DE2030507C3 - Oxazolyl-cumarine, deren Herstellung und Verwendung - Google Patents
Oxazolyl-cumarine, deren Herstellung und VerwendungInfo
- Publication number
- DE2030507C3 DE2030507C3 DE19702030507 DE2030507A DE2030507C3 DE 2030507 C3 DE2030507 C3 DE 2030507C3 DE 19702030507 DE19702030507 DE 19702030507 DE 2030507 A DE2030507 A DE 2030507A DE 2030507 C3 DE2030507 C3 DE 2030507C3
- Authority
- DE
- Germany
- Prior art keywords
- formula
- acetic acid
- benzoxazolyl
- methyl
- parts
- 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
- ZSUCSZHRXKUABW-UHFFFAOYSA-N 3-(1,3-oxazol-2-yl)chromen-2-one Chemical class O=C1OC=2C=CC=CC=2C=C1C1=NC=CO1 ZSUCSZHRXKUABW-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 phenoxy, phenyl Chemical group 0.000 claims description 45
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 235000013350 formula milk Nutrition 0.000 description 79
- 150000001875 compounds Chemical class 0.000 description 68
- 239000000975 dye Substances 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 34
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229960000956 coumarin Drugs 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 235000001671 coumarin Nutrition 0.000 description 17
- 150000001408 amides Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229960001413 acetanilide Drugs 0.000 description 13
- 238000009835 boiling Methods 0.000 description 13
- 239000004744 fabric Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- WMIHEWJRNFUVNR-UHFFFAOYSA-N 2-methylbenzo[f][1,3]benzoxazole Chemical compound C1=CC=C2C=C(OC(C)=N3)C3=CC2=C1 WMIHEWJRNFUVNR-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 7
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000003931 anilides Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 238000005882 aldol condensation reaction Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- XUVVPUSARWFTRS-UHFFFAOYSA-N 2-(1,3-oxazol-2-yl)acetic acid Chemical class OC(=O)CC1=NC=CO1 XUVVPUSARWFTRS-UHFFFAOYSA-N 0.000 description 2
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 2
- PPVPIPDBDKUHPZ-UHFFFAOYSA-N 2-aminooxybenzaldehyde Chemical compound NOC1=CC=CC=C1C=O PPVPIPDBDKUHPZ-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- OPEXAGQSKDXFTB-UHFFFAOYSA-N 2-hydroxy-4-(propylamino)benzaldehyde Chemical compound CCCNC1=CC=C(C=O)C(O)=C1 OPEXAGQSKDXFTB-UHFFFAOYSA-N 0.000 description 2
- JGWOEGYSIHGQPF-UHFFFAOYSA-N 2-morpholin-4-yloxybenzaldehyde Chemical compound O=CC1=CC=CC=C1ON1CCOCC1 JGWOEGYSIHGQPF-UHFFFAOYSA-N 0.000 description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 2
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 2
- XPSLOHMBERQXIX-UHFFFAOYSA-N 4-(diethylamino)-2-ethoxybenzaldehyde Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C=O XPSLOHMBERQXIX-UHFFFAOYSA-N 0.000 description 2
- KURCTZNCAHYQOV-UHFFFAOYSA-N 4-(dimethylamino)-2-hydroxybenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C(O)=C1 KURCTZNCAHYQOV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 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
- 238000005406 washing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- IIEJGTQVBJHMDL-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-[2-oxo-2-[3-(sulfamoylamino)pyrrolidin-1-yl]ethyl]-1,3,4-oxadiazole Chemical group C1CN(CC1NS(=O)(=O)N)C(=O)CC2=NN=C(O2)C3=CN=C(N=C3)NC4CC5=CC=CC=C5C4 IIEJGTQVBJHMDL-UHFFFAOYSA-N 0.000 description 1
- AISFNSXFXXNPPO-UHFFFAOYSA-N 2-aminooxy-3-ethyl-4-(2-hydroxyethyl)benzaldehyde Chemical compound CCC1=C(CCO)C=CC(C=O)=C1ON AISFNSXFXXNPPO-UHFFFAOYSA-N 0.000 description 1
- LTMPNNPIUYTZSU-UHFFFAOYSA-N 2-aminooxy-4-(2-bromoethyl)benzaldehyde Chemical compound NOC1=CC(CCBr)=CC=C1C=O LTMPNNPIUYTZSU-UHFFFAOYSA-N 0.000 description 1
- RXSTZNOIVOCQNC-UHFFFAOYSA-N 2-aminooxy-4-(2-methoxyethyl)benzaldehyde Chemical compound COCCC1=CC=C(C=O)C(ON)=C1 RXSTZNOIVOCQNC-UHFFFAOYSA-N 0.000 description 1
- GVVFCADQIZRJLN-UHFFFAOYSA-N 2-aminooxy-4-(4-ethoxyphenyl)-3-methylbenzaldehyde Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(C=O)C(ON)=C1C GVVFCADQIZRJLN-UHFFFAOYSA-N 0.000 description 1
- YNZGSNCLFDXPGH-UHFFFAOYSA-N 2-aminooxy-4-benzyl-3-methylbenzaldehyde Chemical compound C1=CC(C=O)=C(ON)C(C)=C1CC1=CC=CC=C1 YNZGSNCLFDXPGH-UHFFFAOYSA-N 0.000 description 1
- NGBUGADETFTPEF-UHFFFAOYSA-N 2-hydroxy-4-(2-methylpropylamino)benzaldehyde Chemical compound CC(C)CNC1=CC=C(C=O)C(O)=C1 NGBUGADETFTPEF-UHFFFAOYSA-N 0.000 description 1
- GNCJJPAJKJBWAU-UHFFFAOYSA-N 2-methoxy-3-(methylamino)-4-phenylbenzaldehyde Chemical compound CNC1=C(OC)C(C=O)=CC=C1C1=CC=CC=C1 GNCJJPAJKJBWAU-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
-
- 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
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
- D06P1/40—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes using acid dyes without azo groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702065552 DE2065552A1 (de) | 1970-06-20 | 1970-06-20 | Oxazolyl-essigsaeurederivate |
| DE19702030507 DE2030507C3 (de) | 1970-06-20 | 1970-06-20 | Oxazolyl-cumarine, deren Herstellung und Verwendung |
| DE19702058877 DE2058877A1 (de) | 1970-06-20 | 1970-11-30 | Oxazolyl-essigsaeurederivate und Oxazolyl-cumarine |
| CH715771D CH715771A4 (de) | 1970-06-20 | 1971-05-13 | Verfahren zum Färben oder Bedrucken von organischen Textilfasermaterialien |
| CH1618573A CH587833A5 (enrdf_load_stackoverflow) | 1970-06-20 | 1971-05-13 | |
| CH1618673A CH585250A5 (enrdf_load_stackoverflow) | 1970-06-20 | 1971-06-13 | |
| GB1329043D GB1329043A (en) | 1970-06-20 | 1971-06-18 | Oxazolyl-coumarine dyestuffs |
| JP46043359A JPS5023028B1 (enrdf_load_stackoverflow) | 1970-06-20 | 1971-06-18 | |
| AT527871A AT310707B (de) | 1970-06-20 | 1971-06-18 | Verfahren zum Färben von Ölen und makromolekularen, organischen Materialien |
| GB2870471A GB1329042A (en) | 1970-06-20 | 1971-06-18 | Oxazolyl-acetic acid derivatives |
| AT615272A AT310743B (de) | 1970-06-20 | 1971-06-18 | Verfahren zur Herstellung von neuen Oxazolyl-essigsäurederivaten |
| FR7122352A FR2099247A5 (enrdf_load_stackoverflow) | 1970-06-20 | 1971-06-18 | |
| NL7108436A NL7108436A (enrdf_load_stackoverflow) | 1970-06-20 | 1971-06-18 | |
| BE768722A BE768722A (fr) | 1970-06-20 | 1971-06-18 | Derives d'acide oxazolyl-acetique et oxazolyl-coumarines |
| US05/369,124 US3985763A (en) | 1970-06-20 | 1973-06-12 | Oxazolyl-acetic acid derivatives and oxazolyl-coumarines |
| JP49099075A JPS516266B2 (enrdf_load_stackoverflow) | 1970-06-20 | 1974-08-30 | |
| JP49099076A JPS51526A (en) | 1970-06-20 | 1974-08-30 | Okisazoriruukumarin no seizoho |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702030507 DE2030507C3 (de) | 1970-06-20 | 1970-06-20 | Oxazolyl-cumarine, deren Herstellung und Verwendung |
| DE19702065552 DE2065552A1 (de) | 1970-06-20 | 1970-06-20 | Oxazolyl-essigsaeurederivate |
| DE19702058877 DE2058877A1 (de) | 1970-06-20 | 1970-11-30 | Oxazolyl-essigsaeurederivate und Oxazolyl-cumarine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2030507A1 DE2030507A1 (de) | 1972-01-05 |
| DE2030507B2 DE2030507B2 (de) | 1974-09-19 |
| DE2030507C3 true DE2030507C3 (de) | 1975-05-22 |
Family
ID=27182676
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702030507 Expired DE2030507C3 (de) | 1970-06-20 | 1970-06-20 | Oxazolyl-cumarine, deren Herstellung und Verwendung |
| DE19702065552 Pending DE2065552A1 (de) | 1970-06-20 | 1970-06-20 | Oxazolyl-essigsaeurederivate |
| DE19702058877 Pending DE2058877A1 (de) | 1970-06-20 | 1970-11-30 | Oxazolyl-essigsaeurederivate und Oxazolyl-cumarine |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702065552 Pending DE2065552A1 (de) | 1970-06-20 | 1970-06-20 | Oxazolyl-essigsaeurederivate |
| DE19702058877 Pending DE2058877A1 (de) | 1970-06-20 | 1970-11-30 | Oxazolyl-essigsaeurederivate und Oxazolyl-cumarine |
Country Status (8)
| Country | Link |
|---|---|
| JP (3) | JPS5023028B1 (enrdf_load_stackoverflow) |
| AT (2) | AT310707B (enrdf_load_stackoverflow) |
| BE (1) | BE768722A (enrdf_load_stackoverflow) |
| CH (3) | CH587833A5 (enrdf_load_stackoverflow) |
| DE (3) | DE2030507C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2099247A5 (enrdf_load_stackoverflow) |
| GB (2) | GB1329042A (enrdf_load_stackoverflow) |
| NL (1) | NL7108436A (enrdf_load_stackoverflow) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH593954A5 (enrdf_load_stackoverflow) * | 1975-07-21 | 1977-12-30 | Ciba Geigy Ag | |
| DE2803104A1 (de) * | 1978-01-25 | 1979-07-26 | Bayer Ag | Heterocyclische farbstoffe |
| JPS5533913U (enrdf_load_stackoverflow) * | 1978-08-24 | 1980-03-05 | ||
| DE3067431D1 (en) * | 1979-07-20 | 1984-05-17 | Ciba Geigy Ag | Coumarine compounds, processes for their manufacture as well as the intermediate products used perse and their utilisation for the dyeing or printing of textiles |
| DE2946524A1 (de) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3021947A1 (de) * | 1980-06-12 | 1982-01-14 | Bayer Ag, 5090 Leverkusen | Farbstoffpraeparation sowie deren verwendung als warn- und signalfarbe |
| DE3031326A1 (de) * | 1980-08-20 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | Farbstoffpraeparation sowie deren verwendung als warn- und signalfarbe |
| DE3038599A1 (de) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Substituierte benzazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3038652A1 (de) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | 5-chlor-benzoxazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| JPH01140008U (enrdf_load_stackoverflow) * | 1988-03-22 | 1989-09-25 | ||
| DE19622356A1 (de) * | 1996-06-04 | 1997-12-11 | Bayer Ag | Isoindoleninamidfarbstoffe |
| DE10055093A1 (de) * | 2000-11-07 | 2002-05-16 | Agfa Gevaert Ag | Cyaninfarbstoff |
| GB0205281D0 (en) * | 2002-03-06 | 2002-04-17 | Novartis Ag | Organic compounds |
| JP5221859B2 (ja) * | 2006-03-09 | 2013-06-26 | 株式会社Ａｄｅｋａ | クマリン化合物を含有してなるフィルム、クマリン化合物とマトリクスを含む色変換層、該色変換層を含む色変換フィルタ、補色層、補色フィルタならびに多色発光デバイス |
| JP2012092077A (ja) * | 2010-10-28 | 2012-05-17 | Fujifilm Corp | クマリン化合物 |
| KR102041384B1 (ko) * | 2012-07-31 | 2019-11-07 | 스미또모 가가꾸 가부시키가이샤 | 착색 경화성 수지 조성물 |
| AU2015264336B2 (en) * | 2014-05-19 | 2018-08-30 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic compounds |
| JP6440494B2 (ja) * | 2014-12-26 | 2018-12-19 | 住友化学株式会社 | 化合物 |
| EP3553136A4 (en) * | 2017-02-14 | 2020-03-11 | Konica Minolta, Inc. | AMINOCOUMARIN COMPOUND, AND RESIN PARTICLES WITH ENCAPSULATED AMINOCOUMARIN COMPOUND |
| WO2018150450A1 (ja) * | 2017-02-14 | 2018-08-23 | コニカミノルタ株式会社 | アミノクマリン化合物およびアミノクマリン化合物内包樹脂粒子 |
| JP7261609B2 (ja) * | 2018-03-28 | 2023-04-20 | 日本化薬株式会社 | クマリン化合物、及びこれを含んだ顔料組成物 |
| CN112625033B (zh) * | 2020-12-21 | 2022-03-22 | 青岛科技大学 | 一种检测胺类化合物气体的荧光探针 |
-
1970
- 1970-06-20 DE DE19702030507 patent/DE2030507C3/de not_active Expired
- 1970-06-20 DE DE19702065552 patent/DE2065552A1/de active Pending
- 1970-11-30 DE DE19702058877 patent/DE2058877A1/de active Pending
-
1971
- 1971-05-13 CH CH1618573A patent/CH587833A5/xx not_active IP Right Cessation
- 1971-05-13 CH CH715771D patent/CH715771A4/de unknown
- 1971-06-13 CH CH1618673A patent/CH585250A5/xx not_active IP Right Cessation
- 1971-06-18 AT AT527871A patent/AT310707B/de not_active IP Right Cessation
- 1971-06-18 GB GB2870471A patent/GB1329042A/en not_active Expired
- 1971-06-18 FR FR7122352A patent/FR2099247A5/fr not_active Expired
- 1971-06-18 BE BE768722A patent/BE768722A/xx unknown
- 1971-06-18 GB GB1329043D patent/GB1329043A/en not_active Expired
- 1971-06-18 AT AT615272A patent/AT310743B/de not_active IP Right Cessation
- 1971-06-18 NL NL7108436A patent/NL7108436A/xx not_active Application Discontinuation
- 1971-06-18 JP JP46043359A patent/JPS5023028B1/ja active Pending
-
1974
- 1974-08-30 JP JP49099075A patent/JPS516266B2/ja not_active Expired
- 1974-08-30 JP JP49099076A patent/JPS51526A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1329042A (en) | 1973-09-05 |
| JPS51526A (en) | 1976-01-06 |
| FR2099247A5 (enrdf_load_stackoverflow) | 1972-03-10 |
| JPS5069380A (enrdf_load_stackoverflow) | 1975-06-10 |
| DE2030507A1 (de) | 1972-01-05 |
| JPS5023028B1 (enrdf_load_stackoverflow) | 1975-08-05 |
| BE768722A (fr) | 1971-11-03 |
| AT310707B (de) | 1973-10-10 |
| AT310743B (de) | 1973-10-10 |
| JPS5142125B2 (enrdf_load_stackoverflow) | 1976-11-13 |
| JPS516266B2 (enrdf_load_stackoverflow) | 1976-02-26 |
| CH585250A5 (enrdf_load_stackoverflow) | 1977-02-28 |
| GB1329043A (en) | 1973-09-05 |
| DE2058877A1 (de) | 1972-06-15 |
| CH715771A4 (de) | 1976-06-30 |
| DE2030507B2 (de) | 1974-09-19 |
| NL7108436A (enrdf_load_stackoverflow) | 1971-12-22 |
| DE2065552A1 (de) | 1974-03-07 |
| CH587833A5 (enrdf_load_stackoverflow) | 1977-05-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |