KR20220106959A - Acyl phosphine composition, polymerization initiator, polymerizable composition, cured product, and manufacturing method thereof - Google Patents
Acyl phosphine composition, polymerization initiator, polymerizable composition, cured product, and manufacturing method thereof Download PDFInfo
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- KR20220106959A KR20220106959A KR1020227012422A KR20227012422A KR20220106959A KR 20220106959 A KR20220106959 A KR 20220106959A KR 1020227012422 A KR1020227012422 A KR 1020227012422A KR 20227012422 A KR20227012422 A KR 20227012422A KR 20220106959 A KR20220106959 A KR 20220106959A
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- carbon atoms
- composition
- acylphosphine
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- 239000000203 mixture Substances 0.000 title claims abstract description 264
- -1 Acyl phosphine Chemical compound 0.000 title claims description 215
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 239000003505 polymerization initiator Substances 0.000 title claims description 20
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 title description 5
- 150000001450 anions Chemical class 0.000 claims abstract description 49
- 150000001768 cations Chemical class 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 123
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 238000000034 method Methods 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 30
- 239000003125 aqueous solvent Substances 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 47
- 239000013078 crystal Substances 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000010408 film Substances 0.000 description 33
- 239000000049 pigment Substances 0.000 description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- 230000000704 physical effect Effects 0.000 description 21
- 208000034189 Sclerosis Diseases 0.000 description 19
- 238000003860 storage Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 14
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- JZDGWLGMEGSUGH-UHFFFAOYSA-N phenyl-(2,4,6-trimethylbenzoyl)phosphinic acid Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(O)(=O)C1=CC=CC=C1 JZDGWLGMEGSUGH-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000003086 colorant Substances 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 230000002194 synthesizing effect Effects 0.000 description 7
- BPPZXJZYCOETDA-UHFFFAOYSA-N 1-benzylpiperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC=C1 BPPZXJZYCOETDA-UHFFFAOYSA-N 0.000 description 6
- XHJGXOOOMKCJPP-UHFFFAOYSA-N 2-[tert-butyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(C(C)(C)C)CCO XHJGXOOOMKCJPP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
- 229960002887 deanol Drugs 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 239000012972 dimethylethanolamine Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 239000003759 ester based solvent Substances 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MXFQRSUWYYSPOC-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical class C=CC(=O)OCC(C)(C)COC(=O)C=C MXFQRSUWYYSPOC-UHFFFAOYSA-N 0.000 description 2
- AEBWATHAIVJLTA-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene Chemical group C1CCC2CCCC21 AEBWATHAIVJLTA-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000006041 3-hexenyl group Chemical group 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000006043 5-hexenyl group Chemical group 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical class C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- HMEKVHWROSNWPD-UHFFFAOYSA-N Erioglaucine A Chemical compound [NH4+].[NH4+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 HMEKVHWROSNWPD-UHFFFAOYSA-N 0.000 description 2
- ZMDDERVSCYEKPQ-UHFFFAOYSA-N Ethyl (mesitylcarbonyl)phenylphosphinate Chemical compound C=1C=CC=CC=1P(=O)(OCC)C(=O)C1=C(C)C=C(C)C=C1C ZMDDERVSCYEKPQ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 235000012739 red 2G Nutrition 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229960003138 rose bengal sodium Drugs 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LGZQSRCLLIPAEE-UHFFFAOYSA-M sodium 1-[(4-sulfonaphthalen-1-yl)diazenyl]naphthalen-2-olate Chemical compound [Na+].C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C(S([O-])(=O)=O)C2=C1 LGZQSRCLLIPAEE-UHFFFAOYSA-M 0.000 description 1
- QERXHBDEEFLTOL-UHFFFAOYSA-M sodium 1-[[4-[(4-sulfophenyl)diazenyl]phenyl]diazenyl]naphthalen-2-olate Chemical compound [Na+].Oc1ccc2ccccc2c1N=Nc1ccc(cc1)N=Nc1ccc(cc1)S([O-])(=O)=O QERXHBDEEFLTOL-UHFFFAOYSA-M 0.000 description 1
- VMGPESHNHVBCDP-UHFFFAOYSA-M sodium 3-[(8-acetamido-2-hydroxynaphthalen-1-yl)diazenyl]-5-chloro-2-hydroxybenzenesulfonate Chemical compound [Na+].CC(=O)Nc1cccc2ccc(O)c(N=Nc3cc(Cl)cc(c3O)S([O-])(=O)=O)c12 VMGPESHNHVBCDP-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GNTPCYMJCJNRQB-UHFFFAOYSA-M sodium;2-[[4-(dimethylamino)phenyl]diazenyl]benzoate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1C([O-])=O GNTPCYMJCJNRQB-UHFFFAOYSA-M 0.000 description 1
- SHBDDIJUSNNBLQ-UHFFFAOYSA-M sodium;3-[[4-[(2-chlorophenyl)-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)Cl)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SHBDDIJUSNNBLQ-UHFFFAOYSA-M 0.000 description 1
- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 1
- PMLFOMWMYRKZRF-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]-6-hydroxybenzene-1,3-disulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=C(O)C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 PMLFOMWMYRKZRF-UHFFFAOYSA-M 0.000 description 1
- UWGCNDBLFSEBDW-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]naphthalene-2,7-disulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 UWGCNDBLFSEBDW-UHFFFAOYSA-M 0.000 description 1
- YZORUOZKRBVLEG-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 YZORUOZKRBVLEG-UHFFFAOYSA-M 0.000 description 1
- VVLFAAMTGMGYBS-UHFFFAOYSA-M sodium;4-[[4-(ethylamino)-3-methylphenyl]-(4-ethylimino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-3-sulfobenzenesulfonate Chemical compound [Na+].C1=C(C)C(NCC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S(O)(=O)=O)=C1C=C(C)C(=NCC)C=C1 VVLFAAMTGMGYBS-UHFFFAOYSA-M 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229940099373 sudan iii Drugs 0.000 description 1
- WGPCGCOKHWGKJJ-UHFFFAOYSA-N sulfanylidenezinc Chemical compound [Zn]=S WGPCGCOKHWGKJJ-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OLSOUGWNONTDCK-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3OC)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)OC)=C(O)C2=C1N OLSOUGWNONTDCK-UHFFFAOYSA-J 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- FKVXIGHJGBQFIH-UHFFFAOYSA-K trisodium 5-amino-3-[[4-[4-[(7-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3[O-])N)S(=O)(=O)O)N=NC5=C(C6=C(C=C(C=C6C=C5S(=O)(=O)O)S(=O)(=O)[O-])N)[O-].[Na+].[Na+].[Na+] FKVXIGHJGBQFIH-UHFFFAOYSA-K 0.000 description 1
- FUIZKNBTOOKONL-DPSBJRLESA-K trisodium;5-[(e)-(3-carboxy-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)-(2,6-dichloro-3-sulfonatophenyl)methyl]-3-methyl-2-oxidobenzoate Chemical compound [Na+].[Na+].[Na+].C1=C(C([O-])=O)C(=O)C(C)=C\C1=C(C=1C(=C(C=CC=1Cl)S([O-])(=O)=O)Cl)\C1=CC(C)=C(O)C(C([O-])=O)=C1 FUIZKNBTOOKONL-DPSBJRLESA-K 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PEAGNRWWSMMRPZ-UHFFFAOYSA-L woodstain scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PEAGNRWWSMMRPZ-UHFFFAOYSA-L 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
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- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/037—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
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- C07F9/304—Aromatic acids (P-C aromatic linkage)
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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- C07F9/6533—Six-membered rings
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
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Abstract
아실포스핀 조성물은, 식 (1)로 표시되는 카티온과, 식 (2)로 표시되는 아실포스핀 아니온을 포함하는 2종류 이상의 아니온을 포함하고, 그 아실포스핀 아니온의 몰 당량에 대한 카티온의 몰 당량의 비는, 1.005 이상 1.100 이하이다.The acylphosphine composition contains two or more types of anions containing the cation represented by Formula (1) and the acylphosphine anion represented by Formula (2), The molar equivalent of the acylphosphine anion The ratio of molar equivalents of cations to cations is 1.005 or more and 1.100 or less.
Description
본 발명은, 아실포스핀 조성물, 그 아실포스핀 조성물을 이용한 중합 개시제 및 중합성 조성물과, 그 중합성 조성물의 경화 반응물인 경화물 및 그 제조 방법에 관한 것이다.The present invention relates to an acylphosphine composition, a polymerization initiator and a polymerizable composition using the acylphosphine composition, a cured product that is a curing reaction product of the polymerizable composition, and a method for producing the same.
중합 반응을 이용하여 경화 가능한 중합성 조성물은, 중합 개시제 등의 각종 분야에 있어서 이용되고 있으며, 그 중합성 조성물의 경화 반응물인 경화물도 동일하게, 각종 분야에 있어서 이용되고 있다. 이 때문에, 중합성 조성물의 조성에 관해서는, 다양한 검토가 이루어지고 있다.BACKGROUND ART A polymerizable composition that can be cured using a polymerization reaction is used in various fields such as a polymerization initiator, and a cured product that is a curing reaction product of the polymerizable composition is similarly used in various fields. For this reason, regarding the composition of a polymeric composition, various examination is made|formed.
구체적으로는, 폭넓은 광원에 적응 가능하게 하기 위하여, 아실포스핀 조성물(아실포스핀산염)과 함께 반응성 화합물(특정 반응기를 갖는 화합물)을 포함하는 중합성 조성물(수용성 조성물)이 제안되고 있다(예를 들면, 특허문헌 1 참조.). 또한, 우수한 감도를 얻기 위하여, 아실포스핀옥사이드형의 구조를 갖는 수용성 광중합 개시제와 함께 물 및 중합성 화합물을 포함하는 중합성 조성물(수성 경화성 조성물)이 제안되고 있다(예를 들면, 특허문헌 2 참조.).Specifically, in order to be adaptable to a wide range of light sources, a polymerizable composition (water-soluble composition) comprising a reactive compound (a compound having a specific reactive group) together with an acylphosphine composition (acylphosphinate) has been proposed ( For example, refer to patent document 1.). Furthermore, in order to obtain excellent sensitivity, a polymerizable composition (aqueous curable composition) containing water and a polymerizable compound together with a water-soluble photoinitiator having an acylphosphine oxide-type structure has been proposed (for example, Patent Document 2) Reference.).
아실포스핀 조성물을 포함하는 중합성 조성물의 구성에 관한 검토가 활발히 이루어지고 있지만, 그 중합성 조성물의 물성은 아직 충분하지 않다. 또한, 중합성 조성물의 용도로서 고려되는 중합 개시제의 물성 및 그 중합성 조성물의 경화 반응물인 경화물의 물성도 아직 충분하지 않다. 따라서, 개선의 여지가 있다.Although the examination regarding the structure of the polymeric composition containing an acylphosphine composition is made actively, the physical property of the polymeric composition is still not enough. In addition, the physical properties of the polymerization initiator considered as use of the polymerizable composition and the physical properties of the cured product as a curing reaction product of the polymerizable composition are not yet sufficient. Therefore, there is room for improvement.
본 발명의 목적은, 우수한 물성을 얻는 것이 가능한 아실포스핀 조성물, 중합 개시제, 중합성 조성물과, 경화물 및 그 제조 방법을 제공하는 것에 있다.An object of the present invention is to provide an acylphosphine composition capable of obtaining excellent physical properties, a polymerization initiator, a polymerizable composition, a cured product, and a method for producing the same.
본 발명의 일 실시형태의 아실포스핀 조성물은, 식 (1)로 표시되는 카티온과, 식 (2)로 표시되는 아실포스핀 아니온을 포함하는 2종류 이상의 아니온을 포함하고, 그 아실포스핀 아니온의 몰 당량에 대한 카티온의 몰 당량의 비가 1.005 이상 1.100 이하인 것이다.The acylphosphine composition of one Embodiment of this invention contains the cation represented by Formula (1), and 2 or more types of anions containing the acylphosphine anion represented by Formula (2), The acyl The ratio of the molar equivalent of the cation to the molar equivalent of the phosphine anion is 1.005 or more and 1.100 or less.
N+HY1Y2Y3···(1)N + HY1Y2Y3...(1)
(Y1, Y2 및 Y3의 각각은, 탄소수가 1 이상 6 이하인 직쇄상의 알킬기, 탄소수가 2 이상 6 이하인 직쇄상의 알케닐기, 탄소수가 6 이상 15 이하인 아릴기 및 탄소수가 7 이상 13 이하인 아릴알킬기 중 어느 하나이다. Y1, Y2 및 Y3의 각각의 수소기는, 수산기에 의해 치환되어 있어도 된다. Y1, Y2 및 Y3의 각각의 메틸렌기는, -O-, -S-, -CO- 및 -N+H- 중 어느 하나에 의해 치환되어 있어도 된다. Y1, Y2 및 Y3 중 임의의 2개는, 서로 결합되어 있어도 된다.)(Each of Y1, Y2 and Y3 is a linear alkyl group having 1 to 6 carbon atoms, a linear alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, and an arylalkyl group having 7 to 13 carbon atoms. Any of Y1, Y2 and Y3 each hydrogen group may be substituted with a hydroxyl group. Each methylene group of Y1, Y2 and Y3 is -O-, -S-, -CO- and -N + H It may be substituted by any one of -. Any two of Y1, Y2 and Y3 may be bonded to each other.)
[화학식 1][Formula 1]
(X1은, 탄소수가 6 이상 15 이하인 아릴기이며, 그 아릴기의 수소기의 각각은, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알킬기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알콕시기 및 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알콕시기 중 어느 하나에 의해 치환되어 있어도 된다.(X1 is an aryl group having 6 or more and 15 or less carbon atoms, and each of the hydrogen groups of the aryl group is a linear alkyl group having 1 or more and 8 or less, a branched alkyl group having 3 or more and 8 or less, and 1 or more and 8 or less. A linear halogenated alkyl group having the following or less, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a straight chain halogenated alkyl group having 1 to 8 carbon atoms or less. You may be substituted by either a halogenated alkoxy group and a C3-C8 branched halogenated alkoxy group.
X2는, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기 및 탄소수가 6 이상 15 이하인 아릴기 중 어느 하나이며, 그 아릴기의 수소기의 각각은, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알킬기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알콕시기, 할로겐기, 나이트로기, 사이아노기, 수산기, 아미노기, 카복실기, 메타크릴로일기, 아크릴로일기, 에폭시기, 바이닐기, 바이닐에터기, 머캅토기, 아이소사이아네이트기 및 복소환 함유기 중 어느 하나에 의해 치환되어 있어도 된다. X2의 메틸렌기의 각각은, -O- 및 -S- 중 어느 하나에 의해 치환되어 있어도 된다.)X2 is a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, and 6 carbon atoms. Any of aryl groups of 15 or more, wherein each of the hydrogen groups of the aryl group is a linear alkyl group having 1 or more and 8 or less carbon atoms, a branched alkyl group having 3 or more and 8 or less carbon atoms, and a linear alkyl group having 1 or more and 8 or less carbon atoms. A halogenated alkyl group, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, Branched halogenated alkoxy group having 3 to 8 carbon atoms, halogen group, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl group, vinyl ether group, mercapto group , may be substituted by any one of an isocyanate group and a heterocyclic-containing group. Each of the methylene groups of X2 may be substituted with either -O- or -S-.)
본 발명의 일 실시형태의 중합 개시제는, 아실포스핀 조성물을 포함하고, 그 아실포스핀 조성물이 상기한 본 발명의 일 실시형태의 아실포스핀 조성물의 구성과 동일한 구성을 갖는 것이다.The polymerization initiator of one embodiment of the present invention contains an acylphosphine composition, and the acylphosphine composition has the same constitution as that of the acylphosphine composition of one embodiment of the present invention described above.
본 발명의 일 실시형태의 중합성 조성물은, 아실포스핀 조성물과, 식 (3)으로 표시되는 반응기를 포함하는 반응기 함유 화합물과, 수성 용매를 포함하고, 그 아실포스핀 조성물이 상기한 본 발명의 일 실시형태의 아실포스핀 조성물의 구성과 동일한 구성을 갖는 것이다.The polymerizable composition of one embodiment of the present invention contains an acylphosphine composition, a reactive group-containing compound containing a reactive group represented by formula (3), and an aqueous solvent, and the acylphosphine composition is the present invention described above. It has the same structure as the structure of the acylphosphine composition of one Embodiment of.
[화학식 2][Formula 2]
(R1은, 수소기 및 메틸기 중 어느 하나이다.(R1 is either a hydrogen group or a methyl group.
Z1은, -O- 및 -NR2- 중 어느 하나이며, 그 R2는, 수소기 및 탄소수가 1 이상 20 이하인 탄화 수소기 중 어느 하나이다.Z1 is either -O- or -NR2-, and R2 is any one of a hydrogen group and a hydrocarbon group having 1 or more and 20 or less carbon atoms.
Z2는, 탄소수가 1 이상 6 이하인 알킬렌기이다.Z2 is an alkylene group having 1 or more and 6 or less carbon atoms.
n은, 0 이상 30 이하의 정수(整數)이다.n is an integer of 0 or more and 30 or less.
단, 별표(*)는, 미결합의 결합손을 표시하고 있다.)However, an asterisk (*) indicates an unbonded bond.)
본 발명의 일 실시형태의 경화물은, 중합성 조성물의 경화 반응물이며, 그 중합성 조성물이 상기한 본 발명의 일 실시형태의 중합성 조성물의 구성과 동일한 구성을 갖는 것이다.The cured product of one embodiment of the present invention is a curing reaction product of a polymerizable composition, and the polymerizable composition has the same configuration as that of the polymerizable composition of one embodiment of the present invention described above.
본 발명의 일 실시형태의 경화물의 제조 방법은, 중합성 조성물에 활성 에너지선을 조사하고, 그 중합성 조성물이 상기한 본 발명의 일 실시형태의 중합성 조성물의 구성과 동일한 구성을 갖는 것이다.In the manufacturing method of the hardened|cured material of one Embodiment of this invention, an active energy ray is irradiated to a polymeric composition, The polymeric composition has the structure similar to the structure of the polymeric composition of one Embodiment of this invention mentioned above.
본 발명의 일 실시형태의 아실포스핀 조성물, 중합 개시제 또는 중합성 조성물에 의하면, 그 아실포스핀 조성물이 식 (1)에 나타낸 카티온과 식 (2)에 나타낸 아실포스핀 아니온을 포함하는 2종류 이상의 아니온을 포함하고 있고, 그 아실포스핀 아니온의 몰 당량에 대한 카티온의 몰 당량의 비가 1.005 이상 1.100 이하이므로, 우수한 물성을 얻을 수 있다.According to the acylphosphine composition, polymerization initiator or polymerizable composition of one embodiment of the present invention, the acylphosphine composition contains a cation shown in Formula (1) and an acylphosphine anion shown in Formula (2). Two or more types of anions are included, and since the ratio of the molar equivalent of a cation to the molar equivalent of the acylphosphine anion is 1.005 or more and 1.100 or less, excellent physical properties can be obtained.
또한, 본 발명의 일 실시형태의 경화물에 의하면, 상기한 중합성 조성물의 경화 반응물이므로, 우수한 물성을 얻을 수 있다.In addition, according to the cured product of one embodiment of the present invention, since it is a curing reaction product of the above-described polymerizable composition, excellent physical properties can be obtained.
또, 본 발명의 일 실시형태의 경화물의 제조 방법에 의하면, 상기한 중합성 조성물에 활성 에너지선을 조사하고 있으므로, 우수한 물성을 갖는 경화물을 얻을 수 있다.Moreover, according to the manufacturing method of the hardened|cured material of one Embodiment of this invention, since an active energy ray is irradiated to said polymerizable composition, the hardened|cured material which has outstanding physical properties can be obtained.
이하, 본 발명의 일 실시형태에 관하여 상세하게 설명한다. 설명하는 순서는, 하기와 같다. 단, 본 발명에 관한 상세는, 이하에서 설명하는 양태로 한정되지 않으며, 적절히, 변경 가능하다.Hereinafter, one embodiment of the present invention will be described in detail. The procedure to be described is as follows. However, the detail concerning this invention is not limited to the aspect demonstrated below, It can change suitably.
1. 아실포스핀 조성물1. Acylphosphine composition
2. 중합성 조성물2. Polymerizable composition
3. 경화물 및 그 제조 방법3. Cured product and its manufacturing method
4. 용도(중합 개시제 등)4. Uses (polymerization initiator, etc.)
<1. 아실포스핀 조성물><1. Acylphosphine composition>
먼저, 본 발명의 일 실시형태의 아실포스핀 조성물에 관하여 설명한다.First, the acylphosphine composition of one embodiment of the present invention will be described.
[구성][composition]
여기에서 설명하는 아실포스핀 조성물은, 후술하는 바와 같이, 중합 개시제 등으로서 사용된다. 단, 아실포스핀 조성물의 용도는, 중합 개시제로 한정되지 않으며, 다른 용도여도 된다.The acylphosphine composition demonstrated here is used as a polymerization initiator etc. so that it may mention later. However, the use of an acylphosphine composition is not limited to a polymerization initiator, Another use may be sufficient.
이 아실포스핀 조성물은, 염 구조를 갖고 있다. 구체적으로는, 아실포스핀 조성물은, 식 (1)로 표시되는 제4급 암모늄형의 카티온과, 2종류 이상의 아니온을 포함하고 있고, 그 2종류 이상의 아니온은, 식 (2)로 표시되는 아실포스핀형의 아니온(이하, 「아실포스핀 아니온」이라고 부른다.)을 포함하고 있다.This acylphosphine composition has a salt structure. Specifically, an acylphosphine composition contains the cation of the quaternary ammonium type|mold represented by Formula (1), and two or more types of anions, The two or more types of anions are represented by Formula (2) It contains the indicated acylphosphine type anion (hereinafter referred to as "acyl phosphine anion".).
N+HY1Y2Y3 ···(1)N + HY1Y2Y3 ...(1)
(Y1, Y2 및 Y3의 각각은, 탄소수가 1 이상 6 이하인 직쇄상의 알킬기, 탄소수가 2 이상 6 이하인 직쇄상의 알케닐기, 탄소수가 6 이상 15 이하인 아릴기 및 탄소수가 7 이상 13 이하인 아릴알킬기 중 어느 하나이다. Y1, Y2 및 Y3의 각각의 수소기는, 수산기에 의해 치환되어 있어도 된다. Y1, Y2 및 Y3의 각각의 메틸렌기는, -O-, -S-, -CO- 및 -N+H- 중 어느 하나에 의해 치환되어 있어도 된다. Y1, Y2 및 Y3 중 임의의 2개는, 서로 결합되어 있어도 된다.)(Each of Y1, Y2 and Y3 is a linear alkyl group having 1 to 6 carbon atoms, a linear alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, and an arylalkyl group having 7 to 13 carbon atoms. Any of Y1, Y2 and Y3 each hydrogen group may be substituted with a hydroxyl group. Each methylene group of Y1, Y2 and Y3 is -O-, -S-, -CO- and -N + H It may be substituted by any one of -. Any two of Y1, Y2 and Y3 may be bonded to each other.)
[화학식 3][Formula 3]
(X1은, 탄소수가 6 이상 15 이하인 아릴기이며, 그 아릴기의 수소기의 각각은, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알킬기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알콕시기 및 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알콕시기 중 어느 하나에 의해 치환되어 있어도 된다.(X1 is an aryl group having 6 or more and 15 or less carbon atoms, and each of the hydrogen groups of the aryl group is a linear alkyl group having 1 or more and 8 or less, a branched alkyl group having 3 or more and 8 or less, and 1 or more and 8 or less. A linear halogenated alkyl group having the following or less, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a straight chain halogenated alkyl group having 1 to 8 carbon atoms or less. You may be substituted by either a halogenated alkoxy group and a C3-C8 branched halogenated alkoxy group.
X2는, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기 및 탄소수가 6 이상 15 이하인 아릴기 중 어느 하나이며, 그 아릴기의 수소기의 각각은, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알킬기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알콕시기, 할로겐기, 나이트로기, 사이아노기, 수산기, 아미노기, 카복실기, 메타크릴로일기, 아크릴로일기, 에폭시기, 바이닐기, 바이닐에터기, 머캅토기, 아이소사이아네이트기 및 복소환 함유기 중 어느 하나에 의해 치환되어 있어도 된다. X2의 메틸렌기의 각각은, -O- 및 -S- 중 어느 하나에 의해 치환되어 있어도 된다.)X2 is a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, and 6 carbon atoms. Any of aryl groups of 15 or more, wherein each of the hydrogen groups of the aryl group is a linear alkyl group having 1 or more and 8 or less carbon atoms, a branched alkyl group having 3 or more and 8 or less carbon atoms, and a linear alkyl group having 1 or more and 8 or less carbon atoms. A halogenated alkyl group, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, Branched halogenated alkoxy group having 3 to 8 carbon atoms, halogen group, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl group, vinyl ether group, mercapto group , may be substituted by any one of an isocyanate group and a heterocyclic-containing group. Each of the methylene groups of X2 may be substituted with either -O- or -S-.)
(아니온에 관한 상세)(Details about anion)
2종류 이상의 아니온은, 상기한 바와 같이, 아실포스핀 아니온을 포함하고 있다. 아실포스핀 아니온의 종류는, 1종류만이어도 되고, 2종류 이상이어도 된다.Two or more types of anions contain an acylphosphine anion as mentioned above. One type may be sufficient as the kind of acylphosphine anion, and two or more types may be sufficient as it.
(아실포스핀 아니온)(acylphosphine anion)
아실포스핀 아니온의 구성에 관한 상세는, 이하에서 설명하는 바와 같다.The detail regarding the structure of an acylphosphine anion is as demonstrating below.
(X1)(X1)
아릴기는, 1개 또는 2개 이상의 방향족환을 포함하는 1가의 기의 총칭이다. 아릴기의 구체예는, 탄소수가 6~15이기 때문에, 페닐기, 나프틸기 및 안트라세닐기 등이다. 단, 후술하는 치환기를 포함하고 있는 경우에 있어서의 아릴기의 탄소수는, 그 치환기의 탄소수도 포함하는 전체의 탄소수이다. 이 때문에, 일례를 들면, 트라이메틸페닐기의 탄소수는, 6이 아닌 9이다. 여기에서 설명한 아릴기의 탄소수에 관한 정의는, 이후에 있어서도 동일하다.The aryl group is a generic term for monovalent groups containing one or two or more aromatic rings. Specific examples of the aryl group include a phenyl group, a naphthyl group, and an anthracenyl group since they have 6 to 15 carbon atoms. However, the carbon number of the aryl group in the case of including the substituent mentioned later is the total number of carbon atoms including the carbon number of the substituent. For this reason, for example, the carbon number of a trimethylphenyl group is 9 instead of 6. The definition regarding carbon number of the aryl group demonstrated here is also the same hereafter.
아릴기에 포함되어 있는 1개 또는 2개 이상의 수소기의 각각은, 치환기에 의해 치환되어 있어도 된다. 여기에서 설명하는 치환기는, 상기한 바와 같이, 탄소수가 특정의 범위 내인 직쇄상의 알킬기, 분기상의 알킬기, 직쇄상의 할로겐화 알킬기, 분기상의 할로겐화 알킬기, 직쇄상의 알콕시기, 분기상의 알콕시기, 직쇄상의 할로겐화 알콕시기 및 분기상의 할로겐화 알콕시기 중 어느 하나이다.Each of the 1, 2 or more hydrogen groups contained in the aryl group may be substituted by the substituent. The substituents described herein are, as described above, a linear alkyl group, a branched alkyl group, a linear halogenated alkyl group, a branched halogenated alkyl group, a linear alkoxy group, a branched alkoxy group, and a straight chain alkyl group having a specific range of carbon atoms. either a chain halogenated alkoxy group or a branched halogenated alkoxy group.
직쇄상의 알킬기는, 1개의 탄소 원자를 포함하는 1가의 탄화 수소기 및 직쇄상이 되도록 복수의 탄소 원자가 서로 결합된 1가의 탄화 수소기의 총칭이다. 직쇄상의 알킬기의 구체예는, 탄소수가 1~8이기 때문에, 메틸기, 에틸기, n-프로필기, n-뷰틸기, n-펜틸기, n-헥실기, n-헵틸기 및 n-옥틸기이다.The linear alkyl group is a generic term for a monovalent hydrocarbon group containing one carbon atom and a monovalent hydrocarbon group in which a plurality of carbon atoms are bonded to each other so as to be linear. Specific examples of the linear alkyl group include a methyl group, an ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-octyl group, since they have 1 to 8 carbon atoms. to be.
분기상의 알킬기는, 1개 또는 2개 이상의 측쇄를 갖도록 복수의 탄소 원자가 서로 결합된 1가의 탄화 수소기의 총칭이다. 분기상의 알킬기의 구체예는, 탄소수가 3~8이기 때문에, 아이소프로필기, sec-뷰틸기, 아이소뷰틸기, tert-뷰틸기, sec-펜틸기, 아이소펜틸기, tert-펜틸기, 네오펜틸기, sec-헥실기, 아이소헥실기, tert-헥실기, 네오헥실기, sec-헵틸기, 아이소헵틸기, tert-헵틸기, 네오헵틸기, sec-옥틸기, 아이소옥틸기, tert-옥틸기 및 네오옥틸기이다.The branched alkyl group is a generic term for a monovalent hydrocarbon group in which a plurality of carbon atoms are bonded to each other so as to have one or two or more side chains. Specific examples of the branched alkyl group include 3 to 8 carbon atoms, so isopropyl group, sec-butyl group, isobutyl group, tert-butyl group, sec-pentyl group, isopentyl group, tert-pentyl group, neophene Tyl group, sec-hexyl group, isohexyl group, tert-hexyl group, neohexyl group, sec-heptyl group, isoheptyl group, tert-heptyl group, neoheptyl group, sec-octyl group, isooctyl group, tert-octyl group a tyl group and a neooctyl group.
직쇄상의 할로겐화 알킬기는, 상기한 직쇄상의 알킬기에 포함되어 있는 1개 또는 2개 이상의 수소기의 각각이 할로겐기에 의해 치환된 기이다. 할로겐기의 종류는, 특별히 한정되지 않지만, 불소기, 염소기, 브로민기 및 아이오딘기 등이다. 단, 직쇄상의 할로겐화 알킬기에 포함되는 할로겐기의 종류는, 1종류만이어도 되고, 2종류 이상이어도 된다.The linear halogenated alkyl group is a group in which each of one or two or more hydrogen groups contained in the aforementioned linear alkyl group is substituted with a halogen group. Although the kind of halogen group is not specifically limited, A fluorine group, a chlorine group, a bromine group, an iodine group, etc. are mentioned. However, the number of types of the halogen group contained in the linear halogenated alkyl group may be one, and two or more types may be sufficient as them.
분기상의 할로겐화 알킬기는, 상기한 분기상의 알킬기에 포함되어 있는 1개 또는 2개 이상의 수소기가 할로겐기에 의해 치환된 기이다. 할로겐기의 종류에 관한 상세는, 상기한 바와 같다.The branched halogenated alkyl group is a group in which one or two or more hydrogen groups included in the aforementioned branched alkyl group are substituted with a halogen group. The detail regarding the kind of halogen group is as above-mentioned.
직쇄상의 알콕시기는, 상기한 직쇄상의 알킬기의 말단에 -O-가 결합된 기의 총칭이다. 직쇄상의 알콕시기의 구체예는, 탄소수가 1~8이기 때문에, 메톡시기, 에톡시기, n-프로폭시기, n-뷰톡시기, n-펜톡시기, n-헥속시기, n-헵톡시기 및 n-옥톡시기이다.The linear alkoxy group is a generic term for groups in which -O- is bonded to the terminus of the aforementioned linear alkyl group. Specific examples of the linear alkoxy group include a methoxy group, an ethoxy group, n-propoxy group, n-butoxy group, n-pentoxy group, n-hexoxy group, n-heptoxy group and It is an n-octoxy group.
분기상의 알콕시기는, 상기한 분기상의 알킬기의 말단에 -O-가 결합된 기의 총칭이다. 분기상의 알콕시기의 구체예는, 탄소수가 3~8이기 때문에, 아이소프로폭시기, sec-뷰톡시기, 아이소뷰톡시기, tert-뷰톡시기, sec-펜톡시기, 아이소펜톡시기, tert-펜톡시기, 네오펜톡시기, sec-헥속시기, 아이소헥속시기, tert-헥속시기, 네오헥속시기, sec-헵톡시기, 아이소헵톡시기, tert-헵톡시기, 네오헵톡시기, sec-옥톡시기, 아이소옥톡시기, tert-옥톡시기 및 네오옥톡시기이다.The branched alkoxy group is a generic term for groups in which -O- is bonded to the terminal of the aforementioned branched alkyl group. Specific examples of the branched alkoxy group include, since carbon number is 3 to 8, isopropoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, sec-pentoxy group, isopentoxy group, tert-pentoxy group, Neopentoxy group, sec-hexoxy group, isohexoxy group, tert-hexoxy group, neohexoxy group, sec-heptoxy group, isoheptoxy group, tert-heptoxy group, neoheptoxy group, sec-octoxy group, isooctoxy group, tert-octoxy group and neo-octoxy group.
직쇄상의 할로겐화 알콕시기는, 상기한 직쇄상의 할로겐화 알킬기의 말단에 -O-가 결합된 기의 총칭이다. 직쇄상의 할로겐화 알콕시기의 구체예는, 탄소수가 1~8이기 때문에, 할로겐화 메톡시기, 할로겐화 에톡시기, 할로겐화 n-프로폭시기, 할로겐화 n-뷰톡시기, 할로겐화 n-펜톡시기, 할로겐화 n-헥속시기, 할로겐화 n-헵톡시기 및 할로겐화 n-옥톡시기이다.The linear halogenated alkoxy group is a generic term for groups in which -O- is bonded to the terminal of the aforementioned linear halogenated alkyl group. Specific examples of the linear halogenated alkoxy group include a halogenated methoxy group, a halogenated ethoxy group, a halogenated n-propoxy group, a halogenated n-butoxy group, a halogenated n-pentoxy group, and a halogenated n-hexoxy group, since they have 1 to 8 carbon atoms. group, a halogenated n-heptoxy group and a halogenated n-octoxy group.
분기상의 할로겐화 알콕시기는, 상기한 분기상의 할로겐화 알킬기의 말단에 -O-가 결합된 기의 총칭이다. 분기상의 할로겐화 알콕시기의 구체예는, 탄소수가 3~8이기 때문에, 할로겐화 아이소프로폭시기, 할로겐화 sec-뷰톡시기, 할로겐화 아이소뷰톡시기, 할로겐화 tert-뷰톡시기, 할로겐화 sec-펜톡시기, 할로겐화 아이소펜톡시기, 할로겐화 tert-펜톡시기, 할로겐화 네오펜톡시기, 할로겐화 sec-헥속시기, 할로겐화 아이소헥속시기, 할로겐화 tert-헥속시기, 할로겐화 네오헥속시기, 할로겐화 sec-헵톡시기, 할로겐화 아이소헵톡시기, 할로겐화 tert-헵톡시기, 할로겐화 네오헵톡시기, 할로겐화 sec-옥톡시기, 할로겐화 아이소옥톡시기, 할로겐화 tert-옥톡시기 및 할로겐화 네오옥톡시기이다.The branched halogenated alkoxy group is a generic term for groups in which -O- is bonded to the terminal of the aforementioned branched halogenated alkyl group. Specific examples of the branched halogenated alkoxy group include a halogenated isopropoxy group, a halogenated sec-butoxy group, a halogenated isobutoxy group, a halogenated tert-butoxy group, a halogenated sec-pentoxy group, and a halogenated isopentoxy group, since they have 3 to 8 carbon atoms. Group, halogenated tert-pentoxy group, halogenated neopentoxy group, halogenated sec-hexoxy group, halogenated isohexoxy group, halogenated tert-hexoxy group, halogenated neohexoxy group, halogenated sec-heptoxy group, halogenated isoheptoxy group, halogenated tert-heptoxy group group, a halogenated neoheptoxy group, a halogenated sec-octoxy group, a halogenated isooctoxy group, a halogenated tert-octoxy group and a halogenated neooctoxy group.
그 중에서도, X1은, 1개 또는 2개 이상의 직쇄상의 알킬기가 도입된 아릴기인 것이 바람직하고, 2위, 4위 및 6위의 각각 직쇄상의 알킬기가 도입된 페닐기인 것이 보다 바람직하고, 2위, 4위 및 6위의 각각 메틸기가 도입된 페닐기(2,4,6-트라이메틸-페닐기)인 것이 더 바람직하다. 후술하는 아실포스핀 조성물을 포함하는 중합성 조성물의 경화성이 향상되기 때문이다.Among them, X 1 is preferably an aryl group introduced with one or two or more linear alkyl groups, more preferably a phenyl group introduced with linear alkyl groups at positions 2, 4 and 6, respectively, 2 It is more preferable that the phenyl group (2,4,6-trimethyl-phenyl group) in which a methyl group is introduced in the above, 4th and 6th positions, respectively. It is because sclerosis|hardenability of the polymeric composition containing the acylphosphine composition mentioned later improves.
(X2)(X2)
직쇄상의 알킬기, 분기상의 알킬기, 직쇄상의 알콕시기, 분기상의 알콕시기 및 아릴기의 각각에 관한 상세는, 상기한 바와 같다.The detail regarding each of a linear alkyl group, a branched alkyl group, a linear alkoxy group, a branched alkoxy group, and an aryl group is as above-mentioned.
아릴기에 포함되어 있는 1개 또는 2개 이상의 수소기의 각각은, X1에 관하여 설명한 경우와 동일하게, 치환기에 의해 치환되어 있어도 된다. 이 치환기는, 탄소수가 특정의 범위 내인 직쇄상의 알킬기, 분기상의 알킬기, 직쇄상의 할로겐화 알킬기, 분기상의 할로겐화 알킬기, 직쇄상의 알콕시기, 분기상의 알콕시기, 직쇄상의 할로겐화 알콕시기 및 분기상의 할로겐화 알콕시기 중 어느 하나이다. 또한, 치환기는, 할로겐기, 나이트로기, 사이아노기, 수산기, 아미노기, 카복실기, 메타크릴로일기, 아크릴로일기, 에폭시기, 바이닐기, 바이닐에터기, 머캅토기, 아이소사이아네이트기 및 복소환 함유기 중 어느 하나이다. 할로겐기의 종류에 관한 상세는, 상기한 바와 같다.Each of the one or two or more hydrogen groups contained in the aryl group may be substituted with a substituent in the same manner as in the case of X1. These substituents include a linear alkyl group, a branched alkyl group, a linear halogenated alkyl group, a branched halogenated alkyl group, a linear alkoxy group, a branched alkoxy group, a linear halogenated alkoxy group, and a branched alkyl group having a specific range of carbon atoms. any of the halogenated alkoxy groups. In addition, the substituent is a halogen group, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group and any of the heterocyclic-containing groups. The detail regarding the kind of halogen group is as above-mentioned.
복소환 함유기는, 탄소 원자와 1종류 또는 2종류 이상의 탄소 원자 이외의 원자에 의해 환(복소환)이 구성되는 1가의 기 및 1개 또는 2개 이상의 복소환을 포함하는 1가의 기의 총칭이며, 그 탄소 원자 이외의 원자는, 질소 원자, 산소 원자 및 황 원자 등이다. 복소환 함유기의 구체예는, 싸이아졸, 이미다졸, 옥사졸, 피리딘, 피라진, 피리미딘, 피리다진, 싸이오펜, 퓨란, 바이싸이오펜 및 테르싸이오펜 등의 각각으로부터 1개의 수소기가 이탈한 기 등이다.The heterocycle-containing group is a generic term for monovalent groups in which a ring (heterocycle) is constituted by carbon atoms and atoms other than one or two or more carbon atoms, and monovalent groups containing one or two or more heterocycles, , Atoms other than the carbon atom are a nitrogen atom, an oxygen atom, a sulfur atom, and the like. Specific examples of the heterocyclic-containing group include thiazole, imidazole, oxazole, pyridine, pyrazine, pyrimidine, pyridazine, thiophene, furan, bithiophene, terthiophene, etc. flag, etc.
또한, X2에 포함되어 있는 1개 또는 2개 이상의 메틸렌기의 각각은, 상기한 바와 같이, -O- 및 -S- 중 어느 하나에 의해 치환되어 있어도 된다.In addition, each of the 1, 2 or more methylene groups contained in X2 may be substituted by any one of -O- and -S- as mentioned above.
그 중에서도, X2는, 탄소수가 6~15인 아릴기인 것이 바람직하고, 페닐기인 것이 보다 바람직하다. 아실포스핀 조성물을 포함하는 중합성 조성물의 경화성이 향상되기 때문이다.Especially, it is preferable that it is a C6-C15 aryl group, and, as for X2, it is more preferable that it is a phenyl group. It is because sclerosis|hardenability of the polymeric composition containing an acylphosphine composition improves.
(다른 아니온)(other anions)
상기한 2종류 이상의 아니온은, 아실포스핀 아니온을 포함하고 있으면, 그 아실포스핀 아니온 이외의 다른 아니온을 더 포함하고 있어도 된다. 다른 아니온의 종류는, 1종류만이어도 되고, 2종류 이상이어도 된다.As long as said two or more types of anions contain the acylphosphine anion, other anions other than the acylphosphine anion may be included further. One type may be sufficient as the kind of another anion, and two or more types may be sufficient as it.
다른 아니온의 종류는, 특별히 한정되지 않지만, 할로겐 이온, 6불화 인산 이온(PF6 -), 4불화 붕소 이온(BF4 -), 비스(트라이플루오로메테인설폰일)이미드산 이온((CF3SO2)2N-), 트라이플루오로메테인설폰산 이온(CF3SO3 -), 노나플루오로뷰테인설폰산 이온(C4F9SO3 -), 벤조산 이온, 4-에틸벤조산 이온, p-톨루엔설폰산 이온 및 수산화물 이온(OH-) 등이다. 이 할로겐 이온은, 불소 이온(F-), 염소 이온(Cl-), 브로민 이온(Br-) 및 아이오딘 이온(I-) 등이다.Although the type of the other anion is not particularly limited, halogen ion, hexafluorophosphate ion (PF 6 - ), boron tetrafluoride ion (BF 4 - ), bis(trifluoromethanesulfonyl)imidate ion ((CF 6 - ) 3 SO 2 ) 2 N - ), trifluoromethanesulfonic acid ion (CF 3 SO 3 - ), nonafluorobutanesulfonic acid ion (C 4 F 9 SO 3 - ), benzoate ion, 4-ethylbenzoate ion , p-toluenesulfonic acid ion and hydroxide ion (OH − ), and the like. The halogen ion is a fluorine ion (F − ), a chlorine ion (Cl − ), a bromine ion (Br − ), an iodine ion (I − ), or the like.
그 중에서도, 다른 아니온은, 수산화물 이온인 것이 바람직하다. 아실포스핀 조성물의 안정성이 향상되기 때문이다.Especially, it is preferable that another anion is a hydroxide ion. This is because the stability of the acylphosphine composition is improved.
(카티온에 관한 상세)(the details about the cation)
카티온은, 상기한 바와 같이, 제4급 암모늄형의 카티온(N+HY1Y2Y3)이다. 카티온의 종류는, 1종류만이어도 되고, 2종류 이상이어도 된다. 또한, Y1의 종류는, Y2의 종류와 동일해도 되고, Y2의 종류와 상이해도 된다. 동일하게, Y1의 종류는, Y3의 종류와 동일해도 되고, Y3의 종류와 상이해도 되는 동시에, Y2의 종류는, Y3의 종류와 동일해도 되고, Y3의 종류와 상이해도 된다.A cation is a cation (N + HY1Y2Y3) of a quaternary ammonium type as mentioned above. One type may be sufficient as the kind of cation, and two or more types may be sufficient as it. In addition, the kind of Y1 may be the same as the kind of Y2, and may differ from the kind of Y2. Similarly, the type of Y1 may be the same as the type of Y3 or different from the type of Y3, and the type of Y2 may be the same as the type of Y3 or different from the type of Y3.
직쇄상의 알킬기에 관한 상세는, 탄소수의 범위가 상이한 것을 제외하고, 상기한 바와 같다. 또한, 아릴기에 관한 상세는, 상기한 바와 같다.The detail about the linear alkyl group is as above-mentioned except that the range of carbon number differs. In addition, the detail regarding an aryl group is as above-mentioned.
직쇄상의 알케닐기는, 탄소간 이중 결합(>C=C<)을 가짐과 동시에 직쇄상이 되도록 복수의 탄소 원자가 서로 결합된 1가의 탄화 수소기의 총칭이다. 직쇄상의 알케닐기의 구체예는, 탄소수가 2~6이기 때문에, 바이닐기, 알릴기, 아크릴기 및 메타크릴기 등이다.The linear alkenyl group is a generic term for a monovalent hydrocarbon group in which a plurality of carbon atoms are bonded to each other so as to have a double bond between carbons (>C=C<) and to be linear. Specific examples of the linear alkenyl group include, for example, a vinyl group, an allyl group, an acryl group, and a methacryl group since carbon number is 2-6.
아릴알킬기는, 아릴기와 직쇄상 또는 분기상의 알킬기가 서로 결합된 1가의 기의 총칭이다. 아릴기에 관한 상세는, 상기한 바와 같으며, 직쇄상 또는 분기상의 알킬기에 관한 상세는, 상기한 바와 같다.The arylalkyl group is a generic term for a monovalent group in which an aryl group and a linear or branched alkyl group are bonded to each other. The details regarding the aryl group are as described above, and the details regarding the linear or branched alkyl group are as described above.
Y1, Y2 및 Y3의 각각에 포함되어 있는 1개 또는 2개 이상의 수소기의 각각은, 수산기에 의해 치환되어 있어도 된다. 이 경우에는, Y1, Y2 및 Y3의 각각에 있어서, 말단의 수소기가 수산기에 의해 치환되어 있어도 되고, 도중의 수소기가 수산기에 의해 치환되어 있어도 된다. 말단의 수소기가 수산기에 의해 치환되어 있는 알킬기의 구체예는, 탄소수가 7~13이기 때문에, 하이드록시메틸기, 하이드록시에틸기, 하이드록시프로필기, 하이드록시뷰틸기, 하이드록시펜틸기, 하이드록시헥실기, 하이드록시헵틸기, 하이드록시옥틸기, 하이드록시노닐기, 하이드록시데실기, 하이드록시운데실기, 하이드록시도데실기 및 하이드록시트라이데실기이다.Each of one or two or more hydrogen groups contained in each of Y1, Y2 and Y3 may be substituted with a hydroxyl group. In this case, in each of Y1, Y2, and Y3, the hydrogen group at the terminal may be substituted by the hydroxyl group, and the hydrogen group in the middle may be substituted by the hydroxyl group. Specific examples of the alkyl group in which the terminal hydrogen group is substituted with a hydroxyl group have 7 to 13 carbon atoms, so a hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, hydroxypentyl group, hydroxyhex Sil group, hydroxyheptyl group, hydroxyoctyl group, hydroxynonyl group, hydroxydecyl group, hydroxyundecyl group, hydroxydodecyl group and hydroxytridecyl group.
또한, Y1, Y2 및 Y3의 각각에 포함되어 있는 1개 또는 2개 이상의 메틸렌기의 각각은, -O-, -S-, -CO- 및 -N+H- 중 어느 하나에 의해 치환되어 있어도 된다.In addition, even if each of 1 or 2 or more methylene groups contained in each of Y1, Y2 and Y3 is substituted by any one of -O-, -S-, -CO- and -N + H- do.
또한, Y1, Y2 및 Y3 중 임의의 2개는, 각각 독립적으로, 서로 결합되는 것에 의해, 환을 형성하고 있어도 된다. 즉, Y1 및 Y2가 서로 결합되어 있어도 되고, Y2 및 Y3이 서로 결합되어 있어도 되고, Y1 및 Y3이 서로 결합되어 있어도 된다. 이 경우에는, 1개의 환이 형성되어 있어도 되고, 2개 이상의 환이 형성되어 있어도 된다. 또한, 단결합으로 이루어지는 환이 형성되어 있어도 된다. 또한, Y2 및 Y3이 서로 결합되는 것에 의해, 탄소간 이중 결합이 형성되어 있는 동시에, 그 탄소간 이중 결합 및 Y1이 서로 결합되는 것에 의해, 환이 형성되어 있어도 된다.In addition, any two of Y1, Y2 and Y3 may each independently form a ring by mutually bonding. That is, Y1 and Y2 may be bonded to each other, Y2 and Y3 may be bonded to each other, and Y1 and Y3 may be bonded to each other. In this case, one ring may be formed and two or more rings may be formed. Moreover, the ring which consists of a single bond may be formed. Further, when Y2 and Y3 are bonded to each other, a double bond between carbons is formed, and a ring may be formed when the double bond between carbons and Y1 are bonded to each other.
그 중에서도, Y1, Y2 및 Y3의 일부는, 탄소수가 1~6인 직쇄상의 알킬기임과 동시에, Y1, Y2 및 Y3 중 나머지는, 말단의 1개의 수소기가 수산기에 의해 치환된 탄소수가 1~6인 직쇄상의 알킬기인 것이 바람직하다. 또한, Y1, Y2 및 Y3 중 1개는, 탄소수가 1~6인 직쇄상의 알킬기임과 동시에, Y1, Y2 및 Y3 중 2개의 각각은, 말단의 1개의 수소기가 수산기에 의해 치환된 탄소수가 1~6인 직쇄상의 알킬기인 것이 보다 바람직하다. 아실포스핀 조성물을 포함하는 중합성 조성물의 경화성이 향상되기 때문이다.Among them, a part of Y1, Y2 and Y3 is a linear alkyl group having 1 to 6 carbon atoms, and the rest of Y1, Y2 and Y3 has 1 to carbon atoms in which one hydrogen group at the terminal is substituted with a hydroxyl group. It is preferable that it is a 6-membered linear alkyl group. In addition, one of Y1, Y2 and Y3 is a linear alkyl group having 1 to 6 carbon atoms, and each of two of Y1, Y2 and Y3 has a carbon number in which one hydrogen group at the terminal is substituted with a hydroxyl group. It is more preferable that it is a 1-6 linear alkyl group. It is because sclerosis|hardenability of the polymeric composition containing an acylphosphine composition improves.
(당량비 등)(equivalent ratio, etc.)
여기에서 설명하는 아실포스핀 조성물에서는, 아실포스핀 아니온의 몰 당량에 대한 카티온의 몰 당량의 비(당량비)가 적정화되어 있으며, 구체적으로는 1.005~1.100이다. 아실포스핀 조성물의 용해성이 향상됨과 동시에, 그 아실포스핀 조성물의 안정성이 향상되기 때문이다. 이 당량비는, 당량비=(카티온의 가수×카티온의 몰수)/(아실포스핀 아니온의 가수×아실포스핀 아니온의 몰수)에 의해 산출된다.In the acylphosphine composition demonstrated here, the ratio (equivalent ratio) of the molar equivalent of a cation with respect to the molar equivalent of an acylphosphine anion is optimized, and specifically, it is 1.005-1.100. This is because the solubility of the acylphosphine composition is improved and the stability of the acylphosphine composition is improved. This equivalence ratio is computed by equivalence ratio = (valence of a cation x number of moles of a cation)/(valence of an acylphosphine anion x number of moles of an acylphosphine anion).
또한, 아실포스핀 아니온의 중량에 대한 카티온의 중량의 비(중량비)는, 특별히 한정되지 않지만, 그 중에서도, 0.25~1.00인 것이 바람직하다. 아실포스핀 조성물의 용해성이 보다 향상됨과 동시에, 그 아실포스핀 조성물의 안정성이 보다 향상되기 때문이다.Moreover, although ratio (weight ratio) of the weight of a cation with respect to the weight of an acylphosphine anion is not specifically limited, Especially, it is preferable that it is 0.25-1.00. This is because the solubility of the acylphosphine composition is further improved and the stability of the acylphosphine composition is further improved.
당량비 및 중량비의 각각은, 핵자기 공명(NMR: Nuclear Magnetic Resonance)법을 이용한 아실포스핀 조성물의 분석 결과(1H-NMR의 적분비)에 근거하여 산출 가능하다.Each of the equivalence ratio and the weight ratio can be calculated based on the analysis result (integral ratio of 1H-NMR) of the acylphosphine composition using a nuclear magnetic resonance (NMR) method.
(구체예)(specific example)
아실포스핀 조성물의 구체예는, 식 (1) 및 식 (2)에 나타낸 조건(Y1~Y3, X1 및 X2)을 충족시키는 카티온 및 2종류 이상의 아니온을 포함하는 조성물이면, 특별히 한정되지 않는다.Specific examples of the acylphosphine composition are not particularly limited as long as they are a composition containing a cation and two or more kinds of anions satisfying the conditions (Y1 to Y3, X1 and X2) shown in the formulas (1) and (2). does not
카티온의 구체예는, A1~A42의 각각으로 표시되는 제4급 암모늄형의 카티온 등이다. 단, 카티온은, 식 (1)에 나타낸 조건을 충족시키는 카티온이면, 여기에서 구체예로서 들지 않은 다른 구조를 갖는 카티온이어도 된다.Specific examples of the cation are quaternary ammonium-type cations represented by each of A1 to A42. However, as long as a cation is a cation which satisfies the conditions shown in Formula (1), the cation which has another structure which is not mentioned as a specific example here may be sufficient.
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
아실포스핀 아니온의 구체예는, B1~B16의 각각으로 표시되는 아실포스핀형의 아니온 등이다. 단, 아실포스핀 아니온은, 식 (2)에 나타낸 조건을 충족시키는 아니온이면, 여기에서 구체예로서 들지 않은 다른 구조를 갖는 아니온이어도 된다.Specific examples of the acylphosphine anion are an anion of the acylphosphine type represented by each of B1 to B16. However, as long as the acylphosphine anion is an anion which satisfies the conditions shown in Formula (2), the anion which has another structure not mentioned as a specific example here may be sufficient.
[화학식 7][Formula 7]
[화학식 8][Formula 8]
[제조 방법][Manufacturing method]
아실포스핀 조성물의 제조 방법은, 특별히 한정되지 않는다. 이 때문에, 아실포스핀 조성물은, 기지(旣知)의 제조 방법을 이용하여 제조 가능하다. 또한, 몇가지 아실포스핀 조성물의 구체적인 제조 방법에 관해서는, 후술한다.The manufacturing method of an acylphosphine composition is not specifically limited. For this reason, an acylphosphine composition can be manufactured using a known manufacturing method. In addition, the specific manufacturing method of some acylphosphine compositions is mentioned later.
[작용 및 효과][action and effect]
이 아실포스핀 조성물은, 식 (1)에 나타낸 카티온과, 식 (2)에 나타낸 아실포스핀 아니온을 포함하는 2종류 이상의 아니온을 포함하고 있고, 당량비가 1.005~1.100이다.This acylphosphine composition contains the cation shown in Formula (1), and 2 or more types of anions containing the acylphosphine anion shown in Formula (2), and an equivalence ratio is 1.005-1.100.
이 경우에는, 당량비가 상기한 조건을 충족시키지 않는 경우와 비교해, 상기한 바와 같이, 아실포스핀 조성물의 용해성이 향상됨과 동시에, 그 아실포스핀 조성물의 안정성이 향상된다. 따라서, 아실포스핀 조성물을 포함하는 중합성 조성물의 보존 안정성이 향상됨과 동시에, 그 중합성 조성물의 경화성도 향상되기 때문에, 우수한 물성을 얻을 수 있다.In this case, compared with the case where the equivalence ratio does not satisfy the above-mentioned conditions, the solubility of the acylphosphine composition improves and the stability of the acylphosphine composition improves as mentioned above. Therefore, since the storage stability of the polymeric composition containing an acylphosphine composition improves and sclerosis|hardenability of the polymeric composition also improves, the outstanding physical property can be acquired.
특히, 중량비가 0.25~1.00이면, 아실포스핀 조성물의 용해성이 보다 향상됨과 동시에, 그 아실포스핀 조성물의 안정성이 보다 향상되기 때문에, 보다 높은 효과를 얻을 수 있다.In particular, since the solubility of an acylphosphine composition improves more as weight ratio is 0.25-1.00, and stability of the acylphosphine composition improves more, a higher effect can be acquired.
또한, 식 (2)에 있어서 X1이 2,4,6-트라이메틸페닐기이면, 아실포스핀 조성물을 포함하는 중합성 조성물의 경화성이 향상되기 때문에, 보다 높은 효과를 얻을 수 있다.Moreover, since sclerosis|hardenability of the polymeric composition containing an acylphosphine composition improves that X1 is a 2,4,6- trimethylphenyl group in Formula (2), a higher effect can be acquired.
또한, 식 (2)에 있어서 X2가 페닐기이면, 아실포스핀 조성물을 포함하는 중합성 조성물의 경화성이 향상되기 때문에, 보다 높은 효과를 얻을 수 있다.Moreover, since sclerosis|hardenability of the polymeric composition containing an acylphosphine composition improves that X2 is a phenyl group in Formula (2), a higher effect can be acquired.
또한, 식 (2)에 있어서, Y1, Y2 및 Y3 중 1개는 탄소수가 1~6인 직쇄상의 알킬기임과 동시에, Y1, Y2 및 Y3 중 나머지 2개의 각각은 말단의 1개의 수소기가 수산기에 의해 치환된 탄소수가 1~6인 직쇄상의 알킬기이면, 아실포스핀 조성물을 포함하는 중합성 조성물의 경화성이 향상되기 때문에, 보다 높은 효과를 얻을 수 있다.In the formula (2), one of Y1, Y2 and Y3 is a linear alkyl group having 1 to 6 carbon atoms, and each of the other two of Y1, Y2 and Y3 is a hydrogen group at the terminal. Since sclerosis|hardenability of the polymeric composition containing an acylphosphine composition improves that it is a C1-C6 linear alkyl group substituted by it, a higher effect can be acquired.
<2. 중합성 조성물><2. Polymerizable Composition>
다음으로, 상기한 아실포스핀 조성물을 이용한 본 발명의 일 실시형태의 중합성 조성물에 관하여 설명한다.Next, the polymerizable composition of one embodiment of the present invention using the above-described acylphosphine composition will be described.
[구성][composition]
이 중합성 조성물은, 아실포스핀 조성물과, 반응기 함유 화합물과, 수성 용매를 포함하고 있다. 단, 아실포스핀 조성물의 종류는, 1종류만이어도 되고, 2종류 이상이어도 된다. 이와 같이 종류가 1종류여도 되고 2종류 이상이어도 되는 것은, 반응기 함유 화합물 및 수성 용매의 각각에 관해서도 동일하다.The polymerizable composition contains an acylphosphine composition, a reactive group-containing compound, and an aqueous solvent. However, the number of types of an acylphosphine composition may be one, and two or more types may be sufficient as them. In this way, the number of types may be one or two or more, and it is the same also about each of a reactive group containing compound and an aqueous solvent.
(아실포스핀 조성물)(Acylphosphine composition)
아실포스핀 조성물은, 중합성 조성물의 중합 반응 시에 있어서 중합 개시제로서 기능한다. 또한, 아실포스핀 조성물의 구성에 관한 상세는, 상기한 바와 같다.The acylphosphine composition functions as a polymerization initiator in the polymerization reaction of the polymerizable composition. In addition, the detail regarding the structure of an acylphosphine composition is as above-mentioned.
(함유량)(content)
중합성 조성물 중에 있어서의 아실포스핀 조성물의 함유량은, 특별히 한정되지 않지만, 그 중에서도, 전체 고형분 중에 있어서 0.1질량%~30질량%인 것이 바람직하고, 1질량%~10질량%인 것이 보다 바람직하다. 중합성 조성물의 보존 안정성 및 경화성이 향상되기 때문이다.Although content of the acylphosphine composition in a polymeric composition is not specifically limited, Especially, in total solid, it is preferable that it is 0.1 mass % - 30 mass %, It is more preferable that it is 1 mass % - 10 mass % . It is because the storage stability and sclerosis|hardenability of a polymeric composition improve.
여기에서 설명한 「전체 고형분」이란, 중합성 조성물을 구성하는 일련의 구성요소(액체 성분 및 고체 성분)로부터, 25℃ 및 1 기압의 조건하에 있어서 액체 성분인 수성 용매를 제외한 나머지 고체 성분 전부를 의미하고 있다. 이 때문에, 상기한 아실포스핀 조성물의 함유량은, 전고체 성분의 질량에 대해서 아실포스핀 조성물의 질량이 차지하는 비율을 의미하고 있다. 여기에서 설명한 전체 고형분에 관한 정의는, 이후에 있어서도 동일하다. 또한, 액체 성분에는, 수성 용매뿐만 아니라, 필요에 따라 유기용매 등이 포함되어도 된다.The "total solid content" described herein means all of the remaining solid components from a series of components (liquid components and solid components) constituting the polymerizable composition, excluding the aqueous solvent which is a liquid component under the conditions of 25° C. and 1 atm. are doing For this reason, content of said acylphosphine composition means the ratio which the mass of an acylphosphine composition occupies with respect to the mass of an all-solid component. The definition regarding the total solid content demonstrated here is also the same hereafter. In addition, not only an aqueous solvent but an organic solvent etc. may be contained in a liquid component as needed.
(반응기 함유 화합물)(reactor-containing compound)
반응기 함유 화합물은, 식 (3)으로 표시되는 반응기를 포함하는 화합물이며, 그 반응기 함유 화합물에 포함되는 반응기의 수는, 1개만이어도 되고, 2개 이상이어도 된다.The reactive group-containing compound is a compound containing a reactive group represented by formula (3), and the number of reactive groups contained in the reactive group-containing compound may be one or two or more.
[화학식 9][Formula 9]
(R1은, 수소기 및 메틸기 중 어느 하나이다.(R1 is either a hydrogen group or a methyl group.
Z1은, -O- 및 -NR2 중 어느 하나이며, 그 R2는, 수소기 및 탄소수가 1 이상 20 이하인 탄화 수소기 중 어느 하나이다.Z1 is any one of -O- and -NR2, wherein R2 is any one of a hydrogen group and a hydrocarbon group having 1 or more and 20 or less carbon atoms.
Z2는, 탄소수가 1 이상 6 이하인 알킬렌기이다.Z2 is an alkylene group having 1 or more and 6 or less carbon atoms.
n은, 0 이상 30 이하의 정수이다.n is an integer of 0 or more and 30 or less.
단, 별표(*)는, 미결합의 결합손을 표시하고 있다.)However, an asterisk (*) indicates an unbonded bond.)
식 (3)에서는, 상기한 바와 같이, 별표(*)가 미결합의 결합손을 나타내고 있다. 이 때문에, 식 (3)에서는, 반응기 함유 화합물을 나타내고 있는 것이 아니라, 그 반응기 함유 화합물에 포함되는 반응기만을 나타내고 있다.In Formula (3), as described above, an asterisk (*) indicates an unbonded bond. For this reason, in Formula (3), the reactive group containing compound is not shown, but only the reactive group contained in the reactive group containing compound is shown.
(R1)(R1)
반응기의 수가 2개 이상인 경우에는, 2개 이상의 R1의 종류는, 서로 동일해도 되고, 서로 상이해도 된다. 물론, 반응기의 수가 3개 이상인 경우에는, 3개 이상의 R1 중 일부 R1의 종류만이 서로 동일해도 된다.When the number of reactive groups is two or more, the kind of two or more R<1> may mutually be mutually same, and may mutually differ. Of course, when the number of reactive groups is three or more, only some kinds of R1 among the three or more R1s may be identical to each other.
(Z1)(Z1)
탄소수가 1~20인 탄화 수소기의 종류는, 특별히 한정되지 않는다. 여기에서 설명하는 탄화 수소기란, 수소 및 탄소에 의해 구성되는 1가의 기의 총칭이다. 이 탄화 수소기는, 직쇄상이어도 되고, 분기상이어도 되고, 환상이어도 되며, 그것들의 2종류 이상이 서로 결합된 상태여도 된다. 또한, 탄화 수소기는, 1개 또는 2개 이상의 탄소간 불포화 결합을 포함하고 있어도 된다. 이 탄소간 불포화 탄소 결합은, 탄소간 이중 결합이어도 되고, 탄소간 삼중 결합이어도 되고, 양쪽 다여도 된다.The kind of hydrocarbon group having 1 to 20 carbon atoms is not particularly limited. The hydrocarbon group described herein is a generic term for monovalent groups composed of hydrogen and carbon. The hydrocarbon group may be linear, branched, or cyclic, and may be in a state in which two or more thereof are bonded to each other. Moreover, the hydrocarbon group may contain the 1 or 2 or more carbon unsaturated bond. This intercarbon unsaturated carbon bond may be a double bond between carbons, a triple bond between carbons, or both.
반응기의 수가 2개 이상인 경우에는, 2개 이상의 Z1의 종류는, 서로 동일해도 되고, 서로 상이해도 된다. 물론, 반응기의 수가 3개 이상인 경우에는, 3개 이상의 Z1 의 일부 Z1의 종류만이 서로 동일해도 된다.When the number of reactive groups is two or more, the types of two or more Z1 may mutually be same, and may mutually differ. Of course, when the number of the reactors is three or more, only a part of Z1 of three or more Z1s may be the same as each other.
탄화 수소기의 구체예는, 탄소수가 1~20이기 때문에, 탄소수가 1~20인 알킬기, 탄소수가 2~20인 알케닐기, 탄소수가 3~20인 사이클로알킬기, 탄소수가 4~20인 사이클로알킬알킬기, 탄소수가 6~20인 아릴기 및 탄소수가 7~20인 아릴알킬기 등이다.Specific examples of the hydrocarbon group include, since it has 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and a cycloalkyl group having 4 to 20 carbon atoms. an alkyl group, an aryl group having 6 to 20 carbon atoms, and an arylalkyl group having 7 to 20 carbon atoms.
그 중에서도, 탄소수가 1~10인 알킬기, 탄소수가 2~10인 알케닐기, 탄소수가 3~10인 사이클로알킬기, 탄소수가 4~10인 사이클로알킬알킬기, 탄소수가 6~10인 아릴기 및 탄소수가 7~10인 아릴알킬기 중 어느 하나가 바람직하다. 중합성 조성물의 감도가 향상되기 때문이다.Among them, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkylalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryl group having 6 to 10 carbon atoms. Any one of 7-10 arylalkyl groups is preferable. This is because the sensitivity of the polymerizable composition is improved.
알킬기의 구체예는, 탄소수가 1~20이기 때문에, 메틸기, 에틸기, 프로필기, 아이소프로필기, 뷰틸기, 아이소뷰틸기, sec-뷰틸기, tert-뷰틸기, 아밀기, 아이소아밀기, tert-아밀기, 헥실기, 헵틸기, 옥틸기, 아이소옥틸기, 2-에틸헥실기, tert-옥틸기, 노닐기, 아이소노닐기, 데실기, 아이소데실기, 운데실기, 도데실기, 테트라데실기, 헥사데실기, 옥타데실기 및 아이코실기 등이다.Specific examples of the alkyl group include 1 to 20 carbon atoms, so methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, amyl group, isoamyl group, tert -amyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, tert-octyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tetradecyl group Sil group, hexadecyl group, octadecyl group, icosyl group, and the like.
또한, 탄소수가 1~10인 알킬기의 구체예는, 메틸기, 에틸기, 프로필기, 아이소프로필기, 뷰틸기, 아이소뷰틸기, sec-뷰틸기, tert-뷰틸기, 아밀기, 아이소아밀기, tert-아밀기, 헥실기, 헵틸기, 옥틸기, 아이소옥틸기, 2-에틸헥실기, tert-옥틸기, 노닐기, 아이소노닐기, 데실기 및 아이소데실기 등이다.Specific examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an amyl group, an isoamyl group, tert -amyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, tert-octyl group, nonyl group, isononyl group, decyl group and isodecyl group.
알케닐기의 구체예는, 탄소수가 2~20이기 때문에, 바이닐기, 2-프로펜일기, 3-뷰텐일기, 2-뷰텐일기, 4-펜텐일기, 3-펜텐일기, 2-헥센일기, 3-헥센일기, 5-헥센일기, 2-헵텐일기, 3-헵텐일기, 4-헵텐일기, 3-옥텐일기, 3-노넨일기, 4-데센일기, 3-운데센일기, 4-도데센일기, 3-사이클로헥센일기, 2,5-사이클로헥사다이엔일-1-메틸기 및 4,8,12-테트라데카트라이엔일알릴기 등이다.Since specific examples of the alkenyl group have 2 to 20 carbon atoms, vinyl group, 2-propenyl group, 3-butenyl group, 2-butenyl group, 4-pentenyl group, 3-pentenyl group, 2-hexenyl group, 3 -Hexenyl group, 5-hexenyl group, 2-heptenyl group, 3-heptenyl group, 4-heptenyl group, 3-octenyl group, 3-nonenyl group, 4-decenyl group, 3-undecenyl group, 4-dodecenyl group , a 3-cyclohexenyl group, a 2,5-cyclohexadienyl-1-methyl group, and a 4,8,12-tetradecatrienylallyl group.
또한, 탄소수가 2~10인 알케닐기의 구체예는, 바이닐기, 2-프로펜일기, 3-뷰텐일기, 2-뷰텐일기, 4-펜텐일기, 3-펜텐일기, 2-헥센일기, 3-헥센일기, 5-헥센일기, 2-헵텐일기, 3-헵텐일기, 4-헵텐일기, 3-옥텐일기, 3-노넨일기 및 4-데센일기 등이다.Specific examples of the alkenyl group having 2 to 10 carbon atoms include a vinyl group, 2-propenyl group, 3-butenyl group, 2-butenyl group, 4-pentenyl group, 3-pentenyl group, 2-hexenyl group, 3 -hexenyl group, 5-hexenyl group, 2-heptenyl group, 3-heptenyl group, 4-heptenyl group, 3-octenyl group, 3-nonenyl group and 4-desenyl group.
탄소수가 3~20인 사이클로알킬기란, 3개~20개의 탄소 원자를 갖는 포화 단환식 알킬기 및 포화 다환식 알킬기 중 어느 하나이다. 사이클로알킬기의 구체예는, 탄소수가 3~20이기 때문에, 사이클로프로필기, 사이클로뷰틸기, 사이클로펜틸기, 사이클로헥실기, 사이클로헵틸기, 사이클로옥틸기, 사이클로노닐기, 사이클로데실기, 아다만틸기, 데카하이드로나프틸기, 옥타하이드로펜탈렌기, 바이사이클로[1.1.1]펜타닐기 및 테트라데카하이드로안트라세닐기 등이다.The cycloalkyl group having 3 to 20 carbon atoms is either a saturated monocyclic alkyl group or a saturated polycyclic alkyl group having 3 to 20 carbon atoms. Specific examples of the cycloalkyl group include 3 to 20 carbon atoms, so a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, an adamantyl group , a decahydronaphthyl group, an octahydropentalene group, a bicyclo [1.1.1] fentanyl group, and a tetradecahydroanthracenyl group.
또한, 탄소수가 3~10인 사이클로알킬기의 구체예는, 사이클로프로필기, 사이클로뷰틸기, 사이클로펜틸기, 사이클로헥실기, 사이클로헵틸기, 사이클로옥틸기, 사이클로노닐기, 사이클로데실기, 아다만틸기, 데카하이드로나프틸기, 옥타하이드로펜탈렌기 및 바이사이클로[1.1.1]펜타닐기 등이다.Specific examples of the cycloalkyl group having 3 to 10 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, and an adamantyl group. , a decahydronaphthyl group, an octahydropentalene group, and a bicyclo[1.1.1]fentanyl group.
탄소수가 4~20인 사이클로알킬알킬기란, 알킬기에 포함되어 있는 1개 또는 2개 이상의 수소기가 사이클로알킬기에 의해 치환된 4개~20개의 탄소 원자를 갖는 기의 총칭이다. 사이클로알킬알킬기의 구체예는, 탄소수가 4~20이기 때문에, 사이클로프로필메틸기, 사이클로뷰틸메틸기, 사이클로펜틸메틸기, 사이클로헥실메틸기, 사이클로헵틸메틸기, 사이클로옥틸메틸기, 사이클로노닐메틸기, 사이클로데실메틸기, 2-사이클로뷰틸에틸기, 2-사이클로펜틸에틸기, 2-사이클로헥실에틸기, 2-사이클로헵틸에틸기, 2-사이클로옥틸에틸기, 2-사이클로노닐에틸기, 2-사이클로데실에틸기, 3-사이클로뷰틸프로필기, 3-사이클로펜틸프로필기, 3-사이클로헥실프로필기, 3-사이클로헵틸프로필기, 3-사이클로옥틸프로필기, 3-사이클로노닐프로필기, 3-사이클로데실프로필기, 4-사이클로뷰틸뷰틸기, 4-사이클로펜틸뷰틸기, 4-사이클로헥실뷰틸기, 4-사이클로헵틸뷰틸기, 4-사이클로옥틸뷰틸기, 4-사이클로노닐뷰틸기, 4-사이클로데실뷰틸기, 3-3-아다만틸프로필기 및 데카하이드로나프틸프로필기 등이다.The cycloalkylalkyl group having 4 to 20 carbon atoms is a generic term for a group having 4 to 20 carbon atoms in which one or two or more hydrogen groups included in the alkyl group are substituted by a cycloalkyl group. Specific examples of the cycloalkylalkyl group include 4 to 20 carbon atoms, so cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, cycloheptylmethyl group, cyclooctylmethyl group, cyclononylmethyl group, cyclodecylmethyl group, 2- Cyclobutylethyl group, 2-cyclopentylethyl group, 2-cyclohexylethyl group, 2-cycloheptylethyl group, 2-cyclooctylethyl group, 2-cyclononylethyl group, 2-cyclodecylethyl group, 3-cyclobutylpropyl group, 3-cyclo Pentylpropyl group, 3-cyclohexylpropyl group, 3-cycloheptylpropyl group, 3-cyclooctylpropyl group, 3-cyclononylpropyl group, 3-cyclodecylpropyl group, 4-cyclobutylbutyl group, 4-cyclophene Tylbutyl group, 4-cyclohexylbutyl group, 4-cycloheptylbutyl group, 4-cyclooctylbutyl group, 4-cyclononylbutyl group, 4-cyclodecylbutyl group, 3-3-adamantylpropyl group and decahydro and a naphthylpropyl group.
또한, 탄소수가 4~10인 사이클로알킬알킬기의 구체예는, 사이클로프로필메틸기, 사이클로뷰틸메틸기, 사이클로펜틸메틸기, 사이클로헥실메틸기, 사이클로헵틸메틸기, 사이클로옥틸메틸기, 사이클로노닐메틸기, 2-사이클로뷰틸에틸기, 2-사이클로펜틸에틸기, 2-사이클로헥실에틸기, 2-사이클로헵틸에틸기, 2-사이클로옥틸에틸기, 3-사이클로뷰틸프로필기, 3-사이클로펜틸프로필기, 3-사이클로헥실프로필기, 3-사이클로헵틸프로필기, 4-사이클로뷰틸뷰틸기, 4-사이클로펜틸뷰틸기 및 4-사이클로헥실뷰틸기 등이다.Specific examples of the cycloalkylalkyl group having 4 to 10 carbon atoms include a cyclopropylmethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a cycloheptylmethyl group, a cyclooctylmethyl group, a cyclononylmethyl group, a 2-cyclobutylethyl group, 2-cyclopentylethyl group, 2-cyclohexylethyl group, 2-cycloheptylethyl group, 2-cyclooctylethyl group, 3-cyclobutylpropyl group, 3-cyclopentylpropyl group, 3-cyclohexylpropyl group, 3-cycloheptylpropyl group group, 4-cyclobutylbutyl group, 4-cyclopentylbutyl group and 4-cyclohexylbutyl group.
아릴기의 구체예는, 탄소수가 6~20이기 때문에, 페닐기, 톨릴기, 자일릴기, 에틸페닐기, 나프틸기, 안트릴기 및 페난트렌일기 등이다. 또한, 아릴기의 구체예는, 상기한 알킬기, 알케닐기, 카복실기 및 할로겐기 중 어느 1종류 또는 2종류 이상에 의해 1개 또는 2개 이상의 수소기가 치환된 페닐기, 바이페닐일기, 나프틸기, 안트릴기 등이며, 보다 구체적으로는 4-클로로페닐기, 4-카복실페닐기, 4-바이닐페닐기, 4-메틸페닐기 및 2,4,6-트라이메틸페닐기 등이다.Specific examples of the aryl group include a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group, a naphthyl group, an anthryl group, and a phenanthrenyl group since they have 6 to 20 carbon atoms. In addition, specific examples of the aryl group include a phenyl group, a biphenylyl group, a naphthyl group, in which one or two or more hydrogen groups are substituted by any one or two or more of the above-described alkyl group, alkenyl group, carboxyl group and halogen group, anthryl group, etc., and more specifically, a 4-chlorophenyl group, 4-carboxylphenyl group, 4-vinylphenyl group, 4-methylphenyl group, and 2,4,6-trimethylphenyl group.
또한, 탄소수가 6~10인 아릴기의 구체예는, 페닐기, 톨릴기, 자일릴기, 에틸페닐기 및 나프틸기 등이다. 또한, 아릴기의 구체예는, 상기한 알킬기, 알케닐기, 카복실기 및 할로겐기 중 어느 1종류 또는 2종류 이상에 의해 1개 또는 2개 이상의 수소기가 치환된 페닐기, 바이페닐일기, 나프틸기 및 안트릴기 등이며, 보다 구체적으로는, 4-클로로페닐기, 4-카복실페닐기, 4-바이닐페닐기, 4-메틸페닐기 및 2,4,6-트라이메틸페닐기 등이다.Specific examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group, and a naphthyl group. In addition, specific examples of the aryl group include a phenyl group, a biphenylyl group, a naphthyl group, and anthryl group and the like, and more specifically, a 4-chlorophenyl group, 4-carboxylphenyl group, 4-vinylphenyl group, 4-methylphenyl group, and 2,4,6-trimethylphenyl group.
탄소수가 7~20인 아릴알킬기란, 알킬기에 포함되어 있는 1개 또는 2개 이상의 수소기가 아릴기에 의해 치환된 7개~30개의 탄소 원자를 갖는 기의 총칭이다. 아릴알킬기의 구체예는, 탄소수가 7~20이기 때문에, 벤질기, α-메틸벤질기, α,α-다이메틸벤질기, 페닐에틸기 및 나프틸프로필기 등이다.An arylalkyl group having 7 to 20 carbon atoms is a generic term for a group having 7 to 30 carbon atoms in which one or two or more hydrogen groups included in the alkyl group are substituted with an aryl group. Specific examples of the arylalkyl group include a benzyl group, an α-methylbenzyl group, an α,α-dimethylbenzyl group, a phenylethyl group and a naphthylpropyl group since they have 7 to 20 carbon atoms.
(Z2)(Z2)
반응기의 수가 2개 이상인 경우에는, 2개 이상의 Z2의 종류는, 서로 동일해도 되고, 서로 상이해도 된다. 물론, 반응기의 수가 3개 이상인 경우에는, 3개 이상의 Z2 중 일부 Z2의 종류만이 서로 동일해도 된다.When the number of reactive groups is two or more, the types of two or more Z2 may mutually be mutually same, and may mutually differ. Of course, when the number of reactors is three or more, only some types of Z2 among the three or more Z2s may be the same.
또한, n의 값이 2 이상인 경우에는, 2개 이상의 Z2의 종류는, 서로 동일해도 되고, 서로 상이해도 된다. 물론, n의 값이 3 이상인 경우에는, 3개 이상의 Z2 중 일부 Z2의 종류만이 서로 동일해도 된다.In addition, when the value of n is 2 or more, the kind of two or more Z2 may mutually be mutually same, and may mutually differ. Of course, when the value of n is 3 or more, only some types of Z2 among the three or more Z2s may be the same.
알킬렌기의 구체예는, 탄소수가 1~6이기 때문에, 메틸렌기, 에틸렌기, 프로필렌기, 뷰틸렌기, 펜틸렌기 및 헥실렌기 등의 직쇄상의 알킬렌기여도 되고, 아이소프로필렌기 및 아이소뷰틸렌기 등의 분기쇄상의 알킬렌기여도 된다. 그 중에서도, 알킬렌기는, 탄소수가 1~4인 알킬렌기인 것이 바람직하고, 에틸렌기, 프로필렌기 및 아이소프로필렌기 중 어느 하나인 것이 보다 바람직하다. 반응기 함유 화합물의 수용성이 향상되기 때문이다.Specific examples of the alkylene group include 1 to 6 carbon atoms, so may be a straight-chain alkylene group such as a methylene group, ethylene group, propylene group, butylene group, pentylene group and hexylene group, isopropylene group and isobutylene group It may be a branched alkylene group, such as these. Especially, it is preferable that it is a C1-C4 alkylene group, and, as for an alkylene group, it is more preferable that it is any one of an ethylene group, a propylene group, and an isopropylene group. This is because the water solubility of the reactive group-containing compound is improved.
(n에 관한 상세)(Details about n)
n의 값은, 상기한 바와 같이, 0~30의 정수이기 때문에, 0이어도 된다. n의 값이 0인 경우에는, 반응기는 R1-C(=CH2)-C(=O)-Z1-*로 표시된다.Since the value of n is an integer of 0-30 as mentioned above, 0 may be sufficient. When the value of n is 0, the reactive group is represented by R1-C(=CH 2 )-C(=O)-Z1-*.
(구체예)(specific example)
반응기가 결합되는 모체의 종류는, 특별히 한정되지 않는다. 반응기의 수가 y개인 경우에는, 상기한 모체는, y가의 탄화 수소기 등이다. y=1인 경우에는, 모체는, 상기한 알킬기, 알케닐기, 사이클로알킬기, 사이클로알킬알킬기, 아릴기 및 아릴알킬기 등이며, 그것들의 각 기의 탄소수는, 특별히 한정되지 않는다. y=w(w는, 2 이상의 정수이다.)인 경우에는, 모체는, 상기한 알킬기, 알케닐기, 사이클로알킬기, 사이클로알킬알킬기, 아릴기 및 아릴알킬기의 각각으로부터 (w-1)개의 수소기가 이탈한 기 등이며, 그것들의 탄소수는, 특별히 한정되지 않는다.The kind of parent to which the reactive group is bonded is not particularly limited. When the number of reactive groups is y, the above-described parent is a y-valent hydrocarbon group or the like. When y = 1, the parent is an alkyl group, an alkenyl group, a cycloalkyl group, a cycloalkylalkyl group, an aryl group, an arylalkyl group or the like, and the number of carbon atoms in each group is not particularly limited. When y=w (w is an integer of 2 or more), the parent has (w-1) hydrogen groups from each of the above-described alkyl group, alkenyl group, cycloalkyl group, cycloalkylalkyl group, aryl group and arylalkyl group. It is a group etc. which left|leaved, and the carbon number of those is not specifically limited.
그 중에서도, 반응기 함유 화합물은, 알킬렌옥사이드 변성 (메타)아크릴레이트 화합물 및 (메타)아크릴아마이드 화합물 중 일방 또는 쌍방인 것이 바람직하다. 중합성 조성물이 중합 반응하기 쉬워지기 때문이다.Among them, the reactive group-containing compound is preferably one or both of an alkylene oxide-modified (meth)acrylate compound and a (meth)acrylamide compound. This is because the polymerizable composition is liable to undergo a polymerization reaction.
알킬렌옥사이드 변성 (메타)아크릴레이트 화합물은, 알킬렌옥사이드 변성 아크릴레이트 화합물 및 알킬렌옥사이드 변성 메타크릴레이트 화합물 등이다. (메타)아크릴아마이드 화합물은, 아크릴아마이드 화합물 및 메타크릴아마이드 화합물 등이다.The alkylene oxide-modified (meth)acrylate compound is an alkylene oxide-modified acrylate compound and an alkylene oxide-modified methacrylate compound. The (meth)acrylamide compound is an acrylamide compound, a methacrylamide compound, or the like.
알킬렌옥사이드 변성 아크릴레이트 화합물은, 식 (3)에 있어서, R1이 수소기, Z1이 -O-, n의 값이 1~30인 화합물이다. 알킬렌옥사이드 변성 메타크릴레이트 화합물은, 식 (3)에 있어서, R1이 메틸기, Z1이 -O-, n의 값이 1~30인 화합물이다.The alkylene oxide-modified acrylate compound is a compound in which R1 is a hydrogen group, Z1 is -O-, and the value of n is 1-30 in Formula (3). The alkylene oxide-modified methacrylate compound is a compound in which R1 is a methyl group, Z1 is -O-, and the value of n is 1-30 in Formula (3).
알킬렌옥사이드 변성 아크릴레이트 화합물의 구체예는, 다이에틸렌옥사이드 변성 네오펜틸글라이콜다이아크릴레이트, 다이프로필렌옥사이드 변성 네오펜틸글라이콜다이아크릴레이트, 다이에틸렌옥사이드 변성 1,6-헥세인다이올다이아크릴레이트 및 다이프로필렌옥사이드 변성 1,6-헥세인다이올다이아크릴레이트 등이다.Specific examples of the alkylene oxide-modified acrylate compound include diethylene oxide-modified neopentyl glycol diacrylate, dipropylene oxide-modified neopentyl glycol diacrylate, and diethylene oxide-modified 1,6-hexanediol diacrylate and dipropylene oxide-modified 1,6-hexanediol diacrylate;
알킬렌옥사이드 변성 메타크릴레이트 화합물의 구체예는, 다이에틸렌옥사이드 변성 네오펜틸글라이콜다이메타크릴레이트, 다이프로필렌옥사이드 변성 네오펜틸글라이콜다이메타크릴레이트, 다이에틸렌옥사이드 변성 1,6-헥세인다이올다이메타크릴레이트 및 다이프로필렌옥사이드 변성 1,6-헥세인다이올다이메타크릴레이트 등이다.Specific examples of the alkylene oxide-modified methacrylate compound include diethylene oxide-modified neopentyl glycol dimethacrylate, dipropylene oxide-modified neopentyl glycol dimethacrylate, and diethylene oxide-modified 1,6-hexyl Seindiol dimethacrylate and dipropylene oxide-modified 1,6-hexanediol dimethacrylate.
알킬렌옥사이드 변성 아크릴레이트 화합물 및 알킬렌옥사이드 변성 메타크릴레이트 화합물의 각각으로서는, 시판품을 사용해도 된다. 구체적으로는, 신나카무라 화학공업 주식회사제의 NK에스터 A-600, A-GLY-20E 및 NK에코노마 A-PG5054E 등을 사용할 수 있다.As each of the alkylene oxide modified acrylate compound and the alkylene oxide modified methacrylate compound, you may use a commercial item. Specifically, NK Ester A-600, A-GLY-20E, and NK Economa A-PG5054E manufactured by Shin-Nakamura Chemical Industry Co., Ltd. can be used.
그 중에서도, 알킬렌옥사이드 변성 아크릴레이트 화합물 및 알킬렌옥사이드 변성 메타크릴레이트 화합물의 각각에서는, 식 (3)에 있어서, Z2는 에틸렌기 및 프로필렌기 중 어느 하나인 것이 바람직하다. 반응기 함유 화합물의 용해성, 특히 수성 용매에 대한 용해성이 향상되기 때문이다. Z2가 에틸렌기인 경우에는, 반응기 함유 화합물의 용해성이 현저하게 향상된다.Especially, in each of an alkylene oxide modified acrylate compound and an alkylene oxide modified methacrylate compound, in Formula (3), it is preferable that Z2 is either an ethylene group and a propylene group. This is because the solubility of the reactive group-containing compound, particularly solubility in an aqueous solvent, is improved. When Z2 is an ethylene group, the solubility of a reactive group containing compound improves remarkably.
알킬렌옥사이드 변성 아크릴레이트 화합물 및 알킬렌옥사이드 변성 메타크릴레이트 화합물의 각각이 1개의 반응기를 갖는 경우에는, 반응기 함유 화합물의 용해성이 담보되기 때문에, n의 값은 6 이상인 것이 바람직하다. 또한, 알킬렌옥사이드 변성 아크릴레이트 화합물 및 알킬렌옥사이드 변성 메타크릴레이트 화합물의 각각이 2개 이상의 반응기를 갖는 경우에는, 반응기 함유 화합물의 용해성이 담보되기 때문에, 2개 이상의 n의 값의 총합은 10 이상인 것이 바람직하다.When each of the alkylene oxide-modified acrylate compound and the alkylene oxide-modified methacrylate compound has one reactive group, the solubility of the reactive group-containing compound is ensured, so that the value of n is preferably 6 or more. In addition, when each of the alkylene oxide-modified acrylate compound and the alkylene oxide-modified methacrylate compound has two or more reactive groups, since solubility of the reactive group-containing compound is ensured, the sum of the two or more n values is 10 more preferably.
아크릴아마이드 화합물은, 식 (3)에 있어서, R1이 수소기, Z1이 -NR2-, n의 값이 0인 화합물이다. 메타크릴아마이드 화합물은, 식 (3)에 있어서, R1이 메틸기, Z1이 -NR2-, n의 값이 0인 화합물이다.An acrylamide compound is a compound in which R1 is a hydrogen group, Z1 is -NR2-, and the value of n is 0 in Formula (3). A methacrylamide compound is a compound in which R1 is a methyl group, Z1 is -NR2-, and the value of n is 0 in Formula (3).
아크릴아마이드 화합물의 구체예는, 하이드록시아크릴아마이드, N-메틸아크릴아마이드, N-에틸아크릴아마이드, N-아이소프로필아크릴아마이드, N-뷰틸아크릴아마이드, 다이아세톤아크릴아마이드, N,N-다이메틸아크릴아마이드, N,N-다이에틸아크릴아마이드, N,N-다이프로필아크릴아마이드, 아크릴로일모폴린, N-n-뷰톡시메틸아크릴아마이드, N-아이소뷰톡시메틸아크릴아마이드 및 N-메톡시메틸아크릴아마이드 등이다.Specific examples of the acrylamide compound include hydroxyacrylamide, N-methyl acrylamide, N-ethyl acrylamide, N-isopropyl acrylamide, N-butyl acrylamide, diacetone acrylamide, N,N-dimethyl acrylamide Amide, N,N-diethylacrylamide, N,N-dipropylacrylamide, acryloylmorpholine, N-n-butoxymethylacrylamide, N-isobutoxymethylacrylamide and N-methoxymethylacrylamide, etc. to be.
메타크릴아마이드 화합물의 구체예는, 하이드록시메타크릴아마이드, N-메틸메타크릴아마이드, N-에틸메타크릴아마이드, N-아이소프로필메타크릴아마이드, N-뷰틸메타크릴아마이드, 다이아세톤메타크릴아마이드, N,N-다이메틸메타크릴아마이드, N,N-다이에틸메타크릴아마이드, N,N-다이프로필메타크릴아마이드, 메타크릴로일모폴린, N-n-뷰톡시메틸메타크릴아마이드, N-아이소뷰톡시메틸메타크릴아마이드 및 N-메톡시메틸메타크릴아마이드 등이다.Specific examples of the methacrylamide compound include hydroxymethacrylamide, N-methylmethacrylamide, N-ethylmethacrylamide, N-isopropylmethacrylamide, N-butylmethacrylamide, diacetonemethacrylamide, N,N-dimethylmethacrylamide, N,N-diethylmethacrylamide, N,N-dipropylmethacrylamide, methacryloylmorpholine, N-n-butoxymethylmethacrylamide, N-isobutoxy methyl methacrylamide and N-methoxymethyl methacrylamide.
아크릴아마이드 화합물 및 메타크릴아마이드 화합물의 각각으로서는, 시판품을 사용해도 된다. 구체적으로는, 후지필름 주식회사제의 FFM-2, FFM-3, FFM-4 및 FFM-5 등을 사용할 수 있다.As each of the acrylamide compound and the methacrylamide compound, you may use a commercial item. Specifically, FFM-2, FFM-3, FFM-4 and FFM-5 manufactured by FUJIFILM Corporation can be used.
(함유량)(content)
중합성 조성물 중에 있어서의 반응기 함유 화합물의 함유량은, 특별히 한정되지 않지만, 그 중에서도, 전체 고형분 중에 있어서 60질량%~99질량%인 것이 바람직하고, 70질량%~95질량%인 것이 보다 바람직하다. 중합성 조성물의 경화성이 향상되기 때문이다.Although content of the reactive group containing compound in a polymeric composition is not specifically limited, Especially, it is preferable that they are 60 mass % - 99 mass % in total solid, It is more preferable that they are 70 mass % - 95 mass %. It is because sclerosis|hardenability of a polymeric composition improves.
(수성 용매)(aqueous solvent)
수성 용매란, 25℃ 및 1기압의 조건하에 있어서 액체임과 동시에, 물 및 물과 혼화 가능한 유기용매를 포함하는 용매의 총칭이다. 즉, 수성 용매는, 물만이어도 되고, 물과 혼화 가능한 유기용매만이어도 되고, 쌍방의 혼합물이어도 된다. 이 물과 혼화 가능한 유기용매란, 20℃에 있어서 100g의 물에 대해서 0.01g 이상 용해되는 유기용매를 의미한다.The aqueous solvent is a generic term for solvents that are liquid and contain water and an organic solvent miscible with water under the conditions of 25°C and 1 atm. That is, only water may be sufficient as an aqueous solvent, and only water miscible organic solvent may be sufficient as it, and both mixture may be sufficient as it. This water-miscible organic solvent means an organic solvent which dissolves 0.01 g or more with respect to 100 g of water at 20°C.
수성 용매를 포함하는 중합성 조성물을 사용함으로써, 이하의 이점을 얻을 수 있다. 첫째, 후술하는 피막의 두께가 제어되기 쉬워진다. 둘째, 후술하는 기체(基體)로서, 유기 용제에 대한 내성이 높은 기체뿐만 아니라, 그 유기 용제에 대한 내성이 낮은 기체도 사용 가능하게 되기 때문에, 그 기체의 종류의 선택에 관한 자유도가 넓어진다. 셋째, 유기 재료(예를 들면, 유기 재료를 포함하는 막) 위에 중합성 조성물을 도포할 때에, 그 유기 재료가 중합성 조성물에 의해 침투되기 어려워진다. 넷째, 수성 용매는 환경친화적이기 때문에, 중합성 조성물의 사용 시에 있어서 환경 부하가 저감된다.By using a polymerizable composition containing an aqueous solvent, the following advantages can be obtained. First, it becomes easy to control the thickness of the film mentioned later. Second, as a gas to be described later, not only a gas having high resistance to organic solvents but also a gas having low resistance to the organic solvent can be used. Third, when a polymerizable composition is applied on an organic material (eg, a film containing an organic material), the organic material becomes difficult to permeate by the polymerizable composition. Fourth, since the aqueous solvent is environmentally friendly, the environmental load at the time of use of the polymerizable composition is reduced.
물의 종류는, 특별히 한정되지 않지만, 구체적으로는, 순수 및 이온 교환수 등이다.Although the kind of water is not specifically limited, Specifically, they are pure water, ion-exchange water, etc.
물과 혼화 가능한 유기용매의 종류는, 특별히 한정되지 않지만, 구체적으로는, 에틸렌글라이콜, 다이에틸렌글라이콜, 트라이에틸렌글라이콜, 프로필렌글라이콜, 다이프로필렌글라이콜, 2-피롤리돈, N-메틸-2-피롤리돈, 1,2-프로페인다이올, 1,3-프로페인다이올, 1,2-뷰테인다이올, 1,3-뷰테인다이올, 1,4-뷰테인다이올, 2,3-뷰테인다이올, 2,2-다이메틸-1,3-프로페인다이올, 2-메틸-1,3-프로페인다이올, 1,2-펜테인다이올, 1,5-펜테인다이올, 2,4-펜테인다이올, 1,2-헥세인다이올, 3,5-다이메틸-3-헥사인-2,5-다이올, 2,5-헥세인다이올, 헥실렌글라이콜, 1,6-헥세인다이올, 2-에틸-1,3-헥세인다이올, 2,2,4-트라이메틸-1,3-펜테인다이올, 2,5-다이메틸-2,5-헥세인다이올, 설포레인, 1,4-사이클로헥세인다이메탄올, 2,2-싸이오다이에탄올, 3-피리딜카비놀, 프로필렌글라이콜모노메틸에터, 다이프로필렌글라이콜메틸에터, 트라이프로필렌글라이콜메틸에터, 프로필렌글라이콜에틸에터, 프로필렌글라이콜n-프로필에터, 다이프로필렌글라이콜n-프로필에터, 트라이프로필렌글라이콜n-프로필에터, 프로필렌글라이콜n-뷰틸에터, 다이프로필렌글라이콜n-뷰틸에터, 트라이프로필렌글라이콜n-뷰틸에터, 프로필렌글라이콜t-뷰틸에터, 다이프로필렌글라이콜t-뷰틸에터, 프로필렌글라이콜페닐에터, 에틸렌글라이콜메틸에터, 다이에틸렌글라이콜메틸에터, 트라이에틸렌글라이콜메틸에터, 에틸렌글라이콜에틸에터, 다이에틸렌글라이콜에틸에터, 트라이에틸렌글라이콜에틸에터, 에틸렌글라이콜n-프로필에터, 에틸렌글라이콜n-뷰틸에터, 다이에틸렌글라이콜n-뷰틸에터, 트라이에틸렌글라이콜n-뷰틸에터, 에틸렌글라이콜n-헥실에터, 다이에틸렌글라이콜n-헥실에터 및 에틸렌글라이콜페닐에터 등이다.The type of organic solvent miscible with water is not particularly limited, but specifically, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 2-P Rollidone, N-methyl-2-pyrrolidone, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1 ,4-Butanediol, 2,3-butanediol, 2,2-dimethyl-1,3-propanediol, 2-methyl-1,3-propanediol, 1,2- Pentanediol, 1,5-pentanediol, 2,4-pentanediol, 1,2-hexanediol, 3,5-dimethyl-3-hexaine-2,5-diol , 2,5-hexanediol, hexylene glycol, 1,6-hexanediol, 2-ethyl-1,3-hexanediol, 2,2,4-trimethyl-1,3 -Pentanediol, 2,5-dimethyl-2,5-hexanediol, sulfolane, 1,4-cyclohexanedimethanol, 2,2-thiodiethanol, 3-pyridylcarbinol , propylene glycol monomethyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol n-propyl ether, dipropylene glycol Col n-propyl ether, tripropylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, tripropylene glycol n-butyl ether, Propylene glycol t-butyl ether, dipropylene glycol t-butyl ether, propylene glycol phenyl ether, ethylene glycol methyl ether, diethylene glycol methyl ether, triethylene glycol Colmethyl ether, ethylene glycol ethyl ether, diethylene glycol ethyl ether, triethylene glycol ethyl ether, ethylene glycol n-propyl ether, ethylene glycol n-butyl ether , diethylene glycol n-butyl ether, triethylene glycol n-butyl ether, ethylene glycol n-hexyl ether, diethylene glycol n-hexyl ether and ethylene glycol phenyl ter, etc.
그 중에서도, 물과 혼화 가능한 유기용매로서는, 탄소수가 5 이하인 저급 알코올이 바람직하다. 물에 대한 용해성이 현저하게 향상되기 때문이다.Among them, as the water-miscible organic solvent, a lower alcohol having 5 or less carbon atoms is preferable. It is because the solubility with respect to water improves remarkably.
(함유량)(content)
중합성 조성물 중에 있어서의 수성 용매의 함유량은, 특별히 한정되지 않지만, 그 중에서도, 10질량%~99질량%인 것이 바람직하고, 30질량%~95질량%인 것이 보다 바람직하고, 50질량%~90질량%인 것이 더 바람직하다. 중합성 조성물의 취급성이 향상됨과 함께, 그 중합성 조성물을 사용하여 형성되는 경화물의 두께가 제어되기 쉬워지기 때문이다.Although content of the aqueous solvent in polymeric composition is not specifically limited, Especially, it is preferable that they are 10 mass % - 99 mass %, It is more preferable that they are 30 mass % - 95 mass %, 50 mass % - 90 mass % It is more preferable that it is mass %. It is because the thickness of the hardened|cured material formed using this polymeric composition becomes easy to control while the handleability of a polymeric composition improves.
또한, 중합성 조성물이 잉크젯용의 잉크 조성물로서 사용되는 경우에는, 그 중합성 조성물 중에 있어서의 수성 용매의 함유량은, 특별히 한정되지 않지만, 그 중에서도, 30질량%~95질량%인 것이 바람직하고, 50질량%~90질량%인 것이 보다 바람직하고, 60질량%~80질량%인 것이 더 바람직하다. 잉크 조성물을 포함하는 잉크의 유동성이 제어되기 쉬워지기 때문이다.In addition, when a polymeric composition is used as an ink composition for inkjet, content of the aqueous solvent in the polymeric composition is although it does not specifically limit, Especially, it is preferable that it is 30 mass % - 95 mass %, It is more preferable that they are 50 mass % - 90 mass %, and it is still more preferable that they are 60 mass % - 80 mass %. It is because the fluidity|liquidity of the ink containing an ink composition becomes easy to control.
또한, 수성 용매 중에 있어서의 물과 혼화 가능한 유기용매의 함유량은, 특별히 한정되지 않지만, 그 중에서도, 40질량% 이하인 것이 바람직하고, 20질량% 이하인 것이 보다 바람직하고, 10질량% 이하인 것이 더 바람직하고, 5질량% 이하인 것이 특히 바람직하다. 중합성 조성물의 사용 시에 있어서 환경 부하가 저감되기 때문이다.In addition, the content of the organic solvent miscible with water in the aqueous solvent is not particularly limited, but among them, it is preferably 40 mass % or less, more preferably 20 mass % or less, and still more preferably 10 mass % or less. , it is particularly preferably 5% by mass or less. It is because the environmental load is reduced at the time of use of a polymeric composition.
(그 밖에)(etc)
또한, 중합성 조성물은, 필요에 따라, 추가로, 다른 성분의 어느 1종류 또는 2종류 이상을 포함하고 있어도 된다. 다른 성분의 종류는, 중합성 조성물의 용도 등에 따라 임의로 설정 가능하다.In addition, the polymerizable composition may contain any 1 type or 2 or more types of other components further as needed. The kind of other components can be arbitrarily set according to the use of a polymeric composition, etc.
구체적으로는, 다른 성분은, 가교제, 감광기, 유기산, 커플링제, 레벨링제, 증감제, 계면활성제, 염기성 화합물, 착색제, 광중합(라디칼) 개시제(아실포스핀 조성물은 제외한다.), 수용성 방부제, 도전성 물질 및 유기 용제 등 중 어느 1종류 또는 2종류 이상이다. 이하에서는, 상기한 일련의 다른 성분을 대표하여, 착색제의 상세에 관해 설명한다.Specifically, the other components include a crosslinking agent, a photosensitive group, an organic acid, a coupling agent, a leveling agent, a sensitizer, a surfactant, a basic compound, a colorant, a photopolymerization (radical) initiator (excluding the acylphosphine composition), a water-soluble preservative , any one or two or more of a conductive substance and an organic solvent. Hereinafter, the detail of a coloring agent is demonstrated on behalf of a series of other components mentioned above.
(착색제)(coloring agent)
또한, 다른 성분은, 착색제이다. 이 착색제는, 중합성 조성물을 착색하는 성분이다. 착색제를 이용하여 중합성 조성물이 착색 가능하게 되기 때문이다. 착색제의 종류는, 1종류만이어도 되고, 2종류 이상이어도 된다.In addition, another component is a coloring agent. This coloring agent is a component which colors a polymeric composition. It is because a polymeric composition becomes colorable using a coloring agent. One type may be sufficient as the kind of coloring agent, and two or more types may be sufficient as it.
이 착색제는, 안료 및 염료 중 어느 1종류 또는 2종류 이상을 포함하고 있다. 이 때문에, 착색제는, 안료만을 포함하고 있어도 되고, 염료만을 포함하고 있어도 되고, 안료 및 염료의 쌍방을 포함하고 있어도 된다. 안료 및 염료의 각각은, 무기 재료여도 되고, 유기 재료여도 되고, 무기 재료 및 유기 재료의 혼합물이어도 된다.This coloring agent contains any 1 type or 2 or more types of a pigment and dye. For this reason, a coloring agent may contain only a pigment, may contain only dye, and may contain both a pigment and dye. Each of the pigment and the dye may be an inorganic material, an organic material, or a mixture of an inorganic material and an organic material.
안료는, 용매에 용해되지 않는 착색용 재료이다. 이 안료에는, 용매에 불필요한 무기 재료 및 유기 재료가 포함될 뿐만 아니라, 무기 염료 및 유기 염료 중 어느 한쪽 또는 양쪽이 레이크화된 재료도 포함된다. 염료는, 수용성이어도 되고, 유용성(油溶性)이어도 된다.A pigment is a coloring material which does not melt|dissolve in a solvent. This pigment includes not only inorganic and organic materials unnecessary to the solvent, but also materials in which either or both of inorganic dyes and organic dyes are laked. The dye may be water-soluble or oil-soluble.
안료의 구체예는, 흑색 안료이다. 이 흑색 안료는, 퍼니스법, 채널법 및 서멀법 중 어느 1종류 또는 2종류 이상에 의해 제조되는 카본 블랙 외에, 아세틸렌 블랙, 케첸 블랙 및 램프 블랙 등이다. 또한, 흑색 안료는, 상기한 흑색 안료가 에폭시 수지에 의해 조정 또는 피복된 재료여도 되고, 상기한 흑색 안료가 미리 용매 중에 있어서 수지 중에 분산 처리됨과 동시에 20mg/g~200mg/g의 수지에 의해 피복된 재료여도 되며, 상기한 흑색 안료가 산성 표면 처리 또는 알칼리성 표면 처리된 재료여도 되고, 평균 입경이 8nm 이상임과 동시에 DBP흡유량이 90ml/100g 이하인 카본 블랙이어도 되며, 950℃에 있어서 휘발분 중의 일산화탄소(CO) 및 이산화탄소(CO2)로부터 산출되는 전체 산소량이 표면적 100m2 당에 있어서 9mg 이상인 카본 블랙이어도 된다. 또한, 흑색 안료는, 흑연화 카본 블랙, 흑연, 활성탄, 탄소섬유, 카본 나노 튜브, 카본 마이크로 코일, 카본 나노 호른, 카본 에어로젤, 풀러렌, 아닐린 블랙, 피그먼트 블랙 7 및 타이타늄 블랙 등이어도 된다.The specific example of a pigment is a black pigment. This black pigment is acetylene black, Ketjen black, lamp black, etc. other than carbon black manufactured by any one type or two or more types of a furnace method, a channel method, and a thermal method. In addition, the black pigment may be a material in which the above-described black pigment is adjusted or coated with an epoxy resin, and the above-mentioned black pigment is previously dispersed in a resin in a solvent and coated with a resin of 20 mg/g to 200 mg/g. may be a material that has been treated with an acidic surface or an alkaline surface, or carbon black having an average particle diameter of 8 nm or more and a DBP oil absorption of 90 ml/100 g or less, and carbon monoxide (CO) in volatile matter at 950 ° C. ) and carbon black with a total amount of oxygen calculated from carbon dioxide (CO 2 ) of 9 mg or more per 100 m 2 of surface area. The black pigment may be graphitized carbon black, graphite, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon airgel, fullerene, aniline black, pigment black 7, titanium black, or the like.
또한, 안료의 구체예는, 유기 안료 및 무기 안료의 유색 안료이며, 그 유색 안료의 색은, 흑색 이외의 색이다. 유기 안료 및 무기 안료의 구체예는, 산화 크로뮴 그린, 밀로리 블루, 코발트 그린, 코발트 블루, 망간계, 페로시안화물, 인산염 군청, 감청, 울트라마린, 세룰리안 블루, 비리디안, 에메랄드 그린, 황산납, 황색납, 아연황, 벵갈라(적색 산화철(III)), 카드뮴 레드, 합성철흑, 엄버 및 레이크 안료 등이다.In addition, the specific example of a pigment is a colored pigment of an organic pigment and an inorganic pigment, The color of this colored pigment is a color other than black. Specific examples of organic pigments and inorganic pigments include chromium oxide green, milory blue, cobalt green, cobalt blue, manganese-based, ferrocyanide, phosphate ultramarine blue, royal blue, ultramarine, cerulean blue, viridian, emerald green, sulfuric acid lead, yellow lead, zinc sulfur, bengala (red iron(III) oxide), cadmium red, synthetic iron black, umber and lake pigments.
그 중에서도, 안료는 흑색 안료인 것이 바람직하고, 카본 블랙인 것이 보다 바람직하다. 우수한 차광성을 얻을 수 있기 때문이다.Especially, it is preferable that it is a black pigment, and, as for a pigment, it is more preferable that it is carbon black. This is because excellent light-shielding properties can be obtained.
또한, 안료는, 시판품이어도 된다. 시판품의 안료의 구체예는, MICROPIGMO WMYW-5, MICROPIGMO WMRD-5, MICROPIGMO WMBN-5, MICROPIGMO WMGN-5, MICROPIGMO WMBK-5, MICROPIGMO WMBE-5, MICROPIGMO WMVT-5, MICROPIGMO WMWE-1, BONJET BLACK CW-1(이상, 오리엔트 화학공업 주식회사제), 피그먼트 레드 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 254, 228, 240, 254, 피그먼트 오렌지 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71, 피그먼트 옐로 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185, 피그먼트 그린 7, 10, 36, 58, 피그먼트 블루 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 22, 24, 56, 60, 61, 62, 64, 피그먼트 바이올렛 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 등이다.In addition, a commercial item may be sufficient as a pigment. The specific example of the pigment of a commercial item is MICROPIGMO WMYW-5, MICROPIGMO WMRD-5, MICROPIGMO WMBN-5, MICROPIGMO WMGN-5, MICROPIGMO WMBK-5, MICROPIGMO WMBE-5, MICROPIGMO WMVT-5, MICROPIGMO WMWE-1, BONJET WMWE-1 CW-1 (above, manufactured by Orient Chemical Industries, Ltd.), Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 254, 228, 240, 254, pigment orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64 , 65, 71, Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185, pigmented Green 7, 10, 36, 58, Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 22, 24, 56, 60, 61, 62, 64, Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 and the like.
염료의 구체예는, 금속 착체 화합물 등이다. 금속 착체 화합물의 구체예는, 나이트로소 화합물, 나이트로 화합물, 아조 화합물, 다이아조 화합물, 크산텐 화합물, 퀴놀린 화합물, 안트라퀴논 화합물, 쿠마린 화합물, 사이아닌 화합물, 프탈로사이아닌 화합물, 아이소인돌린온 화합물, 아이소인돌린 화합물, 퀴나크리돈 화합물, 안탄트론 화합물, 페린온 화합물, 페릴렌 화합물, 다이케토피롤로피롤 화합물, 싸이오인디고 화합물, 다이옥사진 화합물, 트라이페닐메테인 화합물, 퀴노프탈론 화합물, 나프탈렌테트라카복실산, 아조 염료 및 사이아닌 염료 등이다.Specific examples of the dye are metal complex compounds and the like. Specific examples of the metal complex compound include a nitroso compound, a nitro compound, an azo compound, a diazo compound, a xanthene compound, a quinoline compound, an anthraquinone compound, a coumarin compound, a cyanine compound, a phthalocyanine compound, isoin Dolinone compound, isoindoline compound, quinacridone compound, ananthrone compound, perinone compound, perylene compound, diketopyrrolopyrrole compound, thioindigo compound, dioxazine compound, triphenylmethane compound, quinope talon compounds, naphthalenetetracarboxylic acid, azo dyes, and cyanine dyes.
또한, 염료는, 시판품이어도 된다. 시판품의 염료의 구체예는, WATER YELLOW 1, WATER YELLOW 2, WATER YELLOW 6C, WATER YELLOW 6CL, WATER ORANGE 18, WATER ORANGE 25, WATER RED 1, WATER RED 2S, WATER RED 3, WATER RED 9, WATER RED 27, WATER PINK 2S, WATER BROWN 16, WATER GREEN 8, WATER BLUE 3, WATER BLUE 9, WATER BLUE 105S, WATER BLUE 106, WATER BLUE 117-L, WATER VIOLET 7, WATER BLACK 31, WATER BLACK 191-L, WATER BLACK 256-L, WATER BLACK R-455, WATER BLACK R-510, BONJET YELLOW 161-L, BONJET MAGENTA XXX, BONJET CYAN XXX, BONJET BLACK 891-L, VALIFAST YELLOW 1101, VALIFAST YELLOW 3150, VALIFAST RED 1308, VALIFAST RED 2320, VALIFAST PINK 1364, VALIFAST PINK 2310N, VALIFAST VIOLET 1701, VALIFAST BLACK 1815, VALIFAST BLACK 1807, VALIFAST BLACK 3804, VALIFAST BLACK 3810, VALIFAST BLACK 3820, VALIFAST BLACK 3830, VALIFAST BLACK 3840, VALIFAST BLACK 3866, VALIFAST BLACK 3870, VALIFAST ORANGE 2210, VALIFAST BROWN 3402, VALIFAST BLUE 1613 및 VALIFAST BLUE 1605(이상, 오리엔트 화학공업 주식회사제), Acid Green 1, Acid Green 3, Acid Green 5, Acid Green 9, Acid Green 27, Acid Green 50, Acid Green A, Alizarin Cyanin Green F, Basic Green 1, Basic Green 5, Bromocresol Green, Bromocresol Green Sodium Salt, Erio Green B, Fast Green FCF, Fiter Blue Green Sodium Salt, Indocyanine Green, Janus Green B, Leuco Malachite Green, Malachite Green, Oxalate, Methyl Green, Palatine Chrome Green, Quinizarin Green SS, Acid Red 1, Acid Red 9, Acid Red 13, Acid Red 18, Acid Red 26, Acid Red 27, Acid Red 52, Acid Red 87, Acid Red 88, Acid Red 91, Acid Red 92, Acid Red 94, Acid Red 112, Acid Red 114, Acid Red 151, Acid Red 289, Alizarin, Allura Red AC, Astrazon Red 6B, Azo Rubine, Basic Red 5, Benzopurpurine 4B, Bordezux Red, Chlorantine Fast Red 5B, Chromotrope 2B, Chromotrope 2R, Congo Red, Cresol Red, Crezol Red Sodium Salt, Crocein Scarlet 3B, Direct Fast Red 3B, Direct Red 80, Direct Scarlet B, Eriochrome Red B, 4-Ethoxychrysoidine Hydrochloride, Ethyl Red, Fast Red B Salt, Fast Red ITR Base, Lake Red CBA, Lithol Rubin BCA, Methoxy Red, Methyl Red, Methyl Red Sodium Salt, Oralith Brilliant Pink R, Para Red, Phenol Red Sodium Salt, Pigment Red, Pigment Red 254, Rhodamine 6G, Sudan II, Sudan III, Sudan R, 2,3,5-Triphenyltetrazolium Chloride, Acid Black 1, Acid Blue 1, Acid Blue 9, Acid Blue 92, Acid Blue 3 Sodium Salt, Acid Red 91, Azo Blue, Basic Blue 1, Basic Blue 7, Basic Blue 12, Basic Blue 17, Basic Blue 24, Basic Blue 26, Briliant Blue G, Brilliant Blue R, Bromocresol Blue, Bromophenol Blue, Bromothymol Blue, Chrome Pure Blue BX, Coomassie Brilliant Blue G-250, Coomassie Brilliant Blue R-250, Direct Blue 1, Direct Blue 2, Direct Blue 14, Direct Sky Blue, Disperse Blue 14, Eriochrome Blue Black B, Eriochrome Cyanine R, Evans Blue, Filter Blue Green Sodium Salt, Indigo Carmine, Indigo, Methylene Blue Hydrate, Mordant Black 17, Mordant Blue 13, Mordant Blue 29, Omega Chrome Black Blue G, Pigment Blue 15, Quinizarin Blue, Sudan Blue, Thymol Blue, Xylene Cyanol FF, Acid Orange 5, Acid Orange 7, 1-Amino-2-methylanthraquione, Astrazon Orange R, Basic Orange 14, Crocein Orange G, Ethyl Orange, Methyl Orange, Mordant Orange 1, α-Naphtol Orange, Oil Orange, Orange G, Permanent Orange, Pyrazolone Orange, Sudan I 및 Sudan II(이상, 도쿄 화성공업 주식회사제) 등이다.In addition, a commercial item may be sufficient as dye. Specific examples of commercially available dyes are WATER YELLOW 1, WATER YELLOW 2, WATER YELLOW 6C, WATER YELLOW 6CL, WATER ORANGE 18, WATER ORANGE 25, WATER RED 1, WATER RED 2S, WATER RED 3, WATER RED 9, WATER RED 27, WATER PINK 2S, WATER BROWN 16, WATER GREEN 8, WATER BLUE 3, WATER BLUE 9, WATER BLUE 105S, WATER BLUE 106, WATER BLUE 117-L, WATER VIOLET 7, WATER BLACK 31, WATER BLACK 191-L, WATER BLACK 256-L, WATER BLACK R-455, WATER BLACK R-510, BONJET YELLOW 161-L, BONJET MAGENTA XXX, BONJET CYAN XXX, BONJET BLACK 891-L, VALIFAST YELLOW 1101, VALIFAST YELLOW 3150, VALIFAST RED 1308 VALIFAST RED 2320, VALIFAST PINK 1364, VALIFAST PINK 2310N, VALIFAST VIOLET 1701, VALIFAST BLACK 1815, VALIFAST BLACK 1807, VALIFAST BLACK 3804, VALIFAST BLACK 3810, VALIFAST BLACK 3820, VALIFAST BLACK 3830, VALIFAST BLACK 3830, VALIFAST BLACK 3830, VALIFAST BLACK 3840 3870, VALIFAST ORANGE 2210, VALIFAST BROWN 3402, VALIFAST BLUE 1613 and VALIFAST BLUE 1605 (above, manufactured by Orient Chemical Industry Co., Ltd.), Acid Green 1, Acid Green 3, Acid Green 5, Acid Green 9, Acid Green 27, Acid Green 50, Acid Green A, Alizarin Cyanin Green F, Basic Green 1, Basic Green 5, Bromocresol Green, Bromocresol Green Sodium Salt, Erio Green B, Fast Green FCF, Filter Blue Green Sodium Salt, Indocyanine Green, Janus Green B, Leuco Malachite Green, Malachite Green, Oxalate, Methyl Green, Palatine Chrome Green, Quinizarin Green SS, Acid Red 1, Acid Red 9, Acid Red 13, Acid Red 18, Acid Red 26, Acid Red 27, Acid Red 52, Acid Red 87, Acid Red 88, Acid Red 91, Acid Red 92, Acid Red 94, Acid Red 112, Acid Red 114, Acid Red 151, Acid Red 289, Alizarin, Allura Red AC, Astrazon Red 6B, Azo Rubine, Basic Red 5, Benzopurpurine 4B, Bordezux Red, Chlorantine Fast Red 5B, Chromotrope 2B, Chromotrope 2R, Congo Red, Cresol Red, Crezol Red Sodium Salt, Crocein Scarlet 3B, Direct Fast Red 3B, Direct Red 80, Direct Scarlet B, Eriochrome Red B, 4-Ethoxychrysoidine Hydrochloride, Ethyl Red, Fast Red B Salt, Fast Red ITR Base, Lake Red CBA, Lithol Rubin BCA, Methoxy Red, Methyl Red, Methyl Red Sodium Salt, Oralith Brilliant Pink R, Para Red, Phenol Red Sodium Salt, Pigment Red, Pigment Red 254, Rhodamine 6G, Sudan II, Sudan III, Sudan R, 2,3,5-Triphenyltetrazolium Chloride, Acid Black 1, Acid Blue 1 , Acid Blue 9, Acid Blue 92, Acid Blue 3 Sodium Salt, Acid Red 91, Azo Blue, Basic Blue 1, Basic Blue 7, Basic Blue 12, Basic Blue 17, Basic Blue 24, Basic Blue 26, Brilliant Blue G, Brilliant Blue R, Bromocresol Blue, Bromophenol Blue, Bromothymol Blue, Chrome Pure Blue BX, Coomassie Brilliant Blue G-250, Coomassie Brilliant Blue R-250, Direct Blue 1, Direct Blue 2, Direct Blue 14, Direct Sky Blue, Disperse Blue 14, Eriochrome Blue Black B, Eriochrome Cyanine R, Evans Blue, Filter Blue Green Sodium Salt, Indigo Carmine, Indigo, Methylene Blue Hydrate, Mordant Black 17, Mordant Blue 13, Mordant Blue 29, Omega Chrome Black Blue G, Pigment Blue 15 , Quinizarin Blue, Sudan Blue, Thymol Blue, Xylene Cyanol FF, Acid Orange 5, Acid Orange 7, 1-Amino-2-methylanthraquione, Astrazon Orange R, Basi c Orange 14, Crocein Orange G, Ethyl Orange, Methyl Orange, Mordant Orange 1, α-Naphtol Orange, Oil Orange, Orange G, Permanent Orange, Pyrazolone Orange, Sudan I and Sudan II (above, manufactured by Tokyo Chemical Industry Co., Ltd.), etc. to be.
(증감제)(sensitizer)
증감제의 종류는, 특별히 한정되지 않지만, 구체적으로는, 싸이오크산톤 및 벤조페논 등이다.Although the kind of sensitizer is not specifically limited, Specifically, they are thioxanthone, benzophenone, etc.
(광중합(라디칼) 개시제)(photopolymerization (radical) initiator)
광중합(라디칼) 개시제의 종류는, 특별히 한정되지 않지만, 구체적으로는, 벤조인에터, 벤질케탈, α-하이드록시아세토페논, α-아미노아세토페논 및 옥심에스터 등이다.The type of the photopolymerization (radical) initiator is not particularly limited, and specific examples thereof include benzoin ether, benzyl ketal, α-hydroxyacetophenone, α-aminoacetophenone, and oxime ester.
(유기 용제)(organic solvent)
여기에서 설명하는 유기 용제는, 상기한 수성 용매 이외의 용매의 총칭이다. 유기 용제의 종류는, 특별히 한정되지 않지만, 구체적으로는, 케톤류, 에터계 용제, 에스터계 용제, 셀로솔브계 용제, 알코올계 용제(단, 수성 용매에 해당되는 알코올계 용제는 제외한다.), 에터에스터계 용제, BTX계 용제, 지방족 탄화 수소계 용제, 터펜 탄화 수소유, 할로겐화 지방족 탄화 수소계 용제 및 할로겐화 방향족 탄화 수소계 용제 등이다.The organic solvent demonstrated here is a generic name of solvents other than the above-mentioned aqueous solvent. The type of the organic solvent is not particularly limited, but specifically, ketones, ether solvents, ester solvents, cellosolve solvents, alcohol solvents (however, alcohol solvents corresponding to aqueous solvents are excluded), Ether ester solvents, BTX solvents, aliphatic hydrocarbon solvents, terpene hydrocarbon oil, halogenated aliphatic hydrocarbon solvents, halogenated aromatic hydrocarbon solvents, and the like.
케톤류는, 메틸에틸케톤, 아세톤 및 사이클로헥사논 등이다. 에터계 용제는, 옥세인, 테트라하이드로퓨란 및 1,2-다이메톡시에테인 등이다. 에스터계 용제는, 아세트산 메틸, 아세트산 에틸 및 아세트산 프로필 등이다. 셀로솔브계 용제는, 에틸렌글라이콜모노메틸에터 및 에틸렌글라이콜모노에틸에터 등이다. 알코올계 용제는, 메탄올 및 에탄올 등이다. 에터에스터계 용제는, 에틸렌글라이콜모노메틸아세테이트 및 에틸렌글라이콜모노에틸아세테이트 등이다. BTX계 용제는, 벤젠, 톨루엔 및 자일렌 등이다. 지방족 탄화 수소계 용제는, 헥세인, 헵테인, 옥테인 및 사이클로헥세인 등이다. 터펜 탄화 수소유는, 테레빈유, D-리모넨 및 피넨 등이다. 할로겐화 지방족 탄화 수소계 용제는, 사염화탄소, 클로로폼, 트라이클로로에틸렌, 염화 메틸렌 및 1,2-다이클로로에테인 등이다. 할로겐화 방향족 탄화 수소계 용제는, 클로로벤젠 등이다. 이 외, 유기 용제는, 아닐린, 트라이에틸아민, 피리딘, 아세트산, 아세토나이트릴, 2황화 탄소, N,N-다이메틸폼아마이드, N,N-다이메틸아세트아마이드, N-메틸피롤리돈 및 다이메틸설폭사이드 등이어도 된다.Ketones are methyl ethyl ketone, acetone, cyclohexanone, etc. Ether solvents include oxane, tetrahydrofuran and 1,2-dimethoxyethane. Ester solvents are methyl acetate, ethyl acetate, and propyl acetate. Cellosolve solvents include ethylene glycol monomethyl ether and ethylene glycol monoethyl ether. Alcoholic solvents are methanol, ethanol, etc. Ether ester solvents include ethylene glycol monomethyl acetate and ethylene glycol monoethyl acetate. BTX solvents include benzene, toluene, and xylene. The aliphatic hydrocarbon-based solvent is hexane, heptane, octane and cyclohexane. The terpene hydrocarbon oil is turpentine, D-limonene, pinene, or the like. The halogenated aliphatic hydrocarbon solvents include carbon tetrachloride, chloroform, trichloroethylene, methylene chloride and 1,2-dichloroethane. The halogenated aromatic hydrocarbon solvent is chlorobenzene or the like. In addition, organic solvents include aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and Dimethyl sulfoxide etc. may be sufficient.
중합 조성물 중에 있어서의 유기 용제의 함유량은, 특별히 한정되지 않지만, 그 중에서도, 5질량% 이하인 것이 바람직하고, 3질량% 이하인 것이 보다 바람직하고, 1질량% 이하인 것이 더 바람직하다. 중합성 조성물의 사용 시에 있어서 환경 부하가 저감되기 때문이다.Although content of the organic solvent in a polymerization composition is not specifically limited, Especially, it is preferable that it is 5 mass % or less, It is more preferable that it is 3 mass % or less, It is more preferable that it is 1 mass % or less. It is because the environmental load is reduced at the time of use of a polymeric composition.
[제조 방법][Manufacturing method]
이 중합성 조성물을 제조하는 경우에는, 수성 용매 중에 아실포스핀 조성물 및 반응기 함유 화합물을 투입한 후, 그 수성 용매를 교반한다. 이 경우에는, 추가로, 수성 용매 중에 착색제 등을 첨가해도 된다. 이로써, 수성 용매 중에 있어서 아실포스핀 조성물 및 반응기 함유 화합물의 각각이 분산 또는 용해되기 때문에, 중합성 조성물이 조제된다.When producing this polymerizable composition, after the acylphosphine composition and the reactive group-containing compound are put in an aqueous solvent, the aqueous solvent is stirred. In this case, you may further add a coloring agent etc. in an aqueous solvent. Thereby, since each of an acylphosphine composition and a reactive group containing compound disperse|distributes or melt|dissolves in an aqueous solvent, a polymeric composition is prepared.
[작용 및 효과][action and effect]
이 중합성 조성물에 의하면, 수성 용매와 함께 아실포스핀 조성물 및 반응기 함유 화합물을 포함하고 있고, 그 아실포스핀 조성물이 상기한 구성을 갖고 있다. 따라서, 중합성 조성물의 보존 안정성 및 경화성이 담보됨으로써, 그 중합성 조성물을 이용하여 양호한 경화물이 제조되기 쉬워지기 때문에, 우수한 물성을 얻을 수 있다. 또한, 중합성 조성물에 관한 다른 작용 및 효과는, 아실포스핀 조성물에 관한 다른 작용 및 효과와 동일하다.According to this polymerizable composition, an acylphosphine composition and a reactive group containing compound are contained with an aqueous solvent, and this acylphosphine composition has an above-mentioned structure. Therefore, since the storage stability and sclerosis|hardenability of a polymeric composition are ensured, since favorable hardened|cured material becomes easy to be manufactured using this polymeric composition, the outstanding physical property can be acquired. In addition, other actions and effects related to the polymerizable composition are the same as other actions and effects related to the acylphosphine composition.
<3. 경화물 및 그 제조 방법><3. Cured product and its manufacturing method>
다음으로, 상기한 중합성 조성물을 이용한 본 발명의 일 실시형태의 경화물 및 그 제조 방법에 관하여 설명한다.Next, the hardened|cured material of one Embodiment of this invention using the above-mentioned polymeric composition, and its manufacturing method are demonstrated.
[구성][composition]
여기에서 설명하는 경화물은, 상기한 바와 같이, 중합성 조성물의 경화 반응물이다. 보다 구체적으로는, 경화물은, 중합 개시제로서 기능하는 아실포스핀 조성물을 통하여 반응기 함유 화합물이 중합 반응(광라디칼 중합 반응)함으로써 형성되는 반응물이다. 따라서, 기체(基體)의 표면에 중합성 조성물이 도포된 후, 그 중합성 조성물이 중합 반응함으로써, 그 기체의 표면에 중합성 조성물의 경화 반응물(경화물)을 포함하는 피막이 형성된다.The cured product described herein is a curing reaction product of the polymerizable composition as described above. More specifically, the cured product is a reaction product formed by a polymerization reaction (photoradical polymerization reaction) of a reactive group-containing compound through an acylphosphine composition functioning as a polymerization initiator. Therefore, after a polymeric composition is apply|coated to the surface of a base|substrate, the polymeric composition polymerizes and reacts, and the film containing the hardening reaction material (hardened|cured material) of the polymeric composition is formed on the surface of the base|substrate.
[제조 방법][Manufacturing method]
이 경화물을 제조하는 경우에는, 처음에, 상기한 순서에 따라, 중합성 조성물을 조제한다. 계속해서, 기체의 표면에 중합성 조성물을 도포한 후, 그 중합성 조성물을 건조시킨다. 이로써, 기체의 표면에, 중합성 조성물을 포함하는 도막이 형성된다.When manufacturing this hardened|cured material, first, a polymeric composition is prepared according to an above-mentioned procedure. Then, after apply|coating a polymeric composition to the surface of a base|substrate, the polymeric composition is dried. Thereby, the coating film containing a polymeric composition is formed on the surface of a base|substrate.
기체의 종류는, 특별히 한정되지 않지만, 일례를 들면, 금속, 목재, 고무, 플라스틱, 유리, 세라믹, 종이 및 천 등 중 어느 1종류 또는 2종류 이상이다. 중합성 조성물의 도포 방법은, 특별히 한정되지 않지만, 일례를 들면, 스핀 코터, 바 코터, 롤 코터, 커튼 코터, 각종 인쇄법 및 침지법 등이다.The type of the substrate is not particularly limited, and for example, any one type or two or more types of metal, wood, rubber, plastic, glass, ceramic, paper, and cloth. Although the application method of a polymeric composition is not specifically limited, For example, a spin coater, a bar coater, a roll coater, a curtain coater, various printing methods, an immersion method, etc. are mentioned.
마지막으로, 도막에 활성 에너지선을 조사한다. 활성 에너지선의 종류는, 특별히 한정되지 않지만, 일례를 들면, 수은 램프 등을 광원으로 한 자외선광 등이다. 자외선광의 파장, 조사 강도 및 조사 시간 등의 조사 조건은, 임의로 설정 가능하다.Finally, the coating film is irradiated with an active energy ray. Although the kind of active energy ray is not specifically limited, For example, it is the ultraviolet light etc. which made a mercury lamp etc. a light source. Irradiation conditions, such as the wavelength of ultraviolet light, irradiation intensity, and irradiation time, can be set arbitrarily.
조사 조건은, 일례를 들면, 이하와 같다. 파장은, 200nm~400nm이다. 조사 강도는, 1mW/cm~500mW/cm, 바람직하게는 5mW/cm~300mW/cm이며, 조사량으로 환산하면, 10mJ/cm2~1000mJ/cm2이고, 바람직하게는 100mJ/cm2~500mJ/cm2이다. 조사 시간은, 1초간~500초간, 바람직하게는 5초간~300초간이다.Irradiation conditions are as follows, giving an example. The wavelength is 200 nm to 400 nm. Irradiation intensity is 1 mW/cm to 500 mW/cm, preferably 5 mW/cm to 300 mW/cm, and when converted into irradiation amount, 10 mJ/cm 2 to 1000 mJ/cm 2 , preferably 100 mJ/cm 2 to 500 mJ/ cm2 . Irradiation time is 1 second - 500 second, Preferably they are 5 second - 300 second.
이로써, 도막 중에 있어서 아실포스핀 조성물(중합 개시제)을 통하여 반응기 함유 화합물의 중합 반응이 진행되기 때문에, 중합성 조성물의 경화 반응물(경화물)이 형성된다. 따라서, 경화물을 포함하는 피막이 형성된다.Thereby, since the polymerization reaction of a reactive group containing compound advances through an acylphosphine composition (polymerization initiator) in a coating film, the hardening reaction material (hardened|cured material) of a polymeric composition is formed. Thus, a film containing the cured product is formed.
또한, 피막을 형성하는 경우에는, 상기한 피막의 형성 순서를 반복함으로써, 복수의 피막을 서로 적층시켜도 된다.In addition, when forming a film, you may laminate|stack a some film on each other by repeating the formation procedure of the said film.
[작용 및 효과][action and effect]
이 경화물에 의하면, 중합성 조성물의 경화 반응물이며, 그 중합성 조성물이 상기한 구성을 갖고 있다. 따라서, 중합성 조성물에 관하여 설명한 경우와 동일한 이유에 의해, 우수한 물성을 얻을 수 있다. 또한, 경화물에 관한 다른 작용 및 효과는, 중합성 조성물에 관한 다른 작용 및 효과와 동일하다.According to this hardened|cured material, it is a hardening reaction product of a polymeric composition, and this polymeric composition has an above-described structure. Therefore, excellent physical properties can be obtained for the same reasons as those described for the polymerizable composition. In addition, other actions and effects related to the cured product are the same as other actions and effects related to the polymerizable composition.
또한, 경화물의 제조 방법에 의하면, 상기한 중합성 조성물에 활성 에너지선을 조사하고 있으므로, 그 활성 에너지의 조사에 따라 중합성 조성물의 중합 반응이 안정되고 충분하며 안정적으로 진행된다. 따라서, 상기한 우수한 물성을 갖는 경화물을 얻을 수 있다.Moreover, according to the manufacturing method of hardened|cured material, since the said polymerizable composition is irradiated with an active energy ray, the polymerization reaction of a polymeric composition progresses stably, sufficient and stably by irradiation of the active energy. Accordingly, a cured product having the above-described excellent physical properties can be obtained.
이 경우에는, 특히, 우수한 물성을 갖는 경화물을 얻기 위하여, 중합성 조성물에 대한 활성 에너지선의 조사 처리만 실시하면 될 뿐만 아니라, 그 중합성 조성물에 대한 활성 에너지선의 조사량이 적어도 되기 때문에, 그 우수한 물성을 갖는 경화물을 용이하게 안정적으로 제조할 수 있다. 즉, 경화물의 제조 공정이 짧아짐과 동시에, 기체가 데미지를 받기 어려워지는 것에 더해, 패터닝(원하는 패턴이 되도록 경화물을 제조하는 것)이 가능하게 되는 점 등에 있어서, 이점을 얻을 수 있다.In this case, in particular, in order to obtain a cured product having excellent physical properties, not only the polymerizable composition needs only to be irradiated with an active energy ray, but the amount of active energy ray irradiation to the polymerizable composition is small, so the excellent A cured product having physical properties can be easily and stably manufactured. That is, the manufacturing process of hardened|cured material becomes short, and an advantage can be acquired in the point etc. which make the base|substrate hard to receive damage, and patterning (manufacturing of hardened|cured material so that it may become a desired pattern) becomes possible.
<4. 용도(중합 개시제 등)><4. Applications (Polymerization Initiator, etc.)>
상기한 아실포스핀 조성물, 중합성 조성물 및 경화물의 각각의 용도는, 특별히 한정되지 않지만, 일례를 들면, 각종 렌즈, 각종 필름 및 각종 기능막 등이다.Although each use of said acylphosphine composition, polymeric composition, and hardened|cured material is not specifically limited, For example, various lenses, various films, various functional films, etc. are mentioned.
구체적으로는, 안경, 촬상용 렌즈, 대전 방지 필름, 광학 필름, 도전성 필름, 보호 필름, 열선 차폐재, 전사박(轉寫箔), 인쇄판, 절연 바니시, 절연 시트, 적층판, 프린트 기판, 플렉시블 디스플레이용 기판, 터치 패널용 기판, 인쇄용 마스크, 성형 재료, 접착제, 건재(建材), 네일 재료, 화장품, 사이딩, 유리 섬유 함침제, 충전제, 반도체용 및 태양전지용 등의 패시베이션막, 층간 절연막, 보호막, 액정 표시 장치의 백 라이트용의 프리즘 렌즈 시트, 프로젝션텔레비전의 스크린용 프레넬 렌즈 시트, 렌티큘러 렌즈 시트용 렌즈 시트의 렌즈부, 그 시트를 이용한 백 라이트 등, 액정 컬러 필터용 보호막·스페이서, DNA 분리 칩, 마이크로 리엑터, 나노 바이오 디바이스, 하드 디스크용 기록 재료, 고체 촬상 소자, 태양전지 패널, 발광 다이오드, 유기 발광 디바이스, 전극 보호재, 루미네센트 필름, 형광 필름, MEMS 소자, 엑츄얼레이터, 홀로그램, 플라즈몬 디바이스, 편광판, 편광 필름, 배향막, 마이크로 렌즈, 광학 소자, 위상차 필름, 광커넥터, 광도파로, 광학적 조형용 주형제(注型劑), 식품, 음료 용기, 식품용 포장재, 치과 재료, 위생 도기, 주택 설비기기 등이다. 이 주택 설비기기는, 욕조 등이다.Specifically, glasses, imaging lenses, antistatic films, optical films, conductive films, protective films, heat ray shielding materials, transfer foils, printing plates, insulating varnishes, insulating sheets, laminates, printed circuit boards, flexible displays Substrate, touch panel substrate, printing mask, molding material, adhesive, building material, nail material, cosmetics, siding, glass fiber impregnating agent, filler, passivation film for semiconductors and solar cells, etc., interlayer insulating film, protective film, liquid crystal A prism lens sheet for a backlight of a display device, a Fresnel lens sheet for a screen of a projection TV, a lens part of a lens sheet for a lenticular lens sheet, a backlight using the sheet, a protective film/spacer for liquid crystal color filters, a DNA separation chip , microreactor, nanobio device, hard disk recording material, solid-state image sensor, solar cell panel, light emitting diode, organic light emitting device, electrode protective material, luminescent film, fluorescent film, MEMS element, actuator, hologram, plasmon Device, polarizing plate, polarizing film, alignment film, microlens, optical element, retardation film, optical connector, optical waveguide, casting agent for optical molding, food, beverage container, food packaging material, dental material, sanitary ware, housing equipment, etc. This house equipment is a bathtub etc.
특히, 아실포스핀 조성물은, 상기한 바와 같이, 중합 반응을 필요로 하는 용도에 있어서 중합 개시제로서 사용되는 것이 바람직하다. 아실포스핀 조성물의 용해성이 담보되면서, 그 아실포스핀 조성물을 포함하는 중합성 조성물의 보존 안정성 및 경화성이 향상되기 때문이다. 이로써, 중합성 조성물을 이용하여 양호한 경화물이 형성된다.In particular, it is preferable that an acylphosphine composition is used as a polymerization initiator in the use which requires a polymerization reaction as mentioned above. This is because the storage stability and curability of the polymerizable composition containing the acylphosphine composition are improved while the solubility of the acylphosphine composition is ensured. Thereby, a favorable hardened|cured material is formed using a polymeric composition.
실시예Example
이하, 본 발명의 실시예에 관하여 상세하게 설명한다.Hereinafter, embodiments of the present invention will be described in detail.
(실험예 1~45)(Experimental Examples 1-45)
우선, 이하에서 설명하는 순서에 따라, 아실포스핀 조성물을 합성함과 동시에, 그 아실포스핀 조성물을 이용하여 중합성 조성물을 조제한 후, 그 중합성 조성물을 이용하여 피막(경화물)을 제조함으로써, 아실포스핀 조성물, 중합성 조성물 및 경화물의 각각의 물성을 평가했다.First, according to the procedure described below, an acylphosphine composition is synthesized, a polymerizable composition is prepared using the acylphosphine composition, and then a film (cured product) is prepared using the polymerizable composition. , the acylphosphine composition, the polymerizable composition, and each physical property of the cured product were evaluated.
[아실포스핀 조성물의 합성][Synthesis of acylphosphine composition]
C1~C5로 표시되는 5종류의 아실포스핀 조성물을 합성했다. 아실포스핀 조성물에 관한 당량비 및 중량비의 각각은, 표 1 및 표 2에 나타낸 바와 같다.Five types of acylphosphine compositions represented by C1-C5 were synthesized. Each of the equivalent ratio and weight ratio regarding the acylphosphine composition is as shown in Tables 1 and 2.
[화학식 10][Formula 10]
C1에 나타낸 아실포스핀 조성물을 합성하는 경우에는, 처음에, 질소 분위기 중에서, 반응 플라스크 안에, 페닐(2,4,6-트라이메틸벤조일)포스핀산 50.0g(173.4mmol)과, 다이클로로메테인 500ml(=500cm3)를 투입했다. 계속해서, 반응 플라스크 안의 혼합물을 실온에서 교반함으로써, 페닐(2,4,6-트라이메틸벤조일)포스핀산을 완전히 용해시켰다. 계속해서, 반응 플라스크 안에 뷰틸다이에탄올아민 26.6g(164.8mmol)을 첨가한 후, 반응 플라스크 안의 혼합물을 실온에서 교반(교반시간=5시간)함으로써, 반응 용액을 얻었다. 마지막으로, 반응 용액을 탈용매한 후, 감압 건조(건조 온도=40℃)시킴으로써, C1에 나타낸 아실포스핀 조성물인 담황색의 결정을 얻었다(실험예 1).When synthesizing the acylphosphine composition shown in C1, 50.0 g (173.4 mmol) of phenyl (2,4,6-trimethylbenzoyl) phosphinic acid and dichloromethane in a reaction flask in a nitrogen atmosphere first 500ml (=500cm 3 ) was added. Then, the mixture in the reaction flask was stirred at room temperature to completely dissolve phenyl(2,4,6-trimethylbenzoyl)phosphinic acid. Subsequently, after adding 26.6 g (164.8 mmol) of butyldiethanolamine into the reaction flask, the mixture in the reaction flask was stirred at room temperature (stirring time = 5 hours) to obtain a reaction solution. Finally, after desolving the reaction solution, it was dried under reduced pressure (drying temperature = 40°C) to obtain pale yellow crystals of the acylphosphine composition shown in C1 (Experimental Example 1).
뷰틸다이에탄올아민의 첨가량을 28.0g(173.4mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 2). 뷰틸다이에탄올아민의 첨가량을 28.1g(174.3mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 3). 뷰틸다이에탄올아민의 첨가량을 28.3g(175.2mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 4). 뷰틸다이에탄올아민의 첨가량을 29.4g(182.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 5). 뷰틸다이에탄올아민의 첨가량을 30.2g(187.3mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 6). 뷰틸다이에탄올아민의 첨가량을 30.8g(190.7mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 7). 뷰틸다이에탄올아민의 첨가량을 33.6g(208.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 8).A pale yellow crystal was obtained according to the same procedure except that the amount of butyldiethanolamine was changed to 28.0 g (173.4 mmol) (Experimental Example 2). A pale yellow crystal was obtained according to the same procedure except that the amount of butyldiethanolamine was changed to 28.1 g (174.3 mmol) (Experimental Example 3). A pale yellow crystal was obtained according to the same procedure except that the amount of butyldiethanolamine was changed to 28.3 g (175.2 mmol) (Experimental Example 4). A pale yellow crystal was obtained according to the same procedure except that the amount of butyldiethanolamine was changed to 29.4 g (182.1 mmol) (Experimental Example 5). A pale yellow crystal was obtained according to the same procedure except that the amount of butyldiethanolamine was changed to 30.2 g (187.3 mmol) (Experimental Example 6). A pale yellow crystal was obtained according to the same procedure except that the amount of butyldiethanolamine was changed to 30.8 g (190.7 mmol) (Experimental Example 7). A pale yellow crystal was obtained according to the same procedure except that the amount of butyldiethanolamine was changed to 33.6 g (208.1 mmol) (Experimental Example 8).
C2에 나타낸 아실포스핀 조성물을 합성하는 경우에는, 처음에, 질소 분위기 중에서, 반응 플라스크 안에, 페닐(2,4,6-트라이메틸벤조일)포스핀산 50.0g(173.4mmol)과, 다이클로로메테인 500ml(=500cm3)를 투입했다. 계속해서, 반응 플라스크 안의 혼합물을 실온에서 교반함으로써, 페닐(2,4,6-트라이메틸벤조일)포스핀산을 완전히 용해시켰다. 계속해서, 반응 플라스크 안에 4-메틸모폴린 15.8g(156.1mmol)을 첨가한 후, 반응 플라스크 안의 혼합물을 실온에서 교반(교반시간=5시간)함으로써, 반응 용액을 얻었다. 마지막으로, 반응 용액을 탈용매한 후, 감압 건조(건조 온도=40℃)시킴으로써, C2에 나타낸 아실포스핀 조성물인 담황색의 결정을 얻었다(실험예 9).When synthesizing the acylphosphine composition shown in C2, 50.0 g (173.4 mmol) of phenyl (2,4,6-trimethylbenzoyl) phosphinic acid and dichloromethane in a reaction flask in a nitrogen atmosphere first 500ml (=500cm 3 ) was added. Then, the mixture in the reaction flask was stirred at room temperature to completely dissolve phenyl(2,4,6-trimethylbenzoyl)phosphinic acid. Subsequently, after adding 15.8 g (156.1 mmol) of 4-methylmorpholine to the reaction flask, the mixture in the reaction flask was stirred at room temperature (stirring time = 5 hours) to obtain a reaction solution. Finally, after desolving the reaction solution, it was dried under reduced pressure (drying temperature = 40°C) to obtain pale yellow crystals of the acylphosphine composition shown in C2 (Experimental Example 9).
4-메틸모폴린의 첨가량을 17.5g(173.4mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 10). 4-메틸모폴린의 첨가량을 17.6g(174.3mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 11). 4-메틸모폴린의 첨가량을 18.1g(178.6mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 12). 4-메틸모폴린의 첨가량을 19.2g(189.01mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 13). 4-메틸모폴린의 첨가량을 19.3g(190.7mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 14). 4-메틸모폴린의 첨가량을 21.0g(208.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 15).A pale yellow crystal was obtained according to the same procedure except that the amount of 4-methylmorpholine was changed to 17.5 g (173.4 mmol) (Experimental Example 10). A pale yellow crystal was obtained according to the same procedure except that the amount of 4-methylmorpholine was changed to 17.6 g (174.3 mmol) (Experimental Example 11). A pale yellow crystal was obtained according to the same procedure except that the amount of 4-methylmorpholine was changed to 18.1 g (178.6 mmol) (Experimental Example 12). A pale yellow crystal was obtained according to the same procedure except that the amount of 4-methylmorpholine was changed to 19.2 g (189.01 mmol) (Experimental Example 13). A pale yellow crystal was obtained according to the same procedure except that the amount of 4-methylmorpholine was changed to 19.3 g (190.7 mmol) (Experimental Example 14). Light yellow crystals were obtained according to the same procedure except that the amount of 4-methylmorpholine was changed to 21.0 g (208.1 mmol) (Experimental Example 15).
C3에 나타낸 아실포스핀 조성물을 합성하는 경우에는, 처음에, 질소 분위기 중에서, 반응 플라스크 안에, 페닐(2,4,6-트라이메틸벤조일)포스핀산 50.0g(173.4mmol)과, 다이클로로메테인 500ml(=500cm3)를 투입했다. 계속해서, 반응 플라스크 안의 혼합물을 실온에서 교반함으로써, 페닐(2,4,6-트라이메틸벤조일)포스핀산을 완전히 용해시켰다. 계속해서, 반응 플라스크 안에 1-벤질-4-하이드록시피페리딘 29.9g(156.1mmol)을 첨가한 후, 반응 플라스크 안의 혼합물을 실온에서 교반(교반시간=5시간)함으로써, 반응 용액을 얻었다. 마지막으로, 반응 용액을 탈용매한 후, 감압 건조(건조 온도=40℃)시킴으로써, C3에 나타낸 아실포스핀 조성물인 담황색의 결정을 얻었다(실험예 16).When synthesizing the acylphosphine composition shown in C3, 50.0 g (173.4 mmol) of phenyl (2,4,6-trimethylbenzoyl) phosphinic acid and dichloromethane in a reaction flask in a nitrogen atmosphere first 500ml (=500cm 3 ) was added. Then, the mixture in the reaction flask was stirred at room temperature to completely dissolve phenyl(2,4,6-trimethylbenzoyl)phosphinic acid. Subsequently, after adding 29.9 g (156.1 mmol) of 1-benzyl-4-hydroxypiperidine into the reaction flask, the mixture in the reaction flask was stirred at room temperature (stirring time = 5 hours) to obtain a reaction solution. Finally, after desolving the reaction solution, it was dried under reduced pressure (drying temperature = 40°C) to obtain pale yellow crystals of the acylphosphine composition shown in C3 (Experimental Example 16).
1-벤질-4-하이드록시피페리딘의 첨가량을 33.2g(173.4mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 17). 1-벤질-4-하이드록시피페리딘의 첨가량을 33.3g(174.3mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 18). 1-벤질-4-하이드록시피페리딘의 첨가량을 33.9g(176.9mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 19). 1-벤질-4-하이드록시피페리딘의 첨가량을 36.5g(190.7mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 20). 1-벤질-4-하이드록시피페리딘의 첨가량을 39.8g(208.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 21).The same procedure was followed except that the amount of 1-benzyl-4-hydroxypiperidine was changed to 33.2 g (173.4 mmol), to obtain pale yellow crystals (Experimental Example 17). The same procedure was followed except that the amount of 1-benzyl-4-hydroxypiperidine was changed to 33.3 g (174.3 mmol) to obtain pale yellow crystals (Experimental Example 18). A pale yellow crystal was obtained in the same procedure except that the amount of 1-benzyl-4-hydroxypiperidine was changed to 33.9 g (176.9 mmol) (Experimental Example 19). Light yellow crystals were obtained in the same procedure except that the amount of 1-benzyl-4-hydroxypiperidine was changed to 36.5 g (190.7 mmol) (Experimental Example 20). A pale yellow crystal was obtained according to the same procedure except that the amount of 1-benzyl-4-hydroxypiperidine was changed to 39.8 g (208.1 mmol) (Experimental Example 21).
C4에 나타낸 아실포스핀 조성물을 합성하는 경우에는, 처음에, 질소 분위기 중에서, 반응 플라스크 안에, 페닐(2,4,6-트라이메틸벤조일)포스핀산 50.0g(173.4mmol)과, 다이클로로메테인 500ml(=500cm3)를 투입했다. 계속해서, 반응 플라스크 안의 혼합물을 실온에서 교반함으로써, 페닐(2,4,6-트라이메틸벤조일)포스핀산을 완전히 용해시켰다. 계속해서, 반응 플라스크 안에 다이메틸에탄올아민 14.0g(156.1mmol)을 첨가한 후, 반응 플라스크 안의 혼합물을 실온에서 교반(교반시간=5시간)함으로써, 반응 용액을 얻었다. 마지막으로, 반응 용액을 탈용매한 후, 감압 건조(건조 온도=40℃)시킴으로써, C4에 나타낸 아실포스핀 조성물인 담황색의 결정을 얻었다(실험예 22).When synthesizing the acylphosphine composition shown in C4, 50.0 g (173.4 mmol) of phenyl (2,4,6-trimethylbenzoyl) phosphinic acid and dichloromethane in a reaction flask in a nitrogen atmosphere first 500ml (=500cm 3 ) was added. Then, the mixture in the reaction flask was stirred at room temperature to completely dissolve phenyl(2,4,6-trimethylbenzoyl)phosphinic acid. Subsequently, after adding 14.0 g (156.1 mmol) of dimethylethanolamine to the reaction flask, the mixture in the reaction flask was stirred at room temperature (stirring time = 5 hours) to obtain a reaction solution. Finally, after desolving the reaction solution, it was dried under reduced pressure (drying temperature = 40°C) to obtain pale yellow crystals of the acylphosphine composition shown in C4 (Experimental Example 22).
다이메틸에탄올아민의 첨가량을 15.4g(173.4mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 23). 다이메틸에탄올아민의 첨가량을 15.5g(174.3mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 24). 다이메틸에탄올아민의 첨가량을 16.0g(178.6mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 25). 다이메틸에탄올아민의 첨가량을 17.0g(190.7mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 26). 다이메틸에탄올아민의 첨가량을 18.6g(208.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 27).A pale yellow crystal was obtained according to the same procedure except that the amount of dimethylethanolamine was changed to 15.4 g (173.4 mmol) (Experimental Example 23). A pale yellow crystal was obtained according to the same procedure except that the amount of dimethylethanolamine was changed to 15.5 g (174.3 mmol) (Experimental Example 24). A pale yellow crystal was obtained according to the same procedure except that the amount of dimethylethanolamine was changed to 16.0 g (178.6 mmol) (Experimental Example 25). A pale yellow crystal was obtained according to the same procedure except that the amount of dimethylethanolamine was changed to 17.0 g (190.7 mmol) (Experimental Example 26). A pale yellow crystal was obtained according to the same procedure except that the amount of dimethylethanolamine was changed to 18.6 g (208.1 mmol) (Experimental Example 27).
C5에 나타낸 아실포스핀 조성물을 합성하는 경우에는, 처음에, 질소 분위기 중에서, 반응 플라스크 안에, 페닐(2,4,6-트라이메틸벤조일)포스핀산 50.0g(173.4mmol)과, 다이클로로메테인 500ml(=500cm3)를 투입했다. 계속해서, 반응 플라스크 안의 혼합물을 실온에서 교반함으로써, 페닐(2,4,6-트라이메틸벤조일)포스핀산을 완전히 용해시켰다. 계속해서, 반응 플라스크 안에 tert-뷰틸다이에탄올아민 25.2g(156.1mmol)을 첨가한 후, 반응 플라스크 안의 혼합물을 실온에서 교반(교반시간=5시간)함으로써, 반응 용액을 얻었다. 마지막으로, 반응 용액을 탈용매한 후, 감압 건조(건조 온도=40℃)시킴으로써, C5에 나타낸 아실포스핀 조성물인 담황색의 결정을 얻었다(실험예 28).When synthesizing the acylphosphine composition shown in C5, 50.0 g (173.4 mmol) of phenyl (2,4,6-trimethylbenzoyl) phosphinic acid and dichloromethane in a reaction flask in a nitrogen atmosphere first 500ml (=500cm 3 ) was added. Then, the mixture in the reaction flask was stirred at room temperature to completely dissolve phenyl(2,4,6-trimethylbenzoyl)phosphinic acid. Subsequently, after adding 25.2 g (156.1 mmol) of tert-butyldiethanolamine into the reaction flask, the mixture in the reaction flask was stirred at room temperature (stirring time = 5 hours) to obtain a reaction solution. Finally, after desolving the reaction solution, it was dried under reduced pressure (drying temperature = 40°C) to obtain pale yellow crystals of the acylphosphine composition shown in C5 (Experimental Example 28).
tert-뷰틸다이에탄올아민의 첨가량을 28.0g(173.4mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 29). tert-뷰틸다이에탄올아민의 첨가량을 28.1g(174.3mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 30). tert-뷰틸다이에탄올아민의 첨가량을 28.6g(178.6mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 31). tert-뷰틸다이에탄올아민의 첨가량을 30.8g(190.7mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 32). tert-뷰틸다이에탄올아민의 첨가량을 33.6g(208.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 33).A pale yellow crystal was obtained according to the same procedure except that the amount of tert-butyldiethanolamine was changed to 28.0 g (173.4 mmol) (Experimental Example 29). A pale yellow crystal was obtained according to the same procedure except that the amount of tert-butyldiethanolamine was changed to 28.1 g (174.3 mmol) (Experimental Example 30). A pale yellow crystal was obtained according to the same procedure except that the amount of tert-butyldiethanolamine was changed to 28.6 g (178.6 mmol) (Experimental Example 31). A pale yellow crystal was obtained according to the same procedure except that the amount of tert-butyldiethanolamine was changed to 30.8 g (190.7 mmol) (Experimental Example 32). A pale yellow crystal was obtained according to the same procedure except that the amount of tert-butyldiethanolamine was changed to 33.6 g (208.1 mmol) (Experimental Example 33).
[다른 조성물의 합성][Synthesis of other compositions]
또한, 비교를 위해서, C6 및 C7의 각각으로 표시되는 다른 조성물도 합성했다. 다른 조성물에 관한 당량비 및 중량비의 각각은, 표 2에 나타낸 바와 같다.In addition, for comparison, other compositions represented by each of C6 and C7 were also synthesized. Each of the equivalence ratio and weight ratio regarding other compositions is as shown in Table 2.
C6에 나타낸 다른 조성물을 합성하는 경우에는, 처음에, 환류 반응 플라스크 안에, 2,4,6-트라이메틸벤조일페닐포스핀산 에틸에스터 7.3g(23mmol)과, 2-뷰탄온(메틸에틸케톤) 40g을 투입했다. 계속해서, 환류 반응 플라스크 안의 혼합물을 질소 기류하 및 실온에서 교반함으로써, 2,4,6-트라이메틸벤조일페닐포스핀산 에틸에스터를 완전히 용해시켰다. 계속해서, 환류 반응 플라스크 안에 아이오딘화 나트륨 3.3g(22mmol)을 첨가한 후, 환류 반응 플라스크 안의 혼합물을 실온에서 교반(교반시간=15분간)했다. 계속해서, 반응 용액의 온도를 65℃까지 승온시킨 후, 그 온도인 그대로 반응 용액을 교반(교반시간=8시간)함으로써, 반응 용액을 얻었다. 마지막으로, 실온이 될 때까지 반응 용액의 온도를 냉각한 후, 그 반응 용액 중의 석출물을 여과함으로써, C6에 나타낸 다른 조성물인 백색의 결정을 얻었다(실험예 34).When synthesizing the other composition shown in C6, first, in a reflux reaction flask, 7.3 g (23 mmol) of 2,4,6-trimethylbenzoylphenylphosphinic acid ethyl ester and 40 g of 2-butanone (methylethyl ketone) was put in Then, 2,4,6-trimethylbenzoylphenylphosphinic acid ethyl ester was completely dissolved by stirring the mixture in the reflux reaction flask under a nitrogen stream and at room temperature. Then, 3.3 g (22 mmol) of sodium iodide was added into the reflux reaction flask, and then the mixture in the reflux reaction flask was stirred at room temperature (stirring time = 15 minutes). Then, after raising the temperature of the reaction solution to 65 degreeC, the reaction solution was obtained by stirring the reaction solution as it is at that temperature (stirring time = 8 hours). Finally, after cooling the temperature of the reaction solution to room temperature, the precipitate in the reaction solution was filtered to obtain white crystals of the other composition represented by C6 (Experimental Example 34).
아이오딘화 나트륨의 첨가량을 3.4g(23mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 백색의 결정을 얻었다(실험예 35). 아이오딘화 나트륨의 첨가량을 3.5g(23.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 백색의 결정을 얻었다(실험예 36). 아이오딘화 나트륨의 첨가량을 3.6g(24mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 백색의 결정을 얻었다(실험예 37). 아이오딘화 나트륨의 첨가량을 3.7g(25mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 백색의 결정을 얻었다(실험예 38). 아이오딘화 나트륨의 첨가량을 4.2g(28mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 백색의 결정을 얻었다(실험예 39).White crystals were obtained according to the same procedure except that the amount of sodium iodide was changed to 3.4 g (23 mmol) (Experimental Example 35). White crystals were obtained according to the same procedure except that the addition amount of sodium iodide was changed to 3.5 g (23.1 mmol) (Experimental Example 36). White crystals were obtained according to the same procedure except that the amount of sodium iodide added was changed to 3.6 g (24 mmol) (Experimental Example 37). White crystals were obtained according to the same procedure except that the amount of sodium iodide was changed to 3.7 g (25 mmol) (Experimental Example 38). White crystals were obtained according to the same procedure except that the amount of sodium iodide was changed to 4.2 g (28 mmol) (Experimental Example 39).
C7에 나타낸 다른 조성물을 합성하는 경우에는, 처음에, 질소 분위기 중에서, 반응 플라스크 안에, 페닐(2,4,6-트라이메틸벤조일)포스핀산 50.0g(173.4mmol)과, 다이클로로메테인 500ml(=500cm3)를 투입했다. 계속해서, 반응 플라스크 안의 혼합물을 실온에서 교반함으로써, 페닐(2,4,6-트라이메틸벤조일)포스핀산을 완전히 용해시켰다. 계속해서, 반응 플라스크 안에 피페라진 무수물 7.10g(82.4mmol)을 첨가한 후, 반응 플라스크 안의 혼합물을 실온에서 교반(교반시간=5시간)함으로써, 반응 용액을 얻었다. 마지막으로, 반응 용액을 탈용매한 후, 감압 건조(건조 온도=40℃)시킴으로써, C7에 나타낸 다른 조성물인 담황색의 결정을 얻었다(실험예 40).When synthesizing the other composition shown in C7, first, in a nitrogen atmosphere, in a reaction flask, 50.0 g (173.4 mmol) of phenyl (2,4,6-trimethylbenzoyl) phosphinic acid, and 500 ml of dichloromethane ( =500cm 3 ) was introduced. Then, the mixture in the reaction flask was stirred at room temperature to completely dissolve phenyl(2,4,6-trimethylbenzoyl)phosphinic acid. Then, after adding 7.10 g (82.4 mmol) of piperazine anhydride into the reaction flask, the mixture in the reaction flask was stirred at room temperature (stirring time = 5 hours) to obtain a reaction solution. Finally, after desolving the reaction solution, it was dried under reduced pressure (drying temperature = 40°C) to obtain pale yellow crystals of the other composition shown in C7 (Experimental Example 40).
피페라진 무수물의 첨가량을 7.47g(86.7mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 41). 피페라진 무수물의 첨가량을 7.50g(87.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 42). 피페라진 무수물의 첨가량을 7.80g(92.8mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 43). 피페라진 무수물의 첨가량을 8.22g(95.4mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 44). 피페라진 무수물의 첨가량을 8.97g(104.1mmol)으로 변경한 것을 제외하고는 동일한 순서에 따라, 담황색의 결정을 얻었다(실험예 45).A pale yellow crystal was obtained according to the same procedure except that the amount of piperazine anhydride was changed to 7.47 g (86.7 mmol) (Experimental Example 41). A pale yellow crystal was obtained according to the same procedure except that the amount of piperazine anhydride was changed to 7.50 g (87.1 mmol) (Experimental Example 42). A pale yellow crystal was obtained according to the same procedure except that the amount of piperazine anhydride was changed to 7.80 g (92.8 mmol) (Experimental Example 43). A pale yellow crystal was obtained according to the same procedure except that the amount of piperazine anhydride was changed to 8.22 g (95.4 mmol) (Experimental Example 44). A pale yellow crystal was obtained according to the same procedure except that the amount of piperazine anhydride was changed to 8.97 g (104.1 mmol) (Experimental Example 45).
[중합성 조성물의 조제][Preparation of polymerizable composition]
중합성 조성물을 조제하는 경우에는, 처음에, 수성 용매(이온 교환수) 70질량부와, 반응기 함유 화합물(KJ케미컬즈 주식회사제의 아크릴로일모폴린 ACMO(등록상표)) 22.5질량부와, 반응기 함유 화합물(신나카무라 화학공업 주식회사제의 알콕시화 글리세린아크릴레이트 A-GLY-20E) 5.7질량부와, 중합 개시제(C1~C5의 각각에 나타낸 아실포스핀 조성물) 1.5질량부와, 레벨링제(EVONIC사제의 폴리에터 변성 폴리실록세인 코폴리머 TEGOglide 100) 0.3질량부를 칭량했다. 여기에서 사용한 아실포스핀 조성물(C1~C5)은, C1~C5의 각각에 나타낸 아니온(아실포스핀 아니온)과 함께 다른 아니온(수산화물 이온)을 포함하고 있다. 계속해서, 수성 용매 중에 반응기 함유 화합물, 중합 개시제 및 레벨링제를 투입한 후, 그 수성 용매를 교반(수성 용매의 온도=25℃, 교반시간=10분간)했다. 마지막으로, 0.45μm의 필터를 이용하여 수성 용매를 여과함으로써, 중합성 조성물을 얻었다.When preparing the polymerizable composition, first, 70 parts by mass of an aqueous solvent (ion-exchanged water), 22.5 parts by mass of a reactive group-containing compound (acryloylmorpholine ACMO (registered trademark) manufactured by KJ Chemicals Co., Ltd.), and a reactor 5.7 parts by mass of a compound containing (Alkoxylated glycerin acrylate A-GLY-20E manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 1.5 parts by mass of a polymerization initiator (acyl phosphine composition shown in each of C1 to C5), and a leveling agent (EVONIC) 0.3 mass parts of polyether-modified polysiloxane copolymer TEGOglide 100) manufactured by the company was weighed out. The acylphosphine compositions (C1 to C5) used herein contain other anions (hydroxide ions) along with the anions (acylphosphine anions) shown in each of C1 to C5. Then, after injecting|throwing-in a reactor containing compound, a polymerization initiator, and a leveling agent in an aqueous solvent, the aqueous solvent was stirred (aqueous solvent temperature = 25 degreeC, stirring time = 10 minutes). Finally, a polymerizable composition was obtained by filtering the aqueous solvent using a 0.45 µm filter.
또한, 비교를 위해, 아실포스핀 조성물(C1~C5) 대신에 다른 조성물(C6 및 C7)을 사용한 것을 제외하고는 동일한 순서에 따라, 중합성 조성물을 조제했다. 여기에서 사용한 다른 조성물(C6 및 C7)은, C6 및 C7의 각각에 나타낸 아니온(아실포스핀 아니온)과 함께 다른 아니온(수산화물 이온)을 포함하고 있다.In addition, for comparison, the polymerizable composition was prepared according to the same procedure except having used the other compositions (C6 and C7) instead of the acylphosphine compositions (C1-C5). The other compositions (C6 and C7) used herein contain other anions (hydroxide ions) together with the anions (acylphosphine anions) shown in each of C6 and C7.
[경화물의 제조][Production of cured product]
코팅 기구(스핀 코터)를 이용하여 기체(코닝사제의 유리판 이글 XG)의 표면에 중합성 조성물을 도포한 후, 그 중합성 조성물을 건조(건조 온도=90℃, 건조 시간=2분간)시켰다. 이로써, 중합성 조성물의 도막(두께=2μm)이 형성되었다. 이 후, 광원으로서 고압 수은 램프를 이용하여, 도막에 활성 에너지선(자외선광, 조도=20mW/cm2, 조사량=500mJ/cm2)을 조사했다. 이로써, 중합성 조성물 중에 있어서 반응기 함유 화합물이 중합 개시제(아실포스핀 조성물 및 다른 조성물)를 통하여 중합 반응했기 때문에, 경화물을 포함하는 피막이 형성되었다.After coating the polymerizable composition on the surface of the substrate (glass plate Eagle XG manufactured by Corning Corporation) using a coating device (spin coater), the polymerizable composition was dried (drying temperature = 90°C, drying time = 2 minutes). Thereby, the coating film (thickness = 2 micrometers) of a polymeric composition was formed. Thereafter, the coating film was irradiated with active energy rays (ultraviolet light, illuminance = 20 mW/cm 2 , irradiation amount = 500 mJ/cm 2 ) using a high-pressure mercury lamp as a light source. As a result, in the polymerizable composition, the reactive group-containing compound was subjected to a polymerization reaction via a polymerization initiator (acyl phosphine composition and other compositions), and thus a film containing a cured product was formed.
[물성의 평가][Evaluation of physical properties]
아실포스핀 조성물의 물성(용해성)과, 중합성 조성물의 물성(보존 안정성)과, 경화물의 물성(경화성)을 평가한 바, 표 1 및 표 2에 나타낸 결과가 얻어졌다. 단, 다른 조성물을 이용한 경우에 있어서도 동일하게, 용해성, 보존 안정성 및 경화성을 평가했다.When the physical properties (solubility) of the acylphosphine composition, the physical properties (storage stability) of the polymerizable composition, and the physical properties (curability) of the cured product were evaluated, the results shown in Tables 1 and 2 were obtained. However, also when another composition was used, solubility, storage stability, and sclerosis|hardenability were evaluated similarly.
용해성을 조사하는 경우에는, 이온 교환수(온도=25℃) 95g에 아실포스핀 조성물 5g을 첨가한 후, 그 이온 교환수를 교반(교반시간=1시간)했다. 이 결과, 이온 교환수 상태를 육안으로 관찰함으로써, 아실포스핀 조성물의 용해 상태를 판정했다. 구체적으로는, 아실포스핀 조성물이 균일하게 용해되어 있어, 불용물이 잔존하지 않은 경우에는, A로 판정했다. 아실포스핀 조성물이 균일하게 용해되어 있지 않아, 불용물이 잔존한 경우에는, B로 판정했다.When examining solubility, after adding 5 g of acylphosphine composition to 95 g of ion-exchange water (temperature = 25 degreeC), the ion-exchange water was stirred (stirring time = 1 hour). As a result, the dissolved state of the acylphosphine composition was determined by visually observing the state of the ion-exchanged water. When the acylphosphine composition was melt|dissolved uniformly specifically, and an insoluble material did not remain|survive, it determined with A. When the acylphosphine composition did not melt|dissolve uniformly and an insoluble material remained, it determined with B.
보존 안정성을 조사하는 경우에는, 저온 환경 중(온도=5℃)에서 중합성 조성물을 보관(보관 시간=10일간)했다. 이 결과, 중합성 조성물 상태를 육안으로 관찰함으로써, 그 중합성 조성물의 보존 상태를 판정했다. 구체적으로는, 중합 조성물의 색이 균일하게 투명하여, 그 중합성 조성물 상태가 조제 후 상태에서 변하지 않은 경우에는, A로 판정했다. 중합 조성물이 백탁하거나, 또는 중합성 조성물 중에 석출물이 발생하여, 그 중합성 조성물 상태가 조제 후 상태에서 변화한 경우에는, B로 판정했다.When investigating storage stability, the polymerizable composition was stored (storage time = 10 days) in a low-temperature environment (temperature = 5 degreeC). As a result, the storage state of the polymerizable composition was determined by visually observing the state of the polymerizable composition. Specifically, when the color of the polymerization composition was uniformly transparent and the state of the polymerizable composition did not change from the state after preparation, it was determined as A. When the polymerization composition became cloudy or a precipitate was generated in the polymerizable composition and the state of the polymerizable composition changed from the state after preparation, it was determined as B.
경화성을 조사하는 경우에는, 경화물의 상태를 육안 및 촉진(觸診)으로 조사함으로써, 그 경화물의 경화 상태를 판정했다. 구체적으로는, 중합성 조성물이 충분히 경화되어, 균일하게 투명한 피막이 얻어진 경우에는, A로 판정했다. 중합성 조성물이 경화되었지만, 피막의 표면이 백탁한 경우에는, B로 판정했다. 중합성 조성물이 충분히 경화되어 있지 않아, 즉 중합성 조성물이 경화되어 있지 않아, 피막이 달라붙은 경우에는, C로 판정했다.When sclerosis|hardenability was investigated, the hardened|cured state of the hardened|cured material was judged by irradiating the state of hardened|cured material by visual observation and acceleration|stimulation. When the polymerizable composition fully hardened|cured specifically, and the transparent film uniformly was obtained, it determined with A. Although the polymerizable composition was hardened, when the surface of the film was cloudy, it was determined as B. When the polymerizable composition did not fully harden|cure, ie, the polymeric composition was not hardened|cured and the film adhered, it determined with C.
또한, 표 1 및 표 2에 나타낸 「종합 평가」의 란에는, 물성(용해성, 보존 안정성 및 경화성)에 관한 종합적인 평가를 나타내고 있다. 구체적으로는, 용해성의 판정 결과, 보존 안정성의 판정 결과 및 경화성의 판정 결과가 모두 A인 경우에는, 종합 평가를 A로 했다. 이에 대해서, 용해성의 판정 결과, 보존 안정성의 판정 결과 및 경화성의 판정 결과 중 어느 하나가 B 또는 C인 경우에는, 종합 평가를 B로 했다.In addition, in the column of "comprehensive evaluation" shown in Table 1 and Table 2, the comprehensive evaluation regarding physical properties (solubility, storage stability, and sclerosis|hardenability) is shown. Specifically, when all of the determination result of solubility, the determination result of storage stability, and the determination result of sclerosis|hardenability were A, comprehensive evaluation was made into A. On the other hand, when any one of the determination result of solubility, the determination result of storage stability, and sclerosis|hardenability determination result was B or C, comprehensive evaluation was made into B.
[표 1][Table 1]
[표 2][Table 2]
[고찰][Review]
표 1 및 표 2에 나타낸 바와 같이, 용해성, 보존 안정성 및 경화성의 각각은, 중합성 조성물의 구성에 따라 크게 변동되었다.As shown in Table 1 and Table 2, each of solubility, storage stability, and sclerosis|hardenability fluctuated largely with the structure of a polymeric composition.
구체적으로는, 중합성 조성물이 본 발명의 아실포스핀 조성물을 포함하지 않고, 즉 중합성 조성물이 다른 조성물을 포함하고 있는 경우(실험예 34~45)에는, 용해성, 보존 안정성 및 경화성 모두에 관하여 양호한 결과가 얻어지지 않았기 때문에, 양호한 종합 평가를 얻을 수 없었다.Specifically, when the polymerizable composition does not contain the acylphosphine composition of the present invention, that is, the polymerizable composition contains other compositions (Experimental Examples 34 to 45), both solubility, storage stability and curability are Since favorable results were not obtained, favorable overall evaluation could not be obtained.
이에 대해서, 중합성 조성물이 본 발명의 아실포스핀 조성물을 포함하고 있는 경우(실험예 1~33)에는, 당량비에 따라 용해성, 보존 안정성 및 경화성 각각이 변동되었다.On the other hand, when the polymerizable composition contained the acylphosphine composition of this invention (Experimental Examples 1-33), each of solubility, storage stability, and sclerosis|hardenability fluctuate|varied according to an equivalence ratio.
상세하게는, 당량비가 적정한 조건(당량비=1.005~1.100)을 충족시키지 않은 경우(실험예 1, 2, 8 등)에는, 여전히, 용해성, 보존 안정성 및 경화성 모두에 관하여 양호한 결과가 얻어지지 않았기 때문에, 양호한 종합 평가를 얻을 수 없었다. 그러나, 당량비가 적정한 조건을 충족시키고 있는 경우(실험예 3~7 등)에는, 용해성, 보존 안정성 및 경화성 모두에 관하여 양호한 결과가 얻어졌기 때문에, 양호한 종합 평가를 얻을 수 있었다.Specifically, when the equivalence ratio does not satisfy the appropriate conditions (equivalent ratio = 1.005 to 1.100) (Experimental Examples 1, 2, 8, etc.), good results are still not obtained with respect to both solubility, storage stability and curability. , a good overall evaluation could not be obtained. However, when the equivalence ratio satisfies the appropriate conditions (Experimental Examples 3 to 7, etc.), good results were obtained with respect to all of solubility, storage stability, and hardenability, and therefore a good comprehensive evaluation was obtained.
특히, 당량비가 적정한 조건을 충족시키고 있는 경우에는, 중량비도 적정한 조건(중량비=0.25~1.00)을 충족시키고 있으면, 용해성, 보존 안정성 및 경화성 모두에 관하여 충분한 결과가 얻어졌다.In particular, when the equivalence ratio satisfies the appropriate conditions, and the weight ratio also satisfies the appropriate conditions (weight ratio = 0.25 to 1.00), sufficient results were obtained with respect to all of solubility, storage stability and curability.
[정리][organize]
표 1 및 표 2에 나타낸 결과로부터, 아실포스핀 조성물이 식 (1)에 나타낸 카티온과 식 (2)에 나타낸 아실포스핀 아니온을 포함하는 2종류 이상의 아니온을 포함하고 있고, 당량비가 1.005~1.100이면, 우수한 용해성이 얻어졌다. 이 경우에는, 아실포스핀 조성물을 포함하는 중합성 조성물에 있어서 우수한 보존 안정성이 얻어짐과 함께, 그 중합성 조성물을 이용하여 형성된 피막(경화물)에 있어서 우수한 경화성이 얻어졌다. 또한, 상기한 중합성 조성물에 활성 에너지선을 조사함으로써 얻어진 피막(경화물)에서는, 우수한 경화성이 얻어졌다. 따라서, 아실포스핀 조성물(중합 개시제), 중합성 조성물 및 경화물의 각각에 있어서, 우수한 물성이 얻어짐과 함께, 그 경화물의 제조 방법에 의해, 우수한 물성을 갖는 경화물이 얻어졌다.From the results shown in Tables 1 and 2, the acylphosphine composition contains two or more kinds of anions including the cation shown in Formula (1) and the acylphosphine anion shown in Formula (2), and the equivalent ratio is If it was 1.005-1.100, the outstanding solubility was obtained. In this case, while the excellent storage stability was acquired in the polymeric composition containing an acylphosphine composition, sclerosis|hardenability excellent in the film (hardened|cured material) formed using this polymeric composition was acquired. Moreover, in the film (hardened|cured material) obtained by irradiating an active energy ray to said polymeric composition, the outstanding sclerosis|hardenability was obtained. Therefore, in each of the acylphosphine composition (polymerization initiator), the polymerizable composition, and the cured product, excellent physical properties were obtained, and a cured product having excellent physical properties was obtained by the method for producing the cured product.
이상, 일 실시형태 및 실시예를 들면서 본 발명에 관하여 설명했지만, 본 발명의 양태는 실시형태 및 실시예에 있어서 설명한 양태로 한정되지 않기 때문에, 그 양태에 관해서는 다양한 변형이 가능하다.As mentioned above, although this invention was demonstrated giving one Embodiment and an Example, since the aspect of this invention is not limited to the aspect demonstrated in embodiment and an Example, various deformation|transformation is possible about the aspect.
본 출원은, 일본 특허청에 있어서 2019년 11월 25일에 출원된 일본특허출원 번호 제2019-212569호를 기초로 하여 우선권을 주장하는 것이며, 이 출원의 모든 내용을 참조에 의해 본 출원에 원용한다.This application claims priority on the basis of Japanese Patent Application No. 2019-212569 for which it applied to the Japan Patent Office on November 25, 2019, All content of this application is used for this application by reference. .
당업자라면, 설계상의 요건이나 다른 요인에 따라, 다양한 수정, 콤비네이션, 서브 콤비네이션, 및 변경에 이를 수 있지만, 그것은 첨부한 청구범위의 취지나 그 균등물의 범위에 포함된다는 것을 이해해야 한다.Various modifications, combinations, sub-combinations, and changes will occur to those skilled in the art depending on design requirements or other factors, but it should be understood that they are included within the spirit of the appended claims and their equivalents.
Claims (9)
식 (2)로 표시되는 아실포스핀 아니온을 포함하는 2종류 이상의 아니온
을 포함하고,
상기 아실포스핀 아니온의 몰 당량에 대한 상기 카티온의 몰 당량의 비가 1.005 이상 1.100 이하인,
아실포스핀 조성물.
N+HY1Y2Y3 ···(1)
(Y1, Y2 및 Y3의 각각은, 탄소수가 1 이상 6 이하인 직쇄상의 알킬기, 탄소수가 2 이상 6 이하인 직쇄상의 알케닐기, 탄소수가 6 이상 15 이하인 아릴기 및 탄소수가 7 이상 13 이하인 아릴알킬기 중 어느 하나이다. Y1, Y2 및 Y3의 각각의 수소기는, 수산기에 의해 치환되어 있어도 된다. Y1, Y2 및 Y3의 각각의 메틸렌기는, -O-, -S-, -CO- 및 -N+H- 중 어느 하나에 의해 치환되어 있어도 된다. Y1, Y2 및 Y3 중 임의의 2개는, 서로 결합되어 있어도 된다.)
[화학식 1]
(X1은, 탄소수가 6 이상 15 이하인 아릴기이며, 그 아릴기의 수소기의 각각은, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알킬기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알콕시기 및 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알콕시기 중 어느 하나에 의해 치환되어 있어도 된다.
X2는, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기 및 탄소수가 6 이상 15 이하인 아릴기 중 어느 하나이며, 그 아릴기의 수소기의 각각은, 탄소수가 1 이상 8 이하인 직쇄상의 알킬기, 탄소수가 3 이상 8 이하인 분기상의 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알킬기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알킬기, 탄소수가 1 이상 8 이하인 직쇄상의 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 알콕시기, 탄소수가 1 이상 8 이하인 직쇄상의 할로겐화 알콕시기, 탄소수가 3 이상 8 이하인 분기상의 할로겐화 알콕시기, 할로겐기, 나이트로기, 사이아노기, 수산기, 아미노기, 카복실기, 메타크릴로일기, 아크릴로일기, 에폭시기, 바이닐기, 바이닐에터기, 머캅토기, 아이소사이아네이트기 및 복소환 함유기 중 어느 하나에 의해 치환되어 있어도 된다. X2의 메틸렌기의 각각은, -O- 및 -S- 중 어느 하나에 의해 치환되어 있어도 된다.)A cation represented by Formula (1),
Two or more kinds of anions containing an acylphosphine anion represented by formula (2)
including,
The ratio of the molar equivalent of the cation to the molar equivalent of the acylphosphine anion is 1.005 or more and 1.100 or less,
An acylphosphine composition.
N + HY1Y2Y3 ...(1)
(Each of Y1, Y2 and Y3 is a linear alkyl group having 1 to 6 carbon atoms, a linear alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, and an arylalkyl group having 7 to 13 carbon atoms. Any of Y1, Y2 and Y3 each hydrogen group may be substituted with a hydroxyl group. Each methylene group of Y1, Y2 and Y3 is -O-, -S-, -CO- and -N + H It may be substituted by any one of -. Any two of Y1, Y2 and Y3 may be bonded to each other.)
[Formula 1]
(X1 is an aryl group having 6 or more and 15 or less carbon atoms, and each of the hydrogen groups in the aryl group is a linear alkyl group having 1 or more and 8 or less, a branched alkyl group having 3 or more and 8 or less, and 1 or more and 8 or less. A linear halogenated alkyl group having the following or less, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a linear halogenated alkyl group having 1 to 8 carbon atoms or less. You may be substituted with either a halogenated alkoxy group and a C3-C8 branched halogenated alkoxy group.
X2 is a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, and 6 carbon atoms. It is any one of the aryl groups of 15 or more, and each of the hydrogen groups of the aryl group is a linear alkyl group having 1 or more and 8 or less, a branched alkyl group having 3 or more and 8 or less, and a straight chain having 1 or more and 8 or less. A halogenated alkyl group, a branched halogenated alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, Branched halogenated alkoxy group having 3 to 8 carbon atoms, halogen group, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl group, vinyl ether group, mercapto group , may be substituted by any one of an isocyanate group and a heterocyclic-containing group. Each of the methylene groups of X2 may be substituted with either -O- or -S-.)
상기 아실포스핀 아니온의 중량에 대한 상기 카티온의 중량의 비는, 0.25 이상 1.00 이하인,
아실포스핀 조성물.According to claim 1,
The ratio of the weight of the cation to the weight of the acylphosphine anion is 0.25 or more and 1.00 or less,
An acylphosphine composition.
상기 X1은, 2,4,6-트라이메틸페닐기인,
아실포스핀 조성물.3. The method of claim 1 or 2,
Wherein X1 is a 2,4,6-trimethylphenyl group,
An acylphosphine composition.
상기 X2는, 페닐기인,
아실포스핀 조성물.4. The method according to any one of claims 1 to 3,
Wherein X2 is a phenyl group,
An acylphosphine composition.
상기 Y1, Y2 및 Y3 중 1개는, 상기 탄소수가 1 이상 6 이하인 직쇄상의 알킬기이며,
상기 Y1, Y2 및 Y3 중 나머지 2개의 각각은, 말단의 1개의 상기 수소기가 상기 수산기에 의해 치환된 상기 탄소수가 1 이상 6 이하인 직쇄상의 알킬기인,
아실포스핀 조성물.5. The method according to any one of claims 1 to 4,
One of Y1, Y2 and Y3 is a linear alkyl group having 1 or more and 6 or less carbon atoms,
each of the other two of Y1, Y2 and Y3 is a linear alkyl group having 1 to 6 carbon atoms in which one hydrogen group at the terminal is substituted with the hydroxyl group,
An acylphosphine composition.
중합 개시제.A composition comprising the acylphosphine composition according to any one of claims 1 to 5,
polymerization initiator.
식 (3)으로 표시되는 반응기를 포함하는 반응기 함유 화합물과,
수성 용매
를 포함하는, 중합성 조성물.
[화학식 2]
(R1은, 수소기 및 메틸기 중 어느 하나이다.
Z1은, -O- 및 -NR2- 중 어느 하나이며, 그 R2는, 수소기 및 탄소수가 1 이상 20 이하인 탄화 수소기 중 어느 하나이다.
Z2는, 탄소수가 1 이상 6 이하인 알킬렌기이다.
n은, 0 이상 30 이하의 정수이다.
단, 별표(*)는, 미결합의 결합손을 표시하고 있다.)The acylphosphine composition according to any one of claims 1 to 5;
A reactive group-containing compound comprising a reactive group represented by formula (3);
aqueous solvent
A polymerizable composition comprising a.
[Formula 2]
(R1 is either a hydrogen group or a methyl group.
Z1 is either -O- or -NR2-, and R2 is any one of a hydrogen group and a hydrocarbon group having 1 or more and 20 or less carbon atoms.
Z2 is an alkylene group having 1 or more and 6 or less carbon atoms.
n is an integer of 0 or more and 30 or less.
However, an asterisk (*) indicates an unbonded bond.)
경화물.A curing reaction product of the polymerizable composition according to claim 7,
hardened material.
경화물의 제조 방법.Irradiating an active energy ray to the polymerizable composition according to claim 7,
A method for producing a cured product.
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