DE1644206C3

DE1644206C3 - Wasserlösliche Reaktivfarbstoffe, deren Herstellung und Verwendung zum Färben von Cellulosematerialien, Wolle, Seide, Polyamid- und Polyurethanfasern

Wasserlösliche Reaktivfarbstoffe, deren Herstellung und Verwendung zum Färben von Cellulosematerialien, Wolle, Seide, Polyamid- und Polyurethanfasern

Info

Publication number: DE1644206C3
Authority: DE; Germany
Prior art keywords: amino; acid; sulfonic acid; dyes; parts
Prior art date: 1967-04-07
Legal status : Expired

Application number

DE1967F0052059

Other languages

German (de)

English (en)

Other versions

DE1644206A1 (de

DE1644206B2 (de

Inventor

Hans-Samuel Dr. 5673 Burscheid Bien

Erich Dr. 5074 Odenthal Klauke

Klaus Dr. 5090 Leverkusen Wunderlich

Current Assignee

Bayer AG

Original Assignee

Bayer AG

Priority date

1967-04-07

Filing date

1967-04-07

Publication date

1978-06-01

1967-04-07 Application filed by Bayer AG filed Critical Bayer AG

1967-04-07 Priority to DE1967F0052059 priority Critical patent/DE1644206C3/de

1968-02-09 Priority to CH1836868A priority patent/CH510091A/de

1968-02-09 Priority to CH1836968A priority patent/CH499603A/de

1968-03-29 Priority to FR1568321D priority patent/FR1568321A/fr

1968-04-02 Priority to NL6804608A priority patent/NL6804608A/xx

1968-04-03 Priority to BE713141D priority patent/BE713141A/xx

1968-04-05 Priority to JP2218368A priority patent/JPS4822873B1/ja

1968-04-05 Priority to GB1648468A priority patent/GB1184165A/en

1970-10-29 Publication of DE1644206A1 publication Critical patent/DE1644206A1/de

1977-10-13 Publication of DE1644206B2 publication Critical patent/DE1644206B2/de

1978-06-01 Application granted granted Critical

1978-06-01 Publication of DE1644206C3 publication Critical patent/DE1644206C3/de

Status Expired legal-status Critical Current

Links

239000000985 reactive dye Substances 0.000 title claims description 25
239000000463 material Substances 0.000 title claims description 19
238000004043 dyeing Methods 0.000 title claims description 12
210000002268 wool Anatomy 0.000 title claims description 7
229920006306 polyurethane fiber Polymers 0.000 title claims 2
229920002678 cellulose Polymers 0.000 title description 17
239000001913 cellulose Substances 0.000 title description 17
239000004952 Polyamide Substances 0.000 title description 3
229920002647 polyamide Polymers 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title description 2
239000000975 dye Substances 0.000 claims description 149
230000008878 coupling Effects 0.000 claims description 42
238000005859 coupling reaction Methods 0.000 claims description 42
238000010168 coupling process Methods 0.000 claims description 40
239000010949 copper Substances 0.000 claims description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
229910052802 copper Inorganic materials 0.000 claims description 14
239000000987 azo dye Substances 0.000 claims description 13
125000000542 sulfonic acid group Chemical group 0.000 claims description 13
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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 7
150000004056 anthraquinones Chemical class 0.000 claims description 7
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052804 chromium Inorganic materials 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
239000001007 phthalocyanine dye Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
229910002480 Cu-O Inorganic materials 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 4
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 4
239000001000 anthraquinone dye Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
150000002790 naphthalenes Chemical class 0.000 claims description 2
239000004627 regenerated cellulose Substances 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
239000004753 textile Substances 0.000 claims 1
239000002253 acid Substances 0.000 description 101
239000000306 component Substances 0.000 description 59
239000000243 solution Substances 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
-1 pyrimidinyl radicals Chemical class 0.000 description 52
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 42
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 35
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 28
WZGAMTYFRMRZNL-UHFFFAOYSA-N 3,4,5,6-tetrafluoropyridazine Chemical compound FC1=NN=C(F)C(F)=C1F WZGAMTYFRMRZNL-UHFFFAOYSA-N 0.000 description 27
238000000034 method Methods 0.000 description 27
239000011734 sodium Substances 0.000 description 24
229920000742 Cotton Polymers 0.000 description 22
235000002639 sodium chloride Nutrition 0.000 description 22
239000011780 sodium chloride Substances 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 18
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
239000004744 fabric Substances 0.000 description 16
230000008569 process Effects 0.000 description 15
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 13
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 13
230000010933 acylation Effects 0.000 description 13
238000005917 acylation reaction Methods 0.000 description 13
125000003277 amino group Chemical group 0.000 description 13
239000000203 mixture Substances 0.000 description 13
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 11
159000000000 sodium salts Chemical class 0.000 description 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 10
239000004202 carbamide Substances 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000010979 ruby Substances 0.000 description 10
229910001750 ruby Inorganic materials 0.000 description 10
229910000029 sodium carbonate Inorganic materials 0.000 description 10
235000011121 sodium hydroxide Nutrition 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
239000002243 precursor Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 8
239000011651 chromium Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
238000001035 drying Methods 0.000 description 8
239000002609 medium Substances 0.000 description 8
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 8
239000000843 powder Substances 0.000 description 8
206010039587 Scarlet Fever Diseases 0.000 description 7
238000009833 condensation Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
238000003756 stirring Methods 0.000 description 7
238000006193 diazotization reaction Methods 0.000 description 6
150000003254 radicals Chemical group 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
230000008719 thickening Effects 0.000 description 6
229920003043 Cellulose fiber Polymers 0.000 description 5
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
125000003368 amide group Chemical group 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 4
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 4
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 4
235000019233 fast yellow AB Nutrition 0.000 description 4
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
239000000344 soap Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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 3
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 3
JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 3
LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 3
YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 3
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 3
KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 3
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 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
241000092161 Pithys Species 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000009471 action Effects 0.000 description 3
229940072056 alginate Drugs 0.000 description 3
235000010443 alginic acid Nutrition 0.000 description 3
229920000615 alginic acid Polymers 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000003086 colorant Substances 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
150000004699 copper complex Chemical class 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910001385 heavy metal Inorganic materials 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
239000000661 sodium alginate Substances 0.000 description 3
235000010413 sodium alginate Nutrition 0.000 description 3
229940005550 sodium alginate Drugs 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
QJGHJWKPZQIOSN-UHFFFAOYSA-N (4-aminophenyl)methanesulfonic acid Chemical compound NC1=CC=C(CS(O)(=O)=O)C=C1 QJGHJWKPZQIOSN-UHFFFAOYSA-N 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Polymers CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
DCYBHNIOTZBCFS-UHFFFAOYSA-N 2-amino-5-[(4-sulfophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 DCYBHNIOTZBCFS-UHFFFAOYSA-N 0.000 description 2
LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 2
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 2
FOINSAWEWXUXPQ-UHFFFAOYSA-N 4-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 FOINSAWEWXUXPQ-UHFFFAOYSA-N 0.000 description 2
APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 2
KKBQCLVIBFUKGQ-UHFFFAOYSA-N 4-amino-5-methylbenzene-1,3-disulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1N KKBQCLVIBFUKGQ-UHFFFAOYSA-N 0.000 description 2
UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 2
HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 2
ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
150000001868 cobalt Chemical class 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
235000019646 color tone Nutrition 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
229910000365 copper sulfate Inorganic materials 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
239000000835 fiber Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
238000005185 salting out Methods 0.000 description 2
KWVVTSALYXIJSS-UHFFFAOYSA-L silver(ii) fluoride Chemical compound [F-].[F-].[Ag+2] KWVVTSALYXIJSS-UHFFFAOYSA-L 0.000 description 2
229910052979 sodium sulfide Inorganic materials 0.000 description 2
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 2
YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 2
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
238000007747 plating Methods 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000002964 rayon Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000002791 soaking Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
MAZKAODOCXYDCM-UHFFFAOYSA-N tetrazone Chemical group N\N=N\N MAZKAODOCXYDCM-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
239000004552 water soluble powder Substances 0.000 description 1