DE1644578A1 - Verfahren zur Herstellung von Anthrachinonyl-sulfonen - Google Patents
Verfahren zur Herstellung von Anthrachinonyl-sulfonenInfo
- Publication number
- DE1644578A1 DE1644578A1 DE19641644578 DE1644578A DE1644578A1 DE 1644578 A1 DE1644578 A1 DE 1644578A1 DE 19641644578 DE19641644578 DE 19641644578 DE 1644578 A DE1644578 A DE 1644578A DE 1644578 A1 DE1644578 A1 DE 1644578A1
- Authority
- DE
- Germany
- Prior art keywords
- anthraquinone
- parts
- blue
- diamino
- amino
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 13
- JOJOBXILPDFSGO-UHFFFAOYSA-N 1-(9,10-dioxoanthracen-1-yl)sulfonylanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)C1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O JOJOBXILPDFSGO-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- -1 alkaline earth metal salts Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical class 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000003457 sulfones Chemical class 0.000 claims description 6
- 125000005362 aryl sulfone group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
- 239000000975 dye Substances 0.000 description 53
- 239000000835 fiber Substances 0.000 description 50
- 229920000728 polyester Polymers 0.000 description 39
- 150000004056 anthraquinones Chemical class 0.000 description 25
- YZZOFFUTSZLDMY-UHFFFAOYSA-N 1-(benzenesulfonyl)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)C1=CC=CC=C1 YZZOFFUTSZLDMY-UHFFFAOYSA-N 0.000 description 24
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000009835 boiling Methods 0.000 description 21
- 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 19
- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- 239000002253 acid Substances 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 12
- 229920000139 polyethylene terephthalate Polymers 0.000 description 10
- 239000005020 polyethylene terephthalate Substances 0.000 description 10
- 239000003086 colorant Substances 0.000 description 8
- BLDUUWWNHUUEJH-UHFFFAOYSA-N 2-methylsulfonylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)C)=CC=C3C(=O)C2=C1 BLDUUWWNHUUEJH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000009998 heat setting Methods 0.000 description 7
- 229920002284 Cellulose triacetate Polymers 0.000 description 6
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- KXTIQESEQCOMSB-UHFFFAOYSA-N 1-methylsulfonylanthracene-9,10-dione Chemical compound CS(=O)(=O)C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O KXTIQESEQCOMSB-UHFFFAOYSA-N 0.000 description 5
- VTSDGYDTWADUJQ-UHFFFAOYSA-N 2-bromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 VTSDGYDTWADUJQ-UHFFFAOYSA-N 0.000 description 5
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229960001156 mitoxantrone Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- JRVJSYADKXRGRH-UHFFFAOYSA-N 1-ethylsulfonylanthracene-9,10-dione Chemical compound C(C)S(=O)(=O)C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O JRVJSYADKXRGRH-UHFFFAOYSA-N 0.000 description 4
- CMUSFGOGIIXRDU-UHFFFAOYSA-N 2-(benzenesulfonyl)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(=C2)S(=O)(=O)C1=CC=CC=C1 CMUSFGOGIIXRDU-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- 150000003455 sulfinic acids Chemical class 0.000 description 4
- XRIGHGYEGNDPEU-UHFFFAOYSA-N 1-anilinoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 XRIGHGYEGNDPEU-UHFFFAOYSA-N 0.000 description 3
- UWXCCBKRJAVWST-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfinic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)O UWXCCBKRJAVWST-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000282376 Panthera tigris Species 0.000 description 3
- 241000033695 Sige Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RWDJJOUSDATHMI-UHFFFAOYSA-N benzenesulfinic acid;sodium Chemical compound [Na].OS(=O)C1=CC=CC=C1 RWDJJOUSDATHMI-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 235000019646 color tone Nutrition 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- IEWDGUMBUFXBCC-UHFFFAOYSA-N 1,4-diamino-2-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Br)C=C2N IEWDGUMBUFXBCC-UHFFFAOYSA-N 0.000 description 2
- MSSQDESMUMSQEN-UHFFFAOYSA-N 1-amino-2-bromo-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Br)=C2N MSSQDESMUMSQEN-UHFFFAOYSA-N 0.000 description 2
- PRARPUUKJGGSOO-UHFFFAOYSA-N 1-sulfonyl-2H-anthracene-9,10-dione Chemical compound S(=O)(=O)=C1CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O PRARPUUKJGGSOO-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- PVHJWGFOGUKLQQ-UHFFFAOYSA-L C.[Na+].[Na+].[O-]S([O-])(=O)=O Chemical compound C.[Na+].[Na+].[O-]S([O-])(=O)=O PVHJWGFOGUKLQQ-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical compound CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 description 2
- RHDUOFVTCTUTFX-UHFFFAOYSA-N methanesulfinic acid;sodium Chemical compound [Na].CS(O)=O RHDUOFVTCTUTFX-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 229920006304 triacetate fiber Polymers 0.000 description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 2
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 1
- ORZMSMCZBZARKY-UHFFFAOYSA-N 1,3,2$l^{6}-benzodioxathiole 2,2-dioxide Chemical compound C1=CC=C2OS(=O)(=O)OC2=C1 ORZMSMCZBZARKY-UHFFFAOYSA-N 0.000 description 1
- KZYAYVSWIPZDKL-UHFFFAOYSA-N 1,4-diamino-2,3-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Cl)C(Cl)=C2N KZYAYVSWIPZDKL-UHFFFAOYSA-N 0.000 description 1
- UWSIIZNBRWDPSW-UHFFFAOYSA-N 1,4-diamino-2-(benzenesulfonyl)-5-nitroanthracene-9,10-dione Chemical compound NC1=C(C=C(C=2C(C3=C(C=CC=C3C(C12)=O)[N+](=O)[O-])=O)N)S(=O)(=O)C1=CC=CC=C1 UWSIIZNBRWDPSW-UHFFFAOYSA-N 0.000 description 1
- VNOZXTBRPCYXOC-UHFFFAOYSA-N 1,4-diamino-2-benzylsulfonylanthracene-9,10-dione Chemical compound NC1=CC(=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O)S(=O)(=O)CC1=CC=CC=C1 VNOZXTBRPCYXOC-UHFFFAOYSA-N 0.000 description 1
- FAOCCNVWFNGPAC-UHFFFAOYSA-N 1,4-diamino-2-methylsulfonylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(S(=O)(=O)C)=CC(N)=C3C(=O)C2=C1 FAOCCNVWFNGPAC-UHFFFAOYSA-N 0.000 description 1
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 description 1
- KNOYUKKOVLJJRM-UHFFFAOYSA-N 1,5-diamino-2,4,6,8-tetrabromoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C(Br)=CC(Br)=C2C(=O)C2=C1C(Br)=CC(Br)=C2N KNOYUKKOVLJJRM-UHFFFAOYSA-N 0.000 description 1
- DQGQBUGJFBAERK-UHFFFAOYSA-N 1-(2-methoxyethylsulfonyl)anthracene-9,10-dione Chemical compound COCCS(=O)(=O)C1=CC=CC=2C(C3=CC=CC=C3C(C1=2)=O)=O DQGQBUGJFBAERK-UHFFFAOYSA-N 0.000 description 1
- ZINRVIQBCHAZMM-UHFFFAOYSA-N 1-Amino-2,4-dibromoanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(Br)=C2N ZINRVIQBCHAZMM-UHFFFAOYSA-N 0.000 description 1
- TVEOQRWKLZDKEC-UHFFFAOYSA-N 1-amino-2-(benzenesulfonyl)anthracene-9,10-dione Chemical compound C1=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1S(=O)(=O)C1=CC=CC=C1 TVEOQRWKLZDKEC-UHFFFAOYSA-N 0.000 description 1
- SPDRRRCQUXHHLH-UHFFFAOYSA-N 1-amino-2-bromo-4-(4-methylanilino)anthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1NC1=CC(Br)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O SPDRRRCQUXHHLH-UHFFFAOYSA-N 0.000 description 1
- VQTYRGPRIOXCEK-UHFFFAOYSA-N 1-amino-2-bromo-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Br)C=C2OC VQTYRGPRIOXCEK-UHFFFAOYSA-N 0.000 description 1
- MVRDXWVWKOUPDO-UHFFFAOYSA-N 1-amino-2-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Br)=C2N MVRDXWVWKOUPDO-UHFFFAOYSA-N 0.000 description 1
- NNYSRWRYJYMHFI-UHFFFAOYSA-N 1-ethylsulfinylethane;methylsulfinylmethane Chemical compound CS(C)=O.CCS(=O)CC NNYSRWRYJYMHFI-UHFFFAOYSA-N 0.000 description 1
- KJGPMAHVCDFRBN-UHFFFAOYSA-N 2,6-dichloroanthracene-9,10-dione Chemical compound ClC1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 KJGPMAHVCDFRBN-UHFFFAOYSA-N 0.000 description 1
- GTMIUYOWIKJTSM-UHFFFAOYSA-N 2-(benzenesulfonyl)-1,4-dihydroxyanthracene-9,10-dione Chemical compound OC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(O)=CC=1S(=O)(=O)C1=CC=CC=C1 GTMIUYOWIKJTSM-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- CLWMYQQCXBSIBF-UHFFFAOYSA-N 2-amino-3-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(Br)=C2 CLWMYQQCXBSIBF-UHFFFAOYSA-N 0.000 description 1
- BPUAQNKWCBCCAA-UHFFFAOYSA-N 2-bromo-1,4-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(Br)C=C2O BPUAQNKWCBCCAA-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WLPRUDLQOPCFNL-UHFFFAOYSA-N 2-methylpropane-1-sulfinic acid Chemical compound CC(C)CS(O)=O WLPRUDLQOPCFNL-UHFFFAOYSA-N 0.000 description 1
- SKVNXVIZRCDAPH-UHFFFAOYSA-N 3-methoxypropane-1-sulfinic acid Chemical compound COCCCS(O)=O SKVNXVIZRCDAPH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- FXJVNINSOKCNJP-UHFFFAOYSA-M 4-methylbenzenesulfinate Chemical compound CC1=CC=C(S([O-])=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-M 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- QMXBNDOLWASDNK-UHFFFAOYSA-N C(C)SC1=CC=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O Chemical compound C(C)SC1=CC=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O QMXBNDOLWASDNK-UHFFFAOYSA-N 0.000 description 1
- UEOOMGIEXKMOHE-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C=1C=CC=2C(C3=CC(=CC=C3C(C2C1)=O)S(=O)(=O)C1=CC=CC=C1)=O Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C=CC=2C(C3=CC(=CC=C3C(C2C1)=O)S(=O)(=O)C1=CC=CC=C1)=O UEOOMGIEXKMOHE-UHFFFAOYSA-N 0.000 description 1
- QPMRCKFDOBNCQW-UHFFFAOYSA-N CC(C)CS(=O)(=O)C1=C(N)C2=C(C(N)=C1)C(=O)C1=CC=CC=C1C2=O Chemical compound CC(C)CS(=O)(=O)C1=C(N)C2=C(C(N)=C1)C(=O)C1=CC=CC=C1C2=O QPMRCKFDOBNCQW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- QQIKCJHZOFWRQI-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O QQIKCJHZOFWRQI-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 241000344726 Iris spuria Species 0.000 description 1
- 241000985630 Lota lota Species 0.000 description 1
- 240000000233 Melia azedarach Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- OZEHKGNAAYQWOB-UHFFFAOYSA-N NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)N)S(=O)(=O)CCC Chemical compound NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)N)S(=O)(=O)CCC OZEHKGNAAYQWOB-UHFFFAOYSA-N 0.000 description 1
- NUBDBQOHBMQLGL-UHFFFAOYSA-N NC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)S(=O)O Chemical class NC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)S(=O)O NUBDBQOHBMQLGL-UHFFFAOYSA-N 0.000 description 1
- ZCXFEJFNQIAQNC-UHFFFAOYSA-N O=C(C1=CC=CC=C11)C(C=CC=C2S(CCCl)(=O)=O)=C2C1=O Chemical compound O=C(C1=CC=CC=C11)C(C=CC=C2S(CCCl)(=O)=O)=C2C1=O ZCXFEJFNQIAQNC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- LTUSOFINFRSGGG-UHFFFAOYSA-M S(=O)(=O)([O-])O.[Na+].S(=O)(=O)(O)O.C1=CC=CC=C1 Chemical compound S(=O)(=O)([O-])O.[Na+].S(=O)(=O)(O)O.C1=CC=CC=C1 LTUSOFINFRSGGG-UHFFFAOYSA-M 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003830 anthracite Substances 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- 150000004832 aryl thioethers Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- RQIFXTOWUNAUJC-UHFFFAOYSA-N ethanesulfinic acid Chemical compound CCS(O)=O RQIFXTOWUNAUJC-UHFFFAOYSA-N 0.000 description 1
- ZBAICKQMXSAONA-UHFFFAOYSA-N ethanesulfinic acid;sodium Chemical compound [Na].CCS(O)=O ZBAICKQMXSAONA-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- HBTBNXFVJYRYGI-UHFFFAOYSA-N hexadecane-1-sulfinic acid Chemical class CCCCCCCCCCCCCCCCS(O)=O HBTBNXFVJYRYGI-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CQGDBBBZCJYDRY-UHFFFAOYSA-N methoxyanthraquinone Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OC CQGDBBBZCJYDRY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- OLRICEKEOLIEMY-UHFFFAOYSA-N trichloromethanesulfinic acid Chemical compound OS(=O)C(Cl)(Cl)Cl OLRICEKEOLIEMY-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0042955 | 1964-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1644578A1 true DE1644578A1 (de) | 1970-09-10 |
Family
ID=7099337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641644578 Ceased DE1644578A1 (de) | 1964-05-22 | 1964-05-22 | Verfahren zur Herstellung von Anthrachinonyl-sulfonen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE662074A (cs) |
| CH (1) | CH464407A (cs) |
| DE (1) | DE1644578A1 (cs) |
| GB (1) | GB1053455A (cs) |
| NL (1) | NL6504223A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681402A (en) * | 1969-05-06 | 1972-08-01 | Guido R Genta | Anthraquinone dyestuff manufacture |
-
0
- GB GB1053455D patent/GB1053455A/en active Active
-
1964
- 1964-05-22 DE DE19641644578 patent/DE1644578A1/de not_active Ceased
-
1965
- 1965-03-09 CH CH327865A patent/CH464407A/de unknown
- 1965-04-02 NL NL6504223A patent/NL6504223A/xx unknown
- 1965-04-05 BE BE662074D patent/BE662074A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6504223A (cs) | 1965-11-23 |
| CH464407A (de) | 1968-10-31 |
| GB1053455A (cs) | |
| BE662074A (cs) | 1965-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |