DE108836C - - Google Patents

Info

Publication number

DE108836C

DE108836C DENDAT108836D DE108836DA DE108836C DE 108836 C DE108836 C DE 108836C DE NDAT108836 D DENDAT108836 D DE NDAT108836D DE 108836D A DE108836D A DE 108836DA DE 108836 C DE108836 C DE 108836C

Authority

DE

Germany

Prior art keywords

anthraquinone

resorcinol

dyes

condensation

derivatives

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.)

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• GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 30
• 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 claims description 15
• 150000004056 anthraquinones Chemical class 0.000 claims description 15
• 239000000975 dye Substances 0.000 claims description 13
• 238000009833 condensation Methods 0.000 claims description 10
• 230000005494 condensation Effects 0.000 claims description 10
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical class [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 238000002386 leaching Methods 0.000 claims 1
• 239000002904 solvent Substances 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 239000003513 alkali Substances 0.000 description 6
• 239000000155 melt Substances 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 239000001044 red dye Substances 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
• NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
• 239000001049 brown dye Substances 0.000 description 3
• 235000005074 zinc chloride Nutrition 0.000 description 3
• 239000011592 zinc chloride Substances 0.000 description 3
• YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 2
• RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 239000007859 condensation product Substances 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 239000001632 sodium acetate Substances 0.000 description 2
• 235000017281 sodium acetate Nutrition 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• XZSUEVFAMOKROK-UHFFFAOYSA-N 1,2-dihydroxy-3-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(O)C([N+]([O-])=O)=C2 XZSUEVFAMOKROK-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000012670 alkaline solution Substances 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 150000002828 nitro derivatives Chemical class 0.000 description 1
• 235000011118 potassium hydroxide Nutrition 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 150000004053 quinones Chemical class 0.000 description 1
• RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
• 229960005369 scarlet red Drugs 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 210000002268 wool Anatomy 0.000 description 1