JP5299838B2 - 10−ヒドロキシ−10−ナフチルメチルアントラセン−9(10h)−オン化合物及びその光ラジカル重合開始剤としての用途。 - Google Patents
10−ヒドロキシ−10−ナフチルメチルアントラセン−9(10h)−オン化合物及びその光ラジカル重合開始剤としての用途。 Download PDFInfo
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- JP5299838B2 JP5299838B2 JP2008068908A JP2008068908A JP5299838B2 JP 5299838 B2 JP5299838 B2 JP 5299838B2 JP 2008068908 A JP2008068908 A JP 2008068908A JP 2008068908 A JP2008068908 A JP 2008068908A JP 5299838 B2 JP5299838 B2 JP 5299838B2
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- Prior art keywords
- hydroxy
- compound
- methyl
- naphthylmethyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 10-hydroxy-10-naphthylmethylanthracen-9 (10H) -one compound Chemical class 0.000 title claims abstract description 64
- 239000007870 radical polymerization initiator Substances 0.000 title claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 238000000859 sublimation Methods 0.000 abstract description 20
- 230000008022 sublimation Effects 0.000 abstract description 20
- 238000003776 cleavage reaction Methods 0.000 abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 9
- 239000003505 polymerization initiator Substances 0.000 abstract description 9
- 125000004434 sulfur atom Chemical group 0.000 abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 5
- 125000004429 atom Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 27
- 150000003254 radicals Chemical class 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000003999 initiator Substances 0.000 description 21
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 16
- 229940076442 9,10-anthraquinone Drugs 0.000 description 15
- 125000001624 naphthyl group Chemical group 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- DDDDZNDLXAOAOF-UHFFFAOYSA-N 10-hydroxy-10-(naphthalen-1-ylmethyl)anthracen-9-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC=C2C1(O)CC1=CC=CC2=CC=CC=C12 DDDDZNDLXAOAOF-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 9
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 9
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 230000007017 scission Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 239000005456 alcohol based solvent Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000006356 dehydrogenation reaction Methods 0.000 description 5
- 238000004455 differential thermal analysis Methods 0.000 description 5
- 239000004210 ether based solvent Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- KOGHAOQITVWULR-UHFFFAOYSA-N 10-hydroxy-10h-anthracen-9-one Chemical group C1=CC=C2C(O)C3=CC=CC=C3C(=O)C2=C1 KOGHAOQITVWULR-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000005453 ketone based solvent Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XPCZSIPRUSOJFO-UHFFFAOYSA-N 1,4,4a,9a-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2C1CC=CC2 XPCZSIPRUSOJFO-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 2
- MPCHQYWZAVTABQ-UHFFFAOYSA-N 2-(chloromethyl)naphthalene Chemical compound C1=CC=CC2=CC(CCl)=CC=C21 MPCHQYWZAVTABQ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical group C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 2
- ZLKBPPIGNPAPDC-UHFFFAOYSA-N OC1(C=2C=CC=CC2C(C2=CC=CC=C12)=O)CC1=CC=C(C2=CC=CC=C12)OC Chemical compound OC1(C=2C=CC=CC2C(C2=CC=CC=C12)=O)CC1=CC=C(C2=CC=CC=C12)OC ZLKBPPIGNPAPDC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000852 hydrogen donor Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 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 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- RZJGKPNCYQZFGR-UHFFFAOYSA-N 1-(bromomethyl)naphthalene Chemical compound C1=CC=C2C(CBr)=CC=CC2=C1 RZJGKPNCYQZFGR-UHFFFAOYSA-N 0.000 description 1
- VQADZLUXFHDBJH-UHFFFAOYSA-N 1-(chloromethyl)-2-ethylnaphthalene Chemical compound C1=CC=CC2=C(CCl)C(CC)=CC=C21 VQADZLUXFHDBJH-UHFFFAOYSA-N 0.000 description 1
- CGSYKRJQLUCLOR-UHFFFAOYSA-N 1-(chloromethyl)-2-methoxynaphthalene Chemical compound C1=CC=CC2=C(CCl)C(OC)=CC=C21 CGSYKRJQLUCLOR-UHFFFAOYSA-N 0.000 description 1
- STBYRSZXHDPASK-UHFFFAOYSA-N 1-(chloromethyl)-2-methylnaphthalene Chemical compound C1=CC=CC2=C(CCl)C(C)=CC=C21 STBYRSZXHDPASK-UHFFFAOYSA-N 0.000 description 1
- ZRQUOLGLNFIGNF-UHFFFAOYSA-N 1-(chloromethyl)-4-ethoxynaphthalene Chemical compound C1=CC=C2C(OCC)=CC=C(CCl)C2=C1 ZRQUOLGLNFIGNF-UHFFFAOYSA-N 0.000 description 1
- ZGNNXILHNOLGQO-UHFFFAOYSA-N 1-(chloromethyl)-4-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=C(CCl)C2=C1 ZGNNXILHNOLGQO-UHFFFAOYSA-N 0.000 description 1
- QHXSBKTZBDHBKF-UHFFFAOYSA-N 1-(chloromethyl)-4-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(CCl)C2=C1 QHXSBKTZBDHBKF-UHFFFAOYSA-N 0.000 description 1
- LOXGELNNCVYJGJ-UHFFFAOYSA-N 1-(chloromethyl)-6-methoxynaphthalene Chemical compound ClCC1=CC=CC2=CC(OC)=CC=C21 LOXGELNNCVYJGJ-UHFFFAOYSA-N 0.000 description 1
- ZTUJCHLKVRVOHI-UHFFFAOYSA-N 1-(chloromethyl)-6-methylnaphthalene Chemical compound Cc1ccc2c(CCl)cccc2c1 ZTUJCHLKVRVOHI-UHFFFAOYSA-N 0.000 description 1
- XQXNMQAQDHEQSB-UHFFFAOYSA-N 1-(iodomethyl)naphthalene Chemical compound C1=CC=C2C(CI)=CC=CC2=C1 XQXNMQAQDHEQSB-UHFFFAOYSA-N 0.000 description 1
- JDASKBNBZDGJKX-UHFFFAOYSA-N 1-bromo-3-(chloromethyl)naphthalene Chemical compound ClCc1cc(Br)c2ccccc2c1 JDASKBNBZDGJKX-UHFFFAOYSA-N 0.000 description 1
- AVHPSHRBXHDYIR-UHFFFAOYSA-N 1-bromo-4-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=C(Br)C2=C1 AVHPSHRBXHDYIR-UHFFFAOYSA-N 0.000 description 1
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 1
- BEHRVPLBZSVTAO-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)naphthalene Chemical compound ClCc1cc(Cl)c2ccccc2c1 BEHRVPLBZSVTAO-UHFFFAOYSA-N 0.000 description 1
- AZFWKWBXGOGJOI-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=C(Cl)C2=C1 AZFWKWBXGOGJOI-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical group O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 description 1
- XSFPJYHPSAVIOC-UHFFFAOYSA-N 1-methyl-10h-anthracen-9-one Chemical compound C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C XSFPJYHPSAVIOC-UHFFFAOYSA-N 0.000 description 1
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical group O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- INPHIYULSHLAHR-UHFFFAOYSA-N 1-pentylanthracene-9,10-dione Chemical group O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCCC INPHIYULSHLAHR-UHFFFAOYSA-N 0.000 description 1
- BGJQNPIOBWKQAW-UHFFFAOYSA-N 1-tert-butylanthracene-9,10-dione Chemical group O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)(C)C BGJQNPIOBWKQAW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SAKIJMSLTKGUQV-UHFFFAOYSA-N 2,7-dibromoanthracene-9,10-dione Chemical compound C1=C(Br)C=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 SAKIJMSLTKGUQV-UHFFFAOYSA-N 0.000 description 1
- HQUNBWGQFXPVES-UHFFFAOYSA-N 2,7-dichloroanthracene-9,10-dione Chemical compound C1=C(Cl)C=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 HQUNBWGQFXPVES-UHFFFAOYSA-N 0.000 description 1
- UPYAOZCJHKIOHD-UHFFFAOYSA-N 2,7-diethylanthracene-9,10-dione Chemical compound C1=C(CC)C=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 UPYAOZCJHKIOHD-UHFFFAOYSA-N 0.000 description 1
- BNQIMPXNGWHMGE-UHFFFAOYSA-N 2,7-difluoroanthracene-9,10-dione Chemical compound FC1=CC=2C(C3=CC(=CC=C3C(C=2C=C1)=O)F)=O BNQIMPXNGWHMGE-UHFFFAOYSA-N 0.000 description 1
- RATJDSXPVPAWJJ-UHFFFAOYSA-N 2,7-dimethylanthracene-9,10-dione Chemical compound C1=C(C)C=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 RATJDSXPVPAWJJ-UHFFFAOYSA-N 0.000 description 1
- GDNGHUJEIRASIR-UHFFFAOYSA-N 2,7-ditert-butylanthracene-9,10-dione Chemical compound C1=C(C(C)(C)C)C=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 GDNGHUJEIRASIR-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Description
以下の記述において、アントラセン−9(10H)−オン骨格とは、一般式(1)における下記構造式(4)の部分を称し、ナフタレン骨格とは、一般式(1)における下記構造式(5)または構造式(6)の部分を称する。
(1)融点:ゲレンキャンプ社製の融点測定装置、型式MFB−595(JIS K0064に準拠)
(2)赤外線(IR)分光光度計:日本分光社製、型式IR−810
(3)核磁気共鳴装置(NMR):日本電子社製、型式GSX FT NMR Spectorometer
(4)Massスペクトル:島津製作所社製、質量分析計、型式GCMS−QP5000
示差熱測定装置(DTA):島津製作所製 DTG50H型
9,10−アントラキノン2.4g(11.4ミリモル)、1,4,4a,9a−テトラヒドロアントラキノン 2.5g(11.4ミリモル)、水酸化ナトリウム1g(25ミリモル)、水18gを100mlオートクレーブに仕込み、窒素雰囲気下、110℃のオイルバスに浸漬し1時間加熱した。反応終了後、オートクレーブを室温まで冷却し、9,10−アントラヒドロキノンのジナトリウム塩の水溶液である深紅の溶液20mlを得た。次に、攪拌機、温度計を装備した容量が300ml三口フラスコに、先に得られた9,10−アントラヒドロキノンのジナトリウム塩20mlの水溶液(9,10−アントラキノン換算で20重量%、22.6ミリモル)を窒素雰囲気下で入れ、次に溶媒としてメタノール26mlを加え、最後に1−クロロメチルナフタレン4.6g(26ミリモル)のメタノール40ml溶液を約0.5時間かけて添加した。反応温度を20〜30℃程度にコントロールしながら、添加から約0.5時間攪拌を続けると次第に結晶が析出した。その後さらに約2時間攪拌後、反応液に水20mlを加えさらに0.5時間攪拌した後、反応液をロータリーエバポレーターを使用して反応液の容量が2/3程度まで減圧濃縮した。沈殿した結晶を吸引濾過・水洗い・乾燥し、薄黄色の結晶を4.2g(11.8ミリモル)得た。9,10−アントラヒドロキノンに対する生成物の収率は52モル%であった。
(2)IR(KBr、cm−1):3480,3055,2960,2940,1654,1600,1582、1462,1322,1298、1221,1200,1178,1034,960、932,760,695.
(3)1H−NMR(CDCl3,270MHz):δ=2.61(s,1H),3.72(s,2H),6.58(d,J=8Hz,1H),7.09(d,J=8Hz,1H),7.15(t,J=8Hz,1H),7.40(t,J=8Hz,2H),7.52(t,J=8Hz,2H),7.68(t,J=8Hz,2H),7.76(d,J=8Hz,2H),7.82(d,J=8Hz,1H),8.02(d,J=8Hz,2H),8.32(d,J=8Hz,1H).
(4)MASSスペクトル(EI−MS)m/z:354(M+)
トリメチロールプロパントリアクリレート100重量部に対し、実施例1で得た10−ヒドロキシ−10−(1−ナフチルメチル)アントラセン−9(10H)−オンを1重量部添加した光ラジカル重合性組成物を調製した。次に、ポリエステルフィルム(東レ製ルミラー膜厚100μm、ルミラーは東レ株式会社の登録商標)上に調製した組成物を膜厚が12μmとなるようにバーコーターを使用して塗布した。この塗布膜に窒素雰囲気下、高圧水銀ランプ(CAMAG社製UVランプ)を使用し、照射強度1.8mw/cm2の条件で照射したところ、硬化していることを確認した。タックフリータイムは30秒であった。
10−ヒドロキシ−10−(1−ナフチルメチル)アントラセン−9(10H)−オン1重量部の代わりに、1−ヒドロキシシクロヘキシルフェニルケトン1重量部を添加した以外は実施例2と同様の方法で重合組成物を調整し、塗布膜を作成し、塗布膜に窒素雰囲気下、実施例2と同様に高圧水銀ランプを照射したところ、フィルム表面が硬化していることを確認した。タックフリータイムは30秒であった。
実施例1で得た10−ヒドロキシ−10−(1−ナフチルメチル)アントラセン−9(10H)−オンを示差熱測定装置(DTA)に10−ヒドロキシ−10−(1−ナフチルメチル)アントラセン−9(10H)−オンの結晶 10mgを入れ、窒素ガス供給速度50ml/分の条件で、10℃/分の速度で昇温し、その間の試料の重量変化を測定した。所定の重量減少値となった時の温度を指標として昇華性を調べた。結果を表1に示す。
1−ヒドロキシシクロヘキシルフェニルケトンをDTA(示差熱分析)により昇華性の評価を行った。評価方法は実施例3と同様に行い、所定の重量減少値となった時の温度を指標として昇華性を調べた。結果を表1に示す。
Claims (3)
- 一般式(1)で表される10−ヒドロキシ−10−ナフチルメチルアントラセン−9(10H)−オン化合物。
- 請求項1記載の10−ヒドロキシ−10−ナフチルメチルアントラセン−9(10H)−オン化合物を有効成分として含有する光ラジカル重合開始剤。
- 一般式(2)で表される9,10−アントラヒドロキノン化合物と一般式(3)で表されるハロゲン化メチルナフタレン化合物を反応させることによる、請求項1記載の10−ヒドロキシ−10−ナフチルメチルアントラセン−9(10H)−オン化合物の製造法。
(一般式(3)において、Wは塩素原子、臭素原子又はヨウ素原子を示し、Zは、水素原子、ハロゲン原子、アルキル基、水酸基又はアルコキシ基を示し、nは1〜7の整数であり、nが2以上のとき、複数あるZは同一でも異なってもよい。)
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