropenylphenylmethylbutyl ether and isopropenylphenylmethylpentyl ether;
For example, monolong-chain alkyl ester-based cyclic monomers of dicarboxylic acids such as vinylphenyl phenylnonyl succinate and vinyl phenylmethyl decyl hexahydrophthalate;
For example, alkenyl group-containing cyclic sulfonic acids such as styrene sulfonic acid and 2-propenyloxybenzene sulfonic acid;
For example, ammonium salts of styrene sulfonic acid such as ammonium styrene sulfonate, monomethyl ammonium styrene sulfonate;
Examples thereof include metal salts of styrene sulfonic acid such as sodium styrene sulfonate.
化合物(b2−2−1)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−イル等の(メタ)アクリル酸環状エステル類が好ましい。 As the compound (b2-2-1), cyclohexyl acrylate, phenyl acrylate, benzyl acrylate, 2-phenoxyethyl acrylate, iso-bornyl acrylate, acrylic from the viewpoint of durability such as heat resistance and water resistance. (Meta) acrylic acid cyclic esters such as dicyclopentanyl acid, dicyclopentanyl diacrylic acid, dicyclopentenyl acrylate, dicyclopentenyl diacrylic acid, and 2-ethyladamantyl-2-yl acrylate are preferable.
化合物(b2−2−2)としては、水酸基を有さず環員原子としてヘテロ原子を含む環状構造および二重結合を有する化合物であれば、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 (b2-2-2) is not particularly limited as long as it does not have a hydroxyl group and has a cyclic structure containing a hetero atom as a ring member atom and a double bond. For example, pentamethylpiperidinyl (b2-2-2). Heterocyclic (meth) acrylic acid esters containing nitrogen atoms such as meta) acrylate and 4- (pyrimidine-2-yl) piperazin-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;
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;
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;
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;
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;
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, vinyl group-containing compounds having a nitrogen atom-containing heterocycle such as 1-vinylpyrrole and 1-vinyl-2-imidazoline;
For example, vinyl group-containing compounds having a nitrogen atom-containing six-membered ring such as 1- (meth) allyl-1H-imidazole and 1- (meth) allyl-2-methyl-1H-imidazole;
For example, nitrogen atom-containing heteropolycyclic ethenyl group-containing compounds such as 1-vinyl-1H-benzimidazole and 1-vinyl-5,6-dimethyl-1H-benzimidazole;
For example, compounds having a nitrogen atom-containing heterocyclic structure such as 1-methyl-4,5-divinyl-1H-imidazole and two or more vinyl groups;
For example, (meth) allyl having a nitrogen atom-containing heterocyclic structure such as 1- (meth) allyl-3,5-dimethyl-1H-pyrazole, 1- (1-methylpropyl) -5 (meth) allylpyrimidine. Group-containing compounds;
For example, (meth) allyl group-containing compounds having a nitrogen atom-containing heteropolycyclic structure such as 2- (meth) allyl-1H-indole and 3- (meth) allyl-1H-indole;
例えば、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オキシエチレン基変性、トリ(メタ)アクリル酸イソシアヌル酸オキシエチレン基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, di (meth) acrylic acid ethoxylated isocyanuric acid, tri (meth) acrylic acid ethoxylated isocyanuric acid, ε-caprolactone-modified tris- (2-acryloyloxyethyl) isocyanurate, di (meth) acrylic acid isocyanurate oxyethylene. (Meta) acrylic acid esters having a heterocyclic structure containing oxygen atoms in addition to nitrogen atoms such as group modification, tri (meth) acrylic acid isocyanuric acid oxyethylene group modification;
例えば、4−アクリロイルモルホリン、β−(2−フリル)(メタ)アクリルアミド等のヘテロ環状アクリルアミド類;
例えば、メチルマレイミド、エチルマレイミド等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;
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;
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;
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等のグリシジル基含有ビニルエステル類;
例えば、2−ビニルチアゾ−ル、4−メチル−5−ビニル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。
Heterocyclic acrylamides such as 4-acryloyl morpholine, β- (2-furyl) (meth) acrylamide;
For example, maleimide derivatives having both nitrogen and oxygen atoms such as methylmaleimide and ethylmaleimide;
For example, vinyl group-containing compounds having a heterocyclic structure containing an oxygen atom in addition to a nitrogen atom such as 2-vinyloxazole and 2-phenyl-4-vinyloxazole;
For example, heterocyclic (meth) acrylic acid esters having an oxygen atom such as glycidyl (meth) acrylate and (3,4-epoxycyclohexyl) methyl (meth) acrylate;
For example, glycidyl group-containing vinyl esters such as glycidyl cinnamate and allyl glycidyl ether;
For example, vinyl group-containing compounds having a heterocyclic structure containing a sulfur atom in addition to a nitrogen atom such as 2-vinylthiazol and 4-methyl-5-vinylthiazole can be mentioned, and only one of these can be used. Alternatively, a plurality of types may be used in combination.
化合物(b2−2−2)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、4−アクリロイルモルホリン等のヘテロ環状アクリルアミド類、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が好ましい。 As the compound (b2-2-2), a hetero having an oxygen atom such as glycidyl acrylate, glycidyl methacrylate, or methyl methacrylate (3,4-epoxycyclohexyl) is considered from the viewpoint of durability such as heat resistance and water resistance. Oxygen atoms in addition to nitrogen atoms such as ring-containing (meth) acrylic acid esters, heterocyclic acrylamides such as 4-acryloylmorpholin, di (meth) acrylic acid ethoxylated isocyanuric acid, and tri (meth) acrylic acid ethoxylated isocyanuric acid. (Meth) acrylic acid esters having a heterocyclic structure containing the above are preferable.
また、化合物(b2−3)としては、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n−ブチル、(メタ)アクリル酸2−エチルヘキシル等の(メタ)アクリル酸アルキルエステル類;
例えば、(メタ)アクリル酸(メタ)アリル、(メタ)アクリル酸ビニル等のさらに二重結合基を含有する(メタ)アクリル酸エステル類;
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等の(メタ)アクリル酸パーフルオロアルキルエステル類;
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−エトキシエチル等のアルコキシ基含有(メタ)アクリル酸エステル類;
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;
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;
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;
Examples of the compound (b2-3) include (meth) acrylics such as methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate. Acid alkyl esters;
For example, (meth) acrylic acid esters containing further double bond groups such as (meth) acrylic acid (meth) allyl and (meth) vinyl chloride;
For example, (meth) acrylic acid perfluoroalkyl esters such as (meth) acrylic acid perfluoromethyl and (meth) acrylic acid perfluoroethyl;
For example, alkoxy group-containing (meth) acrylic acid esters such as 2-methoxyethyl (meth) acrylate and 2-ethoxyethyl (meth) acrylate;
For example, alkylene oxide-containing (meth) acrylic acid derivatives such as an alkylene oxide adduct of (meth) acrylic acid;
For example, aliphatic (meth) acrylic acid esters having one carbonyl group such as (meth) acrylic acid (methoxycarbonyl) methyl and (meth) acrylic acid (methoxycarbonyl) ethyl;
For example, aliphatic (meth) acrylic acid esters having two carbonyl groups such as 2-oxobutanoylethyl (meth) acrylate and 2-oxobutanoylpropyl (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 ] nona-2-yl, (meth) acrylic acid-10-methoxycarbonyl -5-oxo-4-oxa-tricyclo [5.2.1.0 3,8 ] nona-2-yl, (meth) acrylate-4-methoxycarbonyl-6-oxo-7-oxa-bicyclo [3] .2.1] It has a carbonyl group such as octa-2-yl, (meth) acrylate-4-methoxycarbonyl-7-oxo-8-oxa-bicyclo [3.3.1] octa-2-yl ( Meta) Acrylic acid cyclic esters;
例えば、N−(2−オキソブタノイルエチル)(メタ)アクリルアミド等のカルボニル基を有する(メタ)アクリルアミド類;
例えば、アセト酢酸ビニル等のアシル基を有する脂肪族系のビニル化合物類;
例えば、ベンゾイル酢酸ビニル、ベンゾイルプロピオン酸ビニル等のアシル基を有する芳香族系のビニル化合物類;
例えば、アセト酢酸(メタ)アリル、アセトプロピオン酸(メタ)アリル等のアシル基を有する脂肪族系の(メタ)アリル化合物類;
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, (meth) acrylamides having a carbonyl group such as N- (2-oxobutanoylethyl) (meth) acrylamide;
For example, aliphatic vinyl compounds having an acyl group such as vinyl acetoacetic acid;
For example, aromatic vinyl compounds having an acyl group such as vinyl benzoyl acetate and vinyl benzoyl propionate;
For example, aliphatic (meth) allyl compounds having an acyl group such as acetoacetic acid (meth) allyl and acetopropionic acid (meth) allyl;
For example, alkoxysilyl group-containing (meth) acrylic acid esters such as 3- (meth) acryloyloxypropylmethyldimethoxysilane and 3- (meth) acryloyloxypropyltrimethoxysilane;
例えば、ジ(メタ)アクリル酸プロピレンオキサイド、ジ(メタ)アクリル酸ポリプロピレンオキサイド、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1,9−ノナンジオール等の2官能(メタ)アクリル酸エステル類; For example, bifunctional (meth) acrylic acid propylene oxide, di (meth) acrylic acid polypropylene oxide, di (meth) acrylic acid 1,6-hexanediol, di (meth) acrylic acid 1,9-nonanediol and the like. Meta) Acrylic acid 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, tri (meth) acrylic acid 1,2,3-propanetriol, tri (meth) acrylic acid 2-methylpentane-2,4-diol, tri (meth) acrylic acid 2-methylpentane-2,4-diol. Tricaprolactonate, tri (meth) acrylic acid 2,2-dimethylpropan-1,3-diol, tri (meth) acrylate trimethyl hexane, tri (meth) acrylate trimethylol octane, tri (meth) acrylic acid 2,2-bis (hydroxymethyl) 1,3-propanediol, tri (meth) acrylic acid 1,1,1-trishydroxymethylethane, tri (meth) acrylic acid 1,1,1-trishydroxymethylpropane, Trifunctional (meth) acrylates 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, pentaerythritol tetra (meth) acrylate, pentaerythritol ethoxylated tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tetra (meth) acrylate 2, 2-Bis (Hydroxymethyl) 1,3-Propanediol, Tetra (Meta) Acrylic Acid 2,2-Bis (Hydroxymethyl) 1,3-Propandiol Tetracaprolactonate, Tetra (Meta) Acrylic Acid Di1, 2,3-Propanetriol, di2-methylpentane tetra (meth) acrylate-2,4-diol, di2-methylpentane tetra (meth) acrylate-2,4-diol tetracaprolactonate, tetra ( Di,2-dimethylpropane-1,3-diol acrylate, ditrimethylolbutane tetra (meth) acrylate, ditrimethylolhexane tetra (meth) acrylate, ditrimethylol octane tetra (meth) acrylate, etc. Functional (meth) acrylic acid esters;
例えば、酢酸ビニル、プロピオン酸ビニル等のカルボン酸のビニルエステル類;
例えば、メチルビニルエーテル、エチルビニルエーテル等の脂肪族ビニルエーテル類;
例えば、プロピレングリコールジビニルエーテル1,4−シクロヘキサンジオールジビニルエーテル(CHODVE)、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, vinyl esters of carboxylic acids such as vinyl acetate and vinyl propionate;
For example, aliphatic vinyl ethers such as methyl vinyl ether and ethyl vinyl ether;
For example, polyfunctional vinyl ethers such as propylene glycol divinyl ether 1,4-cyclohexanediol divinyl ether (CHODVE), trimethylolpropane trivinyl ether, dipentaerythritol tetravinyl ether, ditrimethylolpropane tetravinyl ether, dipentaerythritol hexavinyl ether;
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)アクリルアミド等のモノまたはジ-アルキルアミノアルキル(メタ)アクリルアミド類;
例えば、(メタ)アクリルアミド、N−メチル(メタ)アクリルアミド等の脂肪族系の(メタ)アクリルアミド類;
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)アクリルアミド等のN−アルコキシ基含有の(メタ)アクリルアミド類;
例えば、(メタ)アクリロニトリル、マレインニトリル、フマロニトリル等のニトリル基含有二重結合基含有化合物類;
例えば、酢酸(メタ)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, mono- or di-alkylaminoalkyl (meth) acrylamides such as dimethylaminoethyl (meth) acrylamide and diethylaminoethyl (meth) acrylamide;
For example, aliphatic (meth) acrylamides such as (meth) acrylamide and N-methyl (meth) acrylamide;
For example, N-alkoxy group-containing (meth) acrylamides such as N-methoxymethyl (meth) acrylamide and N-methoxyethyl (meth) acrylamide;
For example, nitrile group-containing double bond group-containing compounds such as (meth) acrylonitrile, maleine nitrile, and fumaronitrile;
For example, (meth) allyl esters of saturated carboxylic acids such as acetic acid (meth) allyl, coconut oil fatty acid, vinyl pivalate;
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、オキシエチレン基を除く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, (meth) acrylic acid 2-carboxyethyl, (meth) acrylic acid 2-carboxypropyl, (meth) acrylic acid 3-carboxypropyl, (meth) acrylic acid 4-carboxybutyl, (meth) ) Acrylic acid dimer, maleic acid, fumaric acid, monomethylmaleic acid, monomethylfumaric acid, aconitic acid, sorbic acid, silicic acid, α-chlorosorbic acid, glutaconic acid, citraconic acid, mesaconic acid, itaconic acid, tigric acid, Angelica acid, senesioic acid, crotonic acid, isoccrotonic acid, mucobromic acid, mucochloric acid, sorbic acid, muconic acid, aconitic acid, penicic acid, gelanic acid, citronellic acid, 4-acrylamide butanoic acid, 6-acrylamidehexanoic acid, 2- Polylactone-based (meth) acrylic acid ester, oxyethylene group having a carboxyl group at the end due to ring-opening addition of the lactone ring, such as (meth) acryloyloxyethyl succinate, mono (meth) acrylic acid ω-carboxypolycaprolactone ester. A carboxyl group-containing aliphatic α, β- Unsaturated double-bonded group-containing carboxylic acids and their 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等のカルボキシル基含有の脂環や芳香環を有する(メタ)アクリロイル基含有カルボン酸類やその酸無水物類;
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;
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等のヒドラジノ基を有する(メタ)アクリル酸エステル類;
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等の3級アミノ基を有する(メタ)アクリル酸エステル類;
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;
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)アクリルアミド等の3級のアミノ基を有する(メタ)アクリルアミド類;
例えば、ビニルアミン、メチルビニルアミン等の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, (meth) acryloyl group-containing carboxylic acids having a carboxyl group-containing alicyclic or aromatic ring such as 2- (meth) acryloyloxyethyl hexahydrophthalate and 2- (meth) acryloyloxyethyl phthalate and their acid anhydrides. ;
For example, (meth) acrylic acid esters having primary and / or secondary amino groups such as N-methylaminoethyl (meth) acrylate and N-ethylaminoethyl (meth) acrylate;
For example, (meth) acrylic acid esters having a hydrazino group such as (meth) acrylic acid hydrazide, 2- (2-furyl) -3- (5-nitro-2-frill) (meth) acrylic acid hydrazide;
For example, (meth) acrylic acid esters having a tertiary amino group such as dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate;
For example, (meth) acrylamides having primary and / or secondary amino groups such as monomethylaminoethyl (meth) acrylamide and monoethylaminoethyl (meth) acrylamide;
For example, (meth) acrylamides having a tertiary amino group such as dimethylaminoethyl (meth) acrylamide and diethylaminoethyl (meth) acrylamide;
For example, vinyl compounds having a primary and / or secondary amino group such as vinylamine and methylvinylamine;
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;
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;
例えば、マレイミド、メチルマレイミド等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, (meth) allylamine, 4- (meth) allyl-3,5-dimethyl-1H-pyrazole, 5- (1-methylpropyl) -5- (meth) allylpyrimidine, 5- (meth) allyl-5-. It has primary and / or secondary amino groups such as isopropylpyrimidine, 2- (meth) allylpyridine, 4- (meth) allylpyridine, 3,6-dihydro-4- (meth) allylpyridine (meth). Allyl compounds;
For example, vinyl compounds containing a tertiary amino group such as N-ethyl-N-nitrosovinylamine;
Examples thereof include, but are not limited to, heterocyclic double bond group-containing compounds of maleimide derivatives having both a nitrogen atom and an oxygen atom such as maleimide and methylmaleimide. Only one of these may be used, or a plurality of types may be used in combination.
上記、その他の二重結合を有する化合物(b2−3)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、硬化性の良い重合物を得る為には、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 the above-mentioned other compound having a double bond (b2-3), a compound having a (meth) acryloyl group is preferable from the viewpoint of reactivity, and in order to obtain a polymer having good curability, bifunctional or higher functional compounds (b2-3) are preferable. Meta) It is preferable to contain acrylic acid esters.
化合物(b2)において、重合硬化性、重合物の硬化収縮性、及び、耐熱性,耐湿熱性や耐水性等の耐久性の点で化合物(b2)の優位性は、水酸基を含有する(b2−1)ではあるが、水酸基と環状構造の双方が含有されるように適時配合することで、良好な重合性組成物とすることができる。 In the compound (b2), the superiority of the compound (b2) in terms of polymerization curability, curing shrinkage of the polymer, and durability such as heat resistance, moisture heat resistance, and water resistance is that the compound (b2) contains a hydroxyl group (b2-). Although it is 1), a good polymerizable composition can be obtained by blending it in a timely manner so as to contain both a hydroxyl group and a cyclic structure.
化合物(b2)は、以下に示すメーカーの市販品として、容易に入手することができる。例えば、共栄社油脂化学工業(株)社製の「ライトアクリレート」、「ライトエステル」、「エポキシエステル」、「ウレタンアクリレート」及び「高機能性オリゴマー」シリーズ、新中村化学(株)社製の「NKエステル」及び「NKオリゴ」シリーズ、日立化成工業(株)社製の「ファンクリル」シリーズ、東亞合成化学(株)社製の「アロニックスM」シリーズ、大八化学工業(株)社製の「機能性モノマー」シリーズ、大阪有機化学工業(株)社製の「特殊アクリルモノマー」シリーズ、三菱レイヨン(株)社製の「アクリエステル」及び「ダイヤビームオリゴマー」シリーズ、日本化薬(株)社製の「カヤラッド」及び「カヤマー」シリーズ、(株)日本触媒社製の「(メタ)アクリル酸/メタクリル酸エステルモノマー」シリーズ、日本合成化学工業(株)社製の「NICHIGO−UV紫光ウレタンアクリレートリゴマー」シリーズ、信越酢酸ビニル(株)社製の「カルボン酸ビニルエステルモノマー」シリーズ、(株)興人社製の「機能性モノマー」シリーズ等が挙げられる。 Compound (b2) can be easily obtained as a commercially available product of the following manufacturers. For example, "Light Acrylate", "Light Ester", "Epoxy Ester", "Urethane Acrylate" and "Highly Functional Oligomer" series manufactured by Kyoei Co., Ltd., "Light Ester" manufactured by Shin-Nakamura Chemical Co., Ltd. "NK Ester" and "NK Oligo" series, "Funkril" series manufactured by Hitachi Kasei Kogyo Co., Ltd., "Aronix M" series manufactured by Toa Synthetic Chemical Co., Ltd., manufactured by Daihachi Kagaku Kogyo Co., Ltd. "Functional monomer" series, "Special acrylic monomer" series manufactured by Osaka Organic Chemical Industry Co., Ltd., "Acrylate" and "Diabeam oligomer" series manufactured by Mitsubishi Rayon Co., Ltd., Nippon Kayaku Co., Ltd. "Kayarad" and "Kayamer" series manufactured by Nippon Catalyst Co., Ltd., "(Meta) acrylic acid / methacrylic acid ester monomer" series manufactured by Nippon Catalyst Co., Ltd., "NICHIGO-UV purple light urethane" manufactured by Nippon Synthetic Chemical Industry Co., Ltd. Examples include the "acrylate ligomer" series, the "carboxylic acid vinyl ester monomer" series manufactured by Shinetsu Vinyl Acetate Co., Ltd., and the "functional monomer" series manufactured by Kojin Co., Ltd.
さらに、化合物(b2)は、以下に示す文献に記載のものも挙げることができる。例えば、山下晋三ら編、「架橋剤ハンドブック」、(1981年、大成社)や加藤清視編、「UV・EB硬化ハンドブック(原料編)」、(1985年、高分子刊行会)、ラドテック研究会編、赤松清編、「新・感光性樹脂の実際技術」、(1987年、シーエムシー)、遠藤剛編、「熱硬化性高分子の精密化」、(1986年、シーエムシー)、滝山榮一郎著、「ポリエステル樹脂ハンドブック」、(1988年、日刊工業新聞社)、ラドテック研究会編、「UV・EB硬化技術の応用と市場」、(2002年、シーエムシー)が挙げられる。 Further, as the compound (b2), those described in the following documents can also be mentioned. For example, Shinzo Yamashita et al., "Crosslinking Agent Handbook" (1981, Taiseisha) and Kiyomi Kato, "UV / EB Curing Handbook (Raw Materials)", (1985, Polymer Publishing Association), Radtech Research Kai, Kiyoshi Akamatsu, "New Practical Technology for Photosensitive Resins", (1987, CMC), Tsuyoshi Endo, "Precision of Thermosetting Polymers", (1986, CMC), Takiyama Eiichiro's "Polyester Resin Handbook" (1988, Nikkan Kogyo Shimbun), Radtech Study Group, "Application and Market of UV / EB Curing Technology", (2002, CMC).
<酸化還元触媒(C)>
本発明において、酸化還元触媒(C)は、原子価状態が2以上の状態で存在する事の出来る金属塩又は錯体である。酸化還元触媒(C)は、後述する有機還元剤(D)によって変換された過酸化水素を酸化還元反応により分解し、活性ラジカルを発生させる役割を果たしている。
<Redox catalyst (C)>
In the present invention, the redox catalyst (C) is a metal salt or complex that can exist in a valence state of 2 or more. The redox catalyst (C) plays a role of decomposing hydrogen peroxide converted by the organic reducing agent (D) described later by a redox reaction to generate active radicals.
酸化還元触媒(C)の具体例を以下に示すが、本発明に用いる酸化還元触媒(C)は、これらに限定されるものではない。 Specific examples of the redox catalyst (C) are shown below, but the redox catalyst (C) used in the present invention is not limited thereto.
オキシアセチルアセトンバナジウム、オキシ硫酸バナジウム、オキシナフテン酸バナジウム、オキシテトラフェニルポルフィリナトバナジル、オキシオクタエチルポルフィリナトバナジル、オキシテトラ−t−ブチルフタロシアニンバナジル等のオキシバナジウム塩あるいは錯体、第1コバルトアセチルアセトナト、第2コバルトアセチルアセトナト、ナフテン酸第1コバルト、ナフテン酸第2コバルト、ステアリン酸第1コバルト、ステアリン酸第2コバルト、酢酸コバルト、テトラフェニルポルフィリナトコバルト、オクタエチルポルフィリナトコバルト、オキシテトラ−t−ブチルフタロシアニンコバルト等のコバルト塩あるいは錯体、ステアリン酸第1マンガン、ステアリン酸第2マンガン、第1マンガンアセチルアセトナト、第2マンガンアセチルアセトナト、酢酸マンガン、ナフテン酸マンガン、テトラフェニルポルフィリナトマンガン、オクタエチルポルフィリナトマンガン、テトラ−t−ブチルフタロシアニンマンガン等のマンガン塩あるいは錯体、鉄(III)アセチルアセトナト、鉄(III)ベンゾイルアセトナト、テトラフェニルポルフィリナト鉄(III)クロライド、テトラフェニルポルフィリナト鉄(III)クロライド、オクタエチルポルフィリナト鉄(III)クロライド、テトラ−t−ブチルフタロシアニン鉄〈III〉クロライド、ナフテン酸鉄(III)フェロセン、シクロペンタジエニル-クメン鉄ヘキサフルオロホスフェート、鉄(II)−o−フェナントロリン、硫酸鉄(II)、塩化鉄(II)、硝酸鉄(II)、水酸化鉄(II)ヘキシアノ鉄(II)酸塩(フェロシアン化物)、鉄(II)アセチルアセトナト、鉄(II)ベンゾイルアセトナト、テトラフェニルポルフィリナト鉄(II)、テトラフェニルポルフィリナト鉄(II)、オクタエチルポルフィリナト鉄(II)、テトラ−t−ブチルフタロシアニン鉄〈II〉クロライド等の鉄塩あるいは錯体、チタニルアセチルアセトナト、チタノセン、ジシクロペンタジエニルチタニウム(II)ジクロリド、オキシチタニウムアセチルアセトナト等のチタン塩あるいは錯体。硫酸銅(I)、塩化銅硫酸銅(I)、硝酸銅硫酸銅(I)、水酸化銅硫酸銅(I)グルコン酸銅等の銅塩あるいは錯体。 Oxyvanadium salts or complexes such as oxyacetylacetone vanadium, vanadium oxysulfate, vanadium oxynaphthenate, oxytetraphenylporphyrinatovanadyl, oxyoctaethylporphyrinatovanadyl, oxytetra-t-butylphthalocyanine vanadyl, first cobalt acetylacetonato, Second cobalt acetylacetonato, first cobalt naphthenate, second cobalt naphthenate, first cobalt stearate, second cobalt stearate, cobalt acetate, tetraphenylporphyrinato cobalt, octaethylporphyrinato cobalt, oxytetra-t -Cobalt salts or complexes such as butylphthalocyanine cobalt, first manganese stearate, second manganese stearate, first manganese acetylacetonato, second manganese acetylacetonato, manganese acetate, manganese naphthenate, tetraphenylporphyrinato manganese, Manganese salts or complexes such as octaethylporphyrinato manganese, tetra-t-butylphthalocyanine manganese, iron (III) acetylacetonato, iron (III) benzoylacetonato, tetraphenylporphyrinato iron (III) chloride, tetraphenylporphyrinato Iron (III) chloride, octaethylporphyrinato iron (III) chloride, tetra-t-butylphthalocyanine iron <III> chloride, iron naphthenate (III) ferrocene, cyclopentadienyl-cumene iron hexafluorophosphate, iron (II) ) -O-Phenantroline, iron (II) sulfate, iron (II) chloride, iron (II) nitrate, iron (II) hydroxide hexcyano (II) salt (ferrocyanide), iron (II) acetylacetonato , Iron (II) benzoylacetonato, tetraphenylporphyrinato iron (II), tetraphenylporphyrinato iron (II), octaethylporphyrinato iron (II), tetra-t-butylphthalocyanine iron <II> chloride and other irons. Titanium salts or complexes such as salts or complexes, titanylacetylacetonato, titanosen, dicyclopentadienyltitanium (II) dichloride, oxytitanium acetylacetonato. A copper salt or complex such as copper sulfate (I), copper chloride copper sulfate (I), copper nitrate copper sulfate (I), copper hydroxide copper sulfate (I) copper gluconate.
本発明では、酸化還元触媒(C)として、上記の化合物を単独で、または2種類以上組み合わせて使用することが出来る。 In the present invention, the above compounds can be used alone or in combination of two or more as the redox catalyst (C).
酸化還元触媒(C)は、触媒機能の面から、銅(I)、鉄(II)、コバルト(II)が好ましく、入手のし易さ等から硫酸鉄(II)が特に好ましい。 As the redox catalyst (C), copper (I), iron (II), and cobalt (II) are preferable from the viewpoint of catalytic function, and iron (II) sulfate is particularly preferable from the viewpoint of easy availability.
酸化還元触媒(C)は、化合物(B)100質量部に対して、0.001〜5質量部である事が好ましく、0.005〜1質量部であることがより好ましい。0.001質量部以上であると、過酸化水素を分解し発生する活性ラジカルの量が、所望のラジカル重合性(転換率)を得る為に十分な量となることから、十分な硬度を有する重合物を得る事が出来たり、未反応モノマーが重合物中に残留量の削減に繋がり、臭気やマイグレーションの問題改善に繋がる。また、5質量部以下であると、酸化還元触媒(C)由来の重合物の着色が抑制され、重合物の用途拡大に繋がる。 The redox catalyst (C) is preferably 0.001 to 5 parts by mass, and more preferably 0.005 to 1 part by mass with respect to 100 parts by mass of the compound (B). When it is 0.001 part by mass or more, the amount of active radicals generated by decomposing hydrogen peroxide becomes a sufficient amount to obtain a desired radical polymerizable property (conversion rate), and thus has sufficient hardness. A polymer can be obtained, and unreacted monomers lead to a reduction in the residual amount in the polymer, leading to improvement of odor and migration problems. Further, when the amount is 5 parts by mass or less, the coloring of the polymer derived from the redox catalyst (C) is suppressed, which leads to the expansion of applications of the polymer.
<有機還元剤(D)>
本発明において、有機還元剤(D)は、ヒドリド移動による還元、つまりは水素供与体となり得るものである。有機還元剤(D)は、光増感剤(A)に活性エネルギー線を照射する事で発生した一重項酸素に水素を供与して過酸化水素を発生させる役割を果たす。
<Organic Reducing Agent (D)>
In the present invention, the organic reducing agent (D) can be a reduction by hydride transfer, that is, a hydrogen donor. The organic reducing agent (D) plays a role of supplying hydrogen to the singlet oxygen generated by irradiating the photosensitizer (A) with active energy rays to generate hydrogen peroxide.
有機還元剤(D)の具体例を以下に示すが、本発明に用いる有機還元剤(D)は、これらに限定されるものではない。 Specific examples of the organic reducing agent (D) are shown below, but the organic reducing agent (D) used in the present invention is not limited thereto.
アスコルビン酸及びその誘導体、バルビツル酸及びその誘導体、リボフラビン及びその誘導体、カテコール及びその誘導体、レゾルシン及びその誘導体、ハイドロキノン及びその誘導体、亜ジチオン酸アニオン又は亜硫酸アニオンの塩、スルフィン酸、およびスルフィン酸塩。 Ascorbic acid and its derivatives, barbitulic acid and its derivatives, riboflavin and its derivatives, catechol and its derivatives, resorcin and its derivatives, hydroquinone and its derivatives, salts of dithionous acid anion or sulfite anion, sulfinic acid, and sulfinate.
有機還元剤(D)は、化合物(B)100質量部に対して、0.01〜5質量部である事が好ましく、0.05〜2質量部であることがより好ましい。0.01質量部以上であると、一重項酸素を還元して発生する過酸化水素が十分な量となる事で、ラジカル重合性(転換率)が得る事が可能となり、十分な硬度を有する重合物を得る事が出来たり、未反応モノマーが重合物中に残留量の削減に繋がり、臭気やマイグレーションの問題改善に繋がる。 The amount of the organic reducing agent (D) is preferably 0.01 to 5 parts by mass, and more preferably 0.05 to 2 parts by mass with respect to 100 parts by mass of the compound (B). When it is 0.01 part by mass or more, the amount of hydrogen peroxide generated by reducing singlet oxygen becomes a sufficient amount, so that radical polymerizable (conversion rate) can be obtained and the hardness is sufficient. A polymer can be obtained, and unreacted monomers lead to a reduction in the residual amount in the polymer, leading to improvement of odor and migration problems.
<オリゴマー(E)>
本発明において、上記成分に加えて、二重結合を有する化合物(B)に該当しないオリゴマー(E)を含んでも良い。オリゴマー(E)を使用することによって、重合物の硬化収縮抑制効果をより向上させることができる。更に耐熱性又は耐湿熱性を向上させることが容易となる。
<Oligomer (E)>
In the present invention, in addition to the above components, an oligomer (E) which does not correspond to the compound (B) having a double bond may be contained. By using the oligomer (E), the effect of suppressing the curing shrinkage of the polymer can be further improved. Further, it becomes easy to improve heat resistance or moisture heat resistance.
オリゴマー(E)は、少なくとも(メタ)アクリルロイル基を有するモノマーの重合体及び/又は各種化合物に、(メタ)アクリルロイル基を有する置換基を付加して得られる化合物であって、分子内に、1個以上の(メタ)アクリルロイル基を有する。上記オリゴマーは、(メタ)アクリルロイル基の他に、各種官能基を有してもよい。上記オリゴマー(E)は、主鎖がポリエステルである(メタ)アクリロイル基を有するポリエステル系オリゴマー(e1)、主鎖がポリウレタンである(メタ)アクリロイル基を有するポリウレタン系オリゴマー(e2)、主鎖がグリシジル基を有する化合物と水酸基を有する化合物との反応により形成される構造を有し(メタ)アクリロイル基を有するポリエポキシ系オリゴマー(e3)及びポリアクリル系オリゴマー(e4)よりなる群から選ばれる少なくとも1種以上を含み、これらを特に制限なく使用することができる。 The oligomer (E) is a compound obtained by adding a substituent having a (meth) acrylic loyl group to a polymer and / or various compounds of a monomer having at least a (meth) acrylic loyl group, and is contained in the molecule. It has one or more (meth) acrylic loyl groups. The oligomer may have various functional groups in addition to the (meth) acrylic loyl group. The oligomer (E) is a polyester-based oligomer (e1) having a (meth) acryloyl group whose main chain is polyester, a polyurethane-based oligomer (e2) having a (meth) acryloyl group whose main chain is polyurethane, and a main chain. At least selected from the group consisting of polyepoxy-based oligomers (e3) and polyacrylic oligomers (e4) having a structure formed by the reaction of a compound having a glycidyl group and a compound having a hydroxyl group and having a (meth) acryloyl group. One or more of them are included, and these can be used without particular limitation.
(e1)主鎖がポリエステルである(メタ)アクリロイル基を有するポリエステル系オリゴマー
ポリエステル系オリゴマー(e1)としては、主鎖骨格に多塩基酸と多価アルコールを重縮合して得られるポリエステルの末端あるいはポリエステル鎖中の水酸基と(メタ)アクリル酸、マレイン酸などの分子内に1個以上のカルボキシル基を有するα,β−エチレン性不飽和二重結合基含有化合物とのエステル化によって得られる化合物、あるいはポリエステルの末端あるいはポリエステル鎖中のカルボキシル基と(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などの前述の化合物(b2−1−1)とのエステル化によって得られる化合物である。その他、酸無水物と(メタ)アクリル酸グリシジルと少なくとも1個の水酸基を有する化合物とから得られるポリエステルオリゴマー等もポリエステルオリゴマー(e1)として使用可能である。
(E1) Polyester-based oligomer having a (meth) acryloyl group whose main chain is polyester As the polyester-based oligomer (e1), the terminal of polyester obtained by polycondensing a polybasic acid and a polyhydric alcohol on the main chain skeleton or A compound obtained by esterification of a hydroxyl group in a polyester chain with an α, β-ethylene unsaturated double bond group-containing compound having one or more carboxyl groups in the molecule such as (meth) acrylic acid and maleic acid. Alternatively, it is obtained by esterification of the carboxyl group at the end of the polyester or in the polyester chain with the above-mentioned compound (b2-1-1) such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate. It is a compound. In addition, a polyester oligomer obtained from an acid anhydride, glycidyl (meth) acrylate, and a compound having at least one hydroxyl group can also be used as the polyester oligomer (e1).
上記、多塩基酸としては、脂肪族系、脂環族系、及び芳香族系が挙げられ、それぞれ特に制限が無く使用できる。脂肪族系多塩基酸としては、より具体的には、例えば、シュウ酸、マロン酸、コハク酸、アジピン酸、セバチン酸、アゼライン酸、スベリン酸、マレイン酸、クロロマレイン酸、フマル酸、ドデカン二酸、ピメリン酸、シトラコン酸、グルタル酸、イタコン酸、無水コハク酸、無水マレイン酸等が挙げられ、これらの脂肪族ジカルボン酸及びその無水物が利用できる。又、無水コハク酸の誘導体(メチル無水コハク酸物、2,2−ジメチル無水コハク酸、ブチル無水コハク酸、イソブチル無水コハク酸、ヘキシル無水コハク酸、オクチル無水コハク酸、ドデセニル無水コハク酸、フェニル無水コハク酸等)、無水グルタル酸の誘導体(無水グルタル酸、3−アリル無水グルタル酸、2,4−ジメチル無水グルタル酸、2,4−ジエチル無水グルタル酸、ブチル無水グルタル酸、ヘキシル無水グルタル酸等)、無水マレイン酸の誘導体(2−メチル無水マレイン酸、2,3−ジメチル無水マレイン酸、ブチル無水マレイン酸、ペンチル無水マレイン酸、ヘキシル無水マレイン酸、オクチル無水マレイン酸、デシル無水マレイン酸、ドデシル無水マレイン酸、2,3−ジクロロ無水マレイン酸、フェニル無水マレイン酸、2,3−ジフェニル無水マレイン酸等)等の無水物誘導体も利用できる。 Examples of the above-mentioned polybasic acid include aliphatic type, alicyclic group type, and aromatic type, and each of them can be used without particular limitation. More specifically, the aliphatic polybasic acid includes, for example, oxalic acid, malonic acid, succinic acid, adipic acid, sebatic acid, azelaic acid, suberic acid, maleic acid, chloromaleic acid, fumaric acid, and dodecanedi. Examples thereof include acids, pimeric acid, citraconic acid, glutaconic acid, itaconic acid, succinic anhydride, maleic anhydride and the like, and these aliphatic dicarboxylic acids and their anhydrides can be used. Derivatives of succinic anhydride (methyl anhydride, 2,2-dimethylanhydride, butylanhydride, isobutyl anhydride, hexyl anhydride, octyl anhydride, dodecenyl anhydride, phenylanhydride. Succinic acid, etc.), derivatives of glutaric anhydride (glutaric anhydride, 3-allyl maleic anhydride, 2,4-dimethyl maleic anhydride, 2,4-diethyl anhydride, butyl anhydride, hexyl anhydride, etc. ), Derivatives of maleic anhydride (2-methyl maleic anhydride, 2,3-dimethyl maleic anhydride, butyl maleic anhydride, pentyl maleic anhydride, hexyl maleic anhydride, octyl maleic anhydride, decyl maleic anhydride, dodecyl Anhydrous derivatives such as maleic anhydride, 2,3-dichloromaleic anhydride, phenylmaleic anhydride, 2,3-diphenylmaleic anhydride, etc.) can also be used.
脂環族系多塩基酸としては、より具体的には、例えば、脂環族ジカルボン酸としては、例えば、ダイマー酸、シクロプロパン−1α,2α−ジカルボン酸、シクロプロパン−1α,2β−ジカルボン酸、シクロプロパン−1β,2α−ジカルボン酸、シクロブタン−1,2−ジカルボン酸、シクロブタン−1α,2β−ジカルボン酸、シクロブタン−1α,3β−ジカルボン酸、シクロブタン−1α,3α−ジカルボン酸、(1R)−シクロペンタン−1β,2α−ジカルボン酸、trans−シクロペンタン−1,3−ジカルボン酸、(1β,2β)−シクロペンタン−1,3−ジカルボン酸、(1β,3β)−シクロペンタン−1,3−ジカルボン酸、(1S,2S)−1,2−シクロペンタンジカルボン酸、1,2−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、1,4−シクロヘキサンジカルボン酸、1,1−シクロヘプタンジカルボン酸、クバン−1,4−ジカルボン酸、2,3−ノルボルナンジカルボン酸、ヘキサヒドロテレフタル酸、ヘキサヒドロイソフタル酸、ヘキサヒドロフタル酸、テトラヒドロフタル酸等の飽和脂環属ジカルボン酸や、1−シクロブテン−1,2−ジカルボン酸、3−シクロブテン−1,2−ジカルボン酸、1−シクロペンテン−1,2−ジカルボン酸、4−シクロペンテン−1,3−ジカルボン酸、1−シクロヘキセン−1,2−ジカルボン酸、2−シクロヘキセン−1,2−ジカルボン酸、3−シクロヘキセン−1,2−ジカルボン酸、4−シクロヘキセン−1,3−ジカルボン酸、2,5−ヘキサジエン−1α,4α−ジカルボン酸等の環内に不飽和二重結合が1もしくは2個有した不飽和脂環族ジカルボン酸が挙げられ、これらの脂環族ジカルボン酸及びその無水物等が利用できる。 More specifically, as the alicyclic polybasic acid, for example, as the alicyclic dicarboxylic acid, for example, dimer acid, cyclopropane-1α, 2α-dicarboxylic acid, cyclopropane-1α, 2β-dicarboxylic acid. , Cyclopropane-1β, 2α-dicarboxylic acid, cyclobutane-1,2-dicarboxylic acid, cyclobutane-1α, 2β-dicarboxylic acid, cyclobutane-1α, 3β-dicarboxylic acid, cyclobutane-1α, 3α-dicarboxylic acid, (1R) -Cyclopentane-1β, 2α-dicarboxylic acid, trans-cyclopentane-1,3-dicarboxylic acid, (1β, 2β) -cyclopentane-1,3-dicarboxylic acid, (1β, 3β) -cyclopentane-1, 3-dicarboxylic acid, (1S, 2S) -1,2-cyclopentanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 1,1-cycloheptane Saturated alicyclic dicarboxylic acids such as dicarboxylic acid, cuban-1,4-dicarboxylic acid, 2,3-norbornandicarboxylic acid, hexahydroterephthalic acid, hexahydroisophthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, and 1- Cyclobutene-1,2-dicarboxylic acid, 3-cyclobutene-1,2-dicarboxylic acid, 1-cyclopentene-1,2-dicarboxylic acid, 4-cyclopentene-1,3-dicarboxylic acid, 1-cyclohexene-1,2- Dicarboxylic acid, 2-cyclohexene-1,2-dicarboxylic acid, 3-cyclohexene-1,2-dicarboxylic acid, 4-cyclohexene-1,3-dicarboxylic acid, 2,5-hexadien-1α, 4α-dicarboxylic acid, etc. Examples thereof include unsaturated alicyclic dicarboxylic acids having one or two unsaturated double bonds in the ring, and these alicyclic dicarboxylic acids and their anhydrides can be used.
また、ヘキサヒドロ無水フタル酸の誘導体(3−メチル−ヘキサヒドロ無水フタル酸、4−メチル−ヘキサヒドロ無水フタル酸)、テトラヒドロ無水フタル酸の誘導体(1,2,3,6−テトラヒドロ無水フタル酸、3−メチル−1,2,3,6−テトラヒドロ無水フタル酸、4−メチル−1,2,3,6−テトラヒドロ無水フタル酸、メチルブテニル−1,2,3,6−テトラヒドロ無水フタル酸等)等の水素添化した無水フタル酸誘導体も脂環族ジカルボン酸無水物として利用できる。 Derivatives of hexahydrophthalic anhydride (3-methyl-hexahydrophthalic anhydride, 4-methyl-hexahydrophthalic anhydride), derivatives of tetrahydrophthalic anhydride (1,2,3,6-tetrahydrophthalic anhydride, 3- Methyl-1,2,3,6-tetrahydrophthalic anhydride, 4-methyl-1,2,3,6-tetrahydrophthalic anhydride, methylbutenyl-1,2,3,6-tetrahydrophthalic anhydride, etc.) A hydrogenated phthalic anhydride derivative can also be used as an alicyclic dicarboxylic acid anhydride.
芳香族系多塩基酸としては、より具体的には、例えば、芳香族ジカルボン酸としては、例えば、o−フタル酸、イソフタル酸、テレフタル酸、トルエンジカルボン酸、2,5−ジメチルテレフタル酸、2,2'−ビフェニルジカルボン酸、4,4−ビフェニルジカルボン酸、1,4−ナフタレンジカルボン酸、2,6−ナフタレンジカルボン酸、ノルボルネンジカルボン酸、ジフェニルメタン−4,4´−ジカルボン酸、フェニルインダンジカルボン酸、1,2−アズレンジカルボン酸、1,3−アズレンジカルボン酸、4,5−アズレンジカルボン酸、(−)−1,3−アセナフテンジカルボン酸、1,4−アントラセンジカルボン酸、1,5−アントラセンジカルボン酸、1,8−アントラセンジカルボン酸、2,3−アントラセンジカルボン酸、1,2−フェナントレンジカルボン酸、4,5−フェナントレンジカルボン酸、3,9−ペリレンジカルボン酸等の芳香族ジカルボン酸や、無水フタル酸、4−メチル無水フタル酸等の芳香族ジカルボン酸無水物が挙げられ、これらの芳香族ジカルボン酸及びその無水物等が利用できる。 More specifically, as the aromatic polybasic acid, for example, as the aromatic dicarboxylic acid, for example, o-phthalic acid, isophthalic acid, terephthalic acid, toluenedicarboxylic acid, 2,5-dimethylterephthalic acid, 2 , 2'-biphenyldicarboxylic acid, 4,4-biphenyldicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, norbornenedicarboxylic acid, diphenylmethane-4,4'-dicarboxylic acid, phenylindandicarboxylic acid , 1,2-azurange carboxylic acid, 1,3-azurange carboxylic acid, 4,5-azurange carboxylic acid, (-)-1,3-acenaftendicarboxylic acid, 1,4-anthracene dicarboxylic acid, 1,5- Aromatic dicarboxylic acids such as anthracene dicarboxylic acid, 1,8-anthracene dicarboxylic acid, 2,3-anthracene dicarboxylic acid, 1,2-phenanthrange carboxylic acid, 4,5-phenanthrange carboxylic acid, and 3,9-perylene dicarboxylic acid , Aromatic dicarboxylic acid anhydrides such as phthalic acid anhydride and 4-methylphthalic anhydride, and these aromatic dicarboxylic acids and their anhydrides can be used.
さらに、無水クロレンド酸、無水ヘット酸、ビフェニルジカルボン酸無水物、無水ハイミック酸、エンドメチレン−1,2,3,6−テトラヒドロ無水フタル酸、メチル−3,6−エンドメチレン−1,2,3,6−テトラヒドロ無水フタル酸、1,2−シクロヘキサンジカルボン酸無水物、1−シクロペンテン−1,2−ジカルボン酸無水物、メチルシクロヘキセンジカルボン酸無水物、1,8−ナフタレンジカルボン酸無水物、オクタヒドロ−1,3−ジオキソ−4,5−イソベンゾフランジカルボン酸無水物等の酸無水物類も多塩基酸として使用可能である。 In addition, chlorendic anhydride, hetic anhydride, biphenyldicarboxylic anhydride, hymic anhydride, endomethylene-1,2,3,6-tetrahydrophthalic anhydride, methyl-3,6-endomethylene-1,2,3 , 6-Tetrahydro phthalic anhydride, 1,2-cyclohexanedicarboxylic acid anhydride, 1-cyclopentene-1,2-dicarboxylic acid anhydride, methylcyclohexene dicarboxylic acid anhydride, 1,8-naphthalenedicarboxylic acid anhydride, octahydro- Acid anhydrides such as 1,3-dioxo-4,5-isobenzofurandicarboxylic acid anhydride can also be used as polybasic acid.
また、多価アルコールとしては、数平均分子量(Mn):約50〜500の比較的低分子量のポリオール類や、数平均分子量(Mn):500〜30,000の比較的高分子量のポリオール類が挙げられ、それぞれ、特に制限が無く使用できる。 The polyhydric alcohols include relatively low molecular weight polyols having a number average molecular weight (Mn) of about 50 to 500 and relatively high molecular weight polyols having a number average molecular weight (Mn) of 500 to 30,000. Each of them can be used without any particular limitation.
比較的低分子量のポリオール類としては、より具体的には、例えば、プロピレングリコール、ジプロピレングリコール、ブチレングリコール、3−メチル−1,5−ペンタンジオール、2,4−ジエチル−1,5−ペンタンジオール、2−メチル−1,8−オクタンジオール、3,3'−ジメチロールヘプタン、2−ブチル−2−エチル−1,3−プロパンジオール、ポリオキシプロピレングリコール、プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、1,9−ノナンジオール、ネオペンチルグリコール、オクタンジオール、ブチルエチルペンタンジオール、2−エチル−1,3−ヘキサンジオール、シクロヘキサンジオール、シクロヘキサンジメタノール,トリシクロデカンジメタノール、シクロペンタジエンジメタノール、ダイマージオール等の脂肪族又は脂環族ジオール類; More specifically, as the polyols having a relatively low molecular weight, for example, propylene glycol, dipropylene glycol, butylene glycol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentane Diol, 2-methyl-1,8-octanediol, 3,3'-dimethylol heptane, 2-butyl-2-ethyl-1,3-propanediol, polyoxypropylene glycol, propanediol, 1,3-butane Diol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, octanediol, butylethylpentanediol, 2-ethyl-1,3- Adipose or alicyclic diols such as hexanediol, cyclohexanediol, cyclohexanedimethanol, tricyclodecanedimethanol, cyclopentadienedimethanol, and dimerdiol;
例えば、1,3−ビス(2−ヒドロキシエトキシ)ベンゼン、1,2−ビス(2−ヒドロキシエトキシ)ベンゼン、1,4−ビス(2−ヒドロキシエトキシ)ベンゼン、4,4'−メチレンジフェノール、4,4'−(2−ノルボルニリデン)ジフェノール、4,4'−ジヒドロキシビフェノール、o−,m−及びp−ジヒドロキシベンゼン、4,4'−イソプロピリデンフェノール、ビスフェノールにアルキレンオキサイドを付加させた付加型ビスフェノール等の芳香族ジオール類等を挙げることができる。 For example, 1,3-bis (2-hydroxyethoxy) benzene, 1,2-bis (2-hydroxyethoxy) benzene, 1,4-bis (2-hydroxyethoxy) benzene, 4,4'-methylenediphenol, Addition of 4,4'-(2-norbornenilidene) diphenol, 4,4'-dihydroxybiphenol, o-, m- and p-dihydroxybenzene, 4,4'-isopropyridenephenol, bisphenol with alkylene oxide added Aromatic diols such as type bisphenol can be mentioned.
付加型ビスフェノールの原料ビスフェノールとしては、ビスフェノールA、ビスフェノールF等が挙げられ、原料アルキレンオキサイドとしては、プロピレンオキサイドが挙げられる。
比較的高分子量のポリオール類としては、より具体的には、例えば、高分子量ポリエステルポリオール、高分子量ポリアミドポリオール、高分子量ポリカーボネートポリオール及び高分子量ポリウレタンポリオールが挙げられる。高分子量ポリカーボネートポリオールは、上記の比較的低分子量のジオールと炭酸エステル又はホスゲンとの反応によって得られる。
Examples of the raw material bisphenol of the addition type bisphenol include bisphenol A and bisphenol F, and examples of the raw material alkylene oxide include propylene oxide.
More specific examples of the relatively high molecular weight polyols include high molecular weight polyester polyols, high molecular weight polyamide polyols, high molecular weight polycarbonate polyols, and high molecular weight polyurethane polyols. The high molecular weight polycarbonate polyol is obtained by reacting the above-mentioned relatively low molecular weight diol with a carbonic acid ester or phosgene.
上記高分子量ポリエステルポリオールの市販品としては、例えば、東洋紡績社製のバイロンシリーズ、クラレ社製のクラレポリオールPシリーズ、協和発酵ケミカル社製のキョーワポールシリーズが挙げられる。
上記高分子量ポリアミドポリオールの市販品としては、富士化成工業社製のTPAE617等を使用できる。
上記高分子量ポリカーボネートポリオールの市販品としては、例えば、パーストープ社製のオキシマーN112、旭化成ケミカルズ社製のPCDLシリーズ、クラレ社製のクラレポリオールPMHCシリーズ、クラレポリオールCシリーズ等が挙げられる。
Examples of commercially available products of the high molecular weight polyester polyol include the Byron series manufactured by Toyobo Co., Ltd., the Kuraray polyol P series manufactured by Kuraray Co., Ltd., and the Kyowa Pole series manufactured by Kyowa Hakko Chemical Co., Ltd.
As a commercially available product of the high molecular weight polyamide polyol, TPAE617 manufactured by Fuji Kasei Kogyo Co., Ltd. or the like can be used.
Examples of commercially available products of the high molecular weight polycarbonate polyol include Oxymer N112 manufactured by Perstop, PCDL series manufactured by Asahi Kasei Chemicals Co., Ltd., Kuraray polyol PMHC series manufactured by Kuraray Co., Ltd., and Kuraray polyol C series.
上記高分子量ポリウレタンポリオールの市販品としては、例えば、東洋紡績社製のバイロンURシリーズ、三井化学ポリウレタン社製のタケラックE158(水酸基価=20mgKOH/g,酸価<3mgKOH/g)、タケラックE551T(水酸基価=30mgKOH/g,酸価<3mgKOH/g)、及び、タケラックY2789(水酸基価=10mgKOH/g,酸価<2mgKOH/g)等が挙げられる。
その他に、ポリカプロラクトンジオール、ポリ(β−メチル−γ−バレロラクトン)ジオール、ポリバレロラクトンジオール等のラクトン類を開環重合して得られるポリエステルポリオール等も、上記高分子量ポリオールとして使用できる高分子量ポリオールに含まれる。
Commercially available products of the above high molecular weight polyurethane polyol include, for example, Byron UR series manufactured by Toyo Spinning Co., Ltd., Takelac E158 manufactured by Mitsui Chemicals Polyurethane Co., Ltd. (hydroxyl value = 20 mgKOH / g, acid value <3 mgKOH / g), Takelac E551T (hydroxyl group). Values = 30 mgKOH / g, acid value <3 mgKOH / g), Takelac Y2789 (hydroxyl value = 10 mgKOH / g, acid value <2 mgKOH / g) and the like.
In addition, polyester polyols obtained by ring-opening polymerization of lactones such as polycaprolactone diols, poly (β-methyl-γ-valerolactone) diols, and polyvalerolactone diols can also be used as the high molecular weight polyols. Included in polyol.
(e2)主鎖がポリウレタンである(メタ)アクリロイル基を有するポリウレタン系オリゴマー
ポリウレタン系オリゴマー(e2)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(メタ)アクリル酸、(メタ)アクリル酸2−カルボキシエチルに代表される脂肪族系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または、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上述の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前記化合物(b2−1−1)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前記化合物(b2−1−1)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ポリウレタン系オリゴマー(e2)に含む。
(E2) Polyurethane-based oligomer having a (meth) acryloyl group whose main chain is polyurethane The polyurethane-based oligomer (e2) includes a compound having at least one isocyanate group, (meth) acrylic acid, and (meth) acrylic acid 2. Aliphatic α, β-unsaturated double-bonding group-containing carboxylic acids typified by −carboxyethyl and their acid anhydrides, or α, β-unsaturated double-bonding group-containing carboxylics having an alicyclic or aromatic ring. A compound obtained by reacting an acid or an acid anhydride thereof, or a urethane prepolymer having a terminal isocyanate group obtained by reacting a compound having at least one isocyanate group with the above-mentioned polyhydric alcohol and the compound (the compound ( A compound obtained by reacting b2-1-1), 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 at least one more. It is a compound obtained by reacting a urethane prepolymer having a terminal isocyanate group obtained by reacting a compound having an amino group with the compound (b2-1-1). Further, the polyurethane-based oligomer (e2) also contains a urea-bonding group obtained by reacting an isocyanate group with an amino group.
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 polyisocyanate and polyfunctional isocyanate, and aromatic polyisocyanate, aliphatic polyisocyanate, aromatic aliphatic polyisocyanate, alicyclic polyisocyanate and the like, respectively. Can be mentioned. More specifically, the monofunctional polyisocyanate includes, for example, methyl isocyanate, ethyl isocyanate, propyl isocyanate, butyl isocyanate, octyl isocyanate, decyl isocyanate, octadecyl isocyanate, stearyl isocyanate, cyclohexyl isocyanate, phenyl isocyanate, benzyl isocyanate, and 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-methylbenzylisocyanate, (R)-(-)-1-(1-naphthyl) ethylisocyanate, (R)-(+)-1-phenylethylisocyanate, ( Examples thereof include S)-(-)-1-phenylethyl isocyanate and p-toluenesulfonyl isocyanate.
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, more specifically, examples of the aromatic polyisocyanate include 1,3-phenylenediocyanate, 4,4'-diphenyldiisocyanate, 1,4-phenylenediocyanate, and 4,4'-diphenylmethane diisocyanate. Also known as: 4,4'-MDI), 2,4-tolylene diisocyanate (also known as 2,4-TDI), 2,6-tolylene diisocyanate, 4,4'-toluidine diisocyanate, 2,4,6-tri Examples thereof 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, and dodeca. Methylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate and the like can be mentioned.
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。 As aromatic aliphatic polyisocyanates, ω, ω'-diisocyanate-1,3-dimethylbenzene, ω, ω'-diisocyanate-1,4-dimethylbenzene, ω, ω'-diisocyanate-1,4-diethylbenzene, 1 , 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。 Examples of the alicyclic polyisocyanate include 3-isocyanate methyl-3,5,5-trimethylcyclohexylisocyanate (also known as IPDI), 1,3-cyclopentanediisocyanate, 1,3-cyclohexanediisocyanate, and 1,4-cyclohexanediisocyanate. Examples thereof include methyl-2,4-cyclohexanediisocyanate, methyl-2,6-cyclohexanediisocyanate, 4,4′-methylenebis (cyclohexylisocyanate), and 1,4-bis (isocyanatemethyl) cyclohexane.
また、(e2)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。 Further, as a part of the component (e2), the above-mentioned 2-methylpentane-2,4-diol adduct of polyisocyanate, trimer having an isocyanurate ring and the like can also be used in combination. Polyphenylmethane polyisocyanate (also known as PAPI), naphthylene diisocyanate, and modified products of these polyisocyanates can be used. As the polyisocyanate modified product, a carbodiimide group, a uretdione group, a uretonimine group, a bullet group reacted with water, an isocyanurate group, or a modified product having two or more of these groups can be used. The reaction product of the polyol and diisocyanate can also be used as a compound having at least two isocyanate groups.
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; Examples of amines having an amino group include aminomethane, aminoethane, 1-aminopropane, 2-aminopropane, 1-aminobutane, 2-aminobutane, 1-aminopentane, 2-aminopentane, 3-aminopentane, and the like. Isoamylamine, 1-aminohexane, 1-aminoheptane, 2-aminoheptane, 2-octylamine, 1-aminononane, 1-aminodecane, 1-aminododecane (laurylamine), 1-aminotridecane, 1-aminohexadecane , 1-Aminotetradecane (myristylamine), 1-aminopentadecane, cetylamine, oleylamine, cocoalkylamine, beef alkylamine, hardened beef alkylamine, allylamine, stearylamine, aminocyclopropane, aminocyclobutane, aminocyclopentane, Aminocyclohexane, aminocyclododecane, 1-amino-2-ethylhexane, 1-amino-2-methylpropane, 2-amino-2-methylpropane, 3-amino-1-propene, 3-aminomethylheptane, 3- Isopropoxypropylamine, 3-butoxypropylamine, 3-isobutoxypropylamine, 2-ethylhexyloxypropylamine, 3-decyloxypropylamine, 3-lauryloxypropylamine, 3-myristyloxypropylamine, 2- Aminomethyl tetrahydrofuran, aniline, o-aminotoluene, m-aminotoluene, p-aminotoluene, o-benzylaniline, p-benzylaniline, 1-anilinonaphthalene, 1-aminoanthraquinone, 2-aminoanthraquinone, 1-amino Anthracene, 2-aminoanthracene, 5-aminoisoquinolin, 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, din-propylamine, din-butylamine, disec-butylamine, N-ethyl-1,2 -Dimethylpropylamine, piperidine, 2-pipecholine, 3-pipecholine, 4-pipecholine, 2,4-lupetidine, 2,6-rupetidine, 3,5-lupetidine, 3-piperidin methanol, 2-piperidinethanol, 4-piperidin 2 such as ethanol, 4-piperidinol, pyrrolidine, 3-aminopyrrolidin, 3-pyrrolidinol, diamilamine, diallylamine, methylaniline, ethylaniline, dibenzylamine, diphenylamine, dicocoalkylamine, di-cured beef fat alkylamine, distearylamine, etc. Class amines;
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, ethylene diamine, propylene diamine [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, dimerdiamine, dicyclohexylmethane-4,4'-diamine, diethylene glycol bis (3-amino) Propyl) ether, phenylenediamine, xylylene diamine, dicyclohexylmethane-4,4'-diamine, 2,4-tolylene diamine, 2,6-tolylene diamine, diethyltoluenediamine, 3,3'-dichloro-4 , 4'-diaminodiphenylmethane, 4,4'-bis- (sec-butyl) diphenylmethane, glutamine, asparagine, lysine, diaminopropionic acid, ornithine, diaminobenzoic acid, diaminobenzenesulfonic acid, etc. Diamine having two primary amino groups Kind;
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 [also known as isopropylaminoethylamine], N-isopropyl-1,3-diaminopropane [also known as N-isopropyl-1, 3-Propanediamine or Isopropylaminopropylamine], and N-lauryl-1,3-propanediamine [also known as N-lauryl-1,3-diaminopropane or laurylaminopropylamine], triethyltetramine, diethylenetriamine, 2-hydroxy Ethylethylenediamine, hexamethylenediamine 2-hydroxyethylethylenediamine, N- (2-hydroxyethyl) propylenediamine, (2-hydroxyethylpropylene) diamine, (di-2-hydroxyethylethylene) diamine, (di-2-hydroxyethyl) Polyamines having primary and secondary amino groups such as propylene) 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, dihydrazide oxalic acid, dihydrazide malonic acid, dihydrazide succinic acid, dihydrazide glutaric acid, dihydrazide adipic acid, dihydrazide sebacic acid, dihydrazide dodecandioic acid, hexadecandiohydrazide, dihydrazide dihydranoic acid, dihydrazide maleic acid Hydrazides such as dihydrazide, phthalic acid dihydrazide, carbonate 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). , 1,5-Diazabicyclo- [4.3.0] -5-nonen and other tertiary amines;
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が利用できる。 For example, in addition, 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.
(e3)主鎖がグリシジル基を有する化合物と水酸基を有する化合物との反応により形成される構造を有し(メタ)アクリロイル基を有するポリエポキシ系オリゴマー
ポリエポキシ系オリゴマー(e3)は、グリシジル基を有する化合物とヒドロキシエチル(メタ)アクリレート、(メタ)アクリル酸、マレイン酸などの分子内に1個以上の水酸基やカルボキシル基を有する(メタ)アクリロイル基含有化合物との反応により得られる化合物であり、実質的にグリシジル基を有さず、かつ(メタ)アクリロイル基含有化合物を有する化合物である。代表例としてビスフェノール型、エポキシ化油型、フェノールノボラック型、脂環型が挙げられる。ビスフェノール型ポリエポキシ系オリゴマーとしては、ビスフェノール類とエピクロルヒドリンとを反応させて得られるビスフェノール型ジグリシジルエーテルと(メタ)アクリル酸などの分子内に1個以上のカルボキシル基を有する(メタ)アクリロイル基含有化合物とを反応して得られるものである。
(E3) Polyepoxy-based oligomer having a structure in which the main chain is formed by the reaction of a compound having a glycidyl group and a compound having a hydroxyl group and having a (meth) acryloyl group The polyepoxy-based oligomer (e3) has a glycidyl group. It is a compound obtained by reacting a compound having a compound with a (meth) acryloyl group-containing compound having one or more hydroxyl groups or carboxyl groups in the molecule, such as hydroxyethyl (meth) acrylate, (meth) acrylic acid, and maleic acid. It is a compound having substantially no glycidyl group and having a (meth) acryloyl group-containing compound. Typical examples include bisphenol type, epoxidized oil type, phenol novolac type, and alicyclic type. The bisphenol-type polyepoxy oligomer contains a (meth) acryloyl group having one or more carboxyl groups in the molecule such as bisphenol-type diglycidyl ether obtained by reacting bisphenols with epichlorohydrin and (meth) acrylic acid. It is obtained by reacting with a compound.
エポキシ化油ポリエポキシ系オリゴマーとしては、エポキシ化された大豆油等の油とヒドロキシエチル(メタ)アクリレート、(メタ)アクリル酸、マレイン酸などの分子内に1個以上の水酸基やカルボキシル基を有する(メタ)アクリロイル基含有化合物との反応により得られるものを使用できる。ノボラック型ポリエポキシ系オリゴマーとしては、ノボラック型エポキシ樹脂とヒドロキシエチル(メタ)アクリレート、(メタ)アクリル酸、マレイン酸などの分子内に1個以上の水酸基やカルボキシル基を有する(メタ)アクリロイル基含有化合物との反応により得られるものを使用できる。脂環型ポリエポキシ系オリゴマーとしては、脂環型エポキシ樹脂とヒドロキシエチル(メタ)アクリレート、(メタ)アクリル酸、マレイン酸などの分子内に1個以上の水酸基やカルボキシル基を有する(メタ)アクリロイル基含有化合物との反応により合成されたものを使用できる。 Epoxide oil The polyepoxide-based oligomer has one or more hydroxyl groups or carboxyl groups in an oil such as epoxidized soybean oil and a molecule such as hydroxyethyl (meth) acrylate, (meth) acrylic acid, and maleic acid. Those obtained by reaction with a (meth) acryloyl group-containing compound can be used. The novolak type polyepoxy oligomer contains a novolak type epoxy resin and a (meth) acryloyl group having one or more hydroxyl groups or carboxyl groups in the molecule such as hydroxyethyl (meth) acrylate, (meth) acrylic acid, and maleic acid. Those obtained by reaction with a compound can be used. The alicyclic polyepoxy oligomer includes an alicyclic epoxy resin and (meth) acryloyl having one or more hydroxyl groups or carboxyl groups in molecules such as hydroxyethyl (meth) acrylate, (meth) acrylic acid, and maleic acid. Those synthesized by reaction with a group-containing compound can be used.
(e4)ポリアクリル系オリゴマー
本発明では、オリゴマー(E)として、アクリル系オリゴマー(e4)を使用することもできる。使用可能な化合物の具体例として、(メタ)アクリロイル基を有する変性ポリエーテル、アミン変性された(メタ)アクリロイル基含有化合物、並びに、アルキッド樹脂、スピロアセタール樹脂、ポリブタジエン樹脂、ポリチオールポリエン樹脂及び多価アルコール等の各種化合物に(メタ)アクリロイル基を付加させた変性(メタ)アクリロイル基含有化合物、からなる群より選択される1以上の化合物の、オリゴマーまたはプレポリマーを使用することができる。
(E4) Polyacrylic oligomer In the present invention, an acrylic oligomer (e4) can also be used as the oligomer (E). Specific examples of the compounds that can be used include modified polyethers having a (meth) acryloyl group, amine-modified (meth) acryloyl group-containing compounds, and alkyd resins, spiroacetal resins, polybutadiene resins, polythiol polyene resins and polyvalent compounds. An oligomer or prepolymer of one or more compounds selected from the group consisting of modified (meth) acryloyl group-containing compounds in which a (meth) acryloyl group is added to various compounds such as alcohol can be used.
凝集密度に加えて、他成分との相溶性、及び耐熱性と耐湿熱性といった耐久性において、優れた特性を得る観点から、上記オリゴマー(E)の重量平均分子量(以下、Mwと称す。)が他成分との相溶性や良好な耐久性(耐熱性、耐湿熱性)、凝集密度の点で、300〜50,000の範囲であることが好ましく、400〜30,000の範囲であることが好ましい。Mwが50,000以下のオリゴマーを使用することによって、流動性に優れ、かつ上記記載の本発明に必須成分との相溶性にも優れた重合性組成物を容易に提供することができる。また、それに伴って、重合物の硬化収縮等の耐久性の低下を容易に抑制することができる。 The weight average molecular weight (hereinafter referred to as Mw) of the oligomer (E) is determined from the viewpoint of obtaining excellent properties in terms of compatibility with other components, heat resistance and moisture heat resistance in addition to the aggregation density. In terms of compatibility with other components, good durability (heat resistance, moisture heat resistance), and aggregation density, the range is preferably in the range of 300 to 50,000, and preferably in the range of 400 to 30,000. .. By using an oligomer having an Mw of 50,000 or less, it is possible to easily provide a polymerizable composition having excellent fluidity and excellent compatibility with the essential components of the present invention described above. Further, along with this, it is possible to easily suppress a decrease in durability such as curing shrinkage of the polymer.
なお、数平均分子量(Mn)、重量平均分子量(Mw)、酸価(AV)及び水酸基価(OHV)の測定方法については後述する。 The method for measuring the number average molecular weight (Mn), the weight average molecular weight (Mw), the acid value (AV), and the hydroxyl value (OHV) will be described later.
特に限定するものではないが、本発明において、上記オリゴマー(E)は、ポリウレタン系オリゴマー(e2)を含むことが好ましい。上記重合性組成物を造形材料等の用途で使用する場合、硬化物の弾性及び柔軟性は、上記オリゴマー(E)中の結合基に依存して変化する傾向がある。上記結合基がエステル又はエーテル基である場合、優れた柔軟性を得ることが容易である。しかし、弾性が低く、及び耐加水分解性も低い傾向がある。一方、上記成分(e2)を使用した場合、ウレタン結合に基づき、弾性と柔軟性とのバランスをとることが容易である。また、上記成分(e2)は、耐加水分解性も良好であるため、耐水性や耐湿熱性を容易に向上させることができる。
しかし、本発明は、上記成分(e2)以外のオリゴマー成分を使用した場合についても、その他の構成成分を適切に配合することによって、所望とする特性を容易に得ることができる。
Although not particularly limited, in the present invention, the oligomer (E) preferably contains a polyurethane-based oligomer (e2). When the above-mentioned polymerizable composition is used as a molding material or the like, the elasticity and flexibility of the cured product tend to change depending on the bonding group in the above-mentioned oligomer (E). When the bonding group is an ester or ether group, it is easy to obtain excellent flexibility. However, it tends to have low elasticity and low hydrolysis resistance. On the other hand, when the above component (e2) is used, it is easy to balance elasticity and flexibility based on the urethane bond. Further, since the above component (e2) has good hydrolysis resistance, water resistance and moisture heat resistance can be easily improved.
However, in the present invention, even when an oligomer component other than the above component (e2) is used, desired properties can be easily obtained by appropriately blending the other components.
<色材(F)>
本発明において、上記必須成分に加えて、色材(F)を含んでも良い。色材(F)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。
<Color material (F)>
In the present invention, a coloring material (F) may be contained in addition to the above essential components. By using the coloring material (F), it is possible to impart not only design properties but also various functions such as thermal properties, electrical properties, and optical properties depending on the dyes and pigments contained.
色材(F)には、染料や顔料(f1)を分散剤で高濃度に分散させたものも含まれる。染料や顔料(f1)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。 The coloring material (F) also includes a dye or pigment (f1) dispersed in a high concentration with a dispersant. As the dye or pigment (f1), for example, an achromatic pigment such as carbon black, titanium oxide, or calcium carbonate, or a chromatic organic pigment or dye can be used.
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が、これらに限定されるものではない。
For example, organic pigments include insoluble azo pigments such as toluidine red, toluidine maroon, hanza ero, benzidine ero, and pyrazolone red.
Soluble azo pigments such as Ritol Red, Helio Bordeaux, Pigment Scarlet, Permanent Red 2B,
Derivatives from vat dyes such as alizarin, indigo maroon, thioindigo maroon,
Phthalocyanine-based organic pigments such as phthalocyanine blue and phthalocyanine green,
Quinacridone organic pigments such as quinacridone red and quinacridone magenta,
Perylene-based organic pigments such as perylene red and perylene scarlet,
Isoindolinone-based organic pigments such as Isoindolinone Yellow and Isoindolinone Orange,
Pyranthron organic pigments such as Pyranthron red and Pyranthron orange, thioindigo organic pigments, condensed azo organic pigments, benzimidazolone organic pigments,
Kinophthalone-based organic pigments such as quinophthalone yellow,
Isoindoline organic pigments such as isoindoline yellow,
Other pigments include, but are limited to, organic pigments such as flavanthron ero, acylamide ero, nickel azo ero, copper azomethine ero, perinone orange, anthrone orange, dianthraquinonyl red, and dioxazine violet. It is not something that is done.
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が、これらに限定されるものではない。
これら色素誘導体であれば、特に問題無く使用できる。
For example, examples of the dye include, but are not limited to, azo dyes, rhodamine dyes, quinoline dyes, thiazine dyes, thiazole dyes, xanthene dyes, niglosin dyes and the like.
Any of these dye derivatives can be used without any particular problem.
本発明では、顔料の分散性および重合性組成物の保存安定性を向上させるために色材(F)に分散剤を添加するのが好ましい。色材(F)のうち、分散剤としては、水酸基含有カルボン酸エステル、長鎖ポリアミノアマイドと高分子量酸エステルの塩、高分子量ポリカルボン酸の塩、長鎖ポリアミノアマイドと極性酸エステルの塩、高分子量不飽和酸エステル、高分子共重合物、変性ポリウレタン、変性ポリアクリレート、ポリエーテルエステル型アニオン系活性剤、ナフタレンスルホン酸ホルマリン縮合物塩、芳香族スルホン酸ホルマリン縮合物塩、ポリオキシエチレンアルキルリン酸エステル、ポリオキシエチレンノニルフェニルエーテル、ステアリルアミンアセテート等を用いることができる。 In the present invention, it is preferable to add a dispersant to the coloring material (F) in order to improve the dispersibility of the pigment and the storage stability of the polymerizable composition. Among the coloring materials (F), as the dispersant, hydroxyl group-containing carboxylic acid ester, long-chain polyaminoamide and high-molecular-weight acid ester salt, high-molecular-weight polycarboxylic acid salt, long-chain polyaminoamide and polar acid ester salt, High molecular weight unsaturated acid ester, high molecular weight copolymer, modified polyurethane, modified polyacrylate, polyether ester type anionic activator, naphthalene sulfonic acid formalin condensate salt, aromatic sulfonic acid formalin condensate salt, polyoxyethylene alkyl Carboxylic acid ester, polyoxyethylene nonylphenyl ether, stearylamine acetate and the like can be used.
分散剤の具体例としては、BYK Chemie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)」が挙げられるが、これらに限定されるものではない。 Specific examples of the dispersant include "Anti-Terra-U (polyaminoamide phosphate)", "Anti-Terra-203 / 204 (high molecular weight polycarboxylate)" and "Disperbyk-101 (polyamino)" manufactured by BYK Chemie. Amido phosphate and acid ester), 107 (hydroxyl-containing carboxylic acid ester), 110, 111 (acid group-containing copolymer), 130 (polyamide), 161, 162, 163, 164, 165, 166, 170 (high) "Molecular copolymer)", "400", "Bycumen" (high molecular weight unsaturated acid ester), "BYK-P104, P105 (high molecular weight unsaturated acid polycarboxylic acid)", "P104S, 240S (high molecular weight unsaturated acid)" Acid polycarboxylic acid and silicon-based) ”,“ Lactimon (long-chain amine and unsaturated acid polycarboxylic acid and silicon) ”, but are not limited thereto.
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)」が挙げられるが、これらに限定されるものではない。 In addition, "Fuka 44, 46, 47, 48, 49, 54, 63, 64, 65, 66, 71, 701, 764, 766", "Fuka Polymer 100 (modified polyacrylate), 150 (aliphatic)" manufactured by Efka CHEMICALS. System-modified polymer), 400, 401, 402, 403, 450, 451, 452, 453 (modified polyacrylate), 745 (copper phthalocyanine), Kyoeisha Chemical Co., Ltd. "Floren TG-710 (urethane oligomer)," Fronon SH-290, SP-1000 ”,“ Polyflow No. 50E, No. 300 (acrylic copolymer) ”, Kusumoto Kasei Co., Ltd.“ Disparon KS-860, 873SN, 874 (polymer dispersant), # 2150 ( (Adipose polyvalent carboxylic acid), # 7004 (polyether ester type) ”, but is not limited thereto.
さらに、花王社製「デモールRN、N(ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩)、MS、C、SN−B(芳香族スルホン酸ホルマリン縮合物ナトリウム塩)、EP」、「ホモゲノールL−18(ポリカルボン酸型高分子)、「エマルゲン920、930、931、935、950、985(ポリオキシエチレンノニルフェニルエーテル)、「アセタミン24(ココナッツアミンアセテート)、86(ステアリルアミンアセテート)」、アビシア社製「ソルスパーズ5000(フタロシアニンアンモニウム塩系)、13940(ポリエステルアミン系)、17000(脂肪酸アミン系)、24000GR、32000、33000、39000、41000、53000」、日光ケミカル社製「ニッコール T106(ポリオキシエチレンソルビタンモノオレート)、MYS−IEX(ポリオキシエチレンモノステアレート)、Hexagline 4−0(ヘキサグリセリルテトラオレート)」、味の素ファインテクノ社製「アジスパーPB821、822、824」等が挙げられるが、これらに限定されるものではない。 Furthermore, Kao Co., Ltd. "Demor RN, N (Naphthalene Sulfonic Acid Formalin Condensate Sodium Salt), MS, C, SN-B (Aromatic Sulfonic Acid Formalin Condensate Sodium Salt), EP", "Homogenol L-18 (Poly) Carboxylic acid type polymer), "Emulgen 920, 930, 931, 935, 950, 985 (polyoxyethylene nonylphenyl ether)," acetamine 24 (coconut amine acetate), 86 (stearyl amine acetate) ", manufactured by Abyssia. Sol Spurs 5000 (phthalocyanine ammonium salt type), 13940 (polyester amine type), 17000 (fatty acid amine type), 24000GR, 32000, 33000, 39000, 41000, 53000 ", Nikko Chemical Co., Ltd." Nikkor T106 (polyoxyethylene sorbitan monooleate) ), MYS-IEX (polyoxyethylene monostearate), Hexagline 4-0 (hexaglyceryl tetraolate) ", Ajinomoto Fine Techno Co., Ltd." Azisper PB821, 822, 824 ", etc., but are limited to these. It's not a thing.
分散剤は、染料や顔料(f1)100質量部に対し、固形分換算で10〜60質量部の範囲で使用する事が好ましい。分散剤が顔料100質量部に対して10〜60質量部であると、重合性組成物の粘度が必要以上に上昇する事なく分散安定性が向上する事で、重合性組成物の分散安定性、保存安定性が向上する。 The dispersant is preferably used in the range of 10 to 60 parts by mass in terms of solid content with respect to 100 parts by mass of the dye or pigment (f1). When the dispersant is 10 to 60 parts by mass with respect to 100 parts by mass of the pigment, the dispersion stability is improved without increasing the viscosity of the polymerizable composition more than necessary, so that the dispersion stability of the polymerizable composition is improved. , Improves storage stability.
色材(F)は、重合性組成物100質量部に対して、0.1〜30質量部である事が好ましく、1〜10質量部であることがより好ましい。0.1〜30質量部であると、十分な着色効果が得られる。 The color material (F) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 10 parts by mass with respect to 100 parts by mass of the polymerizable composition. When it is 0.1 to 30 parts by mass, a sufficient coloring effect can be obtained.
<その他成分(G)>
本発明の重合性組成物は、本発明による効果を損なわない範囲であれば、各種添加剤等、その他の成分(G)を適宜配合することも可能である。例えば、ラジカル重合性(転換率)向上、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、及び着色向上等の観点から、有機又は無機の充填剤を配合することができる。このような充填剤は、ポリマー、セラミックス、金属、金属酸化物、金属塩の材料から構成されるものであってよい。また、その形状については、特に限定されず、例えば、粒子状及び繊維状等であってよい。なお、上記ポリマー系の材料を配合する場合には、フェノール系、ヒンダードアミン系等の酸化防止剤、シランカップリング剤、光増感剤、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、紫外線吸収剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、発砲剤、防カビ剤、帯電防止剤、磁性体、表面張力調整剤、スリッピング剤、アンチブロッキング剤、レベリング剤、赤外吸収剤、及び消泡剤等の独立した充填剤としてだけではなく、ポリマーブレンド又は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。
<Other ingredients (G)>
The polymerizable composition of the present invention may be appropriately blended with other components (G) such as various additives as long as the effects according to the present invention are not impaired. For example, improvement of radical polymerizable (conversion rate), reduction of polymerization curing shrinkage rate, reduction of thermal expansion rate, improvement of dimensional stability, improvement of elastic modulus, viscosity adjustment, improvement of thermal conductivity, improvement of strength, improvement of toughness, improvement of coloring, etc. From the viewpoint, an organic or inorganic filler can be blended. Such fillers may be composed of materials such as polymers, ceramics, metals, metal oxides and metal salts. The shape thereof is not particularly limited, and may be, for example, particulate or fibrous. When the above polymer-based materials are blended, antioxidants such as phenol-based and hindered amine-based materials, silane coupling agents, photosensitizers, flexibility-imparting agents, plasticizers, flame-retardant agents, and storage stability Agents, UV absorbers, thixotropy-imparting agents, dispersion stabilizers, fluidity-imparting agents, foaming agents, antifungal agents, antistatic agents, polymers, surface tension modifiers, slipping agents, anti-blocking agents, leveling agents, red It can be dissolved, semi-dissolved or micro-dispersed in the polymerizable composition as a polymer blend or polymer alloy, as well as as an independent filler such as an external absorber and antifoaming agent.
本発明の重合性組成物は、重合反応に際して、熱、または紫外線、可視光線、近赤外線、電子線等の活性エネルギー線によるエネルギーの付与により重合し、目的とする重合物を得ることが可能であるが、エネルギーの付与をする光源として、250nm〜750nmの波長領域に発光の主波長を有する光源による可視光線の照射が好ましい。250nm〜750nmの波長領域に発光の主波長を有する光源の例としては、超高圧水銀ランプ、高圧水銀ランプ、低圧水銀ランプ、水銀キセノンランプ、メタルハライドランプ、ハイパワーメタルハライドランプ、キセノンランプ、パルス発光キセノンランプ、重水素ランプ、蛍光灯、Nd−YAG3倍波レーザー、He−Cdレーザー、窒素レーザー、Xe−Clエキシマレーザー、Xe−Fエキシマレーザー、半導体励起固体レーザー、250nm〜750nmの波長領域に発光波長を有するLEDランプ光源などの各種光源が挙げられる。なお本明細書でいう、紫外線や可視光、近赤外線等の活性エネルギー線の定義は久保亮五ら編「岩波理化学辞典第4版」(1987年、岩波)によった。 The polymerizable composition of the present invention can be polymerized by applying energy by heat or active energy rays such as ultraviolet rays, visible rays, near infrared rays, and electron beams during the polymerization reaction to obtain a desired polymer. However, as a light source for applying energy, irradiation of visible light by a light source having a main wavelength of light emission in a wavelength region of 250 nm to 750 nm is preferable. Examples of light sources having a main emission wavelength in the 250 nm to 750 nm wavelength range are ultra-high pressure mercury lamps, high pressure mercury lamps, low pressure mercury lamps, mercury xenon lamps, metal halide lamps, high power metal halide lamps, xenon lamps, pulse emitting xenone. Lamps, heavy hydrogen lamps, fluorescent lamps, Nd-YAG triple wave lasers, He-Cd lasers, nitrogen lasers, Xe-Cl excimer lasers, Xe-F excimer lasers, semiconductor-pumped solid-state lasers, emission wavelengths in the wavelength range of 250 nm to 750 nm. Examples thereof include various light sources such as an LED lamp light source having the above. The definition of active energy rays such as ultraviolet rays, visible light, and near infrared rays in the present specification is based on "Iwanami Physics and Chemistry Dictionary 4th Edition" (1987, Iwanami) edited by Ryogo Kubo et al.
本発明の重合性組成物は、様々な基材上に印字や塗布することが可能であり、重合性組成物を印字や塗布する基材は、ガラス、プラスチック、金属及び紙からなる群から適宜選択することが出来る。更に、複数の基材から構成される複合基材も選択することが出来る。これらの基材は、板、フィルム、紙のように平坦な形状のものでも良いし、立体的な形状のものでも良い。プラスチック製のフィルムとしては、透明であるものが好ましい。 The polymerizable composition of the present invention can be printed or applied on various substrates, and the substrate on which the polymerizable composition is printed or applied is appropriately composed of a group consisting of glass, plastic, metal and paper. You can choose. Furthermore, a composite base material composed of a plurality of base materials can also be selected. These base materials may have a flat shape such as a plate, a film, or paper, or may have a three-dimensional shape. As the plastic film, a transparent film is preferable.
印字や塗布方法としては、例えば、インクジェット法、ブレードコート法、グラビアコート法、グラビアオフセットコート法、バーコート法、ロールコート法、ナイフコート法、エアナイフコート法、コンマコート法、Uコンマコート法、AKKUコート法、スムージングコート法、マイクログラビアコート法、リバースロールコート法、4本乃至5本ロールコート法、ディップコート法、カーテンコート法、スライドコート法、ダイコート法、スプレーコート法等が挙げられる。 Examples of printing and coating methods include an inkjet method, a blade coating method, a gravure coating method, a gravure offset coating method, a bar coating method, a roll coating method, a knife coating method, an air knife coating method, a comma coating method, and a U comma coating method. Examples thereof include an AKKU coating method, a smoothing coating method, a microgravure coating method, a reverse roll coating method, a 4- to 5-roll coating method, a dip coating method, a curtain coating method, a slide coating method, a die coating method, and a spray coating method.
プラスチックの基材としては、例えば、ポリエステル系ポリマー、セルロース系ポリマー、ポリカーボネート系ポリマー、ポリアクリル系ポリマー等の透明ポリマーが挙げられる。ポリエステル系ポリマーとしては、ポリエチレンテレフタレート(PET)、ポリエチレンナフタレート等が挙げられる。セルロース系ポリマーとしては、ジアセチルセルロース、トリアセチルセルロース(TAC)等が挙げられる。ポリアクリル系ポリマーとしては、ポリメチルメタクリレート等が挙げられる。 Examples of the base material of the plastic include transparent polymers such as polyester-based polymers, cellulosic-based polymers, polycarbonate-based polymers, and polyacrylic-based polymers. Examples of the polyester-based polymer include polyethylene terephthalate (PET) and polyethylene naphthalate. Examples of the cellulosic polymer include diacetyl cellulose and triacetyl cellulose (TAC). Examples of the polyacrylic polymer include polymethyl methacrylate and the like.
更にプラスチックの基材として、ポリスチレン系ポリマー、ポリオレフィン系ポリマー、ポリ塩化ビニル系ポリマー、及びポリアミド系ポリマー等の透明ポリマーも挙げられる。ポリスチレン系ポリマーとしては、ポリスチレン、アクリロニトリル・スチレン共重合体ポリマー等が挙げられる。ポリオレフィン系ポリマーとしては、ポリエチレン、ポリプロピレン、環状ないしノルボルネン構造を有するポリオレフィンポリマー、エチレン・プロピレン共重合体ポリマー等が挙げられる。ポリアミド系ポリマーとしては、ナイロンや芳香族ポリアミドポリマー等が挙げられる。 Further, examples of the base material of the plastic include transparent polymers such as polystyrene-based polymers, polyolefin-based polymers, polyvinyl chloride-based polymers, and polyamide-based polymers. Examples of the polystyrene-based polymer include polystyrene, an acrylonitrile / styrene copolymer polymer, and the like. Examples of the polyolefin-based polymer include polyethylene, polypropylene, a polyolefin polymer having a cyclic or norbornene structure, and an ethylene / propylene copolymer polymer. Examples of the polyamide polymer include nylon and aromatic polyamide polymers.
また、ポリイミド系ポリマー、ポリスルホン系ポリマー、ポリエーテルスルホン系ポリマー、ポリエーテルケトン系ポリマー、ポリフェニルスルフィド系ポリマー、ポリビニルアルコール系ポリマー、ポリ塩化ビニリデン系ポリマー、ポリビニルブチラール系ポリマー、ポリアリレート系ポリマー、ポリオキシメチレン系ポリマー、及びポリエポキシ系ポリマー、ならびに前記ポリマーのブレンド物等の透明ポリマー等も挙げられる。特に複屈折率の小さいものが好適に用いられる。 In addition, polyimide-based polymers, polysulfone-based polymers, polyethersulfone-based polymers, polyetherketone-based polymers, polyphenylsulfide-based polymers, polyvinyl alcohol-based polymers, polyvinylidene chloride-based polymers, polyvinyl butyral-based polymers, polyarylate-based polymers, poly Examples thereof include oximethylene-based polymers, polyepoxy-based polymers, and transparent polymers such as blends of the polymers. In particular, those having a small birefringence are preferably used.
重合性組成物の低粘度化、及び基材への濡れ広がり性を向上させるために、重合性組成物中に水または有機溶剤等の溶剤を含有させても良い。 A solvent such as water or an organic solvent may be contained in the polymerizable composition in order to reduce the viscosity of the polymerizable composition and improve the wettability and spreadability to the substrate.
有機溶剤としては、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、ジプロピレングリコールモノメチルエーテルアセテート、エチレングリコールモノメチルエーテルプロピオネート、エチレングリコールモノエチルエーテルプロピオネート、エチレングリコールモノブチルエーテルプロピオネート、ジエチルジグリコール、ジエチレングリコールジアルキルエーテル、テトラエチレングリコールジアルキルエーテル、ジエチレングリコールモノメチルエーテルプロピオネート、ジエチレングリコールモノエチルエーテルプロピオネート、ジエチレングリコールモノブチルエーテルプロピオネート、プロピレングリコールモノメチルエーテルプロピオネート、ジプロピレングリコールモノメチルエーテルプロピオネート、エチレングリコールモノメチルエーテルブチレート、エチレングリコールモノエチルエーテルブチレート、エチレングリコールモノブチルエーテルブチレート、ジエチレングリコールモノメチルエーテルブチレート、ジエチレングリコールモノエチルエーテルブチレート、ジエチレングリコールモノブチルエーテルブチレート、プロピレングリコールモノメチルエーテルブチレート、ジプロピレングリコールモノメチルエーテルブチレート等のグリコールモノアセテート類、エチレングリコールジアセテート、ジエチレングリコールジアセテート、プロピレングリコールジアセテート、ジプロピレングリコールジアセテート、エチレングリコールアセテートプロピオネート、エチレングリコールアセテートブチレート、エチレングリコールプロピオネートブチレート、エチレングリコールジプロピオネート、エチレングリコールアセテートジブチレート、ジエチレングリコールアセテートプロピオネート、ジエチレングリコールアセテートブチレート、ジエチレングリコールプロピオネートブチレート、ジエチレングリコールジプロピオネート、ジエチレングリコールアセテートジブチレート、プロピレングリコールアセテートプロピオネート、プロピレングリコール1アセテートブチレート、プロピレングリコールプロピオネートブチレート、プロピレングリコールジプロピオネート、プロピレングリコールアセテートジブチレート、ジプロピレングリコールアセテートプロピオネート、ジプロピレングリコールアセテートブチレート、ジプロピレングリコールプロピオネートブチレート、ジプロピレングリコールジプロピオネート、ジプロピレングリコールアセテートジブチレート等のグリコールジアセテート類、エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ジプロピレングリコール等のグリコール類、エチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノブチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノブチルエーテル、プロピレングリコールn −プロピルエーテル、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル、トリエチレングリコールモノブチルエーテル、トリプロピレングリコールモノメチルエーテル等のグリコールエーテル類、乳酸メチル、乳酸エチル、乳酸プロピル、乳酸ブチル等の乳酸エステル類が挙げられる。 Organic solvents include ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, and dipropylene glycol monomethyl. Ether acetate, ethylene glycol monomethyl ether propionate, ethylene glycol monoethyl ether propionate, ethylene glycol monobutyl ether propionate, diethyl diglycol, diethylene glycol dialkyl ether, tetraethylene glycol dialkyl ether, diethylene glycol monomethyl ether propionate, diethylene glycol Monoethyl ether propionate, diethylene glycol monobutyl ether propionate, propylene glycol monomethyl ether propionate, dipropylene glycol monomethyl ether propionate, ethylene glycol monomethyl ether butyrate, ethylene glycol monoethyl ether butyrate, ethylene glycol monobutyl ether Glycol monoacetates such as butyrate, diethylene glycol monomethyl ether butyrate, diethylene glycol monoethyl ether butyrate, diethylene glycol monobutyl ether butyrate, propylene glycol monomethyl ether butyrate, dipropylene glycol monomethyl ether butyrate, ethylene glycol diacetate, diethylene glycol di Acetate, Propylene Glycol Diacetate, Dipropylene Glycol Diacetate, Ethylene Glycol Acetate Propionate, Ethylene Glycol Acetate Butyrate, Ethylene Glycol Propionate Butyrate, Ethylene Glycol Dipropionate, Ethylene Glycol Acetate Dibutyrate, Diethylene Glycol Acetate Propio Nate, Diethylene Glycol Acetate Butyrate, Diethylene Glycol Propionate Butyrate, Diethylene Glycol Dipropionate, Diethylene Glycol Acetate Dibutyrate, Propylene Glycol Acetate Propionate, Propylene Glycol 1 Acetate Butyrate, Propylene Glycol Propionate Butyrate, Propylene Glycol Dipropionate, Propylene Glycol Acetate Dibutyrate, Dipropylene Glycol Acetate Propionate, Dipropylene Glycol Acetate Butyrate, Dipropylene Glycol Propionate Butyrate, Dipropylene Glycol diacetates such as glycol dipropionate and dipropylene glycol acetate dibutyrate, glycols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and dipropylene glycol, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol Monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, propylene glycol n-propyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether , Glycol ethers such as triethylene glycol monobutyl ether and tripropylene glycol monomethyl ether, and lactic acid esters such as methyl lactate, ethyl lactate, propyl lactate and butyl lactate.
<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、活性酸素発生用増感剤(A)、化合物(B)、酸化還元触媒(C)、有機還元剤(D)、オリゴマー(E)、色材(F)、およびその他成分(G)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。
<Manufacturing of polymerizable composition>
The polymerizable composition used in the present invention is, if necessary, the above-mentioned sensitizer for generating active oxygen (A), compound (B), redox catalyst (C), organic reducing agent (D), oligomer (E). ), The coloring material (F), and the other component (G) are blended and then uniformly mixed to produce the product.
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 single-screw or multi-screw extruder equipped with a decompression device, a kneader, and a solver. good. The temperature at the time of stirring and mixing is usually 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。 Hereinafter, specific examples of the present invention will be described together with comparative examples, but the present invention is not limited to the following examples. Further, unless otherwise specified, in Examples and Comparative Examples, "parts" and "%" represent "parts by mass" and "% by mass", respectively.
<色材(F)分散体の製造>
[製造例1、2]
二重結合を有する化合物(B)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(F)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、数値は部を表し、空欄は配合していないことを表す。
<Manufacturing of colored material (F) dispersion>
[Manufacturing Examples 1 and 2]
The compound (B) having a double bond and the dispersed resin were stirred, and after confirming that the dispersed resin was completely dissolved, the pigment was added, and the mixture was stirred with a high-speed mixer or the like until it became uniform, and then obtained. The mill base was produced by dispersing in a horizontal sand mill for about 2 hours. Table 1 shows the composition (numerical values represent parts by mass) of the produced color material (F) dispersion (pigment dispersion). In Table 1, the numerical values represent parts, and the blanks indicate that they are not blended.
数平均分子量(Mn)、重量平均分子量(Mw)、酸価(AV)及び水酸基価(OHV)の測定方法について、以下に記載する。
《分子量》
数平均分子量(Mn)と重量平均分子量(Mw)の測定は、東ソー株式会社製GPC(ゲルパーミエーションクロマトグラフィー)「HLC−8320GPC」を用いた。カラムは、「TSKgel SuperHZ 1000」、「TSKgel SuperHZ 2000」、「TSKgel SuperHZM−N」、「TSKgel MultiporeHXL−M」から選択して用い、溶媒としてはテトロヒドロフラン、測定温度40℃で行った。分子量の決定はポリスチレン換算で行った。
The methods for measuring the number average molecular weight (Mn), weight average molecular weight (Mw), acid value (AV) and hydroxyl value (OHV) will be described below.
《Molecular weight》
The number average molecular weight (Mn) and the weight average molecular weight (Mw) were measured by using GPC (gel permeation chromatography) "HLC-8320 GPC" manufactured by Tosoh Corporation. The column was selected from "TSKgel SuperHZ 1000", "TSKgel SuperHZ 2000", "TSKgel SuperHZM-N", and "TSKgel Multipore HXL-M", and the solvent was tetrohydrofuran and the measurement temperature was 40 ° C. The molecular weight was determined in terms of polystyrene.
《水酸基価(OHV)》
共栓三角フラスコ中に試料を、約1gを精密に量り採り、トルエン/エタノール(容量比:トルエン/エタノール=2/1)混合液100mlを加えて溶解した。更にアセチル化剤(無水酢酸25gをピリジンで溶解し、容量100mlとした溶液)を正確に5ml加え、約1時間攪拌した。これに、フェノールフタレイン試液を指示薬として加え、30秒間持続した。その後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定した。
水酸基価は次式により求めた。水酸基価は樹脂の乾燥状態の数値とした(単位:mgKOH/g)。
水酸基価(mgKOH/g)=[{(b−a)×F×28.25}/S]/(不揮発分濃度/100)+D
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
b:空実験の0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
D:酸価(mgKOH/g)
<< Hydroxy group value (OHV) >>
Approximately 1 g of the sample was precisely weighed into a stoppered Erlenmeyer flask, and 100 ml of a toluene / ethanol (volume ratio: toluene / ethanol = 2/1) mixed solution was added and dissolved. Further, exactly 5 ml of an acetylating agent (a solution in which 25 g of acetic anhydride was dissolved in pyridine to make a volume of 100 ml) was added, and the mixture was stirred for about 1 hour. Phenolphthalein test solution was added to this as an indicator and lasted for 30 seconds. Then, it was titrated with 0.1N alcoholic potassium hydroxide solution until the solution became pink.
The hydroxyl value was calculated by the following formula. The hydroxyl value was taken as the value of the dry state of the resin (unit: mgKOH / g).
Hydroxy group value (mgKOH / g) = [{(ba) × F × 28.25} / S] / (nonvolatile content concentration / 100) + D
However, S: sample collection amount (g)
a: Consumption of 0.1N alcoholic potassium hydroxide solution (ml)
b: Consumption (ml) of 0.1N alcoholic potassium hydroxide solution in the blank experiment
F: Titer of 0.1N alcoholic potassium hydroxide solution
D: Acid value (mgKOH / g)
《酸価(AV》
共栓三角フラスコ中に試料を、約1gを精密に量り採り、トルエン/エタノール(容積比:トルエン/エタノール=2/1)混合液100mlを加えて溶解した。これに、フェノールフタレイン試液を指示薬として加え、30秒間保持した後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定した。
乾燥状態の樹脂の値として、酸価(mgKOH/g)を次式により求めた。
酸価(mgKOH/g)={(5.611×a×F)/S}/(不揮発分濃度/100)
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
《Acid value (AV》
Approximately 1 g of the sample was precisely weighed into a stoppered Erlenmeyer flask, and 100 ml of a toluene / ethanol (volume ratio: toluene / ethanol = 2/1) mixed solution was added and dissolved. Phenolphthalein test solution was added as an indicator, held for 30 seconds, and then titrated with 0.1N alcoholic potassium hydroxide solution until the solution turned pink.
The acid value (mgKOH / g) was calculated as the value of the dried resin by the following formula.
Acid value (mgKOH / g) = {(5.611 × a × F) / S} / (nonvolatile content concentration / 100)
However, S: sample collection amount (g)
a: Consumption of 0.1N alcoholic potassium hydroxide solution (ml)
F: Titer of 0.1N alcoholic potassium hydroxide solution
[実施例1〜16][比較例1〜3]
<重合性組成物の製造>
[配合例1〜20]
酸素濃度が10%以下に置換された遮光されたガラス瓶に、表2に示す配合量で材料を仕込み、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それぞれ得た。尚、表2において、数値は部を表し、空欄は配合していないことを表す。表2中、配合例1〜17は本発明の重合性組成物であり、配合例18〜20が本発明の重合性組成物ではない。表3に実施例および比較例で使用した材料の略号を示す。
[Examples 1 to 16] [Comparative Examples 1 to 3]
<Manufacturing of polymerizable composition>
[Formulation Examples 1 to 20]
In a light-shielded glass bottle in which the oxygen concentration is replaced with 10% or less, the material is charged in the blending amount shown in Table 2, the material is sufficiently stirred with a stirrer, and after sufficient defoaming, the polymerization shown in the blending example is performed. The sex compositions were obtained respectively. In Table 2, the numerical values represent parts, and the blanks indicate that they are not blended. In Table 2, Formulation Examples 1 to 17 are the polymerizable compositions of the present invention, and Formulation Examples 18 to 20 are not the polymerizable compositions of the present invention. Table 3 shows the abbreviations of the materials used in Examples and Comparative Examples.
<硬化性評価試験>
調製した重合性組成物を、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、ウェット膜厚が10μmとなるように塗布し、塗布膜を作製した。活性エネルギー線源としてLEDランプ光源であるPEN Bright(株式会社松風 430〜490nm)を用いて、1,200mW/cm2の照射強度で活性エネルギー線を20秒間照射して重合物を作製した。照射後の重合物の表面を綿布で擦って、皮膜に傷がつかなくなるまで照射を繰り返し、合計の照射時間から硬化性を判定した。照射の時間が短いほど硬化性が良いといえる。結果を表4に示す。判断基準は下記の通りである。
<Curability evaluation test>
The prepared polymerizable composition was applied onto a polyethylene terephthalate (PET) substrate using a micrometer-adjustable applicator so as to have a wet film thickness of 10 μm to prepare a coating film. A polymer was prepared by irradiating the active energy ray with an irradiation intensity of 1,200 mW / cm 2 for 20 seconds using PEN Bright (Matsukaze Co., Ltd. 430-490 nm), which is an LED lamp light source, as an active energy ray source. The surface of the polymer after irradiation was rubbed with a cotton cloth, and irradiation was repeated until the film was not scratched, and the curability was judged from the total irradiation time. It can be said that the shorter the irradiation time, the better the curability. The results are shown in Table 4. The judgment criteria are as follows.
判断基準
◎ :20.0〜181.0秒未満。特に良好。
○ :181.0秒以上〜401.0秒未満。良好。
△ :401.0秒以上。やや不良。
× :未硬化。特に不良。
Judgment criteria ◎: 20.0 to less than 181.0 seconds. Especially good.
◯: 181.0 seconds or more and less than 401.0 seconds. Good.
Δ: 401.0 seconds or more. Somewhat bad.
×: Not cured. Especially bad.
<重合物の硬度評価試験>
調製した重合性組成物を、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、塗布後の膜厚が10μmとなるように塗布し、塗布膜を作製した。活性エネルギー線源としてPEN Bright(株式会社松風 照射波長430〜490nm)を用いて、1,200mW/cm2の照射強度で活性エネルギー線を10分間照射して重合物を作製した。綿棒を用いて、重合物の表面を1cm2当たり0.1kgf(0.98N)の荷重で5秒間押し込み続けた際と、押し込み続けた後に綿棒を離した後の重合物の様子を観察し、重合物の硬度の判定を実施した。結果を表4に示す。判断基準は下記の通りである。
<Polymer hardness evaluation test>
The prepared polymerizable composition was applied onto a polyethylene terephthalate (PET) substrate using a micrometer-adjustable applicator so that the film thickness after application was 10 μm to prepare a coating film. A polymer was prepared by irradiating with active energy rays for 10 minutes at an irradiation intensity of 1,200 mW / cm 2 using PEN Bright (Shofu Inc. irradiation wavelength 430 to 490 nm) as an active energy radiation source. Using a cotton swab, observe the state of the polymer when the surface of the polymer was continuously pressed for 5 seconds with a load of 0.1 kgf (0.98N) per 1 cm 2 and after the cotton swab was released after the continuous pressing. The hardness of the polymer was determined. The results are shown in Table 4. The judgment criteria are as follows.
判断基準
◎ :押し込み続けた時、綿棒を離した後共に凹みなし。特に良好。
○ :押し込み続けた時に凹み発生、綿棒を離した後は凹みなし。やや良好。
× :押し込み続けた時にひび割れ発生、または、重合物が崩壊もしくは未硬化。不良。
Judgment criteria ◎: When pushing in continuously, no dents are found after releasing the cotton swab. Especially good.
◯: A dent is generated when the cotton swab is continuously pushed in, and no dent is formed after the cotton swab is released. Somewhat good.
X: Cracks occur when the product is pushed in continuously, or the polymer collapses or is uncured. Bad.
本発明の重合性組成物を使用した際は、硬化性、硬度共に優れた重合物が作製できた(実施例1〜16)。一方、本発明の重合性組成物の必須成分、光増感剤(A)、酸化還元触媒(C)、有機還元剤(D)のいずれかが含まれていない組成物を使用した際は、硬化性、硬度共に問題のある重合物しか得られなかった(比較例1〜3)。 When the polymerizable composition of the present invention was used, a polymer having excellent curability and hardness could be produced (Examples 1 to 16). On the other hand, when a composition containing no of the essential components of the polymerizable composition of the present invention, the photosensitizer (A), the redox catalyst (C), and the organic reducing agent (D) is used, Only polymers having problems in curability and hardness were obtained (Comparative Examples 1 to 3).
[実施例17]
表2記載の配合例5の重合性組成物を用い、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、塗布後の膜厚が10μmとなるように塗布し、塗布膜を作製した。活性エネルギー線源として、ビーム系2mmのアルゴンレーザー(488nmあるいは514nm光)を30J/cm2照射したところ、表面を綿布で擦っても皮膜に傷がつかなく、また綿棒を用いて、重合物の表面を1cm2当たり0.1kgf(0.98N)の荷重で5秒間押し込み続けた際、5秒間押し込み続けた際に凹み発生も、押し込み続けた後に綿棒を離した後は凹みのない、重合物が得られた。
[Example 17]
Using the polymerizable composition of Formulation Example 5 shown in Table 2, a micrometer-adjustable applicator was used to apply the coating film on a polyethylene terephthalate (PET) substrate so that the film thickness after application was 10 μm. Was produced. When a beam system 2 mm argon laser (488 nm or 514 nm light) was irradiated at 30 J / cm 2 as an active energy radiation source, the film was not damaged even if the surface was rubbed with a cotton swab, and the polymer was obtained using a cotton swab. When the surface is pushed in for 5 seconds with a load of 0.1 kgf (0.98N) per 1 cm 2 , dents occur when the surface is pushed in for 5 seconds, but there is no dent after releasing the cotton swab after continuing to push in. was gotten.
[実施例18〜33][比較例4〜6]
<硬化性評価試験>
表2記載の各重合性組成物を用い、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、膜厚が10μmとなるように塗布し、塗布膜を作製した。活性エネルギー線源として、キセノンランプを用いて50mW/cm2(365nm)、70mW/cm2(405nm)の照射強度で活性エネルギー線を20秒間照射して重合物を作製した。照射後の重合物の表面を綿布で擦って、皮膜に傷がつかなくなるまで照射を繰り返し、合計の照射時間から硬化性の判定を実施した。活性エネルギー線照射の時間が短いほど硬化性が良い、つまりラジカル重合性(転換率)が高いと判断した。結果を表5に示す。判断基準は下記の通りである。
[Examples 18 to 33] [Comparative Examples 4 to 6]
<Curability evaluation test>
Each polymerizable composition shown in Table 2 was applied to a polyethylene terephthalate (PET) substrate using a micrometer-adjustable applicator so as to have a film thickness of 10 μm to prepare a coating film. A polymer was prepared by irradiating an active energy ray with an irradiation intensity of 50 mW / cm 2 (365 nm) and 70 mW / cm 2 (405 nm) for 20 seconds using a xenon lamp as an active energy ray source. The surface of the polymer after irradiation was rubbed with a cotton cloth, and irradiation was repeated until the film was not scratched, and the curability was judged from the total irradiation time. It was judged that the shorter the activation energy ray irradiation time, the better the curability, that is, the higher the radical polymerizable (conversion rate). The results are shown in Table 5. The judgment criteria are as follows.
判断基準
◎ :20.0〜181.0秒未満。特に良好。
○ :181.0秒以上〜401.0秒未満。良好。
△ :401.0秒以上。やや不良。
× :未硬化。特に不良。
Judgment criteria ◎: 20.0 to less than 181.0 seconds. Especially good.
◯: 181.0 seconds or more and less than 401.0 seconds. Good.
Δ: 401.0 seconds or more. Somewhat bad.
×: Not cured. Especially bad.
<重合物の硬度評価試験>
表2記載の各重合性組成物を用い、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、膜厚が10μmとなるように塗布し、塗布膜を作製した。活性エネルギー線源としてキセノンランプを用いて50mW/cm2(365nm)、70mW/cm2(405nm)の照射強度で活性エネルギー線を20秒間照射して重合物を作製した。綿棒を用いて、重合物の表面を1cm2当たり0.1kgf(0.98N)の荷重で5秒間押し込み続けた際と、押し込み続けた後に綿棒を離した後の重合物の様子を観察し、重合物の硬度の判定を実施した。結果を表5に示す。判断基準は下記の通りである。
<Polymer hardness evaluation test>
Each polymerizable composition shown in Table 2 was applied to a polyethylene terephthalate (PET) substrate using a micrometer-adjustable applicator so as to have a film thickness of 10 μm to prepare a coating film. A polymer was prepared by irradiating an active energy ray with an irradiation intensity of 50 mW / cm 2 (365 nm) and 70 mW / cm 2 (405 nm) for 20 seconds using a xenon lamp as an active energy ray source. Using a cotton swab, observe the state of the polymer when the surface of the polymer was continuously pressed for 5 seconds with a load of 0.1 kgf (0.98N) per 1 cm 2 and after the cotton swab was released after the continuous pressing. The hardness of the polymer was determined. The results are shown in Table 5. The judgment criteria are as follows.
判断基準
◎ :押し込み続けた時、綿棒を離した後共に凹みなし。特に良好。
○ :押し込み続けた時に凹み発生、綿棒を離した後は凹みなし。やや良好。
× :押し込み続けた時にひび割れ発生、または、重合物が崩壊もしくは未硬化。不良。
Judgment criteria ◎: When pushing in continuously, no dents are found after releasing the cotton swab. Especially good.
◯: A dent is generated when the cotton swab is continuously pushed in, and no dent is formed after the cotton swab is released. Somewhat good.
X: Cracks occur when the product is pushed in continuously, or the polymer collapses or is uncured. Bad.
本発明の重合性組成物を使用した際は、活性エネルギー線源を変更した場合も、硬化性、硬度共に優れた重合物が作製できた(実施例18〜33)。一方、本発明の重合性組成物の必須成分、光増感剤(A)、酸化還元触媒(C)、有機還元剤(D)のいずれかが含まれていない組成物を使用した際は、硬化性、硬度共に問題のある重合物しか得られなかった(比較例4〜6)。 When the polymerizable composition of the present invention was used, a polymer having excellent curability and hardness could be produced even when the active energy radiation source was changed (Examples 18 to 33). On the other hand, when a composition containing no of the essential components of the polymerizable composition of the present invention, the photosensitizer (A), the redox catalyst (C), and the organic reducing agent (D) is used, Only polymers having problems in curability and hardness were obtained (Comparative Examples 4 to 6).
[実施例34〜65]
<重合性組成物の製造>
[配合例21〜52]
酸素濃度が10%以下に置換された遮光されたガラス瓶に、表6に示す配合量で材料を仕込み、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それぞれ得た。尚、表6において、数値は部を表し、空欄は配合していないことを表す。表3に実施例で使用した材料の略号を示す。
[Examples 34 to 65]
<Manufacturing of polymerizable composition>
[Formulation Examples 21 to 52]
In a light-shielded glass bottle in which the oxygen concentration is replaced with 10% or less, the material is charged in the blending amount shown in Table 6, the material is sufficiently stirred with a stirrer, and after sufficient defoaming, the polymerization shown in the blending example is performed. The sex compositions were obtained respectively. In Table 6, the numerical values represent parts, and the blanks indicate that they are not blended. Table 3 shows the abbreviations of the materials used in the examples.
<硬化性評価試験>
調製した重合性組成物を、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、膜厚が10μmとなるように塗布し、塗布膜を作製した。活性エネルギー線源としてPEN Bright(株式会社松風 波長430〜490nm)を用いて、1,200mW/cm2の照射強度で活性エネルギー線を20秒間照射して重合物を作製した。照射後の重合物の表面を綿布で擦って、皮膜に傷がつかなくなるまで照射を繰り返し、合計の照射時間から硬化性の判定を実施した。活性エネルギー線照射の時間が短いほど硬化性が良い、つまりラジカル重合性(転換率)が高いと判断した。結果を表7に示す。判断基準は下記の通りである。
<Curability evaluation test>
The prepared polymerizable composition was applied onto a polyethylene terephthalate (PET) substrate using a micrometer-adjustable applicator so as to have a film thickness of 10 μm to prepare a coating film. A polymer was prepared by irradiating with active energy rays for 20 seconds at an irradiation intensity of 1,200 mW / cm 2 using PEN Bright (Matsukaze Co., Ltd. wavelength 430-490 nm) as an active energy radiation source. The surface of the polymer after irradiation was rubbed with a cotton cloth, and irradiation was repeated until the film was not scratched, and the curability was judged from the total irradiation time. It was judged that the shorter the activation energy ray irradiation time, the better the curability, that is, the higher the radical polymerizable (conversion rate). The results are shown in Table 7. The judgment criteria are as follows.
判断基準
◎ :20.0〜181.0秒未満。特に良好。
○ :181.0秒以上〜401.0秒未満。良好。
△ :401.0秒以上。やや不良。
× :未硬化。特に不良。
Judgment criteria ◎: 20.0 to less than 181.0 seconds. Especially good.
◯: 181.0 seconds or more and less than 401.0 seconds. Good.
Δ: 401.0 seconds or more. Somewhat bad.
×: Not cured. Especially bad.
<重合物の硬度評価試験>
調製した重合性組成物を、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、ウェット膜厚が10μmとなるように塗布し、塗布膜を作製した。活性エネルギー線源としてPEN Bright(株式会社松風 430〜490nm)を用いて、1,200mW/cm2の照射強度で活性エネルギー線を10分間照射して重合物を作製した。綿棒を用いて、重合物の表面を1cm2当たり0.1kgf(0.98N)の荷重で5秒間押し込んだ際と、押し込んだ後の重合物の様子を観察し、重合物の硬度の判定を実施した。結果を表7に示す。判断基準は下記の通りである。
<Polymer hardness evaluation test>
The prepared polymerizable composition was applied onto a polyethylene terephthalate (PET) substrate using a micrometer-adjustable applicator so as to have a wet film thickness of 10 μm to prepare a coating film. A polymer was prepared by irradiating with active energy rays for 10 minutes at an irradiation intensity of 1,200 mW / cm 2 using PEN Bright (SHOFU INC. 430-490 nm) as an active energy radiation source. Using a cotton swab, the surface of the polymer was pushed in with a load of 0.1 kgf (0.98N) per cm 2 for 5 seconds, and the state of the polymer after pushing was observed to determine the hardness of the polymer. carried out. The results are shown in Table 7. The judgment criteria are as follows.
判断基準
◎ :押し込み時、押し込み後共に凹みなし。特に良好。
○ :押し込み時に凹み発生、押し込み後は凹みなし。やや良好。
× :押し込み時にひび割れ発生、または、硬化物が崩壊もしくは未硬化。不良。
Judgment criteria ◎: No dents during and after pushing. Especially good.
◯: A dent is generated when the product is pushed in, and no dent is generated after the product is pushed in. Somewhat good.
×: Cracks occur when pushed in, or the cured product collapses or is uncured. Bad.
本発明の重合性組成物を使用した際は、どのような組成でも硬化性、硬度共に優れた重合物が作製できた(実施例34〜65)。 When the polymerizable composition of the present invention was used, a polymer having excellent curability and hardness could be produced regardless of the composition (Examples 34 to 65).
本発明の重合性組成物を使用することは、種々の用途において、使用制限されることがない。本発明により、高感度化や、硬化物特性、さらには安全性の向上が期待できる用途の例としては、重合あるいは架橋反応を利用した成形樹脂、注型樹脂、光造形用樹脂、封止剤、歯科用重合レジン、印刷インキ、印刷ニス、塗料、印刷版用感光性樹脂、印刷用カラープルーフ、カラーフィルター用レジスト、ブラックマトリクス用レジスト、液晶用フォトスペーサー、リアプロジェクション用スクリーン材料、光ファイバー、プラズマディスプレー用リブ材、ドライフィルムレジスト、プリント基板用レジスト、ソルダーレジスト、半導体用フォトレジスト、マイクロエレクトロニクス用レジスト、マイクロマシン用部品製造用レジスト、エッチング用レジスト、マイクロレンズアレー、絶縁材、ホログラム材料、光学スイッチ、導波路用材料、オーバーコート剤、粉末コーティング、接着剤、粘着剤、離型剤、光記録媒体、粘接着剤、剥離コート剤、マイクロカプセルを用いた画像記録材料のための組成物、各種デバイスなどが挙げられる。 The use of the polymerizable composition of the present invention is not restricted in various uses. Examples of applications that can be expected to improve sensitivity, cured product properties, and safety by the present invention include molding resins, casting resins, opto-molding resins, and sealants that utilize polymerization or cross-linking reactions. , Dental polymerized resin, printing ink, printing varnish, paint, photosensitive resin for printing plate, color proof for printing, resist for color filter, resist for black matrix, photo spacer for liquid crystal, screen material for rear projection, optical fiber, plasma Rib material for display, dry film resist, resist for printed substrate, solder resist, photo resist for semiconductor, resist for microelectronics, resist for manufacturing parts for micromachine, resist for etching, micro lens array, insulating material, hologram material, optical switch Compositions for waveguide materials, overcoating agents, powder coatings, adhesives, adhesives, mold release agents, optical recording media, adhesives, release coating agents, image recording materials using microcapsules, Various devices and the like can be mentioned.
Claims (3)
( 一般式(1) 中、R1〜R10は、それぞれ独立に、水素原子、塩素原子、臭素原子、ヨウ素原子、ニトロ基またはアミノ基を表す。)
(一般式(2)中、R11〜R20は、それぞれ独立に、水素原子、塩素原子、臭素原子、ヨウ素原子、ニトロ基またはアミノ基を表し、L+は、任意のカチオンを表す。) Photosensitizer and (A), a compound having a double bond (B), and a redox catalyst (C), a polymerizable composition comprising an organic reducing agent (D), wherein (A ) Is a compound represented by the following general formula (1) and / or the following general formula (2), and the above (B) is a compound having an acryloyl group and / or a metaacryloyl group. ) Is 0.001 to 20 parts by mass with respect to 100 parts by mass of (B).
(In the general formula (1), R 1 to R 10 independently represent a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group or an amino group.)
(In the general formula (2), R 11 to R 20 independently represent a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group or an amino group, and L + represents an arbitrary cation.)
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