BE428719A - - Google Patents
Info
- Publication number
- BE428719A BE428719A BE428719DA BE428719A BE 428719 A BE428719 A BE 428719A BE 428719D A BE428719D A BE 428719DA BE 428719 A BE428719 A BE 428719A
- Authority
- BE
- Belgium
- Prior art keywords
- dye
- sulfuric acid
- parts
- brown
- hours
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000002140 halogenating Effects 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 118
- 239000000975 dye Substances 0.000 description 86
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 43
- 229920000742 Cotton Polymers 0.000 description 37
- 239000000047 product Substances 0.000 description 37
- 238000003756 stirring Methods 0.000 description 27
- 238000004043 dyeing Methods 0.000 description 25
- 239000000843 powder Substances 0.000 description 24
- 235000010288 sodium nitrite Nutrition 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000007859 condensation product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000005755 formation reaction Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 239000001187 sodium carbonate Substances 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- PXNNPGGYHAWDJW-UHFFFAOYSA-N N-(4-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC=C1 PXNNPGGYHAWDJW-UHFFFAOYSA-N 0.000 description 7
- 210000002268 Wool Anatomy 0.000 description 7
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000005578 chrysene group Chemical group 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M Copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- FWEQPMZEKHHFTB-UHFFFAOYSA-N N-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 229940045803 cuprous chloride Drugs 0.000 description 4
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- PHJHZJIBGMHBQG-UHFFFAOYSA-N 1,2-dibromochrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=C(Br)C(Br)=C4C=CC3=C21 PHJHZJIBGMHBQG-UHFFFAOYSA-N 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 3
- KOJOUCAVSDKDPR-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=1C=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C=1NC(=O)C1=CC=CC=C1 KOJOUCAVSDKDPR-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 230000001034 aminogenic Effects 0.000 description 3
- 125000004432 carbon atoms Chemical group C* 0.000 description 3
- 150000001880 copper compounds Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- -1 organic acid chlorides Chemical class 0.000 description 3
- 238000009991 scouring Methods 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000005406 washing Methods 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
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 2
- IKUFMQMCBFBQJU-UHFFFAOYSA-N 2-bromochrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=C(Br)C=C4C=CC3=C21 IKUFMQMCBFBQJU-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N Hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- FXYMBQQAXFHRGC-UHFFFAOYSA-N N-(5-amino-9,10-dioxoanthracen-1-yl)acetamide Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C FXYMBQQAXFHRGC-UHFFFAOYSA-N 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N Nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 210000004940 Nucleus Anatomy 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N Sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- JBUKJLNBQDQXLI-UHFFFAOYSA-N Sodium perborate Chemical compound [Na+].[Na+].O[B-]1(O)OO[B-](O)(O)OO1 JBUKJLNBQDQXLI-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 150000002829 nitrogen Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229960001922 sodium perborate Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-Chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- XGQWHHCZIMXNHG-UHFFFAOYSA-N 4-aminonaphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 XGQWHHCZIMXNHG-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- FSRBCNUNTORNMI-UHFFFAOYSA-N NC1(CC=CC=2C(C3=CC=CC=C3C(C1=2)=O)=O)C(=O)C1=C(C=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O)N Chemical compound NC1(CC=CC=2C(C3=CC=CC=C3C(C1=2)=O)=O)C(=O)C1=C(C=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O)N FSRBCNUNTORNMI-UHFFFAOYSA-N 0.000 description 1
- MWKMQUZZZYRXBN-UHFFFAOYSA-N NC1=C(C=2C=CC3=C4C=CC=CC4=CC=C3C2C=C1)S(=O)(=O)O Chemical compound NC1=C(C=2C=CC3=C4C=CC=CC4=CC=C3C2C=C1)S(=O)(=O)O MWKMQUZZZYRXBN-UHFFFAOYSA-N 0.000 description 1
- FMJVSVRGYNANAQ-UHFFFAOYSA-N NC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)NC(=O)C1=NC=CC=C1)=O Chemical compound NC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)NC(=O)C1=NC=CC=C1)=O FMJVSVRGYNANAQ-UHFFFAOYSA-N 0.000 description 1
- QYVPCUISWXEVFG-UHFFFAOYSA-N NC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)NC(C=CC1=CC=CC=C1)=O)=O Chemical compound NC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)NC(C=CC1=CC=CC=C1)=O)=O QYVPCUISWXEVFG-UHFFFAOYSA-N 0.000 description 1
- VPKGVGKUQRIENN-UHFFFAOYSA-N NC1C(C=2C=C3C=CC4=CC5=C6C=CC=CC6=CC6=CC=C7C=C(C2C=C1)C3=C4C7=C65)=O Chemical class NC1C(C=2C=C3C=CC4=CC5=C6C=CC=CC6=CC6=CC=C7C=C(C2C=C1)C3=C4C7=C65)=O VPKGVGKUQRIENN-UHFFFAOYSA-N 0.000 description 1
- STYCLHQWDPNDPW-UHFFFAOYSA-N NC=1C=C(C(=O)NC2=CC=CC=3C(C4=CC=CC=C4C(C2=3)=O)=O)C=CC=1 Chemical compound NC=1C=C(C(=O)NC2=CC=CC=3C(C4=CC=CC=C4C(C2=3)=O)=O)C=CC=1 STYCLHQWDPNDPW-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 240000005428 Pistacia lentiscus Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- HMLOTOLZHBXUIA-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=2C=CC3=C4C=CC(=CC4=CC=C3C2C=C1)Br Chemical compound [N+](=O)([O-])C1=CC=2C=CC3=C4C=CC(=CC4=CC=C3C2C=C1)Br HMLOTOLZHBXUIA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KSDIHKMNSYWRFB-UHFFFAOYSA-N chrysen-2-amine Chemical compound C1=CC=CC2=CC=C3C4=CC=C(N)C=C4C=CC3=C21 KSDIHKMNSYWRFB-UHFFFAOYSA-N 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- PNIJRIIGBGFYHF-UHFFFAOYSA-N perborate(2-) Chemical compound O[B-]1(O)OO[B-](O)(O)OO1 PNIJRIIGBGFYHF-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 239000000984 vat dye Substances 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
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE428719A true BE428719A (xx) |
Family
ID=89038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE428719D BE428719A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE428719A (xx) |
-
0
- BE BE428719D patent/BE428719A/fr unknown
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