DE87584C - - Google Patents
Info
- Publication number
- DE87584C DE87584C DENDAT87584D DE87584DA DE87584C DE 87584 C DE87584 C DE 87584C DE NDAT87584 D DENDAT87584 D DE NDAT87584D DE 87584D A DE87584D A DE 87584DA DE 87584 C DE87584 C DE 87584C
- Authority
- DE
- Germany
- Prior art keywords
- yellow
- brown
- soluble
- cone
- water
- 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
- 239000000843 powder Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 239000000987 azo dye Substances 0.000 claims description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-Diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 2
- 235000020127 ayran Nutrition 0.000 claims 4
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 claims 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- -1 methylethyl ammonium Resorcinol Chemical compound 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTAtPATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Zusatz zum Patente JVr 87257 vom 23. April 1895.Addendum to patent JVr 87257 from April 23, 1895.
Patentirt im Deutschen Reiche vom 11. Juni 1895 ab. Längste Dauer: 22. April 1910.Patented in the German Empire on June 11, 1895. Longest duration: April 22, 1910.
Nach dem Verfahren des Patentes Nr. 87257, welches durch Kuppelung von Amidoammoniumbasen der allgemeinen Formel:According to the method of patent no. 87257, which is obtained by coupling amidoammonium bases the general formula:
. Radical) π . Radical) π
mit Aminen oder Phenolen zu basischen Azofarben führt, sind noch weitere werthvolle Azofarbstoffe durch Vereinigung der nachgenannten Componenten dargestellt worden: m-Amidophenyltrimethylammonium which lead to basic azo colors with amines or phenols are also valuable ones Azo dyes have been represented by combining the following components: m-amidophenyltrimethylammonium
m-Amidophenyldimethyläthylammonium m-Amidophenyldimethylethylammonium
m -Amido - p-methylphenyltrimethylammonium m -amido - p-methylphenyltrimethylammonium
p-Amidophenyltrimethylammonium p-amidophenyltrimethylammonium
p-Amidophenyltrimethylammonium p-amidophenyltrimethylammonium
naphtalin,naphthalene,
m-Toluylendiamin m-tolylenediamine
ß-Naphtol,ß-naphtol,
m-Phenylen-m-phenylene
diamin,diamine,
ι oderι or
V2 Mol.V 2 moles.
Resorcin.Resorcinol.
Das bisher noch nicht beschriebene p-Amidophenyltrimethylammonium kann man darstellen durch Umsetzung von Benzyliden-p-Amidodimethylanilin mit Jodmethyl; das entstehende Jodmethylat bildet in Alkohol fast unlösliche weifse Blättchen; durch Säuren, z. B. Salzsäure, wird aus der Verbindung Benzaldehyd abgespalten; das entstehende p-Amidophenyltrimethylammoniumchlorid ist in Wasser sehr leicht löslich und bildet farblose Prismen; es vereinigt sich mit Chlorzink zu einem gut krystallisirenden Zinkdoppelsalz.The hitherto not yet described p-amidophenyltrimethylammonium can be prepared by reacting benzylidene-p-amidodimethylaniline with iodomethyl; the resulting iodine methylate is almost insoluble in alcohol white leaflets; by acids, e.g. B. hydrochloric acid is split off from the compound benzaldehyde; the resulting p-amidophenyltrimethylammonium chloride is very high in water easily soluble and forms colorless prisms; it combines with zinc chloride to form one good crystallizing zinc double salt.
Die Darstellung der Azofarbstoffe aus der ρ - Amidophenyltrimethylammoniumbase erfolgt ebenso, wie es im Haupt-Patent für die isomere Base beschrieben wurde; die Farbstoffe aus der p-Verbindung unterscheiden sich nicht merklich von den aus der m-Verbindung erhaltenen.The azo dyes are represented from the ρ-amidophenyltrimethylammonium base also as described in the parent patent for the isomeric base; the dyes from the p-compound do not noticeably differ from those obtained from the m-compound.
Die neuen Farbstoffe sind ebenfalls rothgelbe bis rothbraune wasserlösliche Pulver, die auf tanningebeizte Baumwolle in eben soichenTönen färben.The new dyes are also red-yellow to red-brown water-soluble powders that are based on Dye tannin-stained cotton in the same shades.
In der folgenden Tabelle sind die Eigenschaften näher angegeben. The properties are specified in the following table.
m-Amidophenyltrimethylammonium m-amidophenyltrimethylammonium
m - Amidophenyldimethyläthyl- ammonium m-Amido-p-methyl-m - amidophenyldimethylethylammonium m-amido-p-methyl-
phenyltrimethyl-phenyltrimethyl-
ammoniumammonium
p-Aniidophenyltrimethylammonium p-Aniidophenyltrimethylammonium
β! β 2-Dioxynaphtaliiiβ! β 2 -Dioxynaphtaliii
Rothbraunes Pulver; löslich in WasserRed-brown powder; soluble in water
mit brauner Farbe; in cone. H^SO4 with brown color; in cone. H ^ SO 4
violett.violet.
Braunes Pulver;Brown powder;
löslich in Wassersoluble in water
mit brauner Farbe;with brown color;
in cone. H1 S O4 in cone. H 1 S O 4
blauviolett.blue-violet.
Rothbraunes
Pulver; löslich in Wasser mit braunerReddish brown
Powder; soluble in water with brown
Farbe; in cone. H^ S O4 gelbbraun.Colour; in cone. H ^ S O 4 yellow-brown.
Claims (1)
methylammoniumm-amidophenyl tri
methylammonium
methyläthyl-
ammoniumm - amidophenyldi
methylethyl
ammonium
farbstoff)Resorcinol (monoazo-
dye)
phenyltrim ethyl-
ammoniumm-amido-p-methyl-
phenyltrim ethyl-
ammonium
methylammoniump-amidopheflyltri-
methylammonium
mit brauner Farbe; in cone. H2SO4
gelbbraun.Tan powder; soluble in water
with brown color; in cone. H 2 SO 4
yellow-brown.
löslich in Wasser
mit reingelber
Farbe; in cone.
H2 S O4 mit gelber
Farbe.Yellow kryst. Powder;
soluble in water
with pure yellow
Colour; in cone.
H 2 SO 4 with yellow
Colour.
kryst.; löslich in
Wasser mit braun-
gelber Farbe; in
cone. H2 S O4 gelb
braun.Brown powder;
kryst .; soluble in
Water with brown
yellow color; in
cone. H 2 S O 4 yellow
Brown.
löslich in Wasser
mit brauner Farbe;
in cone. H2SO4
gelbbraun.Tan powder;
soluble in water
with brown color;
in cone. H 2 SO 4
yellow-brown.
farbstoffeResorcinol (Disazo
dyes
ammoniumρ-amidophenyl trimethyl
ammonium
löslich in Wasser
mit rothgelber
Farbe; in cone.
H2 S O4 mit carmin-
rother Farbe.Yellow-red powder;
soluble in water
with red-yellow
Colour; in cone.
H 2 S O 4 with carmin-
red color.
Pulver; löslich in
Wasser mit bräun
lich gelber Farbe;
in cone. H2 SO4
gelbbraun.Reddish brown
Powder; soluble in
Water with tan
light yellow color;
in cone. H 2 SO 4
yellow-brown.
löslich in Wasser
mit braungelber
Farbe; in cone.
H2 S O4 gelbbraun.Tan powder;
soluble in water
with brownish yellow
Colour; in cone.
H 2 S O 4 yellow-brown.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE87584C true DE87584C (en) |
Family
ID=359546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT87584D Active DE87584C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE87584C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1082998B (en) * | 1955-02-04 | 1960-06-09 | Ciba Geigy | Process for the preparation of monoazo dyes |
| US3518244A (en) * | 1966-04-26 | 1970-06-30 | Hoechst Ag | Water-soluble quaternary amine containing monoazo dyestuffs |
-
0
- DE DENDAT87584D patent/DE87584C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1082998B (en) * | 1955-02-04 | 1960-06-09 | Ciba Geigy | Process for the preparation of monoazo dyes |
| US3518244A (en) * | 1966-04-26 | 1970-06-30 | Hoechst Ag | Water-soluble quaternary amine containing monoazo dyestuffs |
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