DE2215238C3 - Disazo dyes containing sulfonic acid groups, their production and use for dyeing leather, paper and natural or synthetic polyamides - Google Patents
Disazo dyes containing sulfonic acid groups, their production and use for dyeing leather, paper and natural or synthetic polyamidesInfo
- Publication number
- DE2215238C3 DE2215238C3 DE19722215238 DE2215238A DE2215238C3 DE 2215238 C3 DE2215238 C3 DE 2215238C3 DE 19722215238 DE19722215238 DE 19722215238 DE 2215238 A DE2215238 A DE 2215238A DE 2215238 C3 DE2215238 C3 DE 2215238C3
- Authority
- DE
- Germany
- Prior art keywords
- paper
- natural
- sulfonic acid
- acid groups
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 12
- 239000010985 leather Substances 0.000 title claims description 5
- 239000004952 Polyamide Substances 0.000 title claims description 4
- 229920002647 polyamide Polymers 0.000 title claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 3
- 238000004043 dyeing Methods 0.000 title claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000001808 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OCDSFJBMDKBLRJ-UHFFFAOYSA-N 3,5-diamino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC(N)=C(Cl)C(S(O)(=O)=O)=C1 OCDSFJBMDKBLRJ-UHFFFAOYSA-N 0.000 description 1
- 101710032013 IFITM1 Proteins 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N Sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000011528 polyamide (building material) Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Description
SO3HSO 3 H
H2NH 2 N
NH,NH,
mit 2 Mol einer Kupplungskomponente der Formel with 2 moles of a coupling component of the formula
OH
RHNOH
RHN
SO,HSO, H
in wäßriger Lösung bei einem pH von ungefähr O bis 4 umsetzt.in aqueous solution at a pH of about 0 to 4.
Die Erfindung betrifft Farbstoffe die in Form der freien Säuren der allgemeinen Formel 1The invention relates to dyes in the form of the free acids of the general formula 1
mil 2 Mol einer Kupplungskomponente der Formelmil 2 moles of a coupling component of the formula
3535
HO3SHO 3 S
SO3HSO 3 H
HOHO
N = NN = N
OHOH
4040
SO3HSO 3 H
NHRNHR
NHRNHR
entsprechen, in dercorrespond in the
R Wasserstoff, Methyl oder Phenyl ist.R is hydrogen, methyl or phenyl.
Zur Herstellung der Farbstoffe der Formel I
man eine Tetrazoverbindung des Diamins der FormelFor the preparation of the dyes of the formula I.
a tetrazo compound of diamine of the formula
SO3HSO 3 H
H1NH 1 N
in der R die angegebene Bedeutung hat, in wäßriger Lösung bei einem pH von ungefähr 0 bis 4 umsetzen.
Einzelheiten der Herstellung können den Beispielen entnommen werden.in which R has the meaning given, react in aqueous solution at a pH of approximately 0 to 4.
Details of the preparation can be found in the examples.
Die neuen Farbstoffe sind blaustichig rot und eignen sich insbesondere zum Färben von Leder, Papier und natürlichen oder synthetischen Polyamiden, wie Wolle, kann 50 Pelzen oder Polyamid 6.6. Hervorzuheben sind die guten Naß-, Alkali- und Säureechtheiten.The new dyes are bluish red and are particularly suitable for dyeing leather, paper and natural or synthetic polyamides such as wool, 50 furs or polyamide 6.6. The ones that deserve special mention good wet, alkali and acid fastness properties.
Gegenüber einem nächstvergleichbaren, aus der FR-PS 4 17 463 bekannten Farbstoff haben die neuen Farbstoffe überraschenderweise Vorteile in der Lichtechtheit und der Farbtonkonstanz auf verschiedenen Lederarten.Compared to a next comparable dye known from FR-PS 4 17 463, the new Dyes, surprisingly, have advantages in terms of lightfastness and color constancy on various Types of leather.
Im folgenden Beispiel beziehen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht.In the following example, parts and percentages refer to, unless otherwise stated the weight.
22,2 Teile 2,4-Diamino-l-chlorbenzol-6-sulfonsäure werden in t OO Teilen Wasser und 8 Teilen 50prozentiger Natronlauge neutral gelöst und nach Zugabe von 80 Teilen 36prozentiger Salzsäure und 200 Teilen Eis mit einer Lösung von 13,8 Teilen Natriumnitrit bisdiazotiert.22.2 parts of 2,4-diamino-1-chlorobenzene-6-sulfonic acid are 50 percent in t, OO parts of water and 8 parts Sodium hydroxide solution dissolved neutrally and after the addition of 80 parts of 36 percent hydrochloric acid and 200 parts of ice with bisdiazotized a solution of 13.8 parts of sodium nitrite.
Nach ungefähr 20 Minuten bei 0 bis 5°C wird der Nitritüberschuß wie üblich mit Amidosulfonsäure entfernt. Die Bisdiazoverbindung wird dann bei 10 bis 15° C mit der Suspension vereinigt, die man durch Lösen von 47,8 Teilen 2-Amino-8-hydroxynaphthalin-6-sulfon-After about 20 minutes at 0 to 5 ° C, the nitrite excess is as usual with sulfamic acid removed. The bisdiazo compound is then combined at 10 to 15 ° C with the suspension, which is obtained by dissolving of 47.8 parts of 2-amino-8-hydroxynaphthalene-6-sulfone
/ i/ i
säure in 500 Teilen Wasser und ungefähr 14 Teilen wasserfreiem Natriumcarbonat und anschließender Zugabe von 200 Teilen Eis und 22 Teilen 36prozentiger Salzsäure erhältacid in 500 parts of water and approximately 14 parts of anhydrous sodium carbonate and then Addition of 200 parts of ice and 22 parts of 36 percent hydrochloric acid is obtained
Nach dem Zufügen der Bisdiazoverbim! läßt man ungefähr 45 Minuten nachrühren, gib dann zur Vervollständigung der Kupplung ungefähr 80 Teile Natriumacetat (wasserfrei) bis zu einem pH von 4 zu und läßt die Mischung über Nacht rüliren. Danach gibt man 120 Teile Kaliumchlorid zu.After adding the Bisdiazoverbim! let one Stir for about 45 minutes, then add about 80 parts to complete the coupling Sodium acetate (anhydrous) is added to a pH of 4 and the mixture is left to stir overnight. After that there to 120 parts of potassium chloride.
Anschließend wird der Disazofarbstoff abgesaugt und bei 700C getrocknet Man erhält ein dunkles Pulver, das in Wasser mit blaustichig roter Farbe löslich ist und Leder im gleichen Farbton färbt.Subsequently, the disazo dye is suction filtered and dried at 70 0 C. This gives a dark powder which is soluble in water in a bluish red color and dyes leather in the same color.
Die in der folgenden Tabelle aufgeführten Farbstoffe haben ähnliche coloristische Eigenschaften und wurden analog Beispiel 1 hergestellt.The dyes listed in the table below have and were similar in coloristic properties prepared analogously to Example 1.
Beispiel Nr.Example no.
KupplungskomponfnU·Coupling component
HO3SHO 3 S
OHOH
Farbton auf Letk-rShade on letk-r
NHQH5 NHQH 5
violettviolet
NHCH,NHCH,
rolviolettrolviolet
H O, SHO, S
Claims (4)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722215238 DE2215238C3 (en) | 1972-03-29 | Disazo dyes containing sulfonic acid groups, their production and use for dyeing leather, paper and natural or synthetic polyamides | |
| IT4902373A IT980004B (en) | 1972-03-29 | 1973-03-26 | DIAZOCOLORANTS CONTAINING GROUPS OF SULFONIC ACID |
| FR7310972A FR2178065B1 (en) | 1972-03-29 | 1973-03-27 | |
| DD16974873A DD104094A5 (en) | 1972-03-29 | 1973-03-27 | |
| BE129366A BE797446A (en) | 1972-03-29 | 1973-03-28 | DIS-AZOIC DYES WITH SULPHONIC ACID GROUPS |
| GB1484673A GB1415922A (en) | 1972-03-29 | 1973-03-28 | Disazo dyes containing sulpho groups |
| CH445773A CH599303A5 (en) | 1972-03-29 | 1973-03-28 | |
| JP3513573A JPS5735205B2 (en) | 1972-03-29 | 1973-03-29 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722215238 DE2215238C3 (en) | 1972-03-29 | Disazo dyes containing sulfonic acid groups, their production and use for dyeing leather, paper and natural or synthetic polyamides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2215238A1 DE2215238A1 (en) | 1973-10-11 |
| DE2215238B2 DE2215238B2 (en) | 1977-03-31 |
| DE2215238C3 true DE2215238C3 (en) | 1977-11-17 |
Family
ID=
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