BE563037A - - Google Patents

Info

Publication number

BE563037A

BE563037A BE563037DA BE563037A BE 563037 A BE563037 A BE 563037A BE 563037D A BE563037D A BE 563037DA BE 563037 A BE563037 A BE 563037A

Authority

BE

Belgium

Prior art keywords

anthraquinone

amino

formula

residue

defined under

Prior art date

Links

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• 239000002253 acid Substances 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• 239000000984 vat dye Substances 0.000 claims description 7
• -1 azobenzene dicarboxylic acid Chemical class 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 150000001875 compounds Chemical class 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 3
• 238000004043 dyeing Methods 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 2
• 230000000875 corresponding Effects 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims 5
• KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims 1
• 239000001000 anthraquinone dye Substances 0.000 claims 1
• 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
• 239000000463 material Substances 0.000 claims 1
• 239000000975 dye Substances 0.000 description 13
• FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 229920000742 Cotton Polymers 0.000 description 4
• LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
• 239000000203 mixture Substances 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 3
• FWEQPMZEKHHFTB-UHFFFAOYSA-N N-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical class C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• WKUDHZXMMINTJO-UHFFFAOYSA-N FC1=C(C(=O)NC2=CC=CC=3C(C4=C(C=CC=C4C(C23)=O)N)=O)C=CC=C1 Chemical compound FC1=C(C(=O)NC2=CC=CC=3C(C4=C(C=CC=C4C(C23)=O)N)=O)C=CC=C1 WKUDHZXMMINTJO-UHFFFAOYSA-N 0.000 description 2
• JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
• 238000007792 addition Methods 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 150000001991 dicarboxylic acids Chemical class 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 239000000835 fiber Substances 0.000 description 2
• 238000005755 formation reaction Methods 0.000 description 2
• 239000008103 glucose Substances 0.000 description 2
• 239000000155 melt Substances 0.000 description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 1
• BUSZLIXFVJAMHW-UHFFFAOYSA-N 3-aminoanthracene-1,2-dione Chemical class C1=CC=C2C=C(C(=O)C(C(N)=C3)=O)C3=CC2=C1 BUSZLIXFVJAMHW-UHFFFAOYSA-N 0.000 description 1
• BBEWSMNRCUXQRF-UHFFFAOYSA-N 4-Methyl-3-nitrobenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1[N+]([O-])=O BBEWSMNRCUXQRF-UHFFFAOYSA-N 0.000 description 1
• DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
• MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
• AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 125000000751 azo group Chemical group [*]N=N[*] 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
• 239000007844 bleaching agent Substances 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 150000008422 chlorobenzenes Chemical class 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• 239000012065 filter cake Substances 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 125000001188 haloalkyl group Chemical group 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 230000001264 neutralization Effects 0.000 description 1
• 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 239000003638 reducing agent Substances 0.000 description 1
• 239000000344 soap Substances 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 125000000547 substituted alkyl group Chemical group 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 239000001043 yellow dye Substances 0.000 description 1