AT69355B - Process for the preparation of acidic wool dyes of the anthraquinone series. - Google Patents
Process for the preparation of acidic wool dyes of the anthraquinone series.Info
- Publication number
- AT69355B AT69355B AT69355DA AT69355B AT 69355 B AT69355 B AT 69355B AT 69355D A AT69355D A AT 69355DA AT 69355 B AT69355 B AT 69355B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- preparation
- anthraquinone series
- wool dyes
- acidic
- Prior art date
Links
- 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 title claims description 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 239000000975 dye Substances 0.000 title description 4
- 230000002378 acidificating effect Effects 0.000 title description 3
- 238000000034 method Methods 0.000 title description 3
- 210000002268 wool Anatomy 0.000 title description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- GAZYLEJQUACYIG-UHFFFAOYSA-N 2-amino-9,10-dioxoanthracene-1-sulfonic acid Chemical class C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(N)=CC=C3C(=O)C2=C1 GAZYLEJQUACYIG-UHFFFAOYSA-N 0.000 claims description 2
- YHEHZMLCNQADSB-UHFFFAOYSA-N 5-amino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC(S(O)(=O)=O)=CC=C2C(=O)C2=C1C=CC=C2N YHEHZMLCNQADSB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IVJJSNFWOZGKTE-UHFFFAOYSA-N 1,5-diamino-9,10-dioxo-2h-anthracene-1,2-disulfonic acid Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)C2=C1C=CC(S(O)(=O)=O)C2(N)S(O)(=O)=O IVJJSNFWOZGKTE-UHFFFAOYSA-N 0.000 description 1
- BEQOZTJJZZOVBR-UHFFFAOYSA-N 5-amino-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)C2=C1C=CC=C2S(O)(=O)=O BEQOZTJJZZOVBR-UHFFFAOYSA-N 0.000 description 1
- UEZJOQCWOFDUOR-UHFFFAOYSA-N 8-amino-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2N UEZJOQCWOFDUOR-UHFFFAOYSA-N 0.000 description 1
- UGRPYHKFFFMXCA-UHFFFAOYSA-N 8-amino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=C(S(O)(=O)=O)C=C2C(=O)C2=C1C=CC=C2N UGRPYHKFFFMXCA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- -1 benzoylaminoanthraquinone sulfonic acids Chemical class 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von sauren Wollfarbstoffen der Anthrachinonreihe.
Es wurde gefunden, dass die Alkalisalze der Aminoamhrachinonsulfosäuren durch Erhitzen mit Benzoesäure in neue Farbstoffe übergehen, welche sich von den Ausgangsmaterialien durch bessere Echtheitseigenschaften und eine hellere Nuance auszeichnen.
Die Produkte sind identisch mit den im D. R. P. Nr. 223069 (Beispiel 3) beschriebenen Benzoylaminoanthrachinonsulfosäuren. Nach dem genannten Patente erfolgt die Einführung des Benzovlrestes durch Einwirkung von Benzoylchlorid auf die freien Amino- anthrachinonsulfosäuren in Nitrobenzol als Lösungsmittel und bei Gegenwart einer tertiären Base, wie Pyridin, Dimetylanilin oder Chinolin.
EMI1.1
Vorteil, da einerseits die Darstellung der freien Aminoanthrachinousulfosäuren. die wegen des gleichzeitig sauren und basischen Charakters dieser Körper Schwierigkeiten bereitet und andererseits die Überführung der Benzoesäure in Benzoylchlorid sowie endlich die Anwendung von Lösungsmitteln und Kontaktscbstanzen überflüssig gemacht wird.
Das Verfahren wird durch folgendes Beispiel erläutert :
1 Teil Natriumsalz der 1-Aminoanthrachinon-6-sulfosäure und 4 Teile Benzoesäure werden einige Stunden auf 40 bis 2500 erhitzt. Die ebmeizc wird mit Wasser aufgenommen und solange mit Wasserdampf behandelt, bis im Destitiat ke : ne Benzoesänre mehr nachzuweisen ist. Beim Erkalten kristallisiert der im Wasser schwer lösliche Farbstoff in gelben Nädelchen aus.
EMI1.2
EMI1.3
<tb>
<tb>
Farbung <SEP> auf <SEP> ungebeizter <SEP> Welle
<tb> Aminosaure <SEP> Benzoylderivat
<tb> 1-Aminoanthrachinon-6-sulfosäure <SEP> ........ <SEP> ponceauxrot <SEP> gelb
<tb> 1-Aminoanthrachinon-7-sulfosäure <SEP> .......... <SEP> rot <SEP> gelb
<tb> 1-Aminoanthrachinon-5-sulfosäure <SEP> .......... <SEP> braybrit <SEP> gekb
<tb> 1-Aminoanthrachinon-8-sulfosäure <SEP> ........... <SEP> ziegelrot <SEP> gelbgrün
<tb> 1,5-Diaminoanthrachinon-disulfosäure <SEP> ........ <SEP> violert <SEP> rot
<tb> Aminoalizarinsulfosäure <SEP> ......... <SEP> violettbraun <SEP> hraun
<tb>
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of acidic wool dyes of the anthraquinone series.
It has been found that the alkali salts of the aminoamhraquinone sulfonic acids, when heated with benzoic acid, are converted into new dyes which are distinguished from the starting materials by better fastness properties and a lighter shade.
The products are identical to the benzoylaminoanthraquinone sulfonic acids described in D. R. P. No. 223069 (Example 3). According to the patent mentioned, the benzoyl radical is introduced by the action of benzoyl chloride on the free amino anthraquinone sulfonic acids in nitrobenzene as the solvent and in the presence of a tertiary base such as pyridine, dimethylaniline or quinoline.
EMI1.1
Advantage because on the one hand the representation of the free aminoanthraquinous sulfonic acids. which causes difficulties because of the simultaneously acidic and basic character of these bodies and, on the other hand, the conversion of benzoic acid into benzoyl chloride and finally the use of solvents and contact substances are made superfluous.
The procedure is illustrated by the following example:
1 part of the sodium salt of 1-aminoanthraquinone-6-sulfonic acid and 4 parts of benzoic acid are heated to 40-2500 for a few hours. The ebmeizc is absorbed with water and treated with steam until no more benzoic acid can be detected in the destitute. When it cools down, the dye, which is sparingly soluble in water, crystallizes out in yellow needles.
EMI1.2
EMI1.3
<tb>
<tb>
Coloring <SEP> on <SEP> unpickled <SEP> shaft
<tb> amino acid <SEP> benzoyl derivative
<tb> 1-Aminoanthraquinone-6-sulfonic acid <SEP> ........ <SEP> ponce red <SEP> yellow
<tb> 1-Aminoanthraquinone-7-sulfonic acid <SEP> .......... <SEP> red <SEP> yellow
<tb> 1-Aminoanthraquinone-5-sulfonic acid <SEP> .......... <SEP> braybrit <SEP> kb
<tb> 1-Aminoanthraquinone-8-sulfonic acid <SEP> ........... <SEP> brick red <SEP> yellow green
<tb> 1,5-diaminoanthraquinone disulfonic acid <SEP> ........ <SEP> violet <SEP> red
<tb> Aminoalizarin sulfonic acid <SEP> ......... <SEP> violet brown <SEP> brown
<tb>
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT69355T | 1914-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT69355B true AT69355B (en) | 1915-07-10 |
Family
ID=3591175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT69355D AT69355B (en) | 1914-04-20 | 1914-04-20 | Process for the preparation of acidic wool dyes of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT69355B (en) |
-
1914
- 1914-04-20 AT AT69355D patent/AT69355B/en active
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