PL45016B1 - - Google Patents
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- Publication number
- PL45016B1 PL45016B1 PL45016A PL4501659A PL45016B1 PL 45016 B1 PL45016 B1 PL 45016B1 PL 45016 A PL45016 A PL 45016A PL 4501659 A PL4501659 A PL 4501659A PL 45016 B1 PL45016 B1 PL 45016B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- dye
- water
- cobalt
- aminophenol
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001869 cobalt compounds Chemical class 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- -1 diazo 5-nitro-2-aminophenol Chemical compound 0.000 claims 1
- 239000004922 lacquer Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- CVQSVFTZCRZRBT-UHFFFAOYSA-N naphthalen-2-ylsulfamic acid Chemical compound C1=CC=CC2=CC(NS(=O)(=O)O)=CC=C21 CVQSVFTZCRZRBT-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940055237 sodium 1-naphthalenesulfonate Drugs 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Description
Znane jest otrzymywanie barwników mono- azowych przez sprzeganie dwuazowanego 5-ni- tro-2-aminofenolu z 2-naftylamina w tempera¬ turze pokojowej albo z kwasem 2-naftylami- nosulfonowym (—1) w temperaturze 50°C w obecnosci kwasu naftalensulfonowego —1 w osrodku zakwaszonym kwasem octowym lub mineralnym, które za pomoca srodków oddaja¬ cych kobalt daja sie przeprowadzic w organi¬ cznych rozpuszczalnikach, albo wodzie w kom¬ pleksy z metalami w stosunku 2:1. Te kom¬ pleksowe barwniki zawierajace metal w sto¬ sunku 2 :1 sa rozpuszczalne w wodzie i zna¬ ne sa jako barwniki do welny ciagnace w ka¬ pieli obojetnej.Stwierdzono, ze mozna otrzymac barwnik lakowy praktycznie nierozpuszczalny w wo- *) Wlasciciel patentu oswiadczyl, ze wspólr twórcami wynalazku sa: Essbach, dr Kohler i inz. Ducke. dzie jesli 5-nitro-2-aminofenol sprzega sie z kwasem 2-naftyloaminosulfonowym (—1) w srodowisku silnie zakwaszonym kwasem mi¬ neralnym i nastepnie dziala na wyodrebniony barwnik monoazowy w sposób znany zwiazkami kobaltu. Otrzymuje sie barwnik monoazowy, praktycznie nieropuszczalny w wodzie, który rozpuszcza sie dobrze w róznych organicznych rozpuszczalnikach. Barwnik ten moze znalezc wielostronne zastosowanie jako barwnik do przeswiecajacych laków odznaczajacy sie du¬ za trwaloscia na swiatlo.Przyklad 14.4 g 5-nitro-2-aminofenolu 100 %-owego miesza sie w 600 ml wody z 60 g 1-naftalenosulfonianu sodowego w ciagu 90 minut w temperaturze pokojowej* Nastepnie dodaje sie 70 ml kwasu solnego o gestosci 20° Be i dwuazuje w ciagu 20 minut w tem¬ peraturze 15°C (dodatek lodu) dodajac 24.46 °/o-owy roztwór azotynu w ilosci 1/10 roztworu dwuazowaaegOy no czym traktowany roztwórmiesza sie jeszcze godzine. Do 600 ml wody do¬ daje sie 23 g kwasu 2-naftylaminosulfonowe- go (—1) (kwas Tobiasa) co stanowi 0.1 mola + 5°/o i miesza przez noc. Nastepnie doprowa¬ dza sie temperature do 50°C i dwuazuje jeszcze w ciagu 10—15 minut, po czym miesza sie przez 24 godziny, az do zakonczenia sprzega¬ nia utrzymujac stale temperature 50°C. Papie¬ rek Kongo wykazuje niebieska barwe. Osad odsacza sie i wyciska, przemywa 400 ml roz¬ tworu soli kuchennej o gestosci 6° Be. Otrzy¬ many placek miesza sie przez 2 godziny z 1000 ml wody, nastepnie ogrzewa sie do tem¬ peratury 80—85°C i dodaje do roztworu barwni ka 40 ml lugu sodowego 28.8 °/o-owego. Do te¬ go roztworu wlewa sie szybko roztwór 14 g siarczanu kobaltu w 50 ml wody ogrzany do 85°C i miesza w ciagu 30 minut utrzymujac temperature 85°C. Nastepnie zobojetnia sie za pomoca okolo 10 ml kwasu octowego lodowa¬ tego, po czym odsacza sie, przemywa mala iloscia wody i suszy. PLIt is known to prepare monoazo dyes by combining diazotized 5-nitro-2-aminophenol with 2-naphthylamine at room temperature or with 2-naphthylaminesulfonic acid (-1) at 50 ° C in the presence of naphthalensulfonic acid - 1 in a medium acidified with acetic or mineral acid, which can be converted in organic solvents or water into complexes with metals in a ratio of 2: 1 by means of cobalt-releasing agents. These complex dyes containing 2: 1 metal are soluble in water and are known as wool dyes dragging in neutral baths. It has been found that a wax dye that is practically insoluble in water can be obtained *) Patent owner stated that the co-inventors of the invention are: Essbach, Dr. Kohler and Ing. Ducke. day if 5-nitro-2-aminophenol is combined with 2-naphthylaminosulfonic acid (-1) in a highly acidified environment with mineral acid and then acts on the isolated monoazo dye in a manner known by cobalt compounds. A monoazo dye is obtained, practically insoluble in water, which dissolves well in various organic solvents. This dye can be used in many ways as a dye for translucent lakes, characterized by high stability to light. Example 14.4 g of 100% 5-nitro-2-aminophenol are mixed in 600 ml of water with 60 g of sodium 1-naphthalenesulfonate for 90 minutes at room temperature * Then 70 ml of 20 ° B hydrochloric acid are added and diazotized for 20 minutes at 15 ° C (addition of ice) by adding 24.46% nitrite solution to 1/10 of the diazo solution then the treated solution is stirred for another hour. To 600 ml of water, 23 g of 2-naphthylaminosulfonic acid (-1) (Tobias' acid) are added, equal to 0.1 mol + 5%, and stirred overnight. The temperature is then brought to 50 ° C and diazotized for a further 10-15 minutes, followed by stirring for 24 hours, maintaining a constant temperature of 50 ° C until completion of the performance. Congo paper shows a blue color. The precipitate is filtered off and squeezed out, washed with 400 ml of a 6 ° B common salt solution. The resulting cake is mixed with 1000 ml of water for 2 hours, then heated to 80-85 ° C and 40 ml of 28.8% sodium liquor are added to the dye solution. A solution of 14 g of cobalt sulfate in 50 ml of water, heated to 85 ° C, is quickly poured into this solution and stirred for 30 minutes, maintaining the temperature at 85 ° C. It is then neutralized with about 10 ml of glacial acetic acid, then drained, washed with a little water and dried. PL
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL45016B1 true PL45016B1 (en) | 1961-08-15 |
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