DE3021590A1 - 4-halogen-5-(halogenmethyl-phenyl)-oxazol-derivate, ein verfahren zu ihrer herstellung und sie enthaltenden strahlungsempfindliche massen - Google Patents
4-halogen-5-(halogenmethyl-phenyl)-oxazol-derivate, ein verfahren zu ihrer herstellung und sie enthaltenden strahlungsempfindliche massenInfo
- Publication number
- DE3021590A1 DE3021590A1 DE19803021590 DE3021590A DE3021590A1 DE 3021590 A1 DE3021590 A1 DE 3021590A1 DE 19803021590 DE19803021590 DE 19803021590 DE 3021590 A DE3021590 A DE 3021590A DE 3021590 A1 DE3021590 A1 DE 3021590A1
- Authority
- DE
- Germany
- Prior art keywords
- hoechst
- aldehyde
- kalle
- radiation
- branch
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000000460 chlorine Substances 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 73
- 239000003795 chemical substances by application Substances 0.000 claims description 49
- 230000005855 radiation Effects 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 18
- 241000251730 Chondrichthyes Species 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 230000009471 action Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 150000007978 oxazole derivatives Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 230000001960 triggered effect Effects 0.000 claims description 2
- 238000010538 cationic polymerization reaction Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- -1 aromatic radicals Chemical class 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 238000002211 ultraviolet spectrum Methods 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- YEHATNSHSCNOAQ-UHFFFAOYSA-N 4-(trichloromethyl)benzoyl cyanide Chemical compound ClC(Cl)(Cl)C1=CC=C(C(=O)C#N)C=C1 YEHATNSHSCNOAQ-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical class N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 125000004970 halomethyl group Chemical group 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- HJUGFYREWKUQJT-UHFFFAOYSA-N carbon tetrabromide Natural products BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000006303 photolysis reaction Methods 0.000 description 4
- 230000015843 photosynthesis, light reaction Effects 0.000 description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 3
- IBMUHJIDXFMZPI-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O.ClC1=CC=CC=C1C=O IBMUHJIDXFMZPI-UHFFFAOYSA-N 0.000 description 3
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 3
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 3
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004115 Sodium Silicate Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000004069 differentiation Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000019795 sodium metasilicate Nutrition 0.000 description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000004953 trihalomethyl group Chemical group 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 2
- CRBZVDLXAIFERF-UHFFFAOYSA-N 2,4,6-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C=O)C(OC)=C1 CRBZVDLXAIFERF-UHFFFAOYSA-N 0.000 description 2
- ADDZHRRCUWNSCS-UHFFFAOYSA-N 2-Benzofurancarboxaldehyde Chemical compound C1=CC=C2OC(C=O)=CC2=C1 ADDZHRRCUWNSCS-UHFFFAOYSA-N 0.000 description 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
- VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
- CCRGXEYOIOEMDH-UHFFFAOYSA-N 3,5-bis(trichloromethyl)benzoyl cyanide Chemical compound ClC(Cl)(Cl)C1=CC(C(=O)C#N)=CC(C(Cl)(Cl)Cl)=C1 CCRGXEYOIOEMDH-UHFFFAOYSA-N 0.000 description 2
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 2
- LNIAVCRNJMPGGT-UHFFFAOYSA-N 4-(trichloromethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)(Cl)Cl)C=C1 LNIAVCRNJMPGGT-UHFFFAOYSA-N 0.000 description 2
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 2
- RUKJCCIJLIMGEP-ONEGZZNKSA-N 4-dimethylaminocinnamaldehyde Chemical compound CN(C)C1=CC=C(\C=C\C=O)C=C1 RUKJCCIJLIMGEP-ONEGZZNKSA-N 0.000 description 2
- MYLBIQHZWFWSMH-UHFFFAOYSA-N 4-methoxy-3-methylbenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1C MYLBIQHZWFWSMH-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- WGQVKYPDHREEJU-UHFFFAOYSA-N 5-acetyl-2-methoxybenzaldehyde Natural products COC1=CC=C(C(C)=O)C=C1C=O WGQVKYPDHREEJU-UHFFFAOYSA-N 0.000 description 2
- XBWFYFHSIFEXMY-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carbaldehyde Chemical compound C1=CC=C2C(=O)C3=CC(C=O)=CC=C3C(=O)C2=C1 XBWFYFHSIFEXMY-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- WZKXBGJNNCGHIC-UHFFFAOYSA-N Leucomalachite green Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=CC=C1 WZKXBGJNNCGHIC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HSZUHSXXAOWGQY-UHFFFAOYSA-N [2-methyl-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)COC(=O)C=C HSZUHSXXAOWGQY-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- OBRMNDMBJQTZHV-UHFFFAOYSA-N cresol red Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 OBRMNDMBJQTZHV-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229940081310 piperonal Drugs 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
- BATOPAZDIZEVQF-MQQKCMAXSA-N (E,E)-2,4-hexadienal Chemical compound C\C=C\C=C\C=O BATOPAZDIZEVQF-MQQKCMAXSA-N 0.000 description 1
- HZUFMSJUNLSDSZ-OWOJBTEDSA-N (e)-3-(1,3-benzodioxol-5-yl)prop-2-enal Chemical compound O=C\C=C\C1=CC=C2OCOC2=C1 HZUFMSJUNLSDSZ-OWOJBTEDSA-N 0.000 description 1
- ALGQVMMYDWQDEC-OWOJBTEDSA-N (e)-3-(4-nitrophenyl)prop-2-enal Chemical compound [O-][N+](=O)C1=CC=C(\C=C\C=O)C=C1 ALGQVMMYDWQDEC-OWOJBTEDSA-N 0.000 description 1
- POJPQMDDRCILHJ-UHFFFAOYSA-N 1,1,1,2,2,2-hexabromoethane Chemical compound BrC(Br)(Br)C(Br)(Br)Br POJPQMDDRCILHJ-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HOHVUOKYQMRVDO-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(dichloromethyl)-6-methylbenzene Chemical group CC1=C(Cl)C(Cl)=C(C(Cl)Cl)C(Cl)=C1Cl HOHVUOKYQMRVDO-UHFFFAOYSA-N 0.000 description 1
- VNEOTRCBGZQYJT-UHFFFAOYSA-N 1,2-dihydroacenaphthylene-5-carbaldehyde Chemical compound C1CC2=CC=CC3=C2C1=CC=C3C=O VNEOTRCBGZQYJT-UHFFFAOYSA-N 0.000 description 1
- UXTIRLFDCHFIID-UHFFFAOYSA-N 1,3,4-thiadiazole-2-carbaldehyde Chemical compound O=CC1=NN=CS1 UXTIRLFDCHFIID-UHFFFAOYSA-N 0.000 description 1
- DHRHPJZEESEPCU-UHFFFAOYSA-N 1,3,5-trimethylpyrrole-2,4-dicarbaldehyde Chemical compound CC=1C(C=O)=C(C)N(C)C=1C=O DHRHPJZEESEPCU-UHFFFAOYSA-N 0.000 description 1
- ZLHCGLGZSOFCTN-UHFFFAOYSA-N 1,3,5-trimethylpyrrole-2-carbaldehyde Chemical compound CC=1C=C(C)N(C)C=1C=O ZLHCGLGZSOFCTN-UHFFFAOYSA-N 0.000 description 1
- RHKPJTFLRQNNGJ-UHFFFAOYSA-N 1,3-benzothiazole-2-carbaldehyde Chemical compound C1=CC=C2SC(C=O)=NC2=C1 RHKPJTFLRQNNGJ-UHFFFAOYSA-N 0.000 description 1
- 150000000183 1,3-benzoxazoles Chemical group 0.000 description 1
- WRFKSVINLIQRKF-UHFFFAOYSA-N 1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC=N1 WRFKSVINLIQRKF-UHFFFAOYSA-N 0.000 description 1
- LLLBDLDNTMMZHL-UHFFFAOYSA-N 1-benzofuran-5-carbaldehyde Chemical compound O=CC1=CC=C2OC=CC2=C1 LLLBDLDNTMMZHL-UHFFFAOYSA-N 0.000 description 1
- GBRFPPIJEHQBGK-UHFFFAOYSA-N 1-chloro-3,4-dihydronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C(C=O)CCC2=C1 GBRFPPIJEHQBGK-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- SHYBXXMECBHHFH-UHFFFAOYSA-N 10-chloroanthracene-9-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=C(C=O)C2=C1 SHYBXXMECBHHFH-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- CCRRYHDVZLKVNQ-UHFFFAOYSA-N 1h-indene-2-carbaldehyde Chemical compound C1=CC=C2CC(C=O)=CC2=C1 CCRRYHDVZLKVNQ-UHFFFAOYSA-N 0.000 description 1
- WHTZQYDVDPHTAM-UHFFFAOYSA-N 2,2,2-tribromo-1-phenylethanone Chemical compound BrC(Br)(Br)C(=O)C1=CC=CC=C1 WHTZQYDVDPHTAM-UHFFFAOYSA-N 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- QJXCFMJTJYCLFG-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzaldehyde Chemical compound FC1=C(F)C(F)=C(C=O)C(F)=C1F QJXCFMJTJYCLFG-UHFFFAOYSA-N 0.000 description 1
- UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 description 1
- RCPYGAYAQAHJMN-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzaldehyde Chemical compound CC1=CC(C)=C(C)C(C=O)=C1C RCPYGAYAQAHJMN-UHFFFAOYSA-N 0.000 description 1
- DJYRZTCLVDKWBL-UHFFFAOYSA-N 2,3,5-trichlorobenzaldehyde Chemical compound ClC1=CC(Cl)=C(Cl)C(C=O)=C1 DJYRZTCLVDKWBL-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical class N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- DLIGFSPMLJNSMZ-UHFFFAOYSA-N 2,3-dimethyl-1-benzofuran-4-carbaldehyde Chemical compound C1=CC(C=O)=C2C(C)=C(C)OC2=C1 DLIGFSPMLJNSMZ-UHFFFAOYSA-N 0.000 description 1
- JBTXGGQLRIPBIO-UHFFFAOYSA-N 2,4,5,6-tetramethylbenzene-1,3-dicarbaldehyde Chemical compound CC1=C(C)C(C=O)=C(C)C(C=O)=C1C JBTXGGQLRIPBIO-UHFFFAOYSA-N 0.000 description 1
- LXQRQVUSDOKVLD-UHFFFAOYSA-N 2,4,5-trichlorobenzaldehyde Chemical compound ClC1=CC(Cl)=C(C=O)C=C1Cl LXQRQVUSDOKVLD-UHFFFAOYSA-N 0.000 description 1
- IAJBQAYHSQIQRE-UHFFFAOYSA-N 2,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C=O)C=C1OC IAJBQAYHSQIQRE-UHFFFAOYSA-N 0.000 description 1
- FETYGMIOAZZYEJ-UHFFFAOYSA-N 2,4,6-trichloro-1h-pyrimidine-4-carbaldehyde Chemical compound ClC1=CC(Cl)(C=O)N=C(Cl)N1 FETYGMIOAZZYEJ-UHFFFAOYSA-N 0.000 description 1
- TWFSYIOOAAYYAL-UHFFFAOYSA-N 2,4,6-trichlorobenzaldehyde Chemical compound ClC1=CC(Cl)=C(C=O)C(Cl)=C1 TWFSYIOOAAYYAL-UHFFFAOYSA-N 0.000 description 1
- KMFJNFCEVFECME-UHFFFAOYSA-N 2,4,6-triethylbenzaldehyde Chemical compound CCC1=CC(CC)=C(C=O)C(CC)=C1 KMFJNFCEVFECME-UHFFFAOYSA-N 0.000 description 1
- PHQVFKPKBHTDHG-UHFFFAOYSA-N 2,4,6-trimethoxy-1h-pyrimidine-4-carbaldehyde Chemical compound COC1=CC(OC)(C=O)N=C(OC)N1 PHQVFKPKBHTDHG-UHFFFAOYSA-N 0.000 description 1
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 1
- HIKRJHFHGKZKRI-UHFFFAOYSA-N 2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1 HIKRJHFHGKZKRI-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- JGWAODQUCDFPGI-UHFFFAOYSA-N 2,4-diethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C(OCC)=C1 JGWAODQUCDFPGI-UHFFFAOYSA-N 0.000 description 1
- XBCGIUJJUZHWMC-UHFFFAOYSA-N 2,5-dichloroterephthalaldehyde Chemical compound ClC1=CC(C=O)=C(Cl)C=C1C=O XBCGIUJJUZHWMC-UHFFFAOYSA-N 0.000 description 1
- DDCDZJHDWYGVRO-UHFFFAOYSA-N 2,5-diethoxyterephthalaldehyde Chemical compound CCOC1=CC(C=O)=C(OCC)C=C1C=O DDCDZJHDWYGVRO-UHFFFAOYSA-N 0.000 description 1
- PXJJKVNIMAZHCB-UHFFFAOYSA-N 2,5-diformylfuran Chemical compound O=CC1=CC=C(C=O)O1 PXJJKVNIMAZHCB-UHFFFAOYSA-N 0.000 description 1
- AFUKNJHPZAVHGQ-UHFFFAOYSA-N 2,5-dimethoxy-Benzaldehyde Chemical compound COC1=CC=C(OC)C(C=O)=C1 AFUKNJHPZAVHGQ-UHFFFAOYSA-N 0.000 description 1
- AIBJDPZNCNFKMR-UHFFFAOYSA-N 2,5-dimethylterephthalaldehyde Chemical compound CC1=CC(C=O)=C(C)C=C1C=O AIBJDPZNCNFKMR-UHFFFAOYSA-N 0.000 description 1
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 1
- MVCMPKYZHKUBCL-UHFFFAOYSA-N 2,6-dichloropyridine-4-carbaldehyde Chemical compound ClC1=CC(C=O)=CC(Cl)=N1 MVCMPKYZHKUBCL-UHFFFAOYSA-N 0.000 description 1
- QOJQBWSZHCKOLL-UHFFFAOYSA-N 2,6-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C)=C1C=O QOJQBWSZHCKOLL-UHFFFAOYSA-N 0.000 description 1
- XTCAIKSFUUMBTP-UHFFFAOYSA-N 2,6-dimethylpyridine-3-carbaldehyde Chemical compound CC1=CC=C(C=O)C(C)=N1 XTCAIKSFUUMBTP-UHFFFAOYSA-N 0.000 description 1
- AGLQSSYYTNHTMI-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[3,5-bis(trichloromethyl)phenyl]-4-chloro-1,3-oxazole Chemical compound ClC=1N=C(C=2C=C3OCOC3=CC=2)OC=1C1=CC(C(Cl)(Cl)Cl)=CC(C(Cl)(Cl)Cl)=C1 AGLQSSYYTNHTMI-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
- GBBXAIVUMDGTGQ-UHFFFAOYSA-N 2-(trichloromethyl)-5-[2-(trichloromethyl)phenyl]-1,3,4-oxadiazole Chemical compound O1C(C(Cl)(Cl)Cl)=NN=C1C1=CC=CC=C1C(Cl)(Cl)Cl GBBXAIVUMDGTGQ-UHFFFAOYSA-N 0.000 description 1
- HDKNFIJKQHJEPL-UHFFFAOYSA-N 2-(trichloromethyl)benzoyl cyanide Chemical class ClC(Cl)(Cl)C1=CC=CC=C1C(=O)C#N HDKNFIJKQHJEPL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ODRKIKHWTZCVCM-UHFFFAOYSA-N 2-[4-(4-oxaldehydoylphenyl)phenyl]-2-oxoacetaldehyde Chemical compound C1=CC(C(=O)C=O)=CC=C1C1=CC=C(C(=O)C=O)C=C1 ODRKIKHWTZCVCM-UHFFFAOYSA-N 0.000 description 1
- XSQFAWMDRFSIMY-UHFFFAOYSA-N 2-chloro-4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C(Cl)=C1 XSQFAWMDRFSIMY-UHFFFAOYSA-N 0.000 description 1
- OACPOWYLLGHGCR-UHFFFAOYSA-N 2-chloro-6-fluorobenzaldehyde Chemical compound FC1=CC=CC(Cl)=C1C=O OACPOWYLLGHGCR-UHFFFAOYSA-N 0.000 description 1
- VHNJYJXDQKORPF-UHFFFAOYSA-N 2-chloroanthracene-9-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C3=CC(Cl)=CC=C3C=C21 VHNJYJXDQKORPF-UHFFFAOYSA-N 0.000 description 1
- DUVJMSPTZMCSTQ-UHFFFAOYSA-N 2-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC=C1C=O DUVJMSPTZMCSTQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- QVTPWONEVZJCCS-UHFFFAOYSA-N 2-formylbenzonitrile Chemical compound O=CC1=CC=CC=C1C#N QVTPWONEVZJCCS-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- MHSIFDSGOLPDRK-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,3-dicarbaldehyde Chemical compound COC1=C(C=O)C=C(C)C=C1C=O MHSIFDSGOLPDRK-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- VMSMELHEXDVEDE-HWKANZROSA-N 2-nitrocinnamaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1\C=C\C=O VMSMELHEXDVEDE-HWKANZROSA-N 0.000 description 1
- XKJZDFJGFMPBBG-UHFFFAOYSA-N 2-nitroterephthalaldehyde Chemical compound [O-][N+](=O)C1=CC(C=O)=CC=C1C=O XKJZDFJGFMPBBG-UHFFFAOYSA-N 0.000 description 1
- IMPIIVKYTNMBCD-UHFFFAOYSA-N 2-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OC1=CC=CC=C1 IMPIIVKYTNMBCD-UHFFFAOYSA-N 0.000 description 1
- SFYGTWAUBYYUNK-UHFFFAOYSA-N 2-phenyl-1-benzofuran-3-carbaldehyde Chemical compound O1C2=CC=CC=C2C(C=O)=C1C1=CC=CC=C1 SFYGTWAUBYYUNK-UHFFFAOYSA-N 0.000 description 1
- MWAFWBDWAWZJGK-UHFFFAOYSA-N 3,3-diphenylprop-2-enal Chemical compound C=1C=CC=CC=1C(=CC=O)C1=CC=CC=C1 MWAFWBDWAWZJGK-UHFFFAOYSA-N 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- XDDLXZHBWVFPRG-UHFFFAOYSA-N 3,4-bis(phenylmethoxy)benzaldehyde Chemical compound C=1C=CC=CC=1COC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 XDDLXZHBWVFPRG-UHFFFAOYSA-N 0.000 description 1
- NOUWQZZKSKEHCI-UHFFFAOYSA-N 3,4-dimethoxy-5-nitrobenzaldehyde Chemical compound COC1=CC(C=O)=CC([N+]([O-])=O)=C1OC NOUWQZZKSKEHCI-UHFFFAOYSA-N 0.000 description 1
- STQUSGZJANLZAN-UHFFFAOYSA-N 3,5-bis(trichloromethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)(Cl)Cl)=CC(C(Cl)(Cl)Cl)=C1 STQUSGZJANLZAN-UHFFFAOYSA-N 0.000 description 1
- CASRSOJWLARCRX-UHFFFAOYSA-N 3,5-dichlorobenzaldehyde Chemical compound ClC1=CC(Cl)=CC(C=O)=C1 CASRSOJWLARCRX-UHFFFAOYSA-N 0.000 description 1
- SJMJTTXKHFIOEV-UHFFFAOYSA-N 3,5-dimethyl-4-nitrobenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1[N+]([O-])=O SJMJTTXKHFIOEV-UHFFFAOYSA-N 0.000 description 1
- NBEFMISJJNGCIZ-UHFFFAOYSA-N 3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C)=CC(C=O)=C1 NBEFMISJJNGCIZ-UHFFFAOYSA-N 0.000 description 1
- BRUITYMDHWNCIG-UHFFFAOYSA-N 3,5-ditert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1 BRUITYMDHWNCIG-UHFFFAOYSA-N 0.000 description 1
- WLFDEVVCXPTAQA-UHFFFAOYSA-N 3-(4-methoxyphenoxy)benzaldehyde Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC(C=O)=C1 WLFDEVVCXPTAQA-UHFFFAOYSA-N 0.000 description 1
- YZIHNHLGGMSWAD-UHFFFAOYSA-N 3-(4-tert-butylphenoxy)benzaldehyde Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1=CC=CC(C=O)=C1 YZIHNHLGGMSWAD-UHFFFAOYSA-N 0.000 description 1
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
- VYLBRQPAXQBDTF-UHFFFAOYSA-N 3-bromo-1-benzothiophene-7-carbaldehyde Chemical compound C1=CC=C2C(Br)=CSC2=C1C=O VYLBRQPAXQBDTF-UHFFFAOYSA-N 0.000 description 1
- ADHKMYHLJHBOKB-UHFFFAOYSA-N 3-bromo-4-formylbenzonitrile Chemical compound BrC1=CC(C#N)=CC=C1C=O ADHKMYHLJHBOKB-UHFFFAOYSA-N 0.000 description 1
- QZMGMXBYJZVAJN-UHFFFAOYSA-N 3-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1 QZMGMXBYJZVAJN-UHFFFAOYSA-N 0.000 description 1
- DXMIEBMZZMWOKS-UHFFFAOYSA-N 3-ethyl-5-(3-ethyl-5-formyl-2,4-dimethoxyphenyl)-2,4-dimethoxybenzaldehyde Chemical compound CCC1=C(OC)C(C=O)=CC(C=2C(=C(CC)C(OC)=C(C=O)C=2)OC)=C1OC DXMIEBMZZMWOKS-UHFFFAOYSA-N 0.000 description 1
- SOQCZBSZZLWDGU-UHFFFAOYSA-N 3-fluoro-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1F SOQCZBSZZLWDGU-UHFFFAOYSA-N 0.000 description 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
- HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 description 1
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
- AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 1
- JSHLOPGSDZTEGQ-UHFFFAOYSA-N 3-methoxy-4-phenylmethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 JSHLOPGSDZTEGQ-UHFFFAOYSA-N 0.000 description 1
- CRYSZGHMFXHXTP-UHFFFAOYSA-N 3-methoxyphenanthrene-9-carbaldehyde Chemical compound C1=CC=C2C3=CC(OC)=CC=C3C=C(C=O)C2=C1 CRYSZGHMFXHXTP-UHFFFAOYSA-N 0.000 description 1
- GEWPFPUABRRBPS-UHFFFAOYSA-N 3-methyl-1,2-oxazole-5-carbaldehyde Chemical compound CC=1C=C(C=O)ON=1 GEWPFPUABRRBPS-UHFFFAOYSA-N 0.000 description 1
- LSIPLFHSLYDZPC-UHFFFAOYSA-N 3-methyl-1h-indene-2-carbaldehyde Chemical compound C1=CC=C2C(C)=C(C=O)CC2=C1 LSIPLFHSLYDZPC-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 1
- SZXMDUKWIYIKKS-UHFFFAOYSA-N 3-phenyl-1,2-oxazole-5-carbaldehyde Chemical compound O1C(C=O)=CC(C=2C=CC=CC=2)=N1 SZXMDUKWIYIKKS-UHFFFAOYSA-N 0.000 description 1
- JAICGBJIBWDEIZ-UHFFFAOYSA-N 3-phenylmethoxybenzaldehyde Chemical compound O=CC1=CC=CC(OCC=2C=CC=CC=2)=C1 JAICGBJIBWDEIZ-UHFFFAOYSA-N 0.000 description 1
- IDASOVSVRKONFS-UHFFFAOYSA-N 3-phenylprop-2-ynal Chemical compound O=CC#CC1=CC=CC=C1 IDASOVSVRKONFS-UHFFFAOYSA-N 0.000 description 1
- CGKXSPVNHTZZGR-UHFFFAOYSA-N 4,6-dimethoxy-1-benzofuran-2-carbaldehyde Chemical compound COC1=CC(OC)=C2C=C(C=O)OC2=C1 CGKXSPVNHTZZGR-UHFFFAOYSA-N 0.000 description 1
- NUNWUFSBHOTLLY-UHFFFAOYSA-N 4-(1,2,2,2-tetrafluoroethoxy)benzaldehyde Chemical compound FC(F)(F)C(F)OC1=CC=C(C=O)C=C1 NUNWUFSBHOTLLY-UHFFFAOYSA-N 0.000 description 1
- CLXSBHRRZNBTRT-UHFFFAOYSA-N 4-(2-phenylethenyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C=CC1=CC=CC=C1 CLXSBHRRZNBTRT-UHFFFAOYSA-N 0.000 description 1
- HSHBGIDOTCOEGU-UHFFFAOYSA-N 4-(4-phenylphenyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 HSHBGIDOTCOEGU-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- BERFDQAMXIBOHM-UHFFFAOYSA-N 4-Ethoxy-3-methoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1OC BERFDQAMXIBOHM-UHFFFAOYSA-N 0.000 description 1
- NZEZRZPDYCNMAO-UHFFFAOYSA-N 4-[2-(4-formylphenyl)ethenyl]benzonitrile Chemical compound C1=CC(C=O)=CC=C1C=CC1=CC=C(C#N)C=C1 NZEZRZPDYCNMAO-UHFFFAOYSA-N 0.000 description 1
- UQSGGQUYJJLACY-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)ethenyl]benzaldehyde Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=C(C=O)C=C1 UQSGGQUYJJLACY-UHFFFAOYSA-N 0.000 description 1
- KTFKRVMXIVSARW-UHFFFAOYSA-N 4-acetylbenzaldehyde Chemical compound CC(=O)C1=CC=C(C=O)C=C1 KTFKRVMXIVSARW-UHFFFAOYSA-N 0.000 description 1
- MLZBRARCTFICSV-UHFFFAOYSA-N 4-benzoylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C(=O)C1=CC=CC=C1 MLZBRARCTFICSV-UHFFFAOYSA-N 0.000 description 1
- ARIREUPIXAKDAY-UHFFFAOYSA-N 4-butylbenzaldehyde Chemical compound CCCCC1=CC=C(C=O)C=C1 ARIREUPIXAKDAY-UHFFFAOYSA-N 0.000 description 1
- QTQSEDFIGDSHAC-UHFFFAOYSA-N 4-chloro-2-[3-[4-chloro-5-[4-(trichloromethyl)phenyl]-1,3-oxazol-2-yl]phenyl]-5-[4-(trichloromethyl)phenyl]-1,3-oxazole Chemical compound ClC=1N=C(C=2C=C(C=CC=2)C=2OC(=C(Cl)N=2)C=2C=CC(=CC=2)C(Cl)(Cl)Cl)OC=1C1=CC=C(C(Cl)(Cl)Cl)C=C1 QTQSEDFIGDSHAC-UHFFFAOYSA-N 0.000 description 1
- BQWQOMJOQODMGW-UHFFFAOYSA-N 4-chloro-2-[5-[4-chloro-5-[4-(trichloromethyl)phenyl]-1,3-oxazol-2-yl]furan-2-yl]-5-[4-(trichloromethyl)phenyl]-1,3-oxazole Chemical compound ClC=1N=C(C=2OC(=CC=2)C=2OC(=C(Cl)N=2)C=2C=CC(=CC=2)C(Cl)(Cl)Cl)OC=1C1=CC=C(C(Cl)(Cl)Cl)C=C1 BQWQOMJOQODMGW-UHFFFAOYSA-N 0.000 description 1
- JJYNOBGBIOMQAL-UHFFFAOYSA-N 4-chloro-5-[4-(trichloromethyl)phenyl]-1,3-oxazole Chemical compound N1=COC(C=2C=CC(=CC=2)C(Cl)(Cl)Cl)=C1Cl JJYNOBGBIOMQAL-UHFFFAOYSA-N 0.000 description 1
- DDYBAABYDNWVPI-UHFFFAOYSA-N 4-chloronaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(Cl)=CC=C(C=O)C2=C1 DDYBAABYDNWVPI-UHFFFAOYSA-N 0.000 description 1
- QBFNGLBSVFKILI-UHFFFAOYSA-N 4-ethenylbenzaldehyde Chemical compound C=CC1=CC=C(C=O)C=C1 QBFNGLBSVFKILI-UHFFFAOYSA-N 0.000 description 1
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 1
- ZAYJHTQPWWNPHO-UHFFFAOYSA-N 4-ethylsulfonylbenzaldehyde Chemical compound CCS(=O)(=O)C1=CC=C(C=O)C=C1 ZAYJHTQPWWNPHO-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- NIEBHDXUIJSHSL-UHFFFAOYSA-N 4-iodobenzaldehyde Chemical compound IC1=CC=C(C=O)C=C1 NIEBHDXUIJSHSL-UHFFFAOYSA-N 0.000 description 1
- KYHULTSMPDXSLR-UHFFFAOYSA-N 4-methoxy-2,5-dimethylbenzaldehyde Chemical compound COC1=CC(C)=C(C=O)C=C1C KYHULTSMPDXSLR-UHFFFAOYSA-N 0.000 description 1
- NYMCQLLAIMUVSY-UHFFFAOYSA-N 4-methyl-1,3-thiazole-2-carbaldehyde Chemical compound CC1=CSC(C=O)=N1 NYMCQLLAIMUVSY-UHFFFAOYSA-N 0.000 description 1
- IDHCSGVUFOFZJT-UHFFFAOYSA-N 4-methylpyridine-2,6-dicarbaldehyde Chemical compound CC1=CC(C=O)=NC(C=O)=C1 IDHCSGVUFOFZJT-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- QWLHJVDRPZNVBS-UHFFFAOYSA-N 4-phenoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OC1=CC=CC=C1 QWLHJVDRPZNVBS-UHFFFAOYSA-N 0.000 description 1
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 1
- ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 1
- VAUMDUIUEPIGHM-UHFFFAOYSA-N 5-Methyl-2-thiophenecarboxaldehyde Chemical compound CC1=CC=C(C=O)S1 VAUMDUIUEPIGHM-UHFFFAOYSA-N 0.000 description 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
- JTCRVWQJUODOHI-UHFFFAOYSA-N 5-acetyl-2,4-dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C(C)=O)C=C1C=O JTCRVWQJUODOHI-UHFFFAOYSA-N 0.000 description 1
- IJIBRSFAXRFPPN-UHFFFAOYSA-N 5-bromo-2-methoxybenzaldehyde Chemical compound COC1=CC=C(Br)C=C1C=O IJIBRSFAXRFPPN-UHFFFAOYSA-N 0.000 description 1
- GFBVUFQNHLUCPX-UHFFFAOYSA-N 5-bromothiophene-2-carbaldehyde Chemical compound BrC1=CC=C(C=O)S1 GFBVUFQNHLUCPX-UHFFFAOYSA-N 0.000 description 1
- DGAUAVDWXYXXGQ-UHFFFAOYSA-N 5-chlorofuran-2-carbaldehyde Chemical compound ClC1=CC=C(C=O)O1 DGAUAVDWXYXXGQ-UHFFFAOYSA-N 0.000 description 1
- GZQNWVZECIRJHP-UHFFFAOYSA-N 5-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=CC2=C1C=O GZQNWVZECIRJHP-UHFFFAOYSA-N 0.000 description 1
- GCPFDERTUUICNT-UHFFFAOYSA-N 5-methyl-1,3,4-thiadiazole-2-carbaldehyde Chemical compound CC1=NN=C(C=O)S1 GCPFDERTUUICNT-UHFFFAOYSA-N 0.000 description 1
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 description 1
- ZWRVKCFZFHBSLS-UHFFFAOYSA-N 5-methyl-3-phenyl-1-benzofuran-2-carbaldehyde Chemical compound C12=CC(C)=CC=C2OC(C=O)=C1C1=CC=CC=C1 ZWRVKCFZFHBSLS-UHFFFAOYSA-N 0.000 description 1
- RXACCCLYSOFTFW-UHFFFAOYSA-N 5-nitrobenzene-1,3-dicarbaldehyde Chemical compound [O-][N+](=O)C1=CC(C=O)=CC(C=O)=C1 RXACCCLYSOFTFW-UHFFFAOYSA-N 0.000 description 1
- JYJDWOKNSHADGZ-UHFFFAOYSA-N 5-nitronaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1C=O JYJDWOKNSHADGZ-UHFFFAOYSA-N 0.000 description 1
- AVIIWDALERTCOC-UHFFFAOYSA-N 5-phenyl-1,3,4-oxadiazole-2-carbaldehyde Chemical compound O1C(C=O)=NN=C1C1=CC=CC=C1 AVIIWDALERTCOC-UHFFFAOYSA-N 0.000 description 1
- SKGLVVWEUSDARD-UHFFFAOYSA-N 5-phenyl-1,3,4-thiadiazole-2-carbaldehyde Chemical compound S1C(C=O)=NN=C1C1=CC=CC=C1 SKGLVVWEUSDARD-UHFFFAOYSA-N 0.000 description 1
- YPYPBEGIASEWKA-UHFFFAOYSA-N 5-phenyl-1,3-oxazole Chemical compound O1C=NC=C1C1=CC=CC=C1 YPYPBEGIASEWKA-UHFFFAOYSA-N 0.000 description 1
- ASLNRWLKCLXQSM-UHFFFAOYSA-N 6,7-dimethoxy-4-phenylquinoline-2-carbaldehyde Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C=O)=CC=1C1=CC=CC=C1 ASLNRWLKCLXQSM-UHFFFAOYSA-N 0.000 description 1
- UHZKUBULBNDNTD-UHFFFAOYSA-N 6,7-dimethoxyisoquinoline-1-carbaldehyde Chemical compound C1=NC(C=O)=C2C=C(OC)C(OC)=CC2=C1 UHZKUBULBNDNTD-UHFFFAOYSA-N 0.000 description 1
- BCTADYFWWHNBIH-UHFFFAOYSA-N 6,7-dimethylquinoline-2-carbaldehyde Chemical compound C1=C(C=O)N=C2C=C(C)C(C)=CC2=C1 BCTADYFWWHNBIH-UHFFFAOYSA-N 0.000 description 1
- WRZJIHGBMXGHAJ-UHFFFAOYSA-N 6-ethoxyquinoline-2-carbaldehyde Chemical compound N1=C(C=O)C=CC2=CC(OCC)=CC=C21 WRZJIHGBMXGHAJ-UHFFFAOYSA-N 0.000 description 1
- GOFAYQFZGHXFTL-UHFFFAOYSA-N 6-methoxy-1-benzofuran-2-carbaldehyde Chemical compound COC1=CC=C2C=C(C=O)OC2=C1 GOFAYQFZGHXFTL-UHFFFAOYSA-N 0.000 description 1
- WJXUZZRARHSJOF-UHFFFAOYSA-N 6-methoxy-1h-indene-2-carbaldehyde Chemical compound COC1=CC=C2C=C(C=O)CC2=C1 WJXUZZRARHSJOF-UHFFFAOYSA-N 0.000 description 1
- VZBLASFLFFMMCM-UHFFFAOYSA-N 6-methoxynaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(OC)=CC=C21 VZBLASFLFFMMCM-UHFFFAOYSA-N 0.000 description 1
- AHISYUZBWDSPQL-UHFFFAOYSA-N 6-methylpyridine-2-carbaldehyde Chemical compound CC1=CC=CC(C=O)=N1 AHISYUZBWDSPQL-UHFFFAOYSA-N 0.000 description 1
- IMWMEIWYPWVABQ-UHFFFAOYSA-N 6-methylpyridine-3-carbaldehyde Chemical compound CC1=CC=C(C=O)C=N1 IMWMEIWYPWVABQ-UHFFFAOYSA-N 0.000 description 1
- CLBAHSMUCIURDP-UHFFFAOYSA-N 6-nitro-1,3-benzothiazole-2-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C2N=C(C=O)SC2=C1 CLBAHSMUCIURDP-UHFFFAOYSA-N 0.000 description 1
- QGRVIVDVWTXWEA-UHFFFAOYSA-N 9h-fluorene-2,7-dicarbaldehyde Chemical compound O=CC1=CC=C2C3=CC=C(C=O)C=C3CC2=C1 QGRVIVDVWTXWEA-UHFFFAOYSA-N 0.000 description 1
- XUBSJNINNWDBOF-UHFFFAOYSA-N 9h-fluorene-4-carbaldehyde Chemical compound C1C2=CC=CC=C2C2=C1C=CC=C2C=O XUBSJNINNWDBOF-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 229910014265 BrCl Inorganic materials 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000246142 Chamaecytisus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229940127007 Compound 39 Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- DJGQYTUXTCURSC-UHFFFAOYSA-N acenaphthylene-1-carbaldehyde Chemical compound C1=CC(C(C=O)=C2)=C3C2=CC=CC3=C1 DJGQYTUXTCURSC-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- ISOCABSXIKQOOV-UHFFFAOYSA-N acridine-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=NC2=C1 ISOCABSXIKQOOV-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000007854 aminals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- ASEMRXSTATUWKG-UHFFFAOYSA-N anthracene-2-carbaldehyde Chemical compound C1=CC=CC2=CC3=CC(C=O)=CC=C3C=C21 ASEMRXSTATUWKG-UHFFFAOYSA-N 0.000 description 1
- YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- DNAVOCNYHNNEQI-UHFFFAOYSA-N asaronaldehyde Natural products COC1=CC(OC)=C(C=CC=O)C=C1OC DNAVOCNYHNNEQI-UHFFFAOYSA-N 0.000 description 1
- AEKQNAANFVOBCU-UHFFFAOYSA-N benzene-1,3,5-tricarbaldehyde Chemical compound O=CC1=CC(C=O)=CC(C=O)=C1 AEKQNAANFVOBCU-UHFFFAOYSA-N 0.000 description 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IZGKMPFVTHIGMB-UHFFFAOYSA-N benzo[a]anthracene-12-carbaldehyde Chemical compound C1=CC=CC2=C3C(C=O)=C(C=CC=C4)C4=CC3=CC=C21 IZGKMPFVTHIGMB-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- UIZLQMLDSWKZGC-UHFFFAOYSA-N cadmium helium Chemical compound [He].[Cd] UIZLQMLDSWKZGC-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- CEARSHHHRNMBHM-UHFFFAOYSA-N dibenzofuran-2,8-dicarbaldehyde Chemical compound C1=C(C=O)C=C2C3=CC(C=O)=CC=C3OC2=C1 CEARSHHHRNMBHM-UHFFFAOYSA-N 0.000 description 1
- OVJMIWIVPWPZMN-UHFFFAOYSA-N dibenzofuran-2-carbaldehyde Chemical compound C1=CC=C2C3=CC(C=O)=CC=C3OC2=C1 OVJMIWIVPWPZMN-UHFFFAOYSA-N 0.000 description 1
- LFAGMIMSUYTWDN-UHFFFAOYSA-N dibenzothiophene-2,8-dicarbaldehyde Chemical compound C1=C(C=O)C=C2C3=CC(C=O)=CC=C3SC2=C1 LFAGMIMSUYTWDN-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- XZYGRRSTJVFZLS-UHFFFAOYSA-N ethyl 3-formylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C=O)=C1 XZYGRRSTJVFZLS-UHFFFAOYSA-N 0.000 description 1
- BHYVHYPBRYOMGC-UHFFFAOYSA-N ethyl 4-formylbenzoate Chemical compound CCOC(=O)C1=CC=C(C=O)C=C1 BHYVHYPBRYOMGC-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- JGEMYUOFGVHXKV-OWOJBTEDSA-N fumaraldehyde Chemical compound O=C\C=C\C=O JGEMYUOFGVHXKV-OWOJBTEDSA-N 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- QEAGQILEKLFCEK-UHFFFAOYSA-N isoquinoline-7-carbaldehyde Chemical compound C1=CN=CC2=CC(C=O)=CC=C21 QEAGQILEKLFCEK-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- UVSBCUAQEZINCQ-UHFFFAOYSA-N methyl 3-formylbenzoate Chemical compound COC(=O)C1=CC=CC(C=O)=C1 UVSBCUAQEZINCQ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- WSPGRORDDACGQK-UHFFFAOYSA-N naphthalene-2,7-dicarbaldehyde Chemical compound C1=CC(C=O)=CC2=CC(C=O)=CC=C21 WSPGRORDDACGQK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- GKROKAVBUIADBS-UHFFFAOYSA-N phenanthrene-2-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(C=O)C=C3C=CC2=C1 GKROKAVBUIADBS-UHFFFAOYSA-N 0.000 description 1
- LHEOFIBQZSRTNC-UHFFFAOYSA-N phenanthrene-3-carbaldehyde Chemical compound C1=CC=C2C3=CC(C=O)=CC=C3C=CC2=C1 LHEOFIBQZSRTNC-UHFFFAOYSA-N 0.000 description 1
- QECIGCMPORCORE-UHFFFAOYSA-N phenanthrene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC3=CC=CC=C3C2=C1 QECIGCMPORCORE-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- YIYRXCXJFKZQBC-UHFFFAOYSA-N quinazoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=NC=C21 YIYRXCXJFKZQBC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- BATOPAZDIZEVQF-UHFFFAOYSA-N sorbic aldehyde Natural products CC=CC=CC=O BATOPAZDIZEVQF-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000000080 wetting 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/115—Cationic or anionic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/117—Free radical
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/12—Nitrogen compound containing
- Y10S430/121—Nitrogen in heterocyclic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/126—Halogen compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803021590 DE3021590A1 (de) | 1980-06-09 | 1980-06-09 | 4-halogen-5-(halogenmethyl-phenyl)-oxazol-derivate, ein verfahren zu ihrer herstellung und sie enthaltenden strahlungsempfindliche massen |
| ZA00813554A ZA813554B (en) | 1980-06-09 | 1981-05-27 | 4-halogeno-5-(halogenomethyl-phenyl)-oxazole derivatives,a process for the preparation thereof,and radiationsensitive composition containing these derivatives |
| DE8181104170T DE3173182D1 (en) | 1980-06-09 | 1981-06-01 | 4-halogen-5-(trichloromethyl-phenyl)-oxazole derivatives, process for preparing them and radiation-sensitive compositions containing them |
| EP81104170A EP0041675B1 (de) | 1980-06-09 | 1981-06-01 | 4-Halogen-5-(trichlormethyl-phenyl)-oxazol-Derivate, ein Verfahren zu ihrer Herstellung und sie enthaltende strahlungsempfindliche Massen |
| CA000378878A CA1169071A (en) | 1980-06-09 | 1981-06-02 | 4-halogeno-5-(halogenomethyl-phenyl)-oxazole derivatives, a process for the preparation thereof, and radiation-sensitive compositions containing these derivatives |
| AU71377/81A AU542659B2 (en) | 1980-06-09 | 1981-06-05 | Oxazole derivatives and radiation-sensitive compositions |
| JP8703181A JPS5731674A (en) | 1980-06-09 | 1981-06-08 | 4-halogeno-5-(halogenomethyl-phenyl)-oxazole derivative, manufacture and radiation-sensitive composition containing same |
| US06/272,050 US4371607A (en) | 1980-06-09 | 1981-06-09 | 4-Halogeno-5-(halogenomethyl-phenyl)-oxazole derivatives, a process for the preparation thereof, and radiation-sensitive compositions containing these derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803021590 DE3021590A1 (de) | 1980-06-09 | 1980-06-09 | 4-halogen-5-(halogenmethyl-phenyl)-oxazol-derivate, ein verfahren zu ihrer herstellung und sie enthaltenden strahlungsempfindliche massen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3021590A1 true DE3021590A1 (de) | 1981-12-17 |
Family
ID=6104170
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803021590 Withdrawn DE3021590A1 (de) | 1980-06-09 | 1980-06-09 | 4-halogen-5-(halogenmethyl-phenyl)-oxazol-derivate, ein verfahren zu ihrer herstellung und sie enthaltenden strahlungsempfindliche massen |
| DE8181104170T Expired DE3173182D1 (en) | 1980-06-09 | 1981-06-01 | 4-halogen-5-(trichloromethyl-phenyl)-oxazole derivatives, process for preparing them and radiation-sensitive compositions containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181104170T Expired DE3173182D1 (en) | 1980-06-09 | 1981-06-01 | 4-halogen-5-(trichloromethyl-phenyl)-oxazole derivatives, process for preparing them and radiation-sensitive compositions containing them |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4371607A (https=) |
| EP (1) | EP0041675B1 (https=) |
| JP (1) | JPS5731674A (https=) |
| AU (1) | AU542659B2 (https=) |
| CA (1) | CA1169071A (https=) |
| DE (2) | DE3021590A1 (https=) |
| ZA (1) | ZA813554B (https=) |
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0726498A1 (en) | 1995-02-10 | 1996-08-14 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition |
| EP1471387A2 (en) | 2003-03-31 | 2004-10-27 | Fuji Photo Film Co., Ltd. | Photosensitive composition and compound used thereof |
| DE102004022137B3 (de) * | 2004-05-05 | 2005-09-08 | Kodak Polychrome Graphics Gmbh | π-verzweigte Sensibilisatoren enthaltende strahlungsempfindliche Zusammensetzungen und darauf basierende bebilderbare Elemente |
| EP1615073A1 (en) | 2004-07-06 | 2006-01-11 | Fuji Photo Film Co., Ltd. | Photosensitive composition and image recording method using the same |
| EP1662318A1 (en) | 1999-03-09 | 2006-05-31 | Fuji Photo Film Co., Ltd. | 1,3-dihydro-1-oxo-2H-indene derivative |
| EP1701213A2 (en) | 2005-03-08 | 2006-09-13 | Fuji Photo Film Co., Ltd. | Photosensitive composition |
| EP1707352A1 (en) | 2005-03-31 | 2006-10-04 | Fuji Photo Film Co., Ltd. | Method of producing a planographic printing plate |
| EP1952998A2 (en) | 2007-02-01 | 2008-08-06 | FUJIFILM Corporation | Ink-jet recording device |
| EP1955850A2 (en) | 2007-02-07 | 2008-08-13 | FUJIFILM Corporation | Ink-jet head maintenance device, ink-jet recording device and ink-jet head maintenance method |
| EP1955858A1 (en) | 2007-02-06 | 2008-08-13 | FUJIFILM Corporation | Undercoat solution, ink-jet recording method and ink-jet recording device |
| EP1964893A1 (en) | 2007-02-26 | 2008-09-03 | FUJIFILM Corporation | Ink composition, inkjet recording method, printed material, and ink set |
| EP1975213A1 (en) | 2006-07-03 | 2008-10-01 | FUJIFILM Corporation | Ink composition, injet recording method, printed material, and process for producing lithographic printing plate |
| EP1975211A1 (en) | 2007-03-30 | 2008-10-01 | FUJIFILM Corporation | Ink composition and image recording method and image recorded matter using same |
| EP1975160A1 (en) | 2007-03-30 | 2008-10-01 | Fujifilm Corporation | Polymerizable compound, polymer, ink composition, printed articles and inkjet recording method |
| EP1988136A1 (en) | 2007-03-01 | 2008-11-05 | FUJIFILM Corporation | Ink composition, inkjet recording method, printed material, method for producing planographic printing plate, and planographic printing plate |
| EP2042243A2 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Coater and ink-jet recording device using the same |
| EP2042335A2 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Inkjet recording method |
| EP2042572A1 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Ink composition, inkjet recording method, printed material, and process for producing molded printed material |
| EP2088176A1 (en) | 2008-02-07 | 2009-08-12 | FUJIFILM Corporation | Ink composition, inkjet recording method, printed material, and molded printed material |
| EP2093265A1 (en) | 2008-02-25 | 2009-08-26 | FUJIFILM Corporation | Inkjet ink composition, and inkjet recording method and printed material employing same |
| EP2100925A2 (en) | 2008-03-11 | 2009-09-16 | FUJIFILM Corporation | Pigment composition, ink composition, printed article, inkjet recording method and polyallylamine derivative |
| EP2105478A1 (en) | 2008-03-26 | 2009-09-30 | FUJIFILM Corporation | Inkjet recording method and inkjet recording system |
| EP2130881A1 (en) | 2008-06-02 | 2009-12-09 | FUJIFILM Corporation | Pigment dispersion and ink composition using the same |
| EP2166049A1 (en) | 2008-09-19 | 2010-03-24 | Fujifilm Corporation | Ink composition, inkjet recording method and method for producing printed formed article |
| EP2169021A1 (en) | 2008-09-25 | 2010-03-31 | Fujifilm Corporation | Ink composition, inkjet recording method, and printed material |
| EP2216377A1 (en) | 2009-02-09 | 2010-08-11 | FUJIFILM Corporation | Ink composition, and inkjet recording method |
| EP2216378A1 (en) | 2009-02-05 | 2010-08-11 | Fujifilm Corporation | Nonaqueous ink, image-recording method, image-recording apparatus and recorded article |
| EP2230284A1 (en) | 2009-03-17 | 2010-09-22 | Fujifilm Corporation | Ink composition and inkjet recording method |
| EP2230285A1 (en) | 2009-03-19 | 2010-09-22 | Fujifilm Corporation | Ink composition, inkjet recording method, printed material, and process for producing molded printed material |
| EP2236570A2 (en) | 2009-03-31 | 2010-10-06 | Fujifilm Corporation | Ink composition, ink composition for inkjet recording, inkjet recording method, and printed article obtained by inkjet recording method |
| EP2298841A1 (en) | 2009-09-18 | 2011-03-23 | FUJIFILM Corporation | Ink composition, and inkjet recording method |
| EP2311918A1 (en) | 2009-09-29 | 2011-04-20 | FUJIFILM Corporation | Ink composition, and inkjet recording method |
| EP2644664A1 (en) | 2012-03-29 | 2013-10-02 | Fujifilm Corporation | Actinic radiation-curing type ink composition, inkjet recording method, decorative sheet, decorative sheet molded product, process for producing in-mold molded article, and in-mold molded article |
| WO2014136923A1 (ja) | 2013-03-07 | 2014-09-12 | 富士フイルム株式会社 | インクジェットインク組成物、インクジェット記録方法、印刷物、及び、成型印刷物の製造方法 |
| EP2842763A2 (en) | 2013-08-30 | 2015-03-04 | Fujifilm Corporation | Image formation method, decorative sheet, decorative sheet molding, process for producing in-mold molded product, in-mold molded product, and ink set |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3333450A1 (de) * | 1983-09-16 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Trihalogenmethylgruppen enthaltende carbonylmethylenheterocyclen, verfahren zu ihrer herstellung und lichtempfindliches gemisch, das diese verbindungen enthaelt |
| GB2189493B (en) * | 1986-04-11 | 1990-12-19 | James C W Chien | Self-developing resist |
| DE3613632A1 (de) * | 1986-04-23 | 1987-10-29 | Hoechst Ag | Photopolymerisierbares gemisch und dieses enthaltendes photopolymerisierbares aufzeichnungsmaterial |
| DE3706880A1 (de) * | 1987-03-04 | 1988-09-15 | Hoechst Ag | 4-chloroxazol-derivate, verfahren zu ihrer herstellung und ihre verwendung |
| DE3706881A1 (de) * | 1987-03-04 | 1988-09-15 | Hoechst Ag | Neue 4-chloroxazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| DE3738567A1 (de) * | 1987-03-12 | 1988-09-22 | Merck Patent Gmbh | Coreaktive fotoinitiatoren |
| DE3821585A1 (de) * | 1987-09-13 | 1989-03-23 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial fuer hochenergetische strahlung |
| US5216158A (en) * | 1988-03-07 | 1993-06-01 | Hoechst Aktiengesellschaft | Oxadiazole compounds containing 4,6-bis-trichloromethyl-S-triazin-2-yl groups, process for their preparation |
| DE3807381A1 (de) * | 1988-03-07 | 1989-09-21 | Hoechst Ag | 4,6-bis-trichlormethyl-s-triazin-2-ylgruppen enthaltende heterocyclische verbindungen, verfahren zu ihrer herstellung und lichtempfindliches gemisch, das diese verbindung enthaelt |
| JPH01229003A (ja) * | 1988-03-09 | 1989-09-12 | Fuji Photo Film Co Ltd | 光重合性組成物 |
| DE3930087A1 (de) * | 1989-09-09 | 1991-03-14 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial |
| DE3930086A1 (de) * | 1989-09-09 | 1991-03-21 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial |
| DE4006190A1 (de) * | 1990-02-28 | 1991-08-29 | Hoechst Ag | Negativ arbeitendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial |
| JPH0876380A (ja) | 1994-09-06 | 1996-03-22 | Fuji Photo Film Co Ltd | ポジ型印刷版組成物 |
| EP1235104A4 (en) | 2000-08-29 | 2008-10-01 | Jsr Corp | COMPOSITION HAVING SUBSTANTIALLY MODIFIABLE REFRACTION INDEX AND METHOD FOR FORMING REFRACTION INDEX PATTERN |
| CA2431358A1 (en) | 2000-12-11 | 2002-06-20 | Jsr Corporation | Radiation sensitive refractive index changing composition and refractive index changing method |
| CN1225509C (zh) | 2001-02-19 | 2005-11-02 | 捷时雅株式会社 | 感放射线性折射率变化性组合物 |
| RU2275401C2 (ru) | 2001-03-13 | 2006-04-27 | Джей Эс Эр КОРПОРЕЙШН | Радиационно-чувстивительная композиция, изменяющая показатель преломления, и ее применение |
| JP2003043682A (ja) | 2001-08-01 | 2003-02-13 | Jsr Corp | 感放射線性誘電率変化性組成物、誘電率変化法 |
| DE10307453B4 (de) * | 2003-02-21 | 2005-07-21 | Kodak Polychrome Graphics Gmbh | Oxazol-Derivate enthaltende strahlungsempfindliche Zusammensetzungen und darauf basierende bebilderbare Elemente |
| WO2008090640A1 (ja) | 2007-01-23 | 2008-07-31 | Fujifilm Corporation | オキシム化合物、感光性組成物、カラーフィルタ及びその製造方法、並びに液晶表示素子 |
| KR20100061730A (ko) | 2007-09-19 | 2010-06-08 | 후지필름 가부시키가이샤 | 아세틸렌 화합물, 그 염, 그 축합물 및 그 조성물 |
| JP5581219B2 (ja) | 2008-01-25 | 2014-08-27 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | チオフェンおよびホスファチジルイノシトール３−キナーゼ（ｐｉ３ｋ）阻害薬としてのその使用 |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| WO2010090716A1 (en) | 2009-01-30 | 2010-08-12 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
| MX2013001660A (es) | 2010-08-11 | 2013-06-03 | Millenium Pharmaceuticals Inc | Heteroarilos y usos de los mismos. |
| US8859768B2 (en) | 2010-08-11 | 2014-10-14 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| TW201307309A (zh) | 2010-10-13 | 2013-02-16 | Millennium Pharm Inc | 雜芳基化合物及其用途 |
| US9682085B2 (en) | 2013-02-22 | 2017-06-20 | Shifa Biomedical Corporation | Anti-proprotein convertase subtilisin kexin type 9 (anti-PCSK9) compounds and methods of using the same in the treatment and/or prevention of cardiovascular diseases |
| CN105228616B (zh) * | 2013-03-15 | 2019-05-03 | 实发生物医学公司 | 抗前蛋白转化酶枯草杆菌蛋白酶Kexin 9型（抗PCSK9）化合物及其用于治疗和/或预防心血管疾病的方法 |
| WO2014150395A1 (en) | 2013-03-15 | 2014-09-25 | Shifa Biomedical Corporation | Anti-pcsk9 compounds and methods for the treatment and/or prevention of cardiovascular diseases |
| CN109475521B (zh) | 2016-06-21 | 2022-11-15 | 实发生物医学公司 | 抗前蛋白转化酶枯草杆菌蛋白酶Kexin 9型(抗PCSK9)化合物及其用于治疗和/或预防心血管疾病的方法 |
| CN116836334B (zh) * | 2023-08-28 | 2023-11-28 | 兰州大学 | 一种用于分离检测锝的闪烁树脂及其制备方法和应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3842019A (en) * | 1969-04-04 | 1974-10-15 | Minnesota Mining & Mfg | Use of sulfonic acid salts in cationic polymerization |
| US3954475A (en) * | 1971-09-03 | 1976-05-04 | Minnesota Mining And Manufacturing Company | Photosensitive elements containing chromophore-substituted vinyl-halomethyl-s-triazines |
| US3879356A (en) * | 1973-08-29 | 1975-04-22 | Eastman Kodak Co | Light-sensitive polymeric compositions |
| US3912606A (en) * | 1974-11-21 | 1975-10-14 | Eastman Kodak Co | Photosensitive compositions containing benzoxazole sensitizers |
| US4189323A (en) * | 1977-04-25 | 1980-02-19 | Hoechst Aktiengesellschaft | Radiation-sensitive copying composition |
| US4140515A (en) * | 1977-05-12 | 1979-02-20 | Monsanto Company | Aryl-3-isoxazole benzoates as plant growth regulants and herbicides |
| DE2844394A1 (de) * | 1978-10-12 | 1980-04-30 | Hoechst Ag | Neue 4-chloroxazole und verfahren zu deren herstellung |
-
1980
- 1980-06-09 DE DE19803021590 patent/DE3021590A1/de not_active Withdrawn
-
1981
- 1981-05-27 ZA ZA00813554A patent/ZA813554B/xx unknown
- 1981-06-01 EP EP81104170A patent/EP0041675B1/de not_active Expired
- 1981-06-01 DE DE8181104170T patent/DE3173182D1/de not_active Expired
- 1981-06-02 CA CA000378878A patent/CA1169071A/en not_active Expired
- 1981-06-05 AU AU71377/81A patent/AU542659B2/en not_active Ceased
- 1981-06-08 JP JP8703181A patent/JPS5731674A/ja active Granted
- 1981-06-09 US US06/272,050 patent/US4371607A/en not_active Expired - Fee Related
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0726498A1 (en) | 1995-02-10 | 1996-08-14 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition |
| EP1662318A1 (en) | 1999-03-09 | 2006-05-31 | Fuji Photo Film Co., Ltd. | 1,3-dihydro-1-oxo-2H-indene derivative |
| EP1471387A2 (en) | 2003-03-31 | 2004-10-27 | Fuji Photo Film Co., Ltd. | Photosensitive composition and compound used thereof |
| DE102004022137B3 (de) * | 2004-05-05 | 2005-09-08 | Kodak Polychrome Graphics Gmbh | π-verzweigte Sensibilisatoren enthaltende strahlungsempfindliche Zusammensetzungen und darauf basierende bebilderbare Elemente |
| EP1615073A1 (en) | 2004-07-06 | 2006-01-11 | Fuji Photo Film Co., Ltd. | Photosensitive composition and image recording method using the same |
| EP1701213A2 (en) | 2005-03-08 | 2006-09-13 | Fuji Photo Film Co., Ltd. | Photosensitive composition |
| EP1707352A1 (en) | 2005-03-31 | 2006-10-04 | Fuji Photo Film Co., Ltd. | Method of producing a planographic printing plate |
| EP1975213A1 (en) | 2006-07-03 | 2008-10-01 | FUJIFILM Corporation | Ink composition, injet recording method, printed material, and process for producing lithographic printing plate |
| EP1952998A2 (en) | 2007-02-01 | 2008-08-06 | FUJIFILM Corporation | Ink-jet recording device |
| EP1955858A1 (en) | 2007-02-06 | 2008-08-13 | FUJIFILM Corporation | Undercoat solution, ink-jet recording method and ink-jet recording device |
| EP1955850A2 (en) | 2007-02-07 | 2008-08-13 | FUJIFILM Corporation | Ink-jet head maintenance device, ink-jet recording device and ink-jet head maintenance method |
| EP1964893A1 (en) | 2007-02-26 | 2008-09-03 | FUJIFILM Corporation | Ink composition, inkjet recording method, printed material, and ink set |
| EP1988136A1 (en) | 2007-03-01 | 2008-11-05 | FUJIFILM Corporation | Ink composition, inkjet recording method, printed material, method for producing planographic printing plate, and planographic printing plate |
| EP1975211A1 (en) | 2007-03-30 | 2008-10-01 | FUJIFILM Corporation | Ink composition and image recording method and image recorded matter using same |
| EP1975160A1 (en) | 2007-03-30 | 2008-10-01 | Fujifilm Corporation | Polymerizable compound, polymer, ink composition, printed articles and inkjet recording method |
| EP2042335A2 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Inkjet recording method |
| EP2042243A2 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Coater and ink-jet recording device using the same |
| EP2042572A1 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Ink composition, inkjet recording method, printed material, and process for producing molded printed material |
| EP2088176A1 (en) | 2008-02-07 | 2009-08-12 | FUJIFILM Corporation | Ink composition, inkjet recording method, printed material, and molded printed material |
| EP2093265A1 (en) | 2008-02-25 | 2009-08-26 | FUJIFILM Corporation | Inkjet ink composition, and inkjet recording method and printed material employing same |
| EP2100925A2 (en) | 2008-03-11 | 2009-09-16 | FUJIFILM Corporation | Pigment composition, ink composition, printed article, inkjet recording method and polyallylamine derivative |
| EP2105478A1 (en) | 2008-03-26 | 2009-09-30 | FUJIFILM Corporation | Inkjet recording method and inkjet recording system |
| EP2130881A1 (en) | 2008-06-02 | 2009-12-09 | FUJIFILM Corporation | Pigment dispersion and ink composition using the same |
| EP2166049A1 (en) | 2008-09-19 | 2010-03-24 | Fujifilm Corporation | Ink composition, inkjet recording method and method for producing printed formed article |
| EP2169021A1 (en) | 2008-09-25 | 2010-03-31 | Fujifilm Corporation | Ink composition, inkjet recording method, and printed material |
| EP2216378A1 (en) | 2009-02-05 | 2010-08-11 | Fujifilm Corporation | Nonaqueous ink, image-recording method, image-recording apparatus and recorded article |
| EP2216377A1 (en) | 2009-02-09 | 2010-08-11 | FUJIFILM Corporation | Ink composition, and inkjet recording method |
| EP2230284A1 (en) | 2009-03-17 | 2010-09-22 | Fujifilm Corporation | Ink composition and inkjet recording method |
| EP2230285A1 (en) | 2009-03-19 | 2010-09-22 | Fujifilm Corporation | Ink composition, inkjet recording method, printed material, and process for producing molded printed material |
| EP2236570A2 (en) | 2009-03-31 | 2010-10-06 | Fujifilm Corporation | Ink composition, ink composition for inkjet recording, inkjet recording method, and printed article obtained by inkjet recording method |
| EP2298841A1 (en) | 2009-09-18 | 2011-03-23 | FUJIFILM Corporation | Ink composition, and inkjet recording method |
| EP2311918A1 (en) | 2009-09-29 | 2011-04-20 | FUJIFILM Corporation | Ink composition, and inkjet recording method |
| EP2644664A1 (en) | 2012-03-29 | 2013-10-02 | Fujifilm Corporation | Actinic radiation-curing type ink composition, inkjet recording method, decorative sheet, decorative sheet molded product, process for producing in-mold molded article, and in-mold molded article |
| WO2014136923A1 (ja) | 2013-03-07 | 2014-09-12 | 富士フイルム株式会社 | インクジェットインク組成物、インクジェット記録方法、印刷物、及び、成型印刷物の製造方法 |
| EP2842763A2 (en) | 2013-08-30 | 2015-03-04 | Fujifilm Corporation | Image formation method, decorative sheet, decorative sheet molding, process for producing in-mold molded product, in-mold molded product, and ink set |
Also Published As
| Publication number | Publication date |
|---|---|
| AU542659B2 (en) | 1985-02-28 |
| JPS5731674A (en) | 1982-02-20 |
| AU7137781A (en) | 1981-12-10 |
| EP0041675A2 (de) | 1981-12-16 |
| EP0041675B1 (de) | 1985-12-11 |
| CA1169071A (en) | 1984-06-12 |
| JPH034898B2 (https=) | 1991-01-24 |
| US4371607A (en) | 1983-02-01 |
| EP0041675A3 (en) | 1982-06-16 |
| ZA813554B (en) | 1982-06-30 |
| DE3173182D1 (en) | 1986-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0041675B1 (de) | 4-Halogen-5-(trichlormethyl-phenyl)-oxazol-Derivate, ein Verfahren zu ihrer Herstellung und sie enthaltende strahlungsempfindliche Massen | |
| EP0041674B1 (de) | 2-(Trichlormethyl-phenyl)-4-halogen-oxazol-Derivate, ein Verfahren zu ihrer Herstellung und sie enthaltende strahlungsempfindliche Massen | |
| EP0137452B1 (de) | Lichtempfindliche, Trichlormethylgruppen aufweisende Verbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltendes lichtempfindliches Gemisch | |
| EP0062610B1 (de) | Photopolymerisationsverfahren | |
| EP0006626B1 (de) | Strahlungsempfindliches Gemisch und Verfahren zur Herstellung von Reliefbildern | |
| DE2718259C2 (de) | Strahlungsempfindliches Gemisch | |
| DE2610842C3 (de) | Strahlungsempfindliche Kopiermasse | |
| DE3333450A1 (de) | Trihalogenmethylgruppen enthaltende carbonylmethylenheterocyclen, verfahren zu ihrer herstellung und lichtempfindliches gemisch, das diese verbindungen enthaelt | |
| DE69903453T2 (de) | Ungesättigte oxim-derivate und ihre anwendung als latente säuren | |
| EP0062611B1 (de) | Photopolymerisationsverfahren | |
| EP0332044B1 (de) | 4,6-Bis-trichlormethyl-s-triazin-2-ylgruppen enthaltende heterocyclische Verbindungen, Verfahren zu ihrer Herstellung und lichtempfindliches Gemisch, das diese Verbindungen enthält | |
| EP0568496B1 (de) | Photoresistmaterial auf Basis von Polystyrolen | |
| EP0501919A1 (de) | Strahlungsempfindliche Zusammensetzungen auf der Basis von Polyphenolen und Acetalen | |
| DE2635929A1 (de) | Photopolymerisierbare epoxidharze | |
| EP0071571A1 (de) | Photopolymerisationsverfahren | |
| DE3725741A1 (de) | Positiv arbeitendes strahlungsempfindliches gemisch | |
| EP0347381A1 (de) | Ungesättigte beta-Ketoesteracetale und ihre Anwendungen | |
| EP0510443B1 (de) | Negativ arbeitendes strahlungsempfindliches Gemisch und damit hergestelltes strahlungsempfindliches Aufzeichnungsmaterial | |
| EP0502819A1 (de) | Säurekatalytisch vernetzbare Copolymere | |
| EP0475903B1 (de) | Säurelabile Lösungsinhibitoren und darauf basierende positiv und negativ arbeitende strahlungsempfindliche Zusammensetzung | |
| EP0510442A1 (de) | Substituted 1-sulfonyloxy-2-pyridones, process for their preparation and their use | |
| EP0332043B1 (de) | 4,6-Bis-trichlormethyl-s-triazin-2-ylgruppen enthaltende Oxadiazolverbindungen, Verfahren zu ihrer Herstellung und lichtempfindliches Gemisch, das diese Verbindungen enthält | |
| US5216158A (en) | Oxadiazole compounds containing 4,6-bis-trichloromethyl-S-triazin-2-yl groups, process for their preparation | |
| EP0387193A1 (de) | Substituierte ungesättigte bireaktive bicyclische Imide und deren Verwendung | |
| EP0546997A1 (de) | Strahlungsempfindliche Polymere |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |