JPS6228821B2 - - Google Patents
Info
- Publication number
- JPS6228821B2 JPS6228821B2 JP54091054A JP9105479A JPS6228821B2 JP S6228821 B2 JPS6228821 B2 JP S6228821B2 JP 54091054 A JP54091054 A JP 54091054A JP 9105479 A JP9105479 A JP 9105479A JP S6228821 B2 JPS6228821 B2 JP S6228821B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfur
- dinitroanthraquinone
- mixture
- weight
- hours
- 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
- 239000000203 mixture Substances 0.000 claims abstract description 63
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000004043 dyeing Methods 0.000 claims abstract description 19
- 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 claims abstract description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 150000004056 anthraquinones Chemical class 0.000 claims abstract description 8
- 229920002678 cellulose Polymers 0.000 claims abstract description 8
- 239000001913 cellulose Substances 0.000 claims abstract description 8
- FAVDZWIRBSMLOV-UHFFFAOYSA-N 1,7-dinitroanthracene-9,10-dione Chemical class C1=CC([N+]([O-])=O)=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 FAVDZWIRBSMLOV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000006227 byproduct Substances 0.000 claims abstract description 6
- 230000033444 hydroxylation Effects 0.000 claims abstract description 5
- 238000005805 hydroxylation reaction Methods 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 239000000988 sulfur dye Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 15
- 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 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000005987 sulfurization reaction Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 1
- 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 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- 229920000742 Cotton Polymers 0.000 description 15
- 229910052979 sodium sulfide Inorganic materials 0.000 description 14
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 14
- 239000000155 melt Substances 0.000 description 13
- 238000005406 washing Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 9
- 240000007817 Olea europaea Species 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- XVMVHWDCRFNPQR-UHFFFAOYSA-N 1,5-dinitroanthracene-9,10-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O XVMVHWDCRFNPQR-UHFFFAOYSA-N 0.000 description 1
- KRZHUDWUNNCSIV-UHFFFAOYSA-N 2-hydroxy-1-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(O)=CC=C3C(=O)C2=C1 KRZHUDWUNNCSIV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 238000011022 operating instruction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010792 warming Methods 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
- C09B49/00—Sulfur dyes
- C09B49/02—Sulfur dyes from nitro compounds of the benzene, naphthalene or anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782832215 DE2832215A1 (de) | 1978-07-21 | 1978-07-21 | Schwefelfarbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5518481A JPS5518481A (en) | 1980-02-08 |
| JPS6228821B2 true JPS6228821B2 (enExample) | 1987-06-23 |
Family
ID=6045072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9105479A Granted JPS5518481A (en) | 1978-07-21 | 1979-07-19 | Sulfur dyestuff |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4443369A (enExample) |
| JP (1) | JPS5518481A (enExample) |
| CH (1) | CH654972GA3 (enExample) |
| DE (1) | DE2832215A1 (enExample) |
| FR (1) | FR2431524A1 (enExample) |
| GB (1) | GB2027442B (enExample) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE91508C (enExample) * | ||||
| DE234858C (enExample) * | ||||
| US597983A (en) * | 1898-01-25 | isleb | ||
| DE95484C (enExample) * | ||||
| GB191104158A (en) * | 1910-04-23 | 1911-04-27 | Anilin Fabrikation Ag | Manufacture of Acidylated Sulphurised Anthraquinone Derivatives. |
| FR425411A (fr) * | 1911-01-30 | 1911-06-10 | Griesheim Elektron Chem Fab | Procédé pour la production de colorants bruns sulfurés teignant sur cuve |
| US999045A (en) * | 1911-02-09 | 1911-07-25 | Corp Of Chem Fab Griesheim Elektron | Manufacture of brown sulfurized vat dyestuffs. |
| US1061714A (en) * | 1912-02-05 | 1913-05-13 | Basf Ag | Dyes containing sulfur and process of making them. |
-
1978
- 1978-07-21 DE DE19782832215 patent/DE2832215A1/de not_active Withdrawn
-
1979
- 1979-07-17 GB GB7924858A patent/GB2027442B/en not_active Expired
- 1979-07-18 CH CH669779A patent/CH654972GA3/de unknown
- 1979-07-19 JP JP9105479A patent/JPS5518481A/ja active Granted
- 1979-07-20 FR FR7918794A patent/FR2431524A1/fr active Granted
-
1981
- 1981-07-20 US US06/284,918 patent/US4443369A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE2832215A1 (de) | 1980-01-31 |
| JPS5518481A (en) | 1980-02-08 |
| FR2431524A1 (fr) | 1980-02-15 |
| CH654972GA3 (enExample) | 1986-03-27 |
| GB2027442B (en) | 1983-01-12 |
| GB2027442A (en) | 1980-02-20 |
| US4443369A (en) | 1984-04-17 |
| FR2431524B1 (enExample) | 1983-05-13 |
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