JPS6221023B2 - - Google Patents
Info
- Publication number
- JPS6221023B2 JPS6221023B2 JP54005665A JP566579A JPS6221023B2 JP S6221023 B2 JPS6221023 B2 JP S6221023B2 JP 54005665 A JP54005665 A JP 54005665A JP 566579 A JP566579 A JP 566579A JP S6221023 B2 JPS6221023 B2 JP S6221023B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methyl
- phenyl
- acetyl
- lower alkyl
- 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.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- -1 n -propyl Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000006482 condensation reaction Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- YIBBMDDEXKBIAM-UHFFFAOYSA-M potassium;pentoxymethanedithioate Chemical compound [K+].CCCCCOC([S-])=S YIBBMDDEXKBIAM-UHFFFAOYSA-M 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 15
- 239000000835 fiber Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000975 dye Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229920002647 polyamide Polymers 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000990 laser dye Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- QBZXQDLRICAIMA-UHFFFAOYSA-N 4-acetyl-5-methyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C)=C(C)NN1C1=CC=CC=C1 QBZXQDLRICAIMA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000002081 enamines Chemical class 0.000 description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical compound C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 description 2
- FQNKTJPBXAZUGC-UHFFFAOYSA-N 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O FQNKTJPBXAZUGC-UHFFFAOYSA-N 0.000 description 2
- SGLKFWMIZOJHCL-UHFFFAOYSA-N 2-acetylindene-1,3-dione Chemical compound C1=CC=C2C(=O)C(C(=O)C)C(=O)C2=C1 SGLKFWMIZOJHCL-UHFFFAOYSA-N 0.000 description 2
- UTZHUXAPJIBIBQ-UHFFFAOYSA-N 3-acetyl-4-hydroxychromen-2-one Chemical compound C1=CC=C2OC(=O)C(C(=O)C)=C(O)C2=C1 UTZHUXAPJIBIBQ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004287 Dehydroacetic acid Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 150000001767 cationic compounds Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229940061632 dehydroacetic acid Drugs 0.000 description 2
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 2
- 235000019258 dehydroacetic acid Nutrition 0.000 description 2
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- LEIGZDOJLFBMDH-UHFFFAOYSA-N 1-(1-ethyl-3-hydroxyindol-2-yl)ethanone Chemical compound C1=CC=C2N(CC)C(C(C)=O)=C(O)C2=C1 LEIGZDOJLFBMDH-UHFFFAOYSA-N 0.000 description 1
- PHYIZDJWUOUDRP-UHFFFAOYSA-N 1-(2,6-dihydroxy-4,4-dimethylcyclohex-2-en-1-yl)ethanone Chemical compound CC(=O)C1C(O)CC(C)(C)C=C1O PHYIZDJWUOUDRP-UHFFFAOYSA-N 0.000 description 1
- BTFDPHISTXGHRX-UHFFFAOYSA-N 1-(2-hydroxy-1-benzothiophen-3-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(O)SC2=C1 BTFDPHISTXGHRX-UHFFFAOYSA-N 0.000 description 1
- DNJABWNLJPWMHV-UHFFFAOYSA-N 1-(2-hydroxy-3h-1-benzofuran-2-yl)ethanone Chemical compound C1=CC=C2OC(C(=O)C)(O)CC2=C1 DNJABWNLJPWMHV-UHFFFAOYSA-N 0.000 description 1
- OBDZRLYUIDUJHZ-UHFFFAOYSA-N 1-(3-hydroxy-1-benzofuran-2-yl)ethanone Chemical compound C1=CC=C2C(O)=C(C(=O)C)OC2=C1 OBDZRLYUIDUJHZ-UHFFFAOYSA-N 0.000 description 1
- XQNRBPYRMAXIOB-UHFFFAOYSA-N 1-(3-hydroxy-1-benzothiophen-2-yl)ethanone Chemical compound C1=CC=C2C(O)=C(C(=O)C)SC2=C1 XQNRBPYRMAXIOB-UHFFFAOYSA-N 0.000 description 1
- OPDDOMLDXILSMC-UHFFFAOYSA-N 1-benzyl-5-(2-chloroacetyl)-1,3-diazinane-2,4,6-trione Chemical compound O=C1C(C(=O)CCl)C(=O)NC(=O)N1CC1=CC=CC=C1 OPDDOMLDXILSMC-UHFFFAOYSA-N 0.000 description 1
- LDWHGHNLDXDEAL-UHFFFAOYSA-N 1-benzyl-5-propanoyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1C(C(=O)CC)C(=O)NC(=O)N1CC1=CC=CC=C1 LDWHGHNLDXDEAL-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
- WMMYAVXJTPAQEG-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-4-(2-nitroacetyl)-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C[N+]([O-])=O)=C(C)NN1C1=CC=CC(Cl)=C1 WMMYAVXJTPAQEG-UHFFFAOYSA-N 0.000 description 1
- VKNTUFZVTHWDMG-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-methyl-4-propanoyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)CC)=C(C)NN1C1=CC=C(Cl)C=C1 VKNTUFZVTHWDMG-UHFFFAOYSA-N 0.000 description 1
- JIIFWNZHWIEOKS-UHFFFAOYSA-N 2-[4-acetyl-5-(4-chlorophenyl)-3-oxo-1h-pyrazol-2-yl]ethyl acetate Chemical compound O=C1N(CCOC(=O)C)NC(C=2C=CC(Cl)=CC=2)=C1C(C)=O JIIFWNZHWIEOKS-UHFFFAOYSA-N 0.000 description 1
- LYGSTMCNBMHIRA-UHFFFAOYSA-N 2-acetyl-4,5,6,7-tetrachloroindene-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(=O)C(C(=O)C)C2=O LYGSTMCNBMHIRA-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- JKTQHJKAIBONLQ-UHFFFAOYSA-N 2-amino-4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C(N)=C1 JKTQHJKAIBONLQ-UHFFFAOYSA-N 0.000 description 1
- GTGZDNRRWMWLIG-UHFFFAOYSA-N 2-butylimino-n,n-diethyl-3-nitrochromen-7-amine Chemical compound C1=C(N(CC)CC)C=CC2=C1OC(=NCCCC)C([N+]([O-])=O)=C2 GTGZDNRRWMWLIG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- ICWOPJPPQWGEBD-UHFFFAOYSA-N 3-(4-chlorophenyl)-7-piperidin-1-ylchromene-2-thione Chemical compound C1=CC(Cl)=CC=C1C1=CC2=CC=C(N3CCCCC3)C=C2OC1=S ICWOPJPPQWGEBD-UHFFFAOYSA-N 0.000 description 1
- NGXLZSYWEVIMPO-UHFFFAOYSA-N 3-acetyl-4-hydroxy-1-methylquinolin-2-one Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)C)=C(O)C2=C1 NGXLZSYWEVIMPO-UHFFFAOYSA-N 0.000 description 1
- YIEGSQXJNMZGBV-UHFFFAOYSA-N 3-acetylpyrido[1,2-a]pyrimidine-2,4-dione Chemical compound C1=CC=CN2C(=O)C(C(=O)C)C(=O)N=C21 YIEGSQXJNMZGBV-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
- MLNXBDIOCRSFNI-UHFFFAOYSA-N 4,4-diethoxybutan-2-one Chemical compound CCOC(CC(C)=O)OCC MLNXBDIOCRSFNI-UHFFFAOYSA-N 0.000 description 1
- GJNIXYAQTHSSBG-UHFFFAOYSA-N 4-(4-acetyl-5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonamide Chemical compound O=C1C(C(=O)C)=C(C)NN1C1=CC=C(S(N)(=O)=O)C=C1 GJNIXYAQTHSSBG-UHFFFAOYSA-N 0.000 description 1
- HJZQFQGRNAGOHH-UHFFFAOYSA-N 4-(4-acetyl-5-methyl-3-oxo-1h-pyrazol-2-yl)benzoic acid Chemical compound O=C1C(C(=O)C)=C(C)NN1C1=CC=C(C(O)=O)C=C1 HJZQFQGRNAGOHH-UHFFFAOYSA-N 0.000 description 1
- DZBNCUAIPQOTLM-UHFFFAOYSA-N 4-(4-acetyl-5-methyl-3-oxo-1h-pyrazol-2-yl)benzonitrile Chemical compound O=C1C(C(=O)C)=C(C)NN1C1=CC=C(C#N)C=C1 DZBNCUAIPQOTLM-UHFFFAOYSA-N 0.000 description 1
- PLESVVIVRNVEQP-UHFFFAOYSA-N 4-acetyl-1,5-dimethyl-2-phenylpyrazol-3-one Chemical compound O=C1C(C(=O)C)=C(C)N(C)N1C1=CC=CC=C1 PLESVVIVRNVEQP-UHFFFAOYSA-N 0.000 description 1
- OYKNXAFGSOYNGP-UHFFFAOYSA-N 4-acetyl-2,5-dimethyl-1h-pyrazol-3-one Chemical compound CC(=O)C1=C(C)NN(C)C1=O OYKNXAFGSOYNGP-UHFFFAOYSA-N 0.000 description 1
- HFJRZIHNDCVMKF-UHFFFAOYSA-N 4-acetyl-2,5-diphenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C)=C(C=2C=CC=CC=2)NN1C1=CC=CC=C1 HFJRZIHNDCVMKF-UHFFFAOYSA-N 0.000 description 1
- RLKKLLOSWYWJBF-UHFFFAOYSA-N 4-acetyl-2,6-diphenyldiazinane-3,5-dione Chemical compound O=C1C(C(=O)C)C(=O)C(C=2C=CC=CC=2)NN1C1=CC=CC=C1 RLKKLLOSWYWJBF-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
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- 230000010933 acylation Effects 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
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- NPTMFBRRGUJMEF-UHFFFAOYSA-N ethyl 4-acetyl-2-benzyl-3-oxo-1h-pyrazole-5-carboxylate Chemical compound O=C1C(C(C)=O)=C(C(=O)OCC)NN1CC1=CC=CC=C1 NPTMFBRRGUJMEF-UHFFFAOYSA-N 0.000 description 1
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- FMOBMMRTQSAHNA-UHFFFAOYSA-N ethyl n-[7-(diethylamino)-3-phenylchromen-2-ylidene]carbamate Chemical compound CCOC(=O)N=C1OC=2C=C(N(CC)CC)C=CC=2C=C1C1=CC=CC=C1 FMOBMMRTQSAHNA-UHFFFAOYSA-N 0.000 description 1
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- 235000012245 magnesium oxide Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- NJFAOPXBXRFMIC-UHFFFAOYSA-N methyl 4-acetyl-3-oxo-2-propan-2-yl-1h-pyrazole-5-carboxylate Chemical compound COC(=O)C=1NN(C(C)C)C(=O)C=1C(C)=O NJFAOPXBXRFMIC-UHFFFAOYSA-N 0.000 description 1
- FLBHOKAWNBWMOD-UHFFFAOYSA-N n,n,4-trimethyl-2-methylidenechromen-7-amine Chemical compound CC1=CC(=C)OC2=CC(N(C)C)=CC=C21 FLBHOKAWNBWMOD-UHFFFAOYSA-N 0.000 description 1
- XBKYDGMQFYFATR-UHFFFAOYSA-N n,n-diethyl-2-imino-3-(4-nitrophenyl)chromen-7-amine Chemical compound N=C1OC2=CC(N(CC)CC)=CC=C2C=C1C1=CC=C([N+]([O-])=O)C=C1 XBKYDGMQFYFATR-UHFFFAOYSA-N 0.000 description 1
- ZZSUWYHXBHVPKO-UHFFFAOYSA-N n,n-diethyl-2-methylidenechromen-7-amine Chemical compound C1=CC(=C)OC2=CC(N(CC)CC)=CC=C21 ZZSUWYHXBHVPKO-UHFFFAOYSA-N 0.000 description 1
- UCUQPNNTWJWMLR-UHFFFAOYSA-N n-(4-acetyl-3-oxo-2-phenyl-1h-pyrazol-5-yl)acetamide Chemical compound O=C1C(C(C)=O)=C(NC(=O)C)NN1C1=CC=CC=C1 UCUQPNNTWJWMLR-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Coloring (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782803104 DE2803104A1 (de) | 1978-01-25 | 1978-01-25 | Heterocyclische farbstoffe |
| DE19782844606 DE2844606A1 (de) | 1978-10-13 | 1978-10-13 | Heterocyclische farbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54110226A JPS54110226A (en) | 1979-08-29 |
| JPS6221023B2 true JPS6221023B2 (en:Method) | 1987-05-11 |
Family
ID=25773703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP566579A Granted JPS54110226A (en) | 1978-01-25 | 1979-01-23 | Dye |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4260776A (en:Method) |
| JP (1) | JPS54110226A (en:Method) |
| CH (1) | CH654165GA3 (en:Method) |
| FR (1) | FR2415648A1 (en:Method) |
| GB (1) | GB2013703B (en:Method) |
| IT (1) | IT7919536A0 (en:Method) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4948893A (en) * | 1988-05-09 | 1990-08-14 | Eastman Kodak Company | Novel benzofuran dyes |
| US5110825A (en) * | 1989-12-28 | 1992-05-05 | Shionogi & Co., Ltd. | Benzofuran derivative |
| DE4126244A1 (de) * | 1991-08-08 | 1993-02-11 | Bayer Ag | Massefaerben von kunststoffen |
| DE50200247D1 (de) * | 2001-07-03 | 2004-03-25 | Dyomics Gmbh | Verbindungen auf der Basis von 2-bzw. 4-Chromenyliden-Merocyaninen und ihre Verwendung |
| WO2005061519A1 (en) * | 2003-12-19 | 2005-07-07 | Takeda San Diego, Inc. | Kinase inhibitors |
| US20050250829A1 (en) * | 2004-04-23 | 2005-11-10 | Takeda San Diego, Inc. | Kinase inhibitors |
| US7550598B2 (en) * | 2004-08-18 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| DE602005023333D1 (de) * | 2004-10-15 | 2010-10-14 | Takeda Pharmaceutical | Kinaseinhibitoren |
| US8119655B2 (en) * | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| MX2009003793A (es) | 2006-10-09 | 2009-12-14 | Takeda Pharmaceutical | Inhibidores de cinasa. |
| JP2010505961A (ja) * | 2006-10-09 | 2010-02-25 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965486A (en) * | 1958-06-02 | 1960-12-20 | Eastman Kodak Co | Polymethine sensitizing dyes and photographic emulsions |
| BE755575A (fr) * | 1969-09-02 | 1971-03-01 | Ciba Geigy | Nouveaux pigments pyrazoloniques, leur procede de preparation et leur emploi pour la pigmentation de matieres organiques a poids moleculaire eleve |
| US4144243A (en) * | 1970-07-30 | 1979-03-13 | Bayer Aktiengesellschaft | 3-Pyrozolyl-4-triazolyl compounds |
| DE2045049A1 (de) * | 1970-09-11 | 1972-03-23 | Dr Karl Thomae GmbH, 7950 Biberach | Neue Nitrofurandenvate und Ver fahren zu ihrer Herstellung |
-
1979
- 1979-01-23 IT IT7919536A patent/IT7919536A0/it unknown
- 1979-01-23 US US06/005,925 patent/US4260776A/en not_active Expired - Lifetime
- 1979-01-23 GB GB7902332A patent/GB2013703B/en not_active Expired
- 1979-01-23 JP JP566579A patent/JPS54110226A/ja active Granted
- 1979-01-24 CH CH71979A patent/CH654165GA3/de unknown
- 1979-01-24 FR FR7901763A patent/FR2415648A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2013703B (en) | 1982-06-03 |
| JPS54110226A (en) | 1979-08-29 |
| CH654165GA3 (en:Method) | 1986-02-14 |
| IT7919536A0 (it) | 1979-01-23 |
| GB2013703A (en) | 1979-08-15 |
| FR2415648A1 (fr) | 1979-08-24 |
| US4260776A (en) | 1981-04-07 |
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