DE253933C - - Google Patents
Info
- Publication number
- DE253933C DE253933C DENDAT253933D DE253933DA DE253933C DE 253933 C DE253933 C DE 253933C DE NDAT253933 D DENDAT253933 D DE NDAT253933D DE 253933D A DE253933D A DE 253933DA DE 253933 C DE253933 C DE 253933C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- naphthylamine
- sulfonic acid
- parts
- dyes
- 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.)
- Active
Links
- 239000002253 acid Substances 0.000 claims description 7
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 7
- 230000001808 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 210000002268 Wool Anatomy 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-Xylidine Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 1
- GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 description 1
- SBOIKGBWVIHNNT-UHFFFAOYSA-N 2-(aminodiazenyl)benzenesulfonic acid Chemical compound NN=NC1=CC=CC=C1S(O)(=O)=O SBOIKGBWVIHNNT-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- XJQRCFRVWZHIPN-UHFFFAOYSA-N 3-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1Cl XJQRCFRVWZHIPN-UHFFFAOYSA-N 0.000 description 1
- HDUINBMMWMTTLC-UHFFFAOYSA-N 3-amino-4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1N HDUINBMMWMTTLC-UHFFFAOYSA-N 0.000 description 1
- DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N Naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- ZAMOJKJKCBOKFV-UHFFFAOYSA-N aniline;sulfamide Chemical compound NS(N)(=O)=O.NC1=CC=CC=C1 ZAMOJKJKCBOKFV-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 253933 KLASSE 22 a. GRUPPE- M 253933 CLASS 22 a. GROUP
Verfahren zur Darstellung von Azofarbstoffen. Patentiert im Deutschen Reiche vom 10. Oktober 1911 ab.Process for the preparation of azo dyes. Patented in the German Empire on October 10, 1911.
Im amerikanischen Patent 1003293 sind gelbe, waschechte Monoazofarbstoffe für Wolle beschrieben, die durch Kombination der Diazoverbindungen von o-chlorsubstituierten Amino-Verbindungen der Benzolreihe mit Alkylaralkylanilinsulfosäuren erhalten werden.American patent 1003293 describes yellow, washable monoazo dyes for wool described by combining the diazo compounds of o-chloro-substituted amino compounds the benzene series can be obtained with alkylaralkylaniline sulfonic acids.
Es wurde nun gefunden, daß, wenn man die Alkylaralkylanilinsulfosäuren durch die Alkylaralkyl-m-toluidinsulfosäurenIt has now been found that if the alkylaralkylanilinesulfonic acids by the Alkyl aralkyl-m-toluidine sulfonic acids
-N--N-
-CH2 — C6 -CH 2 - C 6
#4# 4
SO3HSO 3 H
/ CH3 / CH 3
(R — Alkyl oder Aralkyl) oder ihre Derivate ersetzt, man auch weniger gut kuppelnde Komponenten als die o-chlorsubstituierten Aminoverbindungen der Benzolreihe verwenden kann, die mit den Alkylaralkylanilinsulfosäuren gar nicht oder nur mit schlechter Ausbeute kuppeln. (R - alkyl or aralkyl) or their derivatives replaced, one can also use less good coupling components than the o-chloro-substituted amino compounds of the benzene series, which couple with the alkylaralkylaniline sulfonic acids only with poor yield or not at all.
Hierdurch ist es möglich, nicht nur gelbe, sondern auch orangefarbene und rote, klare, walkechte Farbstoffe zu erzielen.This makes it possible to use not only yellow, but also orange and red, clear, to achieve stable dyes.
Durch die in o-Stellung zur Azogruppe in der Alkylaralkyl-m-toluidinsulfosäure stehende Methylgruppe wird aber nicht nur die Kuppelung erleichtert und die Ausbeute erhöht, sondern die Walk- und Lichtechtheit der neuen Produkte ist bedeutend besser als die der analogen Farbstoffe mit Alkylaralkylanilinsulfosäuren. By standing in the o-position to the azo group in the alkylaralkyl-m-toluidinsulfonic acid Methyl group is not only facilitated the coupling and increased the yield, but the milled and lightfastness of the new products is significantly better than that of the analogous dyes with alkylaralkylaniline sulfonic acids.
3535
161 Teile 2 · 5-Dichloranilin werden diazotiert und langsam zu einer Lösung von 327 Teilen äthylbenzyl-m-toluidinsulfosaurem Natrium zugegeben. Gleichzeitig läßt man Natriumacetatlösung zufließen, so daß die Reaktion nicht kongosauer wird.161 parts of 2 · 5-dichloroaniline are diazotized and slowly to a solution of 327 parts of ethylbenzyl-m-toluidinsulfosaurem sodium admitted. At the same time, sodium acetate solution is allowed to flow in, so that the reaction does not get sour in the Congo.
Die Kuppelung ist sofort beendet. Man macht mit Soda schwach alkalisch, filtriert den Farbstoff ab und trocknet ihn.The coupling is ended immediately. It is made weakly alkaline with soda, filtered remove the dye and dry it.
Er färbt Wolle aus saurem Bade stark rotstichig gelb an. Die Färbung ist walkecht.It stains wool from an acid bath with a strong reddish yellow. The coloring is whackfast.
223 Teile i-Naphtylamin-5-sulfosäure werden diazotiert und bei 15 ° zu einer Lösung von 327 Teilen äthylbenzyl-m-toluidinsulfosaurem Natrium gegeben.223 parts of i-naphthylamine-5-sulfonic acid become diazotized and at 15 ° to a solution of 327 parts of äthylbenzyl-m-toluidinsulfosaurem Given sodium.
Man stumpft mit Natriumacetatlösung ab bis zur kongoneutralen Reaktion. Sobald die Kuppelung beendet ist, salzt man aus, filtriert ab und trocknet.It is blunted with sodium acetate solution until the Congo-neutral reaction. As soon as the Coupling is complete, it is salted out, filtered off and dried.
Der Farbstoff färbt Wolle in orangefarbenen, walkechten Tönen an.The dye stains wool in orange, mill-proof shades.
60 Beispiel 3. 60 Example 3.
126 Teile 4 · 4'-Diamino-2 · 2'-dichlordiphenyl werden wie üblich diazotiert und bei 10 ° mit einer Lösung von 327 Teilen äthylbenzyl-mtoluidinsulfosaurem Natrium vereinigt. Man stumpft die kongosaure Reaktion allmählich durch Natriumacetatlösung ab. Nach beendeter Kuppelung salzt man den Farbstoff aus126 parts 4x4'-diamino-2x2'-dichlorodiphenyl are diazotized as usual and at 10 ° with a solution of 327 parts of äthylbenzyl-mtoluidinsulfosaurem Sodium combined. The Congo acidic reaction is gradually blunted with sodium acetate solution. After finished Coupling is salting out the dye
und trocknet ihn. Er färbt Wolle in gelbstichig roten, sehr gut walkechten Tönen an. In analoger Weise reagieren andere Diazoverbindungen, wie:and dries it. It dyes wool in yellowish red, very good millfast shades. Other diazo compounds react in a similar way, such as:
5 o-Aminophenyläther, m-Xylidin, o-Chloranilin, 4-Chlor-2-anisidin, 4-Nitro-2-toluidin, m-Aminobenzolsulfamid, 4 -Toluidin - 2 -sulfanilid, Chlor-m-phenylendiaminoxaminsäure, 3-Amino-4-äthoxybenzoesäure, 0 -Aminophenyläther- 4'-sulfosäure, 4-5-Dichlor-2-sulfanilsäure, 6-Chloranilin - 3 - sulfosäure, 4'-Toluidin - 2'- sulfonyl -1-naphtylamin - 5 - sulfosäure, 1 - Naphtylamin - 2-sulfosäure, 1-Naphtylamin-4-sulfosäure, 1-Naphtylamin-5-sulfosäure, 2-Naphtylamin-4 · 8-disulfosäure, 1 · 8-Aminonaphtol-3 · 6-disulfosäure, Acetyl-i ■ 4-naphtylendiamin-6-sulfosäure, Aminoazobenzolmonosulfosäure.5 o-aminophenyl ether, m-xylidine, o-chloroaniline, 4-chloro-2-anisidine, 4-nitro-2-toluidine, m-aminobenzene sulfamide, 4-toluidine - 2-sulfanilide, Chloro-m-phenylenediamineoxamic acid, 3-amino-4-ethoxybenzoic acid, 0-aminophenyl ether 4'-sulfonic acid, 4-5-dichloro-2-sulfanilic acid, 6-chloroaniline - 3 - sulfonic acid, 4'-toluidine - 2'-sulfonyl -1-naphthylamine - 5 - sulfonic acid, 1 - naphthylamine - 2-sulfonic acid, 1-naphthylamine-4-sulfonic acid, 1-naphthylamine-5-sulfonic acid, 2-naphthylamine-4 · 8-disulphonic acid, 1 · 8-aminonaphthol-3 · 6-disulphonic acid, Acetyl-i ■ 4-naphthylenediamine-6-sulfonic acid, aminoazobenzene monosulfonic acid.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE253933C true DE253933C (en) |
Family
ID=512167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT253933D Active DE253933C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE253933C (en) |
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0
- DE DENDAT253933D patent/DE253933C/de active Active
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