US602858A - Karl krekelee and eduard martz - Google Patents
Karl krekelee and eduard martz Download PDFInfo
- Publication number
- US602858A US602858A US602858DA US602858A US 602858 A US602858 A US 602858A US 602858D A US602858D A US 602858DA US 602858 A US602858 A US 602858A
- Authority
- US
- United States
- Prior art keywords
- acid
- brown
- martz
- eduard
- karl
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 description 36
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 30
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 16
- 229960004889 salicylic acid Drugs 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229920000742 Cotton Polymers 0.000 description 12
- 239000000975 dye Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 210000002268 Wool Anatomy 0.000 description 8
- 150000001844 chromium Chemical class 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 6
- 150000001555 benzenes Chemical class 0.000 description 6
- 150000001879 copper Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 4
- TYADOAMDMDRRPS-UHFFFAOYSA-N C1(=CC=C(N)C=C1)C1=CC=C(N)C=C1.C(C=1C(O)=CC=CC1)(=O)O Chemical compound C1(=CC=C(N)C=C1)C1=CC=C(N)C=C1.C(C=1C(O)=CC=CC1)(=O)O TYADOAMDMDRRPS-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000003801 milling Methods 0.000 description 4
- 239000001187 sodium carbonate Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KIEOKOFEPABQKJ-UHFFFAOYSA-N Sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- -1 diphenyl Chemical class 0.000 description 2
- 159000000011 group IA salts Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Definitions
- Our invention relates to the production of a new class of trisazo dyestuffs by diazotizing tetrazo bodies of the general formula in which formula P represents a radical of the benzidin series, such as diphenyl, ditolyl, diphenyl ether, or the like; R, the radical of an orthooxycarbonic acid of the benzene series, such as salicylic acid or cresotinic acid; 0, the radical of the so-called Cleves alphanaphthylamin-beta-sulfonic acid (1.6 or 1. 7)
- the dyestuffs thus obtained have the general formula (P, R, and 0 meaning in this formula the above-defined radicals.) They represent dark powders which dissolve in water with a color varying from yellowish brown to brown and dye cotton from yellowish-brown to brown shades, which, by a treatment with a solution of bichromate of soda or of an analogous chromium salt, with or without the presence of copper salts, become more reddish brown and faster to washing and against the action of light.
- the new coloring-matters are also capable of dyeing wool in acid-baths. The shades thus obtained are similar to those produced on cotton.
- the body having the formula Sa1icy1ic aeid Benzidin (tetrazotized) Cleves naphthylaminsulfo-acid with one molecule of salicylic acid substan-g tially as described.
- the new 1' trisazo dyestuffs obtainable from the diazo derivatives of the disazo compounds, such as the combination of one molecule of tetrazodiphenyl with one molecule of salicylic acid and one molecule of Oleves naphthylaminsulfo-acid, having the general formula:
- P N:N- Oleves naphthylaminsulfo-acid with one molecule of an orthooxycarbonic -acid of the benzene series being dark powders, soluble in water with a color varying from yellowish brownto brown, dyeing unmordanted cotton from yellowish-brown to brown shades which whentreated with solutions of chromium and copper salts become more reddish brown and faster to washing and against the action of light, capable of dyeing wool in acid-baths shades similar to those produced on cotton substantially as described.
- Salicylic acid Benzidin (tetrazotized) Clves naphthylaminsulfo-acid with one molecule of salicylic .acid being an alkaline salt of an acid having the formula Salicylic acid Benzidin (tetrazotized) Clves naphthylaminsulfo-acid (diazotized -salicylic acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
UNITED STATES PATENT @rricn.
KARL KREKELER AND EDUARD MARTZ, OF ELBERFELD, GERMANY, ASSIGNQRS TO THE FARBENFABRIKEN OF ELBERFELD COMPANY,
OF NEW YORK, N. Y.
BROWN TRISAZO DYE.
SPECIFICATION formingpart of Letters Patent No. 602,858, dated April 26, 1898.
Application filed November 23, 1897. Serial No. 659,582. (Specimens) Patented in Germany September 15,1891, No. 65,262; in England December 28, 1891,1111. 22,641; in France A ril 28,1892,N0. 221,233; in Italy June 30,1892,XXVL 32,191, and LXIII, 186, and in hustria Hungary October 3,1892, No. 1,2 12 and No. 16,870.
No. 32,191, Reg. Att., v01. LXIII,N0.186,-
dated June 30, 1892, and in Austria-Hungary, No. 1,242 and No. 16,870, dated October 3, 1892;) and we hereby declare the following to be a clear and exact description of our invention.
Our invention relates to the production of a new class of trisazo dyestuffs by diazotizing tetrazo bodies of the general formula in which formula P represents a radical of the benzidin series, such as diphenyl, ditolyl, diphenyl ether, or the like; R, the radical of an orthooxycarbonic acid of the benzene series, such as salicylic acid or cresotinic acid; 0, the radical of the so-called Cleves alphanaphthylamin-beta-sulfonic acid (1.6 or 1. 7)
and combining the diazo body thus obtained with one molecule of an orthooxycarbonic acid, such as salicylic acid or cresotinic acid. The dyestuffs thus obtained have the general formula (P, R, and 0 meaning in this formula the above-defined radicals.) They represent dark powders which dissolve in water with a color varying from yellowish brown to brown and dye cotton from yellowish-brown to brown shades, which, by a treatment with a solution of bichromate of soda or of an analogous chromium salt, with or without the presence of copper salts, become more reddish brown and faster to washing and against the action of light. The new coloring-matters are also capable of dyeing wool in acid-baths. The shades thus obtained are similar to those produced on cotton.
In carrying out our new process practically we can proceed as follows: 18.4 kilos, by weight, of benzidin are diazotized in the usual manner by means of fourteen kilos, by weight, of sodium nitrite. To the icy-cold diazo solution an icy-cold solution of fourteen kilos, by weight, of salicylic acid and seventy kilos, by weight, of sodium carbonate (Na OO in four hundred liters of water is added with stirring. hen the formation of the intermediate product is finished, a cold solution prepared by dissolving 2&5 kilos, by weight, of the sodium salt of alpha-naphthylaminbeta-monosulfo-acid (1.6) in three hundred liters of water is added. After about athree hours stirring the formation of the intermediate dyestuff is complete. The mixture is subsequently acidulated by means of hydrochloric acid and filtered. The dyestuff acid thus obtained is dissolved in fifteen hundred liters of a 2. 5-per-cent. soda-lye, then quickly mixed with a solution of eight kilos, by weight, of sodium nitrite, flVG hundred kilos, by weight, of ice, and one hundred and fifty kilos, by weight, of hydrochloric acid, (20 Baum.) This mixture is stirred for about twelve hours, and then the resulting insoluble diazo compound is filtered and pressed. Subsequently it is mixed with ice and water to a thin paste, which is slowly stirred into an icy-cold concentrated solution of fourteen kilos, by weight, of salicylic acid and one hundred and forty kilos, by weight, of sodium carbonate. After stirring for twelve hours the mixture is heated to about 70 eentigrade. The dyestufi thus complete is salted out in the usual manner. Then it is filtered ed,
pressed, dried, and pulverized. It is the sodium salt of an acid having the formula and represents a dark-brown powder, soluble in water with a yellowish-brown color and in concentrated sulfuric acid with a blue color. From this solution a dark-brown flaky precipitate is obtained on the addition of a sufficient quantity of ice.
The new coloring-matter dyes unmordanted cotton yellowish-brown shades, which when treated with a solution of a chromium salt, with or without the presence of salts of copper, become more reddish brown and faster to washing and against the action of light.
On unmordanted Wool the coloring-matter produces in acid -baths yellowish brown shades, which on a treatment with chromium salts become fast against milling.
Having now described our invention and in i what manner the same is to be performed, what we claim as new, and desire to secure by Letters Patent, is-
1. The process for producing new trisazoi dyestuifs by combining the'diazo derivatives of the disazo compounds hereinbefore defined such as the combination of one molecule of tetrazodiphenyl with one molecule of sali cylic acid and one molecule of Cleves naphthylaminsulfo-acid, having the general for- N:N-Oleves naphthylaminsulfo-acid with one molecule of an orthooxycarbonic acid of the benzene series substantially as:
hereinbefore described.
the body having the formula Sa1icy1ic aeid Benzidin (tetrazotized) Cleves naphthylaminsulfo-acid with one molecule of salicylic acid substan-g tially as described.
3. As new articles of manufacture the new 1' trisazo dyestuffs obtainable from the diazo derivatives of the disazo compounds, such as the combination of one molecule of tetrazodiphenyl with one molecule of salicylic acid and one molecule of Oleves naphthylaminsulfo-acid, having the general formula:
N:NorthooXycarbonic acid P N:N- Oleves naphthylaminsulfo-acid with one molecule of an orthooxycarbonic -acid of the benzene series, being dark powders, soluble in water with a color varying from yellowish brownto brown, dyeing unmordanted cotton from yellowish-brown to brown shades which whentreated with solutions of chromium and copper salts become more reddish brown and faster to washing and against the action of light, capable of dyeing wool in acid-baths shades similar to those produced on cotton substantially as described.
4. As a new article of manufacture the specific dyestufi obtainable from the diazo derivativeof the body, having the formula:
. Salicylic acid Benzidin (tetrazotized) Clves naphthylaminsulfo-acid with one molecule of salicylic .acid being an alkaline salt of an acid having the formula Salicylic acid Benzidin (tetrazotized) Clves naphthylaminsulfo-acid (diazotized -salicylic acid.
representing in the form of the sodium salt a dark-brown powder, soluble in water with a yellowish-brown color, in concentrated sulfuric acid with a blue color from which solution a dark-brown flaky precipltate is obtained on the addition of a sufficient quantity of ice, dyeing unmordanted cotton yellowish-brown shades which when treated with solutions of chromium and copper salts become more reddish brown and faster to washing and against the action of light, yielding on wool in acid-baths yellowish-brown shades which on a treatment with chromium salts become fast against milling substantially as 2. lhe process for producing a new trisazo described 7 dyestuif by combining the diazo derivative of I In testimony whereof we have signed our names in the presence of two subscribing wit- 5 nesses.
KARL KREKELER. EDUARD MARTZ.
Witnesses:
R. E. JAHN,
OTTO KoNIG.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US602858A true US602858A (en) | 1898-04-26 |
Family
ID=2671490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US602858D Expired - Lifetime US602858A (en) | Karl krekelee and eduard martz |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US602858A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2001072A2 (en) | 2007-06-04 | 2008-12-10 | I-Chuan Lin | Powdered Fuel Cell |
-
0
- US US602858D patent/US602858A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2001072A2 (en) | 2007-06-04 | 2008-12-10 | I-Chuan Lin | Powdered Fuel Cell |
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