US2038081A - Water-insoluble azo-dyestuffs and fiber dyed therewith - Google Patents
Water-insoluble azo-dyestuffs and fiber dyed therewith Download PDFInfo
- Publication number
- US2038081A US2038081A US29730A US2973035A US2038081A US 2038081 A US2038081 A US 2038081A US 29730 A US29730 A US 29730A US 2973035 A US2973035 A US 2973035A US 2038081 A US2038081 A US 2038081A
- Authority
- US
- United States
- Prior art keywords
- water
- dyestuffs
- black
- grams
- insoluble azo
- 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
- 239000000835 fiber Substances 0.000 title description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 6
- 240000001890 Ribes hudsonianum Species 0.000 description 6
- 235000001466 Ribes nigrum Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000008234 soft water Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- JVMUPDOMGALPOW-UHFFFAOYSA-N 4-methoxynaphthalen-1-amine Chemical compound C1=CC=C2C(OC)=CC=C(N)C2=C1 JVMUPDOMGALPOW-UHFFFAOYSA-N 0.000 description 1
- OLCMNCWEUMBNIS-UHFFFAOYSA-N 5-chloro-2,4-dimethoxyaniline Chemical compound COC1=CC(OC)=C(Cl)C=C1N OLCMNCWEUMBNIS-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000009971 piece dyeing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Definitions
- the present invention relates to water-insoluble azo-dyestuifs and to fiber dyed therewith;
- dyestuffs corresponding to the following general formula CONHaryl wherein X stands for hydrogen, halogen or an alkoxy group.
- the new dyestuffs may be used for the production on the fiber of dyeings and printings, as well as for the preparation of pigments.
- the dyestuffs may furthermore be used for the production on the fiber of mixed shades with other dyestufis derived from the group of the 2,3-hydroxynaphthoic acid arylides, for instance, with those from the diazo-compounds of 4-aminodiphenylamines; this is of particular technical importance, since in this manner the tints of those dyestuffs may be darkened as required.
- the yarn pretreated in the usual manner, is impregnated at 30 C. for 30 minutes. After hydro-extracting, the impregnated yarn is developed in a bath containing per liter 4.42 grams of 3,4-dinitrodi phenylamine-l-diazonium chloride of net content of 62 per cent calculated upon the base and 1.8 cc. of acetic acid of 50 per cent strength.
- the material is thoroughly rinsed cold and hot and soaped at boiling temperature. A greenish black shade of good fastness to light is obtained.
- the dyestuff is characterized by the following formula:
- the paste is dissolved in and made up A with hot water to 1 liter.
- the material After printing, the material is dried, then treated with hot sodium carbonate solution (containing 1 to 2 grams of calcined sodium carbonate per liter, rinsed and soaped.
- hot sodium carbonate solution containing 1 to 2 grams of calcined sodium carbonate per liter, rinsed and soaped.
- the impregnated and dried goods are passed on a foulard at 50 C. through this developing solution and then passed through a' steam chest wherein they are steamed -for about half a minute. They are then rinsed and soaped.
- the impregnated and dried material is then passed at about C. on a foulard through the following solution:
- the material is passed through the solution and then through a steam chest in which it is steamed for about half a minute. Then it is rinsed and soaped.
- the black dyestufi so obtained is filtered with suction and washed well.
- pigments it is advantageously used in the form of a paste.
- an object of the present invention is to provide dyestuffs of good fastness properties which dyestuffs are insoluble in water and alkalies, it is to be understood that the aromatic nuclei of the general formula appearing in the appended claims do not contain any substituents which are known to render organic compounds soluble in water or alkalies and to tend to depreciate the fastness of the dyestuffs to alkalies.
- Substituents of this kind are, for instance, the sulfonic acid and the carboxylic acid group.
- R stands for a. radical of the benzene series, yielding, when produced on the fiber, blackcurrant to black dyeings of good fastness properties, particularly of very good fastness to light.
- N NONHON o: I O H C O 'NH'C yielding, when produced on the fiber, greenish black dyeings of good iastness properties, particularly of very good fastness to light.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented Apr. 21 1936 UNITED STATES WATEK-INSOLUBLE AZO-DYESTUFFS AND FIBER DYED THEREWITH Leopold Laska, Offenbach-on-the-Main, Arthur Zitscher, Kronberg-in-the-Taunus, and Wilhelm Seidenfaden,
Offenbach-omthe-Main,
Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application July 3, 1935, Serial No. 29,730. In Germany July 16, 1934 '10 Claims.
The present invention relates to water-insoluble azo-dyestuifs and to fiber dyed therewith;
more particularly it relates to dyestuffs corresponding to the following general formula CONHaryl wherein X stands for hydrogen, halogen or an alkoxy group.
We have found that valuable azo-dyestufis insoluble in water are obtained by coupling the diam-compound of 4-amino-3,4-dinitrodiphenylamine with an arylide of 2,3-hydroxy-naphthoic acid in substance, on the fiber or on a substratum adapted for the production of lakes. In this manner black-currant to black dyeings of remarkable fastness properties, particularly of very good fastness to light, are obtained.
The new dyestuffs may be used for the production on the fiber of dyeings and printings, as well as for the preparation of pigments.
The dyestuffs may furthermore be used for the production on the fiber of mixed shades with other dyestufis derived from the group of the 2,3-hydroxynaphthoic acid arylides, for instance, with those from the diazo-compounds of 4-aminodiphenylamines; this is of particular technical importance, since in this manner the tints of those dyestuffs may be darkened as required.
Similar combinations have been described in U. S. Patents Nos. 1,919,589 and 1,921,362. According to the process of the present invention there are obtained black-currant and black dyeings of great commercial value, whereas according to the processes described in the said patents there are obtained only garnet to blue or violet shades which are, moreover, less fast to light than the combinations obtainable by the process of the present invention. Moreover, the combinations of the present process, when used for dyeing piece goods, have a. greater tinctorial strength than those obtainable according to U. S. Patent No. 1,921,362.
The following examples serve to illustrate the invention, but they are not intended to limit it thereto.
(1) 4 grams of 1-(2',3'-hydroxynaphthoyl)- aminonaphthalene are dissolved by boiling with cc. of Turkey red oil, 12 cc. of caustic soda solution of 34 Be. and 100 cc. of hot soft water, 100 cc. of cold soft water and 4 cc. of formaldehyde of 33 per cent strength are then added to the solution. The formaldehyde is allowed to act for 5 minutes whereupon the grounding liquor is made up to 1000 cc.
In the bath thus prepared, the yarn, pretreated in the usual manner, is impregnated at 30 C. for 30 minutes. After hydro-extracting, the impregnated yarn is developed in a bath containing per liter 4.42 grams of 3,4-dinitrodi phenylamine-l-diazonium chloride of net content of 62 per cent calculated upon the base and 1.8 cc. of acetic acid of 50 per cent strength.
The material is thoroughly rinsed cold and hot and soaped at boiling temperature. A greenish black shade of good fastness to light is obtained. The dyestuff is characterized by the following formula:
In the same manner the following shades are obtained with the 2,3-hydroxynaphthoyl-compound of l-amino-2-methoxybenzene Greenish black, l-amino-Z-methylbenzene Greenish black, 1-amino-4 -methoxy- 2 -methy1- benzene Violet black, 1-amino-2,4-dimethox y- 5 -chlorobenzene Violet black,
1-amino-2,5-dimethoxybenzene Black-currant, 1 amino 4 methoxynaphthalene 1-amino-2,4-dimethoxybenzene 1-amino-2,5-dimethoxy- 4 -chlorobenzene Black-currant,
and with Black currant, Violet-black,
(2) PRINTING N Goons PREPARED WITH 1-(2',3- HYDROXY-NAPHTHOYL) -AMIN0-2-METHYLBENZENE Grounding liquor 15 grams of 1-(2',3-hydroxynaphthoyl) -amino- 2-methylbenzene are made into a paste with 15 cc. of Turkey red oil and 22.5 cc. of caustic soda solution of 34 B. an
the paste is dissolved in and made up A with hot water to 1 liter.
1'7 grams 20 grams 453 grams grams 500 grams 1000 grams.
After printing, the material is dried, then treated with hot sodium carbonate solution (containing 1 to 2 grams of calcined sodium carbonate per liter, rinsed and soaped.
A deep greenish black shade is obtained.
(3) PIECE DYEING Crude desized cotton piece goods are impregnated at 80 C. on a foulard with the following solution:
12 grams of 1-(2',3'-hydroxynaphthoyl)-amino- 2-methoxy-benzene are made into a. paste with 12 cc. of Turkey red oil and.
18 cc. of caustic soda solution of 34 B. The paste is dissolved in hot water and made up to 1 liter.
Then the goods are dried.
Developing bath 10 grams of the diazonium chloride from 4- amino-3,4-dinitro-diphenylamine are dissolved in 10 grams of acetic acid of 50 per cent strength and of hot water and made up to 1 liter.
The impregnated and dried goods are passed on a foulard at 50 C. through this developing solution and then passed through a' steam chest wherein they are steamed -for about half a minute. They are then rinsed and soaped.
A deep greenish black shade is obtained. (4) PREPARATION or A MIXED SHADE 0N COTTON PIECE Goons Bleached cotton material is grounded on a foulard at about 50 C. in the following solution:
grams of 1-(2',3-hydroxynaphthoyl) -amino- Z-methoxy-benzene are made into a paste with 15 cc. of Turkey red oil and 22.5 cc. of caustic soda solution of 34 B. The paste is dissolved in hot Water and madeup to 1 liter.
The impregnated and dried material is then passed at about C. on a foulard through the following solution:
1 liter.
The material is passed through the solution and then through a steam chest in which it is steamed for about half a minute. Then it is rinsed and soaped.
A reddish blue-black shade is obtained.
(5) 11.8 grams of 3,4-dinitrodiphenylamine-4- diazonium chloride of net content of 59 per cent are dissolved in 300 cc. of decinormal acetic acid and 1500 cc. of water.
The following solution is then added, while stirring:
10.6 grams of 2,3-hydroxynaphthoyl-aminobenzene, 200 cc. of decinormal caustic soda solution in 1000 cc. of Water.
The black dyestufi so obtained is filtered with suction and washed well. For the production of pigments it is advantageously used in the form of a paste.
Since an object of the present invention is to provide dyestuffs of good fastness properties which dyestuffs are insoluble in water and alkalies, it is to be understood that the aromatic nuclei of the general formula appearing in the appended claims do not contain any substituents which are known to render organic compounds soluble in water or alkalies and to tend to depreciate the fastness of the dyestuffs to alkalies. Substituents of this kind are, for instance, the sulfonic acid and the carboxylic acid group.
We claim:
1. The water-insoluble azo-dyestuffs of the following general formula:
HO Q
\CO-NH-R wherein R stands for a. radical of the benzene series, yielding, when produced on the fiber, blackcurrant to black dyeings of good fastness properties, particularly of very good fastness to light.
3. The water-insoluble azo-dyestufi of the following formula:
yielding, when produced on the fiber, greenish black dyeings of good fastness properties, particularly of very good fastness to light.
4. The water-insoluble azo-dyestufi of the following formula:
N=NONHON o: I O H C O 'NH'C yielding, when produced on the fiber, greenish black dyeings of good iastness properties, particularly of very good fastness to light.
5. The water-insoluble azo-dyestufi of the following formula:
yielding, when produced on the fiber, violet-black dyeings of good fastness properties, particularly of very good fastness to light.
6. Fiber dyed with the dyestuffs as claimed in claim 1.
'7. Fiber dyed with the dyestuffs as claimed in claim 2.
8. Fiber dyed with the dyestuif as claimed in claim 3.
9. Fiber dyed with the dyestuff as claimed in claim 4.
10. Fiber dyed with the dyestuff as claimed in claim 5.
LEOPOLD LASKA. ARTHUR ZITSCHER. WILHELM SEIDENFADEN.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2038081X | 1934-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2038081A true US2038081A (en) | 1936-04-21 |
Family
ID=7982085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US29730A Expired - Lifetime US2038081A (en) | 1934-07-16 | 1935-07-03 | Water-insoluble azo-dyestuffs and fiber dyed therewith |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2038081A (en) |
-
1935
- 1935-07-03 US US29730A patent/US2038081A/en not_active Expired - Lifetime
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