JP4454309B2 - 光活性化窒素塩基 - Google Patents

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Publication number

JP4454309B2

JP4454309B2 JP2003536239A JP2003536239A JP4454309B2 JP 4454309 B2 JP4454309 B2 JP 4454309B2 JP 2003536239 A JP2003536239 A JP 2003536239A JP 2003536239 A JP2003536239 A JP 2003536239A JP 4454309 B2 JP4454309 B2 JP 4454309B2

Authority

JP

Japan

Prior art keywords

alkyl

substituted

unsubstituted

formula

groups

Prior art date

2001-10-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 150000002829 nitrogen Chemical class 0.000 title 1
• -1 bicyclic amines Chemical class 0.000 claims abstract description 240
• 239000000203 mixture Substances 0.000 claims abstract description 80
• 238000006555 catalytic reaction Methods 0.000 claims abstract description 11
• 238000006467 substitution reaction Methods 0.000 claims abstract description 9
• 150000001875 compounds Chemical class 0.000 claims description 81
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 239000001257 hydrogen Substances 0.000 claims description 32
• 238000000576 coating method Methods 0.000 claims description 31
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 239000011248 coating agent Substances 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 16
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 239000000758 substrate Substances 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 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 claims description 12
• 125000001624 naphthyl group Chemical group 0.000 claims description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
• 238000007259 addition reaction Methods 0.000 claims description 9
• 238000006116 polymerization reaction Methods 0.000 claims description 8
• 238000006482 condensation reaction Methods 0.000 claims description 7
• 238000000465 moulding Methods 0.000 claims description 7
• 230000005494 condensation Effects 0.000 claims description 6
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
• 125000001725 pyrenyl group Chemical group 0.000 claims description 6
• PNZNKBFIWFBSAU-UHFFFAOYSA-N 1-benzyl-10-methyl-3,4,6,7,8,9,10,10a-octahydro-2h-pyrimido[1,2-a]azepine Chemical compound C12C(C)CCCCN2CCCN1CC1=CC=CC=C1 PNZNKBFIWFBSAU-UHFFFAOYSA-N 0.000 claims description 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• BEZORAZYWWXCIP-UHFFFAOYSA-N 1-benzyl-12-methyl-3,4,6,7,8,9,10,11,12,12a-decahydro-2h-pyrimido[1,2-a]azonine Chemical compound C12C(C)CCCCCCN2CCCN1CC1=CC=CC=C1 BEZORAZYWWXCIP-UHFFFAOYSA-N 0.000 claims description 3
• ZIONUNFGMHFISV-UHFFFAOYSA-N 1-benzyl-2,3,4,6,7,8,9,10,11,11a-decahydropyrimido[1,2-a]azocine Chemical compound C1CCN2CCCCCCC2N1CC1=CC=CC=C1 ZIONUNFGMHFISV-UHFFFAOYSA-N 0.000 claims description 3
• RQXFKBIKINJEBU-UHFFFAOYSA-N 1-benzyl-2,3,4,6,7,8,9,10,11,12,13,13a-dodecahydropyrimido[1,2-a]azecine Chemical compound C1CCN2CCCCCCCCC2N1CC1=CC=CC=C1 RQXFKBIKINJEBU-UHFFFAOYSA-N 0.000 claims description 3
• AMDNICFZCMZSPD-UHFFFAOYSA-N 1-benzyl-3,4,6,7,8,9,10,10a-octahydro-2h-pyrimido[1,2-a]azepine Chemical compound C1CCN2CCCCCC2N1CC1=CC=CC=C1 AMDNICFZCMZSPD-UHFFFAOYSA-N 0.000 claims description 3
• 150000002894 organic compounds Chemical class 0.000 claims description 3
• XUICADQNDIQJLU-UHFFFAOYSA-N 1-benzyl-5-ethyl-3,5,6,7,8,8a-hexahydro-2h-imidazo[1,2-a]pyridine Chemical compound C1CN2C(CC)CCCC2N1CC1=CC=CC=C1 XUICADQNDIQJLU-UHFFFAOYSA-N 0.000 claims 1
• PHFLGFSYPGKEDT-UHFFFAOYSA-N 1-benzyl-5-methyl-3,5,6,7,8,8a-hexahydro-2h-imidazo[1,2-a]pyridine Chemical compound C1CN2C(C)CCCC2N1CC1=CC=CC=C1 PHFLGFSYPGKEDT-UHFFFAOYSA-N 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 abstract description 35
• 150000001412 amines Chemical class 0.000 abstract description 20
• 150000001409 amidines Chemical class 0.000 abstract description 10
• 125000001743 benzylic group Chemical group 0.000 abstract description 5
• 239000002585 base Substances 0.000 description 38
• 229920000642 polymer Polymers 0.000 description 27
• 239000002904 solvent Substances 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 229910052757 nitrogen Inorganic materials 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 238000000034 method Methods 0.000 description 19
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 125000003118 aryl group Chemical group 0.000 description 18
• 238000009472 formulation Methods 0.000 description 18
• 239000000178 monomer Substances 0.000 description 17
• 239000000243 solution Substances 0.000 description 17
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• 125000004432 carbon atom Chemical group C* 0.000 description 15
• 238000004132 cross linking Methods 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• 229920000058 polyacrylate Polymers 0.000 description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 239000012965 benzophenone Substances 0.000 description 12
• 229920000647 polyepoxide Polymers 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• 229920000728 polyester Polymers 0.000 description 11
• 229920001577 copolymer Polymers 0.000 description 10
• 238000001723 curing Methods 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• 150000003839 salts Chemical class 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 239000011230 binding agent Substances 0.000 description 9
• 239000003822 epoxy resin Substances 0.000 description 9
• 229910052751 metal Inorganic materials 0.000 description 9
• 239000002184 metal Substances 0.000 description 9
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 229920005989 resin Polymers 0.000 description 9
• 239000011347 resin Substances 0.000 description 9
• 238000003860 storage Methods 0.000 description 9
• 125000001544 thienyl group Chemical group 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 8
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
• 238000010521 absorption reaction Methods 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 125000000304 alkynyl group Chemical group 0.000 description 7
• 238000005815 base catalysis Methods 0.000 description 7
• RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 125000000320 amidine group Chemical group 0.000 description 6
• 150000008366 benzophenones Chemical class 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 150000002431 hydrogen Chemical class 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 6
• BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 6
• 229920000570 polyether Polymers 0.000 description 6
• 150000003141 primary amines Chemical class 0.000 description 6
• 238000007639 printing Methods 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 5
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
• QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
• 239000000654 additive Substances 0.000 description 5
• 125000001931 aliphatic group Chemical group 0.000 description 5
• IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
• 150000001728 carbonyl compounds Chemical class 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 239000000975 dye Substances 0.000 description 5
• 238000000921 elemental analysis Methods 0.000 description 5
• 150000002170 ethers Chemical class 0.000 description 5
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
• 239000012948 isocyanate Substances 0.000 description 5
• 150000002513 isocyanates Chemical class 0.000 description 5
• 239000012280 lithium aluminium hydride Substances 0.000 description 5
• 238000004519 manufacturing process Methods 0.000 description 5
• 238000005580 one pot reaction Methods 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 150000002989 phenols Chemical class 0.000 description 5
• 239000005056 polyisocyanate Substances 0.000 description 5
• 229920001228 polyisocyanate Polymers 0.000 description 5
• 239000004814 polyurethane Substances 0.000 description 5
• 229920002635 polyurethane Polymers 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• 238000006277 sulfonation reaction Methods 0.000 description 5
• 150000003512 tertiary amines Chemical class 0.000 description 5
• 239000008096 xylene Substances 0.000 description 5
• WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 4
• HYQWHUCTTYCIAU-UHFFFAOYSA-N 1-benzyl-3,4,6,7,8,8a-hexahydro-2h-pyrrolo[1,2-a]pyrimidine Chemical compound C1CCN2CCCC2N1CC1=CC=CC=C1 HYQWHUCTTYCIAU-UHFFFAOYSA-N 0.000 description 4
• VMVPYUCMIYVDTQ-UHFFFAOYSA-N 1-benzyl-4-methyl-3,4,6,7,8,8a-hexahydro-2h-pyrrolo[1,2-a]pyrimidine Chemical compound C12CCCN2C(C)CCN1CC1=CC=CC=C1 VMVPYUCMIYVDTQ-UHFFFAOYSA-N 0.000 description 4
• RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
• GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 4
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
• 206010034972 Photosensitivity reaction Diseases 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 4
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
• 238000007792 addition Methods 0.000 description 4
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
• 239000012964 benzotriazole Substances 0.000 description 4
• KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 4
• 229940073608 benzyl chloride Drugs 0.000 description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 239000002131 composite material Substances 0.000 description 4
• BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
• 239000000835 fiber Substances 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• 230000036211 photosensitivity Effects 0.000 description 4
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 230000005855 radiation Effects 0.000 description 4
• 150000003335 secondary amines Chemical class 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• 150000003573 thiols Chemical class 0.000 description 4
• HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• 239000002023 wood Substances 0.000 description 4
• JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
• KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 3
• SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 3
• DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
• KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 3
• ILNCXUYVDNKISU-UHFFFAOYSA-N 3-(1,3-dioxolan-2-yl)propanenitrile Chemical compound N#CCCC1OCCO1 ILNCXUYVDNKISU-UHFFFAOYSA-N 0.000 description 3
• NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
• 239000006096 absorbing agent Substances 0.000 description 3
• 125000002947 alkylene group Chemical group 0.000 description 3
• 150000008064 anhydrides Chemical group 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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