US2732372A - Chromable monoazo dyestuffs - Google Patents
Chromable monoazo dyestuffs Download PDFInfo
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- US2732372A US2732372A US2732372DA US2732372A US 2732372 A US2732372 A US 2732372A US 2732372D A US2732372D A US 2732372DA US 2732372 A US2732372 A US 2732372A
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- chromium
- complex
- nitro
- wool
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- 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 title claims description 18
- 239000000975 dye Substances 0.000 claims description 12
- 210000002268 Wool Anatomy 0.000 description 24
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 22
- 229910052804 chromium Inorganic materials 0.000 description 22
- 150000001845 chromium compounds Chemical class 0.000 description 22
- 239000002253 acid Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000001264 neutralization Effects 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000011651 chromium Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 8
- 239000000047 product 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
- 239000000725 suspension Substances 0.000 description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000001166 ammonium sulphate Substances 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 125000004432 carbon atoms Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001844 chromium Chemical class 0.000 description 4
- 230000001808 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- XKUUMWKWUZRRPD-UHFFFAOYSA-N heptan-2-amine;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.CCCCCC(C)[NH3+].CCCCCC(C)[NH3+] XKUUMWKWUZRRPD-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- YHTOSLOSIDDANE-UHFFFAOYSA-N 2-amino-3-butylphenol Chemical compound CCCCC1=CC=CC(O)=C1N YHTOSLOSIDDANE-UHFFFAOYSA-N 0.000 description 2
- BNZJMDGOLLELRT-UHFFFAOYSA-N 5-hydroxy-7-sulfamoylnaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)N)=CC(O)=C21 BNZJMDGOLLELRT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OKLSBPYGEGGZHQ-UHFFFAOYSA-N C(C=1C(O)=CC=CC1)(=O)[O-].C(C=1C(O)=CC=CC1)(=O)[O-].[NH4+].[NH4+] Chemical compound C(C=1C(O)=CC=CC1)(=O)[O-].C(C=1C(O)=CC=CC1)(=O)[O-].[NH4+].[NH4+] OKLSBPYGEGGZHQ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- PXLIDIMHPNPGMH-UHFFFAOYSA-N Sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000011528 polyamide (building material) Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Definitions
- the present invention concerns the production of monoazo dyestuffs which have no sulphonic acid groups and the attainment of fast, chromium-containing dyeings on wool and on fibers similar thereto under conditions which do not injure the fibres. It also concerns the production of complex chromium compounds of the monoazo dyestuffs in substance.
- 6-nitro-4-tert. butyl-Z- amino-l-hydroxybenzene 6-nitro-4-tert. amyl-Z-amino-lhydroxybenzene, 6-nitro-4-cyclohexyl-Z-amino-l-hydroxybenzene or 6-nitro-4-di-isobutyl 2 amino-l-hydroxybenzene may be employed as diazo components.
- These compounds are obtained, for example, by dinitration of the corresponding p-alkylphenols and reduction of only 1 nitro group to the amino group, e. g. with alkali sulphide or hydrogen sulphite in an aqueous organic or, for example, an aqueous alcoholic solution or suspension.
- diazotisation is performed in the cold with sodium nitrate in a mineral acid solution or suspension and the coupling with the 1-hydroxynaphthalene-3.6-disulphonic acid amide is performed in an aqueous alkaline solution.
- the alkali salts of the complex chromium compounds which are obtained by salting out and drying, are dark powders which dissolve in water with a blue colour. It is expedient to mix them before using them for dyeing with anion active dispersing agents and inorganic salts which have an alkaline reaction such as trisodium phosphate. They dye wool in very level blue shades which are fast to light and wet treatments, from a neutral to weakly acid bath which may contain ammonium salts of organic or inorganic acids such as ammonium acetate or sulphate.
- the new complex chromium compounds form a valuable addition to the group of chromium-containing wool dyestuffs which can be dyed from a neutral to weakly acid bath. Both in their metal-free state and also in the form of their complex chromium compounds, they are distinguished from known similar products by their improved drawing power on to wool from a neutral to weakly acid bath.
- Example 1 22.4 parts of 6-nitro-4-tert. amyl-Z-amino-l-hydroxybenzene with 4 parts of sodium hydroxide are dissolved in 200 parts of water, 6.9 parts of sodium nitrite in 35 parts of water are added and this mixture is added dropwise at a temperature not exceeding 3 to 25 parts by volume of concentrated hydrochloric acid and 100 parts of water. A yellowish-green suspension of the diazo compound is obtained. On completion of the diazotisation, the acidity of the diazo suspension is neutralized'with sodium 'bicarbonate until there is a neutral reaction to Congo red paper, after which a solution of 30.5 parts of 1.3.6-naphtholdisulphamide (M. P.
- the product For use in the aiter-chroming or in the single bath chroming method, it is advantageous to mix the product with about 10% of calcined soda ash and 5% of a dispersing agent.
- the dyestufi dyes wool from an acid bath a red-violet shade which changes on after-chroming to blue.
- reddish-blue dyeings of equal shades and strengths are obtained from a completely exhausted bath.
- the dyeings have very good wet and light fastness properties.
- the dyestuff produced according to the method described above can be chromed as follows:
- the filter cake of the dyestufi is pasted in 1000 parts of water and 10 parts of 25 ammonia, 100 parts by volume of a solution of ammonium disalicylate chromiate (containing 3% of chromium) are added and the whole is heated at 100 for 6-10 hours. After adding parts of sodium chloride, the dyestuii is filtered oii at 7080 and washed with a 5% sodium chloride solution and dried.
- the chromium complex dyestulf so obtained is a dark blue powder which dissolves in hot water with a blue and in concentrated sulfuric acid with a violet colour.
- the product, which for use is advantageously mixed with 20% of a dispersing agent and 20% of sodium carbonate, dyes wool a blue shade from a neutral and from a weakly acid bath. The dyeing has very good fastness to wetness and light.
- the monoazo dyestuffs obtained from 6-nitro-4-tert. butyl-2-amino-l-hydroxybenzene, 6-nitro-4-cyclohexy1-2- amino-l-hydroxybenzene or 6-nitro-4-di-isobutyl-2-aminol-hydroxybenzene and l.3.6-naphtholdisulphamide can be converted into their chromium complexes in the same way. Products are then obtained which are very similar to that described in detail above. In particular, they have the valuable property of dyeing wool from a weakly acid or neutral bath in equal shades and strengths, which dyeings have very good fastness to wetness and light.
- Example 2 10 parts of wool are entered at 50 into a dyebath containing 1 part of anhydrous sodium sulphate, 0.2 part of sodium monochromate, 0.3 part of ammonium sulphate and 0.2 part of the unchromed dyestufi according to Example l in 400 parts of water. The bath is brought to the boil and kept boiling for 1 hour to develop the shade. The wool, which has been dyed blue is rinsed and dried.
Description
United States Patent CHROMABLE MONQAZO DYESTUFFS Werner Kuster and Guido Schetty, Basel, Switzerland, assignors to J. R. Geigy A. G., Basel, Switzerland, :1 Swiss firm No Drawing. Application March 16, 1953, Serial No. 342,712
Claims priority, application Switzerland March 23, 1952 5 Claims. or. 260-151) The present invention concerns the production of monoazo dyestuffs which have no sulphonic acid groups and the attainment of fast, chromium-containing dyeings on wool and on fibers similar thereto under conditions which do not injure the fibres. It also concerns the production of complex chromium compounds of the monoazo dyestuffs in substance.
It has been found that by coupling in an alkaline medium a diazotised 6-nitro-4-alkyl-2-amino-l-hydroxybenzene compound, the alkyl radical of which contains from 4-8 carbon atoms and which may also be cyclo-aliphatic, with l-hydroxynaphthalene-ir.o-disulphonic acid amide, new, valuable monoa'zo dyestuffs which contain no sulphonic acid groups are obtained of the general formula:
OH OH Alkyl These dyestuffs are distinguished by an excellent drawing power on to wool and fibres similar thereto from a neutral to weakly acid bath both when they do not contain any metal and also in the form of their complex chromium compounds. They are suitable therefore, for the attainment of blue shades on wool which have very good light and wet fastness properties both with the salts of hexavalent chromium when they contain no metal and also in the form of their complex chromium compounds. From a neutral to weakly acid bath, if desired in the presence of ammonium salts of organic and inorganic acids, the chromium-containing dyestuffs draw on to fibres similar to wool such as silk, casein fibres, synthetic polyamide and polyurethane fibres. For example, 6-nitro-4-tert. butyl-Z- amino-l-hydroxybenzene, 6-nitro-4-tert. amyl-Z-amino-lhydroxybenzene, 6-nitro-4-cyclohexyl-Z-amino-l-hydroxybenzene or 6-nitro-4-di-isobutyl 2 amino-l-hydroxybenzene may be employed as diazo components. These compounds are obtained, for example, by dinitration of the corresponding p-alkylphenols and reduction of only 1 nitro group to the amino group, e. g. with alkali sulphide or hydrogen sulphite in an aqueous organic or, for example, an aqueous alcoholic solution or suspension. As is usual, diazotisation is performed in the cold with sodium nitrate in a mineral acid solution or suspension and the coupling with the 1-hydroxynaphthalene-3.6-disulphonic acid amide is performed in an aqueous alkaline solution.
Various methods are known for the production of the complex chromium compounds in substance, e. g. treatment of the dyestufi's with aqueous solutions of the salts of trivalent chromium at a raised temperature in organic,
dyestufi molecules is particularly advantageous; it is expedient to use an excess of chroming agent. The alkali salts of the complex chromium compounds, which are obtained by salting out and drying, are dark powders which dissolve in water with a blue colour. It is expedient to mix them before using them for dyeing with anion active dispersing agents and inorganic salts which have an alkaline reaction such as trisodium phosphate. They dye wool in very level blue shades which are fast to light and wet treatments, from a neutral to weakly acid bath which may contain ammonium salts of organic or inorganic acids such as ammonium acetate or sulphate. The new complex chromium compounds form a valuable addition to the group of chromium-containing wool dyestuffs which can be dyed from a neutral to weakly acid bath. Both in their metal-free state and also in the form of their complex chromium compounds, they are distinguished from known similar products by their improved drawing power on to wool from a neutral to weakly acid bath.
The following examples illustrate the invention without limiting it in any way. The parts are given as parts by weight and the temperatures are in degrees centigrade.
Example 1 22.4 parts of 6-nitro-4-tert. amyl-Z-amino-l-hydroxybenzene with 4 parts of sodium hydroxide are dissolved in 200 parts of water, 6.9 parts of sodium nitrite in 35 parts of water are added and this mixture is added dropwise at a temperature not exceeding 3 to 25 parts by volume of concentrated hydrochloric acid and 100 parts of water. A yellowish-green suspension of the diazo compound is obtained. On completion of the diazotisation, the acidity of the diazo suspension is neutralized'with sodium 'bicarbonate until there is a neutral reaction to Congo red paper, after which a solution of 30.5 parts of 1.3.6-naphtholdisulphamide (M. P. 302-304") and 12 parts of sodium hydroxide in 300 parts of water of a temperature of 0-3 is added. After adding 100 parts of pyridine and 10 parts of 25% ammonia, the temperature is kept overnight at 0-3". The dyestuft is then precipitated with 40 parts of sodium chloride, filtered off and washed with 2.5
sodium chloride solution. When dry, it forms a dark blue powder which dissolves in water with a blue, and in concentrated sulphuric acid with a red-violet colour.
For use in the aiter-chroming or in the single bath chroming method, it is advantageous to mix the product with about 10% of calcined soda ash and 5% of a dispersing agent. The dyestufi dyes wool from an acid bath a red-violet shade which changes on after-chroming to blue. When dyed according to the single bath chroming process without or with the slight addition of acid, reddish-blue dyeings of equal shades and strengths are obtained from a completely exhausted bath. The dyeings have very good wet and light fastness properties.
Very similar dyestufis are obtained if, in the above example, the diazo component is replaced by 21.5 parts of 6-nitro-4-tert. butyl-Z-amino-l-hydroxybenzene, 24 parts of 6-n1tro-4-cyclohexyl-2-amino-l-hydroxybenzene or 26.6 parts of 6-nitro-4-di-isobutyl (octyl)-2-amino-1-hydroxybenzene. These dyestutfs are also excellently suitable for dyeing according to the single bath chroming process.
The dyestuff produced according to the method described above can be chromed as follows:
The filter cake of the dyestufi is pasted in 1000 parts of water and 10 parts of 25 ammonia, 100 parts by volume of a solution of ammonium disalicylate chromiate (containing 3% of chromium) are added and the whole is heated at 100 for 6-10 hours. After adding parts of sodium chloride, the dyestuii is filtered oii at 7080 and washed with a 5% sodium chloride solution and dried. The chromium complex dyestulf so obtained is a dark blue powder which dissolves in hot water with a blue and in concentrated sulfuric acid with a violet colour. The product, which for use is advantageously mixed with 20% of a dispersing agent and 20% of sodium carbonate, dyes wool a blue shade from a neutral and from a weakly acid bath. The dyeing has very good fastness to wetness and light.
The monoazo dyestuffs obtained from 6-nitro-4-tert. butyl-2-amino-l-hydroxybenzene, 6-nitro-4-cyclohexy1-2- amino-l-hydroxybenzene or 6-nitro-4-di-isobutyl-2-aminol-hydroxybenzene and l.3.6-naphtholdisulphamide can be converted into their chromium complexes in the same way. Products are then obtained which are very similar to that described in detail above. In particular, they have the valuable property of dyeing wool from a weakly acid or neutral bath in equal shades and strengths, which dyeings have very good fastness to wetness and light.
Example 2 10 parts of wool are entered at 50 into a dyebath containing 1 part of anhydrous sodium sulphate, 0.2 part of sodium monochromate, 0.3 part of ammonium sulphate and 0.2 part of the unchromed dyestufi according to Example l in 400 parts of water. The bath is brought to the boil and kept boiling for 1 hour to develop the shade. The wool, which has been dyed blue is rinsed and dried.
Example 3 OH I H OzN N=N H N 0 2S 8 O zNHa wherein R represents a saturated hydrocarbon radical with from 4 to 8 carbon atoms and (b) the chromium complexes of said dyestuffs containing one chromium atom in complex linkage with two molecules of dyestuif.
2. The complex chromium compound containing one chromium atom in complex linkage with two molecules of a monoazo dyestutf having the formula:
3. The complex chromium compound containing one chromium atom in complex linkage with two molecules of a monoazo dyestuflf having the formula:
OH OH OzN- N N HgNOzS SO ZNH:
4. The complex chromium compound containing one chromium atom in complex linkage with two molecules of a monoazo dyestuff having the formula:
OH OH O 2N N N HzNOzs SO2NHI CH1 OH:
5. The complex chromium compound containing one chromium atom in complex linkage with two molecules of a monoazo dyestufi having the formula:
OH OH O2N N=N HzNOaS 302N111 HaC- CHa mo- -CH;
References Cited in the file of this patent UNITED STATES PATENTS 1,903,600 Schweitzer Apr. 11, 1933 2,633,463 Kuster Mar. 31, 1953
Claims (1)
1. A DYESTUFF SELECTED FROM THE CLASS CONSISTING OF (A) THE MONOAZO DYESTUFFS HAVING THE FORMULA:
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2732372A true US2732372A (en) | 1956-01-24 |
Family
ID=3442069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2732372D Expired - Lifetime US2732372A (en) | Chromable monoazo dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2732372A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5019132A (en) * | 1989-11-28 | 1991-05-28 | Ciba-Geigy Corporation | Process for the preparation of concentrated 1:2 metal complex dye preparations |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1903600A (en) * | 1930-05-24 | 1933-04-11 | Gen Aniline Works Inc | Azo dyestuffs |
| US2633463A (en) * | 1950-06-09 | 1953-03-31 | Geigy Ag J R | Monoazo dyestuffs |
-
0
- US US2732372D patent/US2732372A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1903600A (en) * | 1930-05-24 | 1933-04-11 | Gen Aniline Works Inc | Azo dyestuffs |
| US2633463A (en) * | 1950-06-09 | 1953-03-31 | Geigy Ag J R | Monoazo dyestuffs |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5019132A (en) * | 1989-11-28 | 1991-05-28 | Ciba-Geigy Corporation | Process for the preparation of concentrated 1:2 metal complex dye preparations |
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