GB1569246A - Process for the preparation of azo reactive dyestuffs - Google Patents
Process for the preparation of azo reactive dyestuffs Download PDFInfo
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- GB1569246A GB1569246A GB982078A GB982078A GB1569246A GB 1569246 A GB1569246 A GB 1569246A GB 982078 A GB982078 A GB 982078A GB 982078 A GB982078 A GB 982078A GB 1569246 A GB1569246 A GB 1569246A
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- amino
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- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The reactive azo dyes of the formula <IMAGE> where D is the radical of a diazo component, R1 is hydrogen, methyl or ethyl, R2 and R3 are hydrogen, optionally substituted alkyl, cycloalkyl or aryl, or are together a ring with optional inclusion of a hetero atom, and n is 1 or 2, are prepared by reacting an aminonaphthol sulphonic acid of the formula <IMAGE> with cyanuric fluoride in a molar ratio of 1:1 to acylate the amino group. The resulting condensation product is coupled with a diazotised amine of the formula DNH2 to form the azo dye of the formula <IMAGE> It is then reacted in a molar ratio of 1:1 with an amine of the formula HNR2R3
Description
(54) PROCESS FOR THE PREPARATION OF AZO REACTIVE
DYESTUFFS
(71) We, BAYER AKTIENGESELL
SCHAFT, a body corporate organised under the laws of Federal Republic of Gerrnany, of Leverkusen, Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement::- The invention relates to a process for the reparation of azo reactive dyestuffs of the formula
wherein
D denotes the radical of a diazo com- ponent,
R1 denotes hydrogen, methyl or ethyl, Ra and R1 denote hydrogen or optionally substituted alkyl, cycloalkyl or aryl, it being
possible for R2 and Re to form a ring,
optionally including a hetero-atom, and
n denotes 1 or 2.
The preparation of dyestuffs of the formula
wherein' D, Re, Re and n have the meaning indicated above, is preferred.
The preparation of compounds of the
formula
wherein
D has the meaning indicated above and R2' and R3' represent hydrogen or option
ally substituted alkyl or cycloalkyl, it being
possible for R2' and R3' to form a ruing,
optionally including a hetero-atom, is also preferred.
The preparation of compounds of the formula
wherein R2' and Ra' have the meaning indicated
above and
D' represents the radical of a diazo com
ponent of the benzene or naphthalene series,
in particular a phenyl radical, which can
be optionally substituted by C1-C4-alkyl, ClC4-alkoxy, sulpho, sulpho-C1-C4- alkyl or halogen, especially chlorine, or a
naphthyl radical, which can also contain 1-3 sulpho groups, is particularly preferred.
Suitable alkyl radicals Re and Ra or R2' and R3' are, for example, C1-C4-alkyl, optionally substituted by OH, C1-C4-alkoxy or phenyl, which is optionally further substituted, for example by sulpho.
Suitable aryl radicals Re and Re or R2' and Ra' are, for example, phenyl, optionally substituted by sulpho, C1-C4-alkyl, C1-C4- alkoxy, halogen or carboxyl.
Suitable cycloalkyl radicals are, for example, cyclohexyl.
Suitable radicals Ra or Ra' are, for example, also those of the formula
wherein
R4 optionally substituted alkylene, cyclo
alkylene or arylene,
R2 has the meaning indicated in formula
(I), and preferably represents hydrogen,
and
R1, D and n have the meaning indicated above.
The novel preparation process is characterised in that an aminonaphtholsulphonic acid of the formula
wherein
R1 and n have the meaning indicated above, is first acylated on the amino group with cyanuric fluoride in a molar ratio 1:1 and at a pH of 2 to 5, compounds of the formula
being formed. These are then coupled with diazotised amines of the formula DNH2 (VII) wherein D has the above-mentioned meaning dyestuffs of the formula
being formed. These dyestuffs are then reacted with an amine of the formula
wherein R2 and R, have the above-mentioned meanings in the molar ratio 1:1 and a fluorine atom is replaced by an amino radical, dyestuffs of the formula (I) being formed.
Examples of compounds of the formula (V) are the following: 1 - hydroxy- 3 - sulpho6 - amino - naphthalene, 1 - hydroxy - 3sulpho - 7 - amino - naphthalene, 1 hydroxy3 - sulpho - 8 - amino - naphthalene, 1hydroxy - 3 - sulpho - 5 - amino - naphtha- lene, 1 - hydroxy - 3,5 - disulpho - 6 - aminonaphthalene, 1 hydroxy - 3,6 - disulpho - 7amino - naphthalene, 1 - hydroxy - 4,8disulpho - 6 - amino - naphthalene, 1hydroxy - 5 - sulpho - 8 - amino - naphthalene, 1 - hydroxy - 3,5 - disulpho - 8 - aminonaphthalene, 1 - hydroxy - 3,6 - disulpho- 8 - amino - naphthalene and 1 - hydroxy 4,6 - disulpho - 8 - amino - naphthalene.
Examples which may be mentioned of amines of the formula (VII) are the following: 1 - amino - benzene, 1 - amino - 4methyl - benzene, 1 - amino - 4 - methoxy- benzene, 4 - amino - benzyl - sulphonic acid, 1 - amino - 2 - sulpho - benzene, 1 - amino2 - sulpho - 4 - chloro - benzene, 1 - amino 2 - sulpho - 4 methyl - benzene, 1 - amino 2 - sulpho - 4 - methoxy - benzene, 1 - amino2,5 - disuipho - benzene, 1 - amino - 2,4disulpho - benzene, 1 - amino - 2,5 - disulpho4 - methoxy - benzene, 1 - amino - 2,4 disuipho - 6 - methyl - benzene, 1 - amino2,5 - dichloro - 4 - sulpho - benzene, 2 amino - 1 - sulpho - naphthalene, 2 - amino
1,5 - disulpho - naphthalene, 2 - amino1,5,7 - trisulpho - naphthalene, 1 - amino4,7 - disulpho - naphthalene, 1 - amino - 4,6disulpho - naphthalene, 1 - amino - 3,6disulpho - naphthalene, 1 - amino - 4 - sulphonaphthalene, 1 - amino - 5 - sulpho - naphthalene, 2 - amino - 5 - sulpho - naphthalene, 2 - amino - 4,8 - disulpho - naphthalene, 2amino - 5,7 - disulpho - naphthalene, 2amino - 3,6 - disuipho - naphthalene, 2amino - 6,8 - disulpho - naphthalene, 2amino - 3,6,8 - trisulpho - naphthalene, 4amino - azobenzene - 3,4' - disulphonic acid, 1 - hydroxy - 4 - sulpho - 6 - chlorobenzene - (2 - azo - 2) - I - hydroxy - 3,5disulpho - 6 - amino - naphthalene, 2 - (3' sulphophenyl) - triazolo[1,2-d] - 7 - aminonaphthalene - 5,9 - disulphonic acid and 2 (4' - amino - 3' - sulphophenyl) - triazolo
[1,2-d] - naphthalene - 4,7,9 - trisulphonic acid.
Examples of amines of the formula IX are the following: ammonia, methylamine, dimethylamine, ethyl amine, ethanol amine, diethanolamine, isopropylamine, )3-methoxyethyl- amine, aminoacetic acid, methylaminoacetic acid, taurine, N-methyltaurine, benzylamine,
N - methyl - benzylamine, benzylamine - sulphonic acid, 8-phenylethylamine, aniline, Nmethyl-aniline, o-, m- and p-toluidine, o-, mand p-anisidine, 4-amino-benzylsulphonic acid, o-, m- and p-sulphanilic acid, piperidine, morpholine, amino-cyclohexane, aniline - 2,4disulphonic acid and aniline-2,5-disulphonic acid.
Examples of further suitable amines IX are the reaction products of 1 mol of (VIII) with 1 mol of a diamine, for example mor p-phenylenediamine, 2,4 - diaminotoluene or 1,4-diaminocyclohexane.
The acylation of the aminonaphtholsul phonic acid with cyanuric fluoride is preferably carried out in an aqueous medium at 00, a pH of 2-5, preferably 3-4, being maintained by adding dilute sodium hydroxide solution, sodium carbonate solution or sodium bicarbonate solution.
The diazotised amines of the formula are coupled with the coupling components at a low temperature, for example at 00, and at a pH of 4-9; but the coupling is preferably carried out at pH 5a, which is maintained by adding acid-binding agents, such as dilute sodium hydroxide solution or sodium carbonate solution.
The condensation of the amine with the azo dyestuff is preferably carried out in an aqueous medium at a temperature of 020 and a pH of 5 to 9. The choice of temperatare and pH depends on the basicity of the amine. Thus, in the case of aliphatic amines, a higher pH and a lower temperature is chosen, whilst aromatic amines are subjected to a condensation reaction at a lower pH and
higher temperature.
A simplification of the process consists in
choosing as the acid-binding agent for the
coupling the same amine which is required
for replacing the second fluorine atom. Amines
which are particularly suitable for this are
ammonia and aliphatic amines.
A particularly advantageous process variant
consists in carrying out all the process steps
in a one pot reaction, without isolating inter
mediate products.
In this procedure, the hydroxy-amino naphthalene-sulphonic acid is first reacted with
1 mol of cyanuric fluoride, preferably at pH 2^5, particularly preferably at pH 34, and
at about 0 C, the diazotised amine (VII) is
then reacted in an aqueous medium, also at
about 0 C and at pH 419, particularly pre
ferably at pH 5a, and thereafter the amine
(IX) is added at about e20"C and at pH 5-9. (IX) is preferably used to adjust the
pH value during the coupling with the diazo
tised (VII).
The dyestuffs (I) can be prepared in high
yields and high purity by the process accord
ing to the invention.
Example 1.
31.9 g of 1 - hydroxy - 8 - amino - 3,6 disuipho - naphthalene are stirred into 500 ml of ice-water. 13.5 g of cyanuric fluoride are added dropwise at a pH of 3-4. The
hydrofluoric acid split off is trapped by adding
dilute sodium hydroxide solution, so that the pH of 3-4 is maintained. The mixture is stirred for some minutes and a solution is then added which has been obtained by diazotisation of 9.3 g of aniline and which has been adjusted to a pH of 4 before the addition. A 30% strength aqueous methylamine solution is then added dropwise until the pH reaches 8.5. The temperature is kept at v) by adding ice. The mixture is then further stirred for some time and the dyestuff is isolated by adding 5% by volume of sodium chloride.After the product has been filtered off, dried and ground, a red dyestuff powder is obtained which dissolves in water to give a red-coloured solution. In the form of the free acid, the dyestuff corresponds to the formula
Example 2.
31.9 g of 1 - hydroxy - 8 - amino - 3,6 disuipho - naphthalene are stirred into 500 ml of ice-water. 13.5 g of cyanuric fluoride are added dropwise at a pH of 3-4, dilute sodium hydroxide solution being added at the same time in order to keep the pH between 3 and 4. The mixture is further stirred for some minutes and a solution, adjusted to pH 4, of 9.3 g of diazotised aniline is then added. A 20% strength sodium carbonate solution is subsequently added dropwise until the pH reaches 6.5.The mixture is stirred at pH 6--6.5 until the coupling component can no longer be detected by a spot test in the colourless discharge from the reaction solu tion, ice being added at the same time in order to keep the temperature at 00. A 30% strength aqueous methylamine solution is then added dropwise up to a pH of 8.5-8.7. The mixture is then further stirred for some time under these conditions (0 C and pH 8.58.7) and the dyestuff is salted out with 5% by volume of sodium chloride. After the product has been filtered off, dried and ground, a red dyestuff powder is obtained. The dyestuff is identical to the product obtained according to Example 1.
Example 3.
11.9 g of 6 - amino - 1 - naphthol - 3sulphonic acid are dissolved in 180 ml of water with sodium hydroxide solution at pH 7. The solution is cooled to 0"--5" and 7.1 g of cyanuric fluoride are then added dropwise in the course of 20 minutes; the pH value kept at 4.5-5 by adding 20% strength sodium carbonate solution dropwise at the same time. Thereafter, the reaction mixture is stirred for a further 15 minutes at 0 5 .
After the reaction has ended, a diazonium salt solution, which is obtained by diazotising 8.7 g of 2 - amino - benzenesulphonic acid in the manner described further below, is slowly added. The reaction mixture is then adjusted to pH 6.5 with 10% strength sodium bicarbonate solution. After stirring for 2 hours at 0 5 and at pH 6.5, the coupling reaction has ended.
9 ml of methylamine solution (30 / strength) are then added dropwise in a manner such that the pH of the reaction mixture remains at pH 8-8.5. The mixture is then further stirred for some time and the temperature is subsequently allowed to rise to 20" 350. After the reaction mixture has been adjusted to pH 6, the dyestuff is salted out with 50 g of sodium chloride. The reaction product which has precipitated is filtered off, washed with 15% strength sodium chloride solution and dried at 60".
The resulting dyestuff, which in the form
of the free acid corresponds to the following
formula:
dyes cotton in brilliant orange-coloured shades.
Similar results are achieved if, after adding the diazonium salt solution, the pH value of the reaction mixture is immediately adjusted to pH 8.5 with methylamine solution and is kept at this value.
The abovementioned diazonium salt is prepared as follows: 8.7 g of 2 - amino-benzenesulphonic acid are dissolved in 90 ml of water by adding sodium hydroxide solution, and are then reprecipitated with 15 ml of hydrochloric acid (35% strength). The suspension is cooled to 0"--5" and the benzenesulphonic acid is diazotised by adding 17 ml of sodium nitrite solution (3N) dropwise. The reaction mixture is subsequently stirred at 0 5 for a further 15 minutes and the excess nitrous acid is destroyed with sulphamic acid solution.
Example 4.
11.9 g of 6 - amino - 1 - naphthol - 3sulphonic acid are dissolved in 180 ml of water with sodium hydroxide solution at pH 7. The solution is cooled to 0 -5 and 7.1 g of cyanuric fluoride are then added dropwise in the course of 20 minutes; the pH value being kept at 4.5-5 by adding 20% strength sodium carbonate solution dropwise at the same time. Thereafter, the reaction mixture is stirred at 0 -5 for a further 15 minutes.
After the reaction has ended, a diazonium salt solution, which is obtained by diazotising 8.7 g of 2 - amino - benzenesulphonic acid in the manner described further below, is slowly added. The reaction mixture is then adjusted to pH 6 with 10% strength sodium bicarbonate solution and the temperature is allowed to rise to 20 25 . The pH value is kept at 5.56 during the reaction. As soon as the coupling has ended, 5.6 g of o-toluidine are added dropwise, whilst stirring well. The reaction mixture is then adjusted again to pH 6. After stirring for several hours, the reaction has ended.The reaction product which has precipitated is filtered off, washed with 10% strength sodium chloride solution and dried at 60"C. The resulting dyestuff, which in the form of the free acid corresponds to the following formula:
dyes cotton in brilliant orange-coloured shades.
The abovementioned diazonium salt is prepared as follows: 8.7 g of 2 - amino - benzenesulphonic acid are dissolved in 90 ml of water by adding sodium hydroxide solution, and are then reprecipitated with 15 ml of hydrochloric acid (35% strength). The suspension is then cooled to 0"--5" and the benzenesulphonic acid is diazotised by adding 17 ml of sodium nitrite solution (3N) dropwise. The reaction mixture is subsequently stirred for a further 15 minutes at 0 5 -0 and the excess nitrous acid is destroyed with sulphamic acid solution.
Example 5.
11.9 g of 6 - amino - 1 - naphthol - 3sulphonic acid are dissolved in 180 ml of water with sodium hydroxide solution at pH 7. The solution is cooled to 0 5 -a and 7.1 g of cyanuric fluoride are then added dropwise in the course of 20 minutes; the pH value being kept at 4.5-5 by adding 20% strength sodium carbonate solution at the same time.
Thereafter, the reaction mixture is stirred at 0 5 CO for a further 15 minutes.
After the reaction has ended, a diazonium salt solution, which is obtained by diazotising 8.7 g of 2 - amino - benzenesulphonic acid in the manner described further below, is slowly added. The reaction mixture is then adjusted to pH 6 with 10% strength sodium bicarbonate solution and the temperature is allowed to rise to 20 -25 . The pH value is kept at 5.5-6 during the reaction. As soon as the coupling has ended, a neutral solution of 8.7 g of 3 - amino - benzenesulphonic acid in 50 ml of water is added dropwise, whilst stirring well. Thereafter, the reaction mixture is adjusted to pH 6. After some time, the reaction has ended. The dyestuff is precipitated by adding 90 g of sodium chloride. The reaction product is filtered off, washed with 15% strength sodium chloride solution and dried at 600.
The resulting dyestuff, which in the form of the free acid corresponds to the following formula:
dyes cotton in brilliant orange-coloured shades.
The abovementioned diazonium salt is prepared as follows: 8.7 g of 2 - amino - benzenesulphonic acid are dissolved in 90 ml of water by adding sodium hydroxide solution, and are then reprecipitated with 15 ml of hydrochloric acid (35% strength). The suspension is cooled to 0 5 and the benzenesulphonic acid is diazotised by adding 17 ml of sodium nitrite solution (3N) dropwise. The reaction mixture is subsequently stirred at 0"--5" for a further 15 minutes and the excess nitrous acid is destroyed with sulphamic acid solution.
Example 6.
17.05 g of 8 - amino - 1 - naphthol - 3,6disulphonic acid are dissolved in 200 ml of water with sodium hydroxide solution at pH 5.5. The solution is cooled to 0 5 and 6.75 g of cyanuric fluoride are then added dropwise in the course of 5 minutes, the pH value being kept at 4.0-4.5 by adding 20% strength sodium carbonate solution dropwise at the saone time. Thereafter, the reaction mixture is stirred at 0"--5" for a further 15 minutes.
After the reaction has ended, a diazonium salt suspension, which is obtained by diazotising 8.7 g of 2 - amino - benzenesulphonic add in the manner described further below, is slowly added. The reaction mixture is adjusted to pH 6.0 with 20% strength sodium carbonate solution, and the temperature is kept at 0 -5 . The pH value is kept at 5.56.0 during the reaction. As soon as the coupling has ended, a solution of 8.65 g of 3 - amino benzenesulphonic acid, dissolved in 50 ml ol water with sodium hydroxide solution at pH 6.0, is added dropwise, while stirring well.
The pH value is kept at 6.0-6.3 by adding 20% strength sodium carbonate solution dropwise at the same time, and the temperature is allowed to rise to 20 -25 . After stirring for several hours, the reaction has ended. The reaction product is further salted out with sodium chloride, filtered off, washed with 13% strength sodium chloride solution and dried at 600.
The resulting dyestuff, which in the form of the free acid corresponds to the following formula:
dyes cotton in bluish-tinged red shades.
The abovementioned diazonium salt is prepared as follows: 8.7 g of 2 - amino - benzenesulphonic acid are dissolved in 90 ml of water by added sodium hydroxide solution, and then reprecipitated with 15 ml of hydrochloric acid
(35% strength). The suspension is cooled to 0 5 and the benzenesulphonic acid is diazotised by adding 17 ml of sodium nitrite solution (3N) dropwise. The reaction mixture is subsequently stirred at 0 5 for a further 13 minutes and the excess nitrous acid is destroyed with sulphamic acid solution.
WKAT WE CLAIM IS 1. A process for the production of an azo dyestuff of the general formula
in which
D denotes a radical of a diazo component, Rl denotes a hydrogen atom or a methyl
or ethyl group,
R2 and Re independently denote a hydrogen
atom or an optionally substituted alkyl,
cycloalkyl or aryl group, it being possible
for Re and Re to form a ring, optionally
including a hetero-atom, and
n is 1 or 2, in which an aminonaphtholsulphonic acid of the general formula
in which n and Re have the above-mentioned meanings, is acylated on the amino group with cyanuric fluoride in a molar ratio 1: :1 and at a pH of 2 to 5, the condensation product formed of the general formula
is coupled with a diazotised amine of the general formula D--NH, (VII) in which D has the above-mentioned meaning; to give an azo dyestuff of the general formula
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (14)
1. A process for the production of an azo dyestuff of the general formula
in which
D denotes a radical of a diazo component, Rl denotes a hydrogen atom or a methyl
or ethyl group,
R2 and Re independently denote a hydrogen
atom or an optionally substituted alkyl,
cycloalkyl or aryl group, it being possible
for Re and Re to form a ring, optionally
including a hetero-atom, and
n is 1 or 2, in which an aminonaphtholsulphonic acid of the general formula
in which n and Re have the above-mentioned meanings, is acylated on the amino group with cyanuric fluoride in a molar ratio 1::1 and at a pH of 2 to 5, the condensation product formed of the general formula
is coupled with a diazotised amine of the general formula D--NH, (VII) in which D has the above-mentioned meaning; to give an azo dyestuff of the general formula
and this is then reacted with an amine of the general formula
in a molar ratio 1:1, Re and Re having the above-mentioned meanings.
2. A process according to claim 1, in which an azo dyestuff of the general formula
in which D, R2, Re and n have the same
meanings as in claim 1, is produced.
3. A process according to claim 1, in which an azo dyestuff of the general formula
in which
D has the same meaning as in claim 1, and R21 and Rs1 independently denote a hydro- gen atom or an optionally substituted alkyl or cycloalkyl group, or R11 and Rue1, optionally
together with a further hetero-atom, complete
a ring with the nitrogen atom, is produced.
4. A process according to claim 1, in which
an azo dyestuff of the general formula
in which
R21 and Re1 have the same meaning as in
claim 3, and D1 denotes a phenyl radical
which is optionally substituted by C1 to
C, alkyl, C1 to C4 alkoxy, sulpho, sulpho
C1 to C4 alkyl, or halogen, or a naphthyl
radical which contains 1 to 3 sulpho groups,
is produced.
5. A process according to claim 1, in which the compound of formula (V) is any of those hereinbefore specifically mentioned.
6. A process according to claim 5, in which the compound of formula (V) is 1 - hydroxy8 - amino - 3,6 - disulphonaphthalene, 1hydroxy - 8 - amino - 3,5 - disulphonaphthalene or 1 - hydroxy - 8 - amino - 4,6 - disulphonaphthalene.
7. A process according to claim 1, 5 or 6, in which the amine of formula (VII) is a primary or secondary aliphatic or araliphatic amino.
8. A process according to claim 7, in which
he amine of formula (VII) is any of those hereinbefore specifically mentioned.
9. A process according to claim 8, in which the amine of formula (VII) is aniline, osulphonanilic acid, aniline - 2,5 - disulphonic acid, 2 - amino - 1 - sulpho - naphthalene, 2 - amino - 1,5 - disulphonaphthalene or 2amino - 4,8 - disulphonaphthalene.
10. A process according to any of the foregoing claims, in which the process steps are carried out in a one pot reaction, without intermediate isolation.
11. A process according to claim 1, when
tarried out substantially as described in
Example 1 or 2.
12. A process according to claim 1, when carried out substantially as described in any one of Examples 3 to 6.
13. An azo dyestuff when produced by the process of any of claims 1 to 11.
14. An azo dyestuff when produced by the process of claim 12.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772711150 DE2711150A1 (en) | 1977-03-15 | 1977-03-15 | METHOD OF PREPARING AZOREACTIVE DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1569246A true GB1569246A (en) | 1980-06-11 |
Family
ID=6003646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB982078A Expired GB1569246A (en) | 1977-03-15 | 1978-03-13 | Process for the preparation of azo reactive dyestuffs |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS53113829A (en) |
| CH (1) | CH631733A5 (en) |
| DE (1) | DE2711150A1 (en) |
| FR (1) | FR2384001A1 (en) |
| GB (1) | GB1569246A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2128200A (en) * | 1982-09-17 | 1984-04-26 | Sandoz Ltd | Chloro-triazinyl mondazo compounds |
| US4740597A (en) * | 1984-08-21 | 1988-04-26 | Ciba-Geigy Corporation | Process for the continuous reaction of cyanuric fluoride with sulfo-containing aromatic amines |
| US4988803A (en) * | 1987-07-16 | 1991-01-29 | Bayer Aktiengesellschaft | Fiber reactive azo dyes containing a morpholinyl-, piperazinyl- or piperidnyl- substituted flurotriazinyl radical |
| CN115386244A (en) * | 2022-08-11 | 2022-11-25 | 南通大学 | Double-chromophore pH color-changing reactive dye and preparation and application thereof |
| CN116144194A (en) * | 2023-01-05 | 2023-05-23 | 江苏德美科化工有限公司 | Reactive red dye for cellulose blend fiber and preparation method thereof |
| US12091552B2 (en) | 2022-08-11 | 2024-09-17 | Nantong University | Reactive dyes and preparation methods thereof |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2729240C2 (en) * | 1977-06-29 | 1982-07-29 | Bayer Ag, 5090 Leverkusen | Azo reactive dyes |
| DE2840380C2 (en) * | 1978-09-16 | 1985-05-30 | Bayer Ag, 5090 Leverkusen | Fiber-reactive azo dyes |
| DE2847916C2 (en) * | 1978-11-04 | 1984-04-26 | Basf Ag, 6700 Ludwigshafen | Reactive dyes and their use |
| DE2903594A1 (en) * | 1979-01-31 | 1980-08-14 | Bayer Ag | FLUORTRIAZINE REACTIVE DYES AND METHOD FOR PRODUCING FLUORTRIAZINE DERIVATIVES |
| DE3224786A1 (en) * | 1982-07-02 | 1984-01-05 | Bayer Ag, 5090 Leverkusen | TRIAZINE COMPOUNDS, THEIR PRODUCTION AND THEIR USE |
| JPS61238855A (en) * | 1985-04-17 | 1986-10-24 | Nippon Kayaku Co Ltd | Water-soluble azo compound and dyeing method using same |
| DE3545462A1 (en) * | 1985-12-20 | 1987-07-02 | Bayer Ag | REACTIVE DYES |
| DE4215485A1 (en) * | 1992-05-11 | 1993-11-18 | Bayer Ag | New reactive dyes |
| DE19821347A1 (en) * | 1998-05-13 | 1999-11-18 | Dystar Textilfarben Gmbh & Co | Water-soluble azo compounds containing halogenotriazine, process for their preparation and their use as dyes |
-
1977
- 1977-03-15 DE DE19772711150 patent/DE2711150A1/en not_active Withdrawn
-
1978
- 1978-03-13 JP JP2784078A patent/JPS53113829A/en active Pending
- 1978-03-13 CH CH272078A patent/CH631733A5/en not_active IP Right Cessation
- 1978-03-13 GB GB982078A patent/GB1569246A/en not_active Expired
- 1978-03-14 FR FR7807283A patent/FR2384001A1/en not_active Withdrawn
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2128200A (en) * | 1982-09-17 | 1984-04-26 | Sandoz Ltd | Chloro-triazinyl mondazo compounds |
| US4518391A (en) * | 1982-09-17 | 1985-05-21 | Sandoz Ltd. | Monoazo compounds having a sulfo group-containing diazo component radical and a 6-(2'-chloro-1',3',5'-triazin-6'-ylamino)-1-hydroxy-3-sulfonaphthalene coupling component radical having a substituted amino group in the 4'-position |
| US4740597A (en) * | 1984-08-21 | 1988-04-26 | Ciba-Geigy Corporation | Process for the continuous reaction of cyanuric fluoride with sulfo-containing aromatic amines |
| US4988803A (en) * | 1987-07-16 | 1991-01-29 | Bayer Aktiengesellschaft | Fiber reactive azo dyes containing a morpholinyl-, piperazinyl- or piperidnyl- substituted flurotriazinyl radical |
| CN115386244A (en) * | 2022-08-11 | 2022-11-25 | 南通大学 | Double-chromophore pH color-changing reactive dye and preparation and application thereof |
| CN115386244B (en) * | 2022-08-11 | 2023-10-20 | 南通大学 | Double-color-body pH color-changing reactive dye and preparation and application thereof |
| US12091552B2 (en) | 2022-08-11 | 2024-09-17 | Nantong University | Reactive dyes and preparation methods thereof |
| CN116144194A (en) * | 2023-01-05 | 2023-05-23 | 江苏德美科化工有限公司 | Reactive red dye for cellulose blend fiber and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2711150A1 (en) | 1978-09-28 |
| JPS53113829A (en) | 1978-10-04 |
| CH631733A5 (en) | 1982-08-31 |
| FR2384001A1 (en) | 1978-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |