DE612072C - Process for the production of water-insoluble azo dyes - Google Patents
Process for the production of water-insoluble azo dyesInfo
- Publication number
- DE612072C DE612072C DEI47490D DEI0047490D DE612072C DE 612072 C DE612072 C DE 612072C DE I47490 D DEI47490 D DE I47490D DE I0047490 D DEI0047490 D DE I0047490D DE 612072 C DE612072 C DE 612072C
- Authority
- DE
- Germany
- Prior art keywords
- water
- azo dyes
- production
- insoluble azo
- solution
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- -1 acetoacetyl compound Chemical class 0.000 description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 1
- WOXLPNAOCCIZGP-UHFFFAOYSA-N 4-chloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=CC=C1N WOXLPNAOCCIZGP-UHFFFAOYSA-N 0.000 description 1
- MTHFVMAPCLAACL-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3NC12.S1C=NC=C1 Chemical class C1=CC=CC=2C3=CC=CC=C3NC12.S1C=NC=C1 MTHFVMAPCLAACL-UHFFFAOYSA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical class C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung von wasserunlöslichen Azofarbstoffen Gegenstand des Hauptpatents 6oo ioi ist ein Verfahren zur Herstellung von wasserunlöslichen Azofarbstoffen, darin bestehend, daß Acetessigsäureamide, in denen ein Wasserstoffatom der Amidgruppe durch den Rest des Benzothiazals bzw. des im Benzolkern substituierten Benzothiazols ersetzt ist, mit Diazokomponenten der aromatischen Reihe gekuppelt werden, die keine wasserlöslich machenden Gruppen enthalten.Process for the preparation of water-insoluble azo dyes Subject of the main patent 6oo ioi is a process for the production of water-insoluble Azo dyes, consisting in that acetoacetic acid amides in which a hydrogen atom of the amide group by the remainder of the benzothiazal or that substituted in the benzene nucleus Benzothiazole is replaced, coupled with diazo components of the aromatic series that do not contain any water-solubilizing groups.
Es wurde nun gefunden, daß man an Stelle der im Hauptpatent genannten- Kupplungskomponenten auch Acetessigsäureamide verwenden kann, in denen ein Wasserstoffatom der Amidgruppe durch den Rest eines anderen Thiazols ersetzt ist, z. B. durch den Rest von Naphthothiazolen oder Carbazolthiazolen.It has now been found that instead of the one mentioned in the main patent Coupling components can also use acetoacetic acid amides, in which a hydrogen atom the amide group is replaced by the remainder of another thiazole, e.g. B. by the Remainder of naphthothiazoles or carbazole thiazoles.
Vor den aus der Patentschrift 393 722 bekannten vergleichbaren Farbstoffen zeichnen sich die nach vorliegendem Verfahren erhältlichen Farbstoffe durch im allgemeinen bessere Weißätzbarkeit aus.Before the comparable dyes known from patent specification 393 722 the dyes obtainable by the present process are generally characterized by better white etchability.
Beispiel i 6g2-Acetoacetylamino-(9'-äthyl-a', 3'-carbazol)-thiazol von der Zusammensetzung werden mit 6 ccm Natronlauge 38° Be und 6 ccm Türkischrotöl in -heißem Wasser zu 1 1 gelöst, und in dieser Lösung werden 50 9 g Baumwollgarn unter Zusatz von Kochsalz grundiert. Durch Entwickeln in einer mit Natriumacetat abgestumpften Lösung von 1,q.2 g diazotiertem 2-Amino-5-chlor-i-methvlbenzol erhält man ein klares Goldgelb von guten Echtheitseigenschaften. Beispiel 2 6.g 2-Acetoacetylamino - (3 ', ¢' - acenaphtheno)-thiazol von der Zusammensetzung werden mit 5 ccm Natronlauge 38' B6 und 1o ccm Tü rkischrotöl in heißem Wasser zu 1 1 gelöst. 5o g Baumwollgarn werden in dieser Lösung unter Zusatz von Natriumchlorid grundiert, und die Färbung wird in einer durch Natriumacetat abgestumpften Lösung von 1,42 g diazotiertem i-Amino-2-methyl-5-chlorbenzol entwickelt. Nach dem Spülen und Seifen erhält man ein Orange von guten Echtheitseigenschaften. Beispiel 3 3,:24.- der Acetoacetylverbindung von der Zusammensetzung werden in So ccm Pyridin gelöst und mit der Diazoverbindung von 1,42 g i-Amino-2-methyl-4-chlorbenzol gekuppelt. Man erhält einen rotstichiggelben Farbstoff, der sich zum Färben von Lacken eignet. Beispiel 1,429 2-Acetoacetylaminor(i', 2'-naphtho)-thiazol -von der Zusammensetzung und 1,28 g der Diazoaminoverbindung aus diazotiertem 4-Chlor-2-methoxy-i-aminobenzol und Sarkosin werden mit o,7 ccm Natronlauge 38° Be, 5 g neutraler Chromatlösun,g und 5 g Thiodiglykol angeteigt und in 25 ccm Wasser gelöst. Die Lösung rührt man in Sog neutrale Stärke-Traganit-Verdickung und stellt diese Druckpaste mit Wasser auf ioo g. Nach dem Aufdrucken und Trocknen wird mit essig- und ameisensäurehaltigem Dampf entwickelt. Man erhält ein kräftiges grünstichiges Gelb.Example i 6g2-Acetoacetylamino- (9'-ethyl-a ', 3'-carbazole) -thiazole of the composition are dissolved with 6 ccm sodium hydroxide solution 38 ° Be and 6 ccm Turkish red oil in hot water to 1 liter, and 50 9 g cotton yarn are primed in this solution with the addition of table salt. Developing in a solution of 1.2 g of diazotized 2-amino-5-chloro-i-methylbenzene truncated with sodium acetate gives a clear golden yellow with good fastness properties. Example 2 6.g 2-Acetoacetylamino - (3 ', ¢' - acenaphtheno) -thiazole of the composition are dissolved in hot water to 1 liter with 5 cc sodium hydroxide solution 38 ' B6 and 10 cc turkish red oil. 50 g of cotton yarn are primed in this solution with the addition of sodium chloride, and the color is developed in a solution of 1.42 g of diazotized i-amino-2-methyl-5-chlorobenzene which has been blunted by sodium acetate. After rinsing and soaking, an orange with good fastness properties is obtained. Example 3 3,: 24.- the acetoacetyl compound of the composition are dissolved in 50 cc of pyridine and coupled with the diazo compound of 1.42 g of i-amino-2-methyl-4-chlorobenzene. A reddish-tinged yellow dye is obtained which is suitable for dyeing paints. Example 1,429 2-Acetoacetylaminor (i ', 2'-naphtho) thiazole - of the composition and 1.28 g of the diazoamino compound from diazotized 4-chloro-2-methoxy-i-aminobenzene and sarcosine are made into a paste with 0.7 cc of 38 ° Be sodium hydroxide solution, 5 g of neutral chromate solution, g and 5 g of thiodiglycol and dissolved in 25 cc of water . The solution is stirred in a suction neutral starch-traganite thickening and this printing paste is made up to 100 g with water. After printing and drying, steam containing acetic and formic acid is used to develop. A strong greenish yellow is obtained.
Beispiel 5 1,42 g 2-Acetoacetylamino-(2', i'-naphtho)-th-iazol und 2,o5 g der Diazoaminoverbindung aus diazotiertem 4-Nitro-2-methoxy-i-aininobenzol und i-Mebhylaminobenzol-4-sulfo-2-carbonsäure geben, in gleicher Art wie in Beispiel 4 gedruckt und entwickelt, ein kräftiges Goldgelb. Beispiel 6 3 g 2-Acetoacetylamino- (2',1'-naphtho)-thiazol werden mit 3 ccm Äthylalkohol, 4,5 ccm Natronlauge von 38° Be und 6 ccm Türkischrotöl in heißem Wasser zu 1 1 gelöst. Hiermit werden 50 g Baumwollgarn unter Zusatz von Kochsalz grundiert und darauf in einer mit Natriumacetat abgestumpften Lösung von 2,6g diazotiertem i-Methoxy-2-aminobenzol-4-sulfonsäurediäthylamid entwickelt, gespült und geseift. Man erhält ein klares grünstichiges Gelb von sehr guter Lichtechtheit. Beispiel 7 3 g 2-Acetoacetylamino-6'-methoxy-(i', 2'-naphtho)-thiazol werden mit 6 ccm Natronlauge von 38° Be und 6 ccm Türkischrotöl in heißem Wasser zu 1 1 gelöst und hiermit unter Zusatz von Kochsalz 50 g Baumwollgarn grundiert. Durch Entwickeln in einer mit Natriumacetat abgestumpften Lösung von 2,2g diazotiertem 4-Chlor-2-amino-i, i'-diphenyläther erhält man nach dem Spülen und Seifen ein klares Geld von guten Echtheitseigenschaften. Beispiel 8 Ein Stück Baumwollgewebe wird mit einer wäßrigen Lösung, die io g 2-Acetoacetylamino-(i', 2'-naphtho)-thiazo'1, 8 ccm Natronlauge von 38° Be und io ccm Türkischrotöl im Liter enthält, imprägniert. Daraufhin wird getrocknet und mit einer Lösung von 7 g diazotiertem i-Amino-2-nitro-q.-methoxybenrzol im Liter entwickelt, gespült und geseift. Man erhält ein klares Goldorange von sehr guten Echtheitseigenschaften.Example 5 1.42 g of 2-acetoacetylamino- (2 ', i'-naphtho) -th-iazole and 2.05 g of the diazoamino compound from diazotized 4-nitro-2-methoxy-i-aininobenzene and i-mebhylaminobenzene-4- sulfo-2-carboxylic acid give, printed and developed in the same way as in Example 4, a strong golden yellow. Example 6 3 g of 2-acetoacetylamino (2 ', 1'-naphtho) thiazole are dissolved in 1 liter of hot water with 3 cc of ethyl alcohol, 4.5 cc of sodium hydroxide solution at 38 ° Be and 6 cc of Turkish red oil. With this, 50 g of cotton yarn are primed with the addition of table salt and then developed, rinsed and soaped in a solution of 2.6 g of diazotized i-methoxy-2-aminobenzene-4-sulfonic acid diethylamide truncated with sodium acetate. A clear greenish yellow of very good lightfastness is obtained. Example 7 3 g of 2-acetoacetylamino-6'-methoxy- (i ', 2'-naphtho) -thiazole are dissolved in 1 liter of hot water with 6 cc of 38 ° Be sodium hydroxide solution and 6 cc of Turkish red oil and herewith with the addition of table salt 50 g cotton thread primed. By developing in a solution of 2.2 g of diazotized 4-chloro-2-amino-i, i'-diphenyl ether truncated with sodium acetate, a clear money with good fastness properties is obtained after rinsing and soaping. EXAMPLE 8 A piece of cotton fabric is impregnated with an aqueous solution containing 10 g of 2-acetoacetylamino- (1 ', 2'-naphtho) -thiazo'1, 8 cc of sodium hydroxide solution at 38 ° Be and 10 cc of Turkish red oil per liter. It is then dried and developed, rinsed and soaped with a solution of 7 g of diazotized i-amino-2-nitro-q.-methoxybenrzene per liter. A clear golden orange with very good fastness properties is obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI47490D DE612072C (en) | 1933-05-14 | 1933-05-14 | Process for the production of water-insoluble azo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI47490D DE612072C (en) | 1933-05-14 | 1933-05-14 | Process for the production of water-insoluble azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE612072C true DE612072C (en) | 1935-04-12 |
Family
ID=7192011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI47490D Expired DE612072C (en) | 1933-05-14 | 1933-05-14 | Process for the production of water-insoluble azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE612072C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE928724C (en) * | 1948-12-07 | 1955-06-10 | Ciba Geigy | Process for the preparation of insoluble azo dyes |
-
1933
- 1933-05-14 DE DEI47490D patent/DE612072C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE928724C (en) * | 1948-12-07 | 1955-06-10 | Ciba Geigy | Process for the preparation of insoluble azo dyes |
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