BE362140A - - Google Patents
Info
- Publication number
- BE362140A BE362140A BE362140DA BE362140A BE 362140 A BE362140 A BE 362140A BE 362140D A BE362140D A BE 362140DA BE 362140 A BE362140 A BE 362140A
- Authority
- BE
- Belgium
- Prior art keywords
- tank
- condensing agents
- sulfuric acid
- acid
- carbazol
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000004040 coloring Methods 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000000463 material Substances 0.000 description 4
- 240000007817 Olea europaea Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-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 1
- 229920000742 Cotton Polymers 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
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
"Procédé pour la préparatlon de matières colorantes a. la ouve, de la série de l'anthraquinone."
<Desc/Clms Page number 2>
On a trouvé que les dérivés "dianthrquinonylami- no" conduisent par fermeture de la chaîne de carbazol au moyen d'agents de condensation acides, à des matières colorantes particulièrement précieuses lorsqu'ils con- tiennent un ou plusieurs atomes d'halogène dans l'anneau acridonique. Les matières colorantes à la cuve ainsi ob- tenues se caractérisent, en comparaison des matières colo rantes non halogènées. par un ton plus plein et de meil- leures propriétés de solidité.
La transformation des dérivés "dianthraquinonylamino" en oarbazols peut se faire non seulement par l'acide sul- furique mais aussi par d'autres agents de condensation appropriés,comme par exemple l'acide ohlorosulfonique ou le mélange de chlorure d'aluminium et de sel de cui- sine, etc, à des températures relativemant basses.
Exemple 1-.- 10 parties en poids-Au dérivé "dianthraquinonyl- amino" qui peut être obtenu par condensation de 1 molé-
EMI2.1
cule de trichlorc-anthraquinonA>-acridon(brevet allemand du 12 février 1910/ 258 561/, exemple 4} avec 1 molécule de 1-benzd'ilamino- 5-aninoanthraquinone, sont dissoutes dans 100 parties en poids d'acide sulfurique concentré. La solution qui est d'abord,d'un brun jaunâtre prend rapidement, déjà à la température ordinaire, une coloration d'un brun olive. /
<Desc/Clms Page number 3>
Par l'agitation dans l'eau on obtient une précipitation d'un vert foncé qui devient d'un brun olive foncé en cas d'addition d'un agent d'oxydation approprié comme le ni- trite de sodium ou d'une solution d'hypochlorite de so- dium.
On chauffe encore à environ 70 et on obtient ain- si une matière colorante qui se dissout en bleu foncé dans l'acide sulfurique concentré et teint le coton en des tons d'un brun noir solide, tandis que la matière de dé- part mise en cuve à l'état de poudre donne des colorations d'un gris verdâtre.
Exemple 2:-
EMI3.1
1 molécule du composé "aminolt PCU'V'8nt être ob-/par réduc- est
EMI3.2
tion du chloranthraquinoneacridozi Mitres/condensée avec 1 molécule de 1-benzollamJno-5-ohloroanthraquînone, de la manière usuelle, par chauffage dans un dissolvant à point d'ébullition élevé, en présence d'aoétate de sodium anhydre et de minimes quantités d'un sel de cuivre,pour
EMI3.3
former le dérivé dianthxaquinonylamino'9.g,ue. Celui-ci est agité en vue de la transformation en oarbazol dans 15 parties en poids d'acide chlorosulfonique à la tempéra- ture ordinaire. Il se forme très rapidement une solution d'un bleu foncé d'où on obtient par coulée, dans l'eau une précipitation d'un brun olive foncé.
La matière colo- rante ainsi obtenue est identique à oelle de l'exemple 1.
<Desc/Clms Page number 4>
<Desc / Clms Page number 1>
"Process for the preparation of dyestuffs on the fly, of the anthraquinone series."
<Desc / Clms Page number 2>
It has been found that the "dianthrquinonylamine" derivatives lead, by closing the carbazol chain by means of acidic condensing agents, to particularly valuable coloring materials when they contain one or more halogen atoms in the compound. acridonic ring. The colorants in the tank thus obtained are characterized, in comparison with non-halogenated coloring materials. by a fuller tone and better solidity properties.
The transformation of the "dianthraquinonylamino" derivatives into oarbazols can be carried out not only by sulfuric acid but also by other suitable condensing agents, such as for example ohlorosulfonic acid or the mixture of aluminum chloride and salt. cooking, etc., at relatively low temperatures.
Example 1 - 10 parts by weight - Au derivative "dianthraquinonylamino" which can be obtained by condensation of 1 mol -
EMI2.1
trichlorc-anthraquinonA> -acridon (German patent of February 12, 1910/258 561 /, example 4} with 1 molecule of 1-benzd'ilamino-5-aninoanthraquinone, are dissolved in 100 parts by weight of concentrated sulfuric acid. The solution which is at first of a yellowish brown quickly takes, already at room temperature, an olive brown color. /
<Desc / Clms Page number 3>
By stirring in water a dark green precipitation is obtained which becomes a dark olive brown with the addition of a suitable oxidizing agent such as sodium nitrite or a solution. sodium hypochlorite.
Heat again to about 70 and thus a coloring material is obtained which dissolves dark blue in concentrated sulfuric acid and dyes the cotton in shades of a solid black brown, while the starting material sets. in vat in powder form gives greenish gray colorings.
Example 2: -
EMI3.1
1 molecule of the compound "aminolt PCU'V'8nt be ob- / by reduction- is
EMI3.2
tion of chloranthraquinoneacridozi Miters / condensed with 1 molecule of 1-benzollamJno-5-ohloroanthraquinone, in the usual manner, by heating in a high-boiling point solvent, in the presence of anhydrous sodium aoetate and minimal amounts of a copper salt, for
EMI3.3
form the derivative dianthxaquinonylamino'9.g, ue. This is stirred for conversion to arbazol in 15 parts by weight of chlorosulfonic acid at room temperature. A dark blue solution forms very quickly from which, by pouring, a dark olive brown precipitation is obtained in the water.
The coloring material thus obtained is identical to that of Example 1.
<Desc / Clms Page number 4>
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE362140A true BE362140A (en) |
Family
ID=35102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE362140D BE362140A (en) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE362140A (en) |
-
0
- BE BE362140D patent/BE362140A/fr unknown
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