CA1065308A - Stable modification of a disazo dyestuff - Google Patents
Stable modification of a disazo dyestuffInfo
- Publication number
- CA1065308A CA1065308A CA253,577A CA253577A CA1065308A CA 1065308 A CA1065308 A CA 1065308A CA 253577 A CA253577 A CA 253577A CA 1065308 A CA1065308 A CA 1065308A
- Authority
- CA
- Canada
- Prior art keywords
- dyestuff
- modification
- glance
- formula
- ray diffraction
- 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
Links
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
- C09B43/44—Preparation of azo dyes from other azo compounds by substituting amine groups for hydroxyl groups or hydroxyl groups for amine groups; Desacylation of amino-acyl groups; Deaminating
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
STABLE MODIFICATION OF A DISAZO DYESTUFF
Abstract of the disclosure:
The modification ? being stable under dyeing conditions of the dyestuff of the formula characterized by an X-ray diffraction diagram with the charac-teristic reflexes at the following glance angles a (Figure 3):
angle 0 4.0° 5.0° 8.15° 12.7° 13.5°
intensity 0.31 0.38 1.00 0.92 0.63 said modification allowing dyeings being fast to rubbing ob-tained on textile wound packages of synthetic and semi-synthetic fibrous materials.
Abstract of the disclosure:
The modification ? being stable under dyeing conditions of the dyestuff of the formula characterized by an X-ray diffraction diagram with the charac-teristic reflexes at the following glance angles a (Figure 3):
angle 0 4.0° 5.0° 8.15° 12.7° 13.5°
intensity 0.31 0.38 1.00 0.92 0.63 said modification allowing dyeings being fast to rubbing ob-tained on textile wound packages of synthetic and semi-synthetic fibrous materials.
Description
~ llOE 75/~ 1~3 The prcsent invelrLion relates to a modification of a dis-azo dyestuIf which is stable under the usual dye~ng condition.s.
The known ~-modification of the dyestuff of the formula ( 1 ) OCH~
o2N ~ _ N = N ~ N - N - ~ OT~
is obtained from the dyestuff prepared according to French Patent Specificati.on No. 1,300,806, Example 2. That modifica-tion has the considerable disadvantage that dyeing composition prepared therefrom in the usual manner by grinding it with dispersing agents undergo alteration during the dyeing process.
When dyein~ textile wound packages of synthetic or semisynthe-tic fibrous, for example cross-wound bobbins, this alteration results in dyestuff deposits on the surface of the material to be dyed. Such dyestuff deposits are undesirable since they im-part a specky appearance to the material. to be dyed and the dyestuff deposited on the surface of the material is chafed o~f.
The same disadvantages are also inherent in the B-modi-fication of the said dyestuff, which can be obtained, for exam-ple by heating the ~-modification to 135C for 4 hours.
The said ~-ana B-modifications are characterized by their X-ray diffraction spectra. The following tables show their ~-ray counter tube diagrams (taken by means of a diffractometer
The known ~-modification of the dyestuff of the formula ( 1 ) OCH~
o2N ~ _ N = N ~ N - N - ~ OT~
is obtained from the dyestuff prepared according to French Patent Specificati.on No. 1,300,806, Example 2. That modifica-tion has the considerable disadvantage that dyeing composition prepared therefrom in the usual manner by grinding it with dispersing agents undergo alteration during the dyeing process.
When dyein~ textile wound packages of synthetic or semisynthe-tic fibrous, for example cross-wound bobbins, this alteration results in dyestuff deposits on the surface of the material to be dyed. Such dyestuff deposits are undesirable since they im-part a specky appearance to the material. to be dyed and the dyestuff deposited on the surface of the material is chafed o~f.
The same disadvantages are also inherent in the B-modi-fication of the said dyestuff, which can be obtained, for exam-ple by heating the ~-modification to 135C for 4 hours.
The said ~-ana B-modifications are characterized by their X-ray diffraction spectra. The following tables show their ~-ray counter tube diagrams (taken by means of a diffractometer
- 2 -~T(~ 75/~' 143 10~5308 manuLactured by ~lessrs. ~IILlPS, P~ 1050/30, using Cu-~rays).
The figure given under the heading "Intensity" refers to the height of the signal as compared with the maximum of the spec-trum, to which the figure 1.00 has been attributed.
The accompanying drawings show the X-ray diffraction spec-tra of the dyestuff of formula t1):
Figure 1 - ~-modification; Figure 2 - ~-modification; Figure 3-~-modification.
Spectrum of the CC-modification Glance angle 0 6.5 7.0 7.6 7.9 9.1 10.65 11.8 12.55 Intensity 0. ao o . so o . 40 0.82 0.45 0.35 0.39 1.00 Spectrum of the ~-modification Glance angle 0 5 7 6 4 7 4 8 35 8 85 13 0 14 5 Intensity 0.45 0.26 0.29 0.76 0.47 1.00 0.24 Spectrum of the ~-modification Glance angle 0 4.0 5.0 8.15 12.7 13.5 Intensity 0.31 0.38 1.00 0.92 0.63 The ~C-modification has been known and pertains to the state of the art.
The present invention now provides a new crystal modfi-cation ( ~-modification)of the dyestuff of the above-cited for-mula (1), which is stable under the dyeing conditions and which is characterized by the X-ra~ diffraction diagram as shown in Fig. 3 with the typical reflexes at the following glance angles angle ~ 4.0 5.0 8.15 12.7 13.5 Intensity 0.31 0.38 1.00 0.92 0.63 as well as a process for its preparation.
The X-ray counter tube diagram of this new modification is also disclosed in the preceding Table and has been taken by means of the same diffractometer as have been theO~-and~-modifications.
Dyestuff compositions prepared with this new ~-modification do no longer exhibit the above-cited tinctorial disadvantages of the ~-and~ - difi-cations but rather allow dyeings that are fast to rubbing to be obtained on textile would packages of synthetic and semisynthetic fibrous material, for example of polyesters, especially polyethylene-terephthalates, cellulose-2 1/2-acetate, cellulose triacetate, polyamide, mixtures of plyester and wool, of polyester and spun rayon and of polyester and cottom.
The new ~-modification of the disazo dyestuff in question may be prepared as follows: the modification of the dyestuff of formula (1) which is unstable under dyeing conditions ~o~-modification) and which is characteriz-ed by the X-ray diffraction spectrum as shown in Figure 1, with the typical reflexes at the following glance angles~
Glance 6.5 7.0 ~.6 7.9 9.1 10.65 11.8 12.95angle Intensity 0.80 0.50 0.40 0.82 0.45 0.35 0.39 1.00 is (a) heated in an aqueous suspension at a temperature of from 50 to 95C, or (b) heated in a mixture of water and an organic solvent miscible with water at a temperature of from 50 to 95C, or (c) converted into an alkali metal salt, preferably sodium salt, and the phenol form of the dyestuff is again set free therefrom by adding an acid.
~J
~IOE 7~ 3 10~5308 Accordillg to Ihe above-said process (a), heating may ke performeA in thc presence of surfactants. Sultable are anionic, cationic and nonicnic surface-active compounds, for example the sodium salt of dodecylphenyl-sulfonic acid or of diiso-butyl-naphthalene-sulfonic acid, the addition product of 25 mols of ethylene oxide on 1 mol of stearyl alcohol, a mixture of alkyl-dimethylbenzyl-ammonium chlorides, a fatty acid poly-glycol ester or a tertiary organic phosphoric acid ester of the addition product of 2 mols of ethylene oxide on 1 mol of laur alcohol.
Of the organic solvents miscible with water, which may be used for the said process (b), there may be used, for example, acetic acid, alcohols, such as, for instance, methanol, etha-nol, n-propanol, isopropanol, n-butanol, isobutanol, glycol, methyl-glycol, ethyl-glycol, ethylene-diglycol, acetone, dioxan, N-methyl-pyrrolidone and dimethylformamide, Mixtures of the afore-mentioned organic solvents may also be used.
The phenol form of the dyestuff may be set free from the - alkali metal salt according to process (c) either with inorga-nic or with organic acids, for example with carbonic acid, ace-tic acid, hydrochloric acid, sulfuric acid or phosphoric acid.
Process (a) may be combined with the preparation of the disazo dyestuff of formula (1) by heating the resulting "coup-ling liquor" after the coupling reaction ( 2 ~ N=N ~ NH2 ~3 ~ H) is complete, without isolating the disazo dyestuff formed.
The following Examples illustrate the invention, the ~ IIOE 5/~ 1~3 parts and percentages being by weight unless stated other-wise.
E X A M P L E 1:
300 Parts of the ~-modification of the dyestuff of the above-cited formula were introduced with stirring into 5,000 parts of a 1% sodium hydroxide solution of 90C. Stirring was continued for 15 minutes at 90C, whereupon the dyestuff was converted into its sodium salt. The dyestuff was then preci-pitated again by introducing carbon dioxide. Stirring was con-tinued for 30 minutes without heating further, the dyestuff was suction-filtered and washed until free of ai~ali. The dye-stuff was obtained in the ~-modification. Dyestuff compositions that had been prepared therefrom by means of dispersing agents, for example sodium salt of lignin-sulfonic acid, provided dyeing liquors having good rheological properties.
E X A M P L E 2:
300 Parts of the ~-modification of the dyestuff of the above-cited formula were introduced into 5,000 parts of 10%
~ acetic acid. The mixture was refluxed for 6 hours. The dye-stuff was suction-filtered and washed until free of acid. The dyestuff was obtained in the ~-modification. Dyestuff composi-tions that had ~een prepared therefrom in the usual manner by grinding it with dispersing agents provided dyeing liquors having good rheological properties.
E X A M P L E 3:
200 Parts of the ~-modification of the dyestuff of the above-cited formula were refluxed for 6 hours in a mixture of 2,000 parts by volume of water and 2,000 parts by volume of ~ 0r _?5/ F _~3 10~308 methanol. The mixture was allowed to cool, and the dyestuff was suction-filtered ~o yield the r-modilication.
E X A M P L E 4:
230 Parts of 3-methoxy-4-amino-4'-azo benzen~ were dia-zotized in 1,200 parts by volume of 15% hydrochloric acid with 147 parts of a 40% sodium nitrite solution. The resulting dia-zonium salt solution was added within 30 minutes to a solution of 90 parts of phenol and 130 parts of crystallized sodium acetate in 4,000 parts by volume of water at about 0 to 5C.
During the addition of the diazonium salt solution, ahout ~00 parts of a 33% sodium hydroxide solution were then added so as to maintain a pH of 5 to 6. The temperature was maintained at S to 10C by adding ice from time to time. Stirring was con-tinued for 1 hour, and the temperature was then raised to 85 -90C. At this temperature, stirring was continued for 8 to 12 hours. The dyestuff was then suction-filtered in the form o the ~-modification. The resulting filter cake was washed until free of salt. This dyestuff was used to prepare dyestuff com-~ positions that provided dyeing liquors having good rheological properties.
E X A M P L E 5:
300 parts of the OC-modification of the dyestuff of the above-cited formuIa were introduced into 5,0Q0 parts of a 1~
sodium hydroxide solution of 90C, and the mixture was stirred for 15 mlnutes at 90C. The dyestuff was then precip.itated by adding 50% acetic acid dropwise until a p~l of 8.7 had been rea-ched. Stirring was continued for 30 minu~es without heating, and the dyestuff was suction-filtered in the form o~ the ~`' _J~E 75/- ~3 modification. It was washed with about 4,000 parts by volume of water and used to prepare dyestuff compositions that pro-vided dyeing liquors having good rheological properties.
E X A M P L E 6:
300 Parts of the ~ -modification of the dyestuff of the formula cited further above were introduced into 4,000 parts of water of 90C. Then, 20 parts of sodium dodecyl-phenyl-sulfonate were added. The mixture was stirred for 20 hours at 90C. Then dyestuff was then suction-filtered in the form of - 10 the ~-modification ànd washed. The resulting dyestuff was used to prepare dyestuff compositions that provided dyeing liquors with good rheological properties.
E X A M P L E i:
The dyestuff was prepared as in Example 1 except that the dyestuff was precipitated by adding hydrochloric acid dropwise instead of introducing carbon dioxide, until the dyestuff was again obtained in the ~-modification.
Dyestuff compositions containing the ~-modification of the dyestuff of the above-mer.tioned formula prepared according to Examples 1 to 7 were suitable for the unobjectionable dyeing of wound packages, for example of polyester fibers, such as polyethylene terephthalate fibers, polyamide fibers and mix-tures of polyester fibers and wool or polyester fibers and spun rayon.
E X A M P L E 8:
100 Parts of the ~-modification of the dyestuff of the above-cited formula were stirred for 4 hours at 60C with 300 parts of water and 100 parts of lignin sulfonatc. The ~?~ 75/F 1~3 resulting Inixture was then gLound in a b~ad mi~l. The resul--ting dyestuff composition contained the dyestuff in its ~-modification. It provided dyeing liquors having good rheolo~i-cal properties.
_ 9 _
The figure given under the heading "Intensity" refers to the height of the signal as compared with the maximum of the spec-trum, to which the figure 1.00 has been attributed.
The accompanying drawings show the X-ray diffraction spec-tra of the dyestuff of formula t1):
Figure 1 - ~-modification; Figure 2 - ~-modification; Figure 3-~-modification.
Spectrum of the CC-modification Glance angle 0 6.5 7.0 7.6 7.9 9.1 10.65 11.8 12.55 Intensity 0. ao o . so o . 40 0.82 0.45 0.35 0.39 1.00 Spectrum of the ~-modification Glance angle 0 5 7 6 4 7 4 8 35 8 85 13 0 14 5 Intensity 0.45 0.26 0.29 0.76 0.47 1.00 0.24 Spectrum of the ~-modification Glance angle 0 4.0 5.0 8.15 12.7 13.5 Intensity 0.31 0.38 1.00 0.92 0.63 The ~C-modification has been known and pertains to the state of the art.
The present invention now provides a new crystal modfi-cation ( ~-modification)of the dyestuff of the above-cited for-mula (1), which is stable under the dyeing conditions and which is characterized by the X-ra~ diffraction diagram as shown in Fig. 3 with the typical reflexes at the following glance angles angle ~ 4.0 5.0 8.15 12.7 13.5 Intensity 0.31 0.38 1.00 0.92 0.63 as well as a process for its preparation.
The X-ray counter tube diagram of this new modification is also disclosed in the preceding Table and has been taken by means of the same diffractometer as have been theO~-and~-modifications.
Dyestuff compositions prepared with this new ~-modification do no longer exhibit the above-cited tinctorial disadvantages of the ~-and~ - difi-cations but rather allow dyeings that are fast to rubbing to be obtained on textile would packages of synthetic and semisynthetic fibrous material, for example of polyesters, especially polyethylene-terephthalates, cellulose-2 1/2-acetate, cellulose triacetate, polyamide, mixtures of plyester and wool, of polyester and spun rayon and of polyester and cottom.
The new ~-modification of the disazo dyestuff in question may be prepared as follows: the modification of the dyestuff of formula (1) which is unstable under dyeing conditions ~o~-modification) and which is characteriz-ed by the X-ray diffraction spectrum as shown in Figure 1, with the typical reflexes at the following glance angles~
Glance 6.5 7.0 ~.6 7.9 9.1 10.65 11.8 12.95angle Intensity 0.80 0.50 0.40 0.82 0.45 0.35 0.39 1.00 is (a) heated in an aqueous suspension at a temperature of from 50 to 95C, or (b) heated in a mixture of water and an organic solvent miscible with water at a temperature of from 50 to 95C, or (c) converted into an alkali metal salt, preferably sodium salt, and the phenol form of the dyestuff is again set free therefrom by adding an acid.
~J
~IOE 7~ 3 10~5308 Accordillg to Ihe above-said process (a), heating may ke performeA in thc presence of surfactants. Sultable are anionic, cationic and nonicnic surface-active compounds, for example the sodium salt of dodecylphenyl-sulfonic acid or of diiso-butyl-naphthalene-sulfonic acid, the addition product of 25 mols of ethylene oxide on 1 mol of stearyl alcohol, a mixture of alkyl-dimethylbenzyl-ammonium chlorides, a fatty acid poly-glycol ester or a tertiary organic phosphoric acid ester of the addition product of 2 mols of ethylene oxide on 1 mol of laur alcohol.
Of the organic solvents miscible with water, which may be used for the said process (b), there may be used, for example, acetic acid, alcohols, such as, for instance, methanol, etha-nol, n-propanol, isopropanol, n-butanol, isobutanol, glycol, methyl-glycol, ethyl-glycol, ethylene-diglycol, acetone, dioxan, N-methyl-pyrrolidone and dimethylformamide, Mixtures of the afore-mentioned organic solvents may also be used.
The phenol form of the dyestuff may be set free from the - alkali metal salt according to process (c) either with inorga-nic or with organic acids, for example with carbonic acid, ace-tic acid, hydrochloric acid, sulfuric acid or phosphoric acid.
Process (a) may be combined with the preparation of the disazo dyestuff of formula (1) by heating the resulting "coup-ling liquor" after the coupling reaction ( 2 ~ N=N ~ NH2 ~3 ~ H) is complete, without isolating the disazo dyestuff formed.
The following Examples illustrate the invention, the ~ IIOE 5/~ 1~3 parts and percentages being by weight unless stated other-wise.
E X A M P L E 1:
300 Parts of the ~-modification of the dyestuff of the above-cited formula were introduced with stirring into 5,000 parts of a 1% sodium hydroxide solution of 90C. Stirring was continued for 15 minutes at 90C, whereupon the dyestuff was converted into its sodium salt. The dyestuff was then preci-pitated again by introducing carbon dioxide. Stirring was con-tinued for 30 minutes without heating further, the dyestuff was suction-filtered and washed until free of ai~ali. The dye-stuff was obtained in the ~-modification. Dyestuff compositions that had been prepared therefrom by means of dispersing agents, for example sodium salt of lignin-sulfonic acid, provided dyeing liquors having good rheological properties.
E X A M P L E 2:
300 Parts of the ~-modification of the dyestuff of the above-cited formula were introduced into 5,000 parts of 10%
~ acetic acid. The mixture was refluxed for 6 hours. The dye-stuff was suction-filtered and washed until free of acid. The dyestuff was obtained in the ~-modification. Dyestuff composi-tions that had ~een prepared therefrom in the usual manner by grinding it with dispersing agents provided dyeing liquors having good rheological properties.
E X A M P L E 3:
200 Parts of the ~-modification of the dyestuff of the above-cited formula were refluxed for 6 hours in a mixture of 2,000 parts by volume of water and 2,000 parts by volume of ~ 0r _?5/ F _~3 10~308 methanol. The mixture was allowed to cool, and the dyestuff was suction-filtered ~o yield the r-modilication.
E X A M P L E 4:
230 Parts of 3-methoxy-4-amino-4'-azo benzen~ were dia-zotized in 1,200 parts by volume of 15% hydrochloric acid with 147 parts of a 40% sodium nitrite solution. The resulting dia-zonium salt solution was added within 30 minutes to a solution of 90 parts of phenol and 130 parts of crystallized sodium acetate in 4,000 parts by volume of water at about 0 to 5C.
During the addition of the diazonium salt solution, ahout ~00 parts of a 33% sodium hydroxide solution were then added so as to maintain a pH of 5 to 6. The temperature was maintained at S to 10C by adding ice from time to time. Stirring was con-tinued for 1 hour, and the temperature was then raised to 85 -90C. At this temperature, stirring was continued for 8 to 12 hours. The dyestuff was then suction-filtered in the form o the ~-modification. The resulting filter cake was washed until free of salt. This dyestuff was used to prepare dyestuff com-~ positions that provided dyeing liquors having good rheological properties.
E X A M P L E 5:
300 parts of the OC-modification of the dyestuff of the above-cited formuIa were introduced into 5,0Q0 parts of a 1~
sodium hydroxide solution of 90C, and the mixture was stirred for 15 mlnutes at 90C. The dyestuff was then precip.itated by adding 50% acetic acid dropwise until a p~l of 8.7 had been rea-ched. Stirring was continued for 30 minu~es without heating, and the dyestuff was suction-filtered in the form o~ the ~`' _J~E 75/- ~3 modification. It was washed with about 4,000 parts by volume of water and used to prepare dyestuff compositions that pro-vided dyeing liquors having good rheological properties.
E X A M P L E 6:
300 Parts of the ~ -modification of the dyestuff of the formula cited further above were introduced into 4,000 parts of water of 90C. Then, 20 parts of sodium dodecyl-phenyl-sulfonate were added. The mixture was stirred for 20 hours at 90C. Then dyestuff was then suction-filtered in the form of - 10 the ~-modification ànd washed. The resulting dyestuff was used to prepare dyestuff compositions that provided dyeing liquors with good rheological properties.
E X A M P L E i:
The dyestuff was prepared as in Example 1 except that the dyestuff was precipitated by adding hydrochloric acid dropwise instead of introducing carbon dioxide, until the dyestuff was again obtained in the ~-modification.
Dyestuff compositions containing the ~-modification of the dyestuff of the above-mer.tioned formula prepared according to Examples 1 to 7 were suitable for the unobjectionable dyeing of wound packages, for example of polyester fibers, such as polyethylene terephthalate fibers, polyamide fibers and mix-tures of polyester fibers and wool or polyester fibers and spun rayon.
E X A M P L E 8:
100 Parts of the ~-modification of the dyestuff of the above-cited formula were stirred for 4 hours at 60C with 300 parts of water and 100 parts of lignin sulfonatc. The ~?~ 75/F 1~3 resulting Inixture was then gLound in a b~ad mi~l. The resul--ting dyestuff composition contained the dyestuff in its ~-modification. It provided dyeing liquors having good rheolo~i-cal properties.
_ 9 _
Claims (4)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. The modification ? being stable under dyeing conditions of the dye-stuff of the formula characterized by an X-ray diffraction diagram with the characteristic reflexes at the following glance angles .theta.
angle .theta. 4.0° 5.0° 8.15° 12.7° 13.5°
intensity 0.31 0.38 1.00 0.92 0.63
angle .theta. 4.0° 5.0° 8.15° 12.7° 13.5°
intensity 0.31 0.38 1.00 0.92 0.63
2. Process for the preparation of the modification ? being stable under dyeing conditions of the dyestuff of the formula (1) being characterized by the X-ray diffraction diagram as defined in claim 1, wherein the dyestuff of formula (1) being unstable under dyeing conditions (modification .alpha.) and being characterized by an X-ray diffraction diagram with the characteristic reflexes at the following glance angles Glance 6.5° 7.0° 7.6° 7.9° 9.1° 10.65° 11.8° 12.95°
angle Intensity 0.80 0.50 0.40 0.82 0.45 0.35 0.39 1.00 is (a) heated in an aqueous suspension at a temperature of from 50° to 95°C, or (b) heated in a mixture of water and an organic solvent miscible with water at a temperature of from 50 to 95°C, or (c) converted into an alkali metal salt, and the phenol form of the dyestuff is again set free therefrom by adding an acid.
angle Intensity 0.80 0.50 0.40 0.82 0.45 0.35 0.39 1.00 is (a) heated in an aqueous suspension at a temperature of from 50° to 95°C, or (b) heated in a mixture of water and an organic solvent miscible with water at a temperature of from 50 to 95°C, or (c) converted into an alkali metal salt, and the phenol form of the dyestuff is again set free therefrom by adding an acid.
3. The process as claimed in claim 2a, wherein the heating is per-formed in the presence of a surface active agent.
4. The process as claimed in claim 2b, wherein the heating is carried out in the presence of acetic acid, methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, glycol, methylglycol, ethylglycol, ethylene-glycol, acetone, dioxan, N-methyl-pyrrolidone or dimethyl formamide or mix-tures thereof as organic solvents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752524187 DE2524187C2 (en) | 1975-05-31 | Dye-stable modification of a disazo dye, its preparation and its use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1065308A true CA1065308A (en) | 1979-10-30 |
Family
ID=5947913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA253,577A Expired CA1065308A (en) | 1975-05-31 | 1976-05-28 | Stable modification of a disazo dyestuff |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5943498B2 (en) |
| BE (1) | BE842415A (en) |
| BR (1) | BR7603421A (en) |
| CA (1) | CA1065308A (en) |
| CH (1) | CH599323A5 (en) |
| FR (1) | FR2313433A1 (en) |
| GB (1) | GB1545816A (en) |
| IN (1) | IN144514B (en) |
| IT (1) | IT1060730B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62147697U (en) * | 1986-03-10 | 1987-09-18 | ||
| CN104629493B (en) * | 2013-11-12 | 2018-01-16 | 浙江双冠染料有限公司 | A kind of preparation method of environment-friendly type CI disperse oranges 29 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2007382A (en) * | 1932-08-16 | 1935-07-09 | Celanese Corp | Production of dispersions |
| CH351689A (en) * | 1956-03-05 | 1961-01-31 | Ciba Geigy | Process for the preparation of solutions of azo dyes |
| US3004821A (en) * | 1957-11-19 | 1961-10-17 | Du Pont | Stabilized gasoline-soluble disazo dye compositions and process of preparing same |
| DE1619535A1 (en) * | 1967-07-19 | 1971-05-19 | Bayer Ag | Color-stable disperse dyes |
| DE2313356A1 (en) * | 1973-03-17 | 1974-09-19 | Bayer Ag | METHOD OF COLORING FIBER MATERIALS |
-
1976
- 1976-05-28 IN IN930/CAL/1976A patent/IN144514B/en unknown
- 1976-05-28 BR BR3421/76A patent/BR7603421A/en unknown
- 1976-05-28 IT IT23758/76A patent/IT1060730B/en active
- 1976-05-28 CH CH669776A patent/CH599323A5/xx not_active IP Right Cessation
- 1976-05-28 JP JP51061302A patent/JPS5943498B2/en not_active Expired
- 1976-05-28 CA CA253,577A patent/CA1065308A/en not_active Expired
- 1976-05-31 BE BE167500A patent/BE842415A/en not_active IP Right Cessation
- 1976-05-31 FR FR7616306A patent/FR2313433A1/en active Granted
- 1976-06-01 GB GB22582/76A patent/GB1545816A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51147534A (en) | 1976-12-17 |
| BR7603421A (en) | 1976-12-21 |
| DE2524187B1 (en) | 1976-11-11 |
| IN144514B (en) | 1978-05-13 |
| FR2313433A1 (en) | 1976-12-31 |
| FR2313433B1 (en) | 1980-05-16 |
| JPS5943498B2 (en) | 1984-10-22 |
| BE842415A (en) | 1976-12-01 |
| GB1545816A (en) | 1979-05-16 |
| IT1060730B (en) | 1982-08-20 |
| CH599323A5 (en) | 1978-05-31 |
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