AT101312B - Process for the preparation of substantive cotton dyes. - Google Patents
Process for the preparation of substantive cotton dyes.Info
- Publication number
- AT101312B AT101312B AT101312DA AT101312B AT 101312 B AT101312 B AT 101312B AT 101312D A AT101312D A AT 101312DA AT 101312 B AT101312 B AT 101312B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- dyes
- acid
- weight
- parts
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 9
- 229920000742 Cotton Polymers 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- RPGKFFKUTVJVPY-UHFFFAOYSA-N 2-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(N)=C1 RPGKFFKUTVJVPY-UHFFFAOYSA-N 0.000 claims description 5
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 description 1
- MTIRCEAOVDFRGC-UHFFFAOYSA-N 4-(dichloroamino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(N(Cl)Cl)C=C1 MTIRCEAOVDFRGC-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229940098779 methanesulfonic acid 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
- 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
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung direktziehende Baumwollfarbstoife.
Es wurde gefunden, dass direkt ziehende, lichtechte, violette bis blaue Baumwollfarbstoffe dadurch erhalten werden, dass man Diazoverbindungen der Benzol-oder Naphthalinreihe mit der 4-Methyl-2aminobenzoesäure vereinigt, weiterdiazotiert und mit der 2-Amino-5-naphthol-7-sulfosäure oder ihren Derivaten kuppelt. Die Farbstoffe lassen sich in Substanz oder auf der Faser nachkupfern und erhalten dadurch ohne eine Beeinträchtigung der Klarheit eine hervorragende Lichtechtheit.
Während die 2-Aminobenzoesäure als Mittelkomponente in Azofarbstoffen nur in Form ihrer Methansulfosäure verwendet werden kann, ist die 4-Methyl-2-aminobenzoesäuro hiezu direkt ohne Schutz der Aminogruppe brauchbar.
Beispiel 1 : 24. 2 Gewichtsteile, 2. 5 Dichloranilin-4-sulfosäure werden wie üblich diazotiert und mit 15-1 Gewichtsteilen 4-Methyl-2-aminobenzoesäure essigsauer gekuppelt. Nach beendeter Kupplung wird alkalisch gemacht, mit 6-9 Gewichtsteilen Nitrit versetzt und durch Einlaufenlassen in Salzsäure und Eis weiterdiazotiert. Die fertige Diazotierung lässt man dann in eine sodaalkalischb Lösung von 31-5 Gewichtsteilen Phenyl-2-amino-5-naphthol-7-sulfosäure einfliessen. Nach kurzer Zeit ist die Kupplung beendet, worauf der Farbstoff ausgesalzen wird. Er färbt Baumwolle in blaustichig roten Tönen von vorzüglicher Lichtechtheit. Durch Nachkupfern wird die Nuance in ein violettstichiges Blau verschoben und die Lichtechtheit noch erhöht.
Beispiel 2 : In der gleichen Weise wie im Beispiel 1 ausgeführt, lassen sich 20-3 Gewichtsteile 2-Anisidin-4-sulfosäure mit 15'1 Gewichtsteilen 4-Methyl-2-aminobenzoesäure vereinigen und dann weiter diazotieren und mit 46-1 Gewichtsteilen 5. 5'-Dioxy-2'2'-dinaphthyl-7. 7'-disulfosäure kuppeln. Dieser Farbstoff färbt Baumwolle in blaustichigvioletten Tönen. Durch Nachkupfern wird die Nuance ein violettstichig Blau von ganz besonderer Lichtechtheit.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of substantive cotton dyes.
It has been found that direct, lightfast, violet to blue cotton dyes are obtained by combining diazo compounds of the benzene or naphthalene series with 4-methyl-2aminobenzoic acid, further diazotizing and with 2-amino-5-naphthol-7-sulfonic acid or their derivatives. The dyes can be re-coppered in bulk or on the fiber and thus have excellent lightfastness without impairing the clarity.
While 2-aminobenzoic acid can only be used as a middle component in azo dyes in the form of its methanesulfonic acid, 4-methyl-2-aminobenzoic acid can be used for this purpose directly without protection of the amino group.
Example 1: 24. 2 parts by weight, 2.5 parts by weight dichloroaniline-4-sulfonic acid are diazotized as usual and coupled with 15-1 parts by weight of 4-methyl-2-aminobenzoic acid in acetic acid. When the coupling has ended, the mixture is made alkaline, 6-9 parts by weight of nitrite are added and the mixture is diazotized further by running it into hydrochloric acid and ice. The finished diazotization is then allowed to flow into a soda-alkaline solution of 31-5 parts by weight of phenyl-2-amino-5-naphthol-7-sulfonic acid. After a short time, the coupling is complete, whereupon the dye is salted out. It dyes cotton in bluish red shades of excellent lightfastness. After copper plating, the shade is shifted to a violet-tinged blue and the lightfastness is further increased.
Example 2: In the same way as in Example 1, 20-3 parts by weight of 2-anisidine-4-sulfonic acid can be combined with 15'1 parts by weight of 4-methyl-2-aminobenzoic acid and then further diazotized and with 46-1 parts by weight of 5 5'-Dioxy-2'2'-dinaphthyl-7. Coupling 7'-disulfonic acid. This dye dyes cotton in bluish purple tones. After copper plating, the shade becomes a violet-tinged blue with a very special lightfastness.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF54402D DE416822C (en) | 1923-07-18 | 1923-07-18 | Process for the preparation of substantive cotton azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT101312B true AT101312B (en) | 1925-10-26 |
Family
ID=7107056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT101312D AT101312B (en) | 1923-07-18 | 1924-06-06 | Process for the preparation of substantive cotton dyes. |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT101312B (en) |
| CH (1) | CH110288A (en) |
| DE (1) | DE416822C (en) |
| FR (1) | FR583233A (en) |
| GB (1) | GB219299A (en) |
-
1923
- 1923-07-18 DE DEF54402D patent/DE416822C/en not_active Expired
-
1924
- 1924-06-05 CH CH110288D patent/CH110288A/en unknown
- 1924-06-06 AT AT101312D patent/AT101312B/en active
- 1924-07-01 FR FR583233D patent/FR583233A/en not_active Expired
- 1924-07-04 GB GB1613824A patent/GB219299A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH110288A (en) | 1925-05-16 |
| DE416822C (en) | 1925-07-29 |
| GB219299A (en) | 1925-06-18 |
| FR583233A (en) | 1925-01-08 |
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