CH257018A - Process for the preparation of a new disazo dye. - Google Patents
Process for the preparation of a new disazo dye.Info
- Publication number
- CH257018A CH257018A CH257018DA CH257018A CH 257018 A CH257018 A CH 257018A CH 257018D A CH257018D A CH 257018DA CH 257018 A CH257018 A CH 257018A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- disazo dye
- preparation
- dye
- new disazo
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 239000003518 caustics Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- SBEZNUQJZHDWEU-UHFFFAOYSA-L C(=O)([O-])C(O)C(O)C(=O)[O-].[Cu+2].[Na+] Chemical compound C(=O)([O-])C(O)C(O)C(=O)[O-].[Cu+2].[Na+] SBEZNUQJZHDWEU-UHFFFAOYSA-L 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-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
- DBNPDRYVYQWGFW-UHFFFAOYSA-N N.[Cu]=O Chemical compound N.[Cu]=O DBNPDRYVYQWGFW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- -1 copper sulfate Chemical compound 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/16—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy-amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Disazofarbstoffes. Es wurde gefunden, dass man einen neuen Disazofarbstoff erhält, wenn man tetrazo- tiertes 3,3'-Dioxy-4,4'-diaminodiphenyl in Ge genwart von anorganischen nicht reduzierend wirkenden Ätzlaugen mit 2 Mol 2-Amino-5- oxynaphthalin-1,7-disulfonsäure vereinigt und auf den so erhaltenen Farbstoff kupferab gebende Mittel einwirken lässt.
Der neue Disazofarbstoff stellt getrocknet ein grauschwarzes Pulver dar, das Baum wolle aus alkalischem Bade in reinen blauen Tönen mit guten Echthieitseigenschaften an-. färbt.
Als anorganische nicht reduzierend wir kende Ätzlaugen sind sowohl Ätzalkalien und Ammoniak als auch Lösungen bzw. Auf schlämmungen von Hydroxyden der Erd- alkalimetalle zu verstehen. Als kupferabgebende Mittel kommen z. B.
Salze des zweiwertigen Kupfers wie Kupfer sulfat in Betracht, ferner Verbindungen, die Kupfer in komplexer Bindung enthalten wie Kupferoxydammoniak oder Natriumkupfer- tartrat. Die Einwirkung der kupferabgeben den Mittel erfolgt beispielsweise in schwach .saurem, neutralem oder alkalischem Medium, gegebenenfalls unter Verwendung geeigneter Zusätze; als solche seien genannt:
Alkaii- salze aliphatischer Carbonsäuren: wie Na triumacetat, oder aliphatischer Oxycarbon- säuren wie Natriumtartrat, organische Basen wie Pyridin sowie andere säurebindende Mittel.
Beispiel: 21,6 Teile 3,3'-Dioxy-4,4'-diaminodiphe- nyl, in Form des Chlorhydrates:, werden in 100 Teilen Wasser und 12 Teilen konzen trierter Salzsäure verrührt und bei 5-8 C mit einer wässerigen Lösung von 13,8 Teilen Natriumnitrit tetrazotiert. Nach beendeter Reaktion kühlt man auf 3 C ab, neutralisiert durch Zugabe von 6,4 Teilen Xatriumcarbonat und filtriert die ausgefallene Tetrazoverbin- dung ab.
Eine Aufschlämmung von 66 Teilen 2 -Amino = 5 - oxynaphthalin-1,7-disulfonsäure und 29,6 Teile Calciunahydroxyd in 200 Tei len Wasser wird auf 5 C abgekühlt und die Tetrazoverbindung unter gutem Rühren darin eingetragen. Man kuppelt zuerst während 2 j Stunden bei 5-8 C und beendet die Kupplung durch mehrstündiges Rühren bei 10-20 C. Hierauf verdünnt man mit 2000 Teilen Wasser von 50 C, setzt 6,0 Teile Na- triumcarbonat zu und filtriert vom abgeschie denen Calciumearbonat ab.
Das Filtrat wird mit 140 Teilen 10%iger Salzsäure versetzt und der neue Farbstoff durch Aussalzen ge wonnen. 92 Teile des so erhaltenen Di- natriumsalzes des Disazofarbstoffes werden in 1000 Teilen Wasser gelöst und mit einer natriumcarbonatalkalisch gestellten Lösung aus 55 Teilen Kupfersulfat und 110 Teilen weinsaurem Natrium 15 Minuten bei 80 C verrührt. Die entstandene Kupferverbindung wird durch Zusatz von
Natriumchlorid ab geschieden, abfiltriert und getrocknet.
Process for the preparation of a new disazo dye. It has been found that a new disazo dye is obtained if tetrazo- tated 3,3'-dioxy-4,4'-diaminodiphenyl in the presence of inorganic non-reducing caustic solutions with 2 moles of 2-amino-5-oxynaphthalene-1 , 7-disulfonic acid combined and allowed to act on the resulting dye kupferab donating agent.
The new disazo dye is a gray-black powder when dried, the cotton from an alkaline bath in pure blue tones with good real properties. colors.
Inorganic, non-reducing caustic solutions are both caustic alkalis and ammonia as well as solutions or suspensions of hydroxides of the alkaline earth metals. As copper-releasing agents come z. B.
Salts of divalent copper, such as copper sulfate, are also possible, and also compounds that contain copper in complex bonds, such as copper oxide ammonia or sodium copper tartrate. The agents emit copper, for example, in a weakly acidic, neutral or alkaline medium, optionally using suitable additives; as such are mentioned:
Alkali salts of aliphatic carboxylic acids: such as sodium acetate, or aliphatic oxycarboxylic acids such as sodium tartrate, organic bases such as pyridine and other acid-binding agents.
Example: 21.6 parts of 3,3'-dioxy-4,4'-diaminodiphenyl, in the form of the chlorohydrate: are stirred in 100 parts of water and 12 parts of concentrated hydrochloric acid and at 5-8 ° C. with an aqueous solution tetrazotized by 13.8 parts of sodium nitrite. After the reaction has ended, the mixture is cooled to 3 ° C., neutralized by adding 6.4 parts of sodium carbonate and the precipitated tetrazo compound is filtered off.
A slurry of 66 parts of 2-amino = 5-oxynaphthalene-1,7-disulfonic acid and 29.6 parts of calcium hydroxide in 200 parts of water is cooled to 5 ° C. and the tetrazo compound is introduced into it with thorough stirring. Coupling is first carried out for 2 hours at 5-8 ° C. and the coupling is terminated by stirring for several hours at 10-20 ° C. It is then diluted with 2000 parts of water at 50 ° C., 6.0 parts of sodium carbonate are added and the separated off is filtered off Calcium carbonate.
The filtrate is mixed with 140 parts of 10% hydrochloric acid and the new dye is won by salting out. 92 parts of the disazo dye thus obtained are dissolved in 1000 parts of water and stirred at 80 ° C. for 15 minutes with a solution of 55 parts of copper sulfate and 110 parts of tartrate of sodium, which is made alkaline with sodium carbonate. The resulting copper compound is by adding
Sodium chloride separated off, filtered off and dried.
Claims (1)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH232505T | 1941-02-18 | ||
| CH257018T | 1942-02-02 | ||
| CH609299X | 1942-02-03 | ||
| CH616155X | 1942-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH257018A true CH257018A (en) | 1948-09-15 |
Family
ID=27429732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH257018D CH257018A (en) | 1941-02-18 | 1942-02-02 | Process for the preparation of a new disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH257018A (en) |
-
1942
- 1942-02-02 CH CH257018D patent/CH257018A/en unknown
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