GB2028360A - Fibre-reactive azo dyes, processes for their manufacture and use thereof - Google Patents
Fibre-reactive azo dyes, processes for their manufacture and use thereof Download PDFInfo
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- GB2028360A GB2028360A GB7923812A GB7923812A GB2028360A GB 2028360 A GB2028360 A GB 2028360A GB 7923812 A GB7923812 A GB 7923812A GB 7923812 A GB7923812 A GB 7923812A GB 2028360 A GB2028360 A GB 2028360A
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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
- C09B62/085—Monoazo dyes
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Abstract
The invention provides reactive dyes of the formula <IMAGE> wherein X is sulfomethyl, cyano or carbamoyl, each of R1 and R2 independently is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, Z is a sulfonaphthylamino group and the benzene radical can contain further substituents in addition to the HO3S group. Processes for obtaining these dyes and their use on silk, leather, wool, polyamide and polyurethane, linen and cotton are also disclosed.
Description
SPECIFICATION
Fibre-reactive azo dyes, processes for their manufacture and use thereof
The present invention relates to fibre-reactive azo dyes, processes for their manufacture and use thereof.
The present invention provides reactive dyes of the formula
wherein X is sulfomethyl, cyano or carbamoyl, each of R1 and R2 independently is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, Z is a sulfonaphthylamino group and the benzene radical can contain further substituents in addition to the HO3S group.
R1 and R2 as alkyl of 1 to 4 carbon atoms can be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl ortert-butyl.
In addition to the HOsS group, the benzene radical in formula (1 ) can contain, for example, the following further substituents: alkyl groups of 1 to 4 carbon atoms, such as methyl, ethyl and propyl; alkoxy groups of 1 to 4 carbon atoms, such as methoxy, ethoxy, propyloxy and isopropyloxy; acylamino groups of 1 to 6 carbon atoms, such as acetylamino, propionylamino and benzoylamino groups; amino groups, such as -NH2, methylamino and ethylamino; the ureido, hydroxyl and carboxyl group; and halogen atoms, such as fluorine, chlorine and bromine.
Z can be for example the radical of one of the naphthylaminosulfonic acids which are named as possible starting materials in the description of the process for the manufacture of the azo dyes of the formula (1).
Preferred reactive dyes of the formula (1) are those wherein X is sulfomethyl, cyano or carbamoyl, each of R1 and R2 independently is hydrogen or alkyl of 1 to 4 carbon atoms, and Z is a mono-, di- or trisul- fonaphthylamino group.
An important subgroup of the reactive dyes of the formula (1 ) comprises reactive dyes of the formula
wherein R1 is hydrogen or alkyl of 1 to 4 carbon atoms.
Avaluable reactive dye of the constitution defined above is that of the formula
The dyes of the formula (1 ) are fibre-reactive because they contain a removable chlorine atom in the s-triazine radical.
By fibre-reactive compounds are meant those compounds which are able to react with the hydroxyl groups of cellulose or with the amino groups of natural or synthetic polyamides to form covalent chemical bonds.
The fibre-reactive azo dyes of the formula (1) may be obtained by reacting, in any order, a 6-hydroxypyridone-(2) of the formula
wherein Rf, R2 and X have their previous significance and W is hydrogen or carbamoyl, a diaminobenzene-sulfonic acid of the formula
2,4,6 - trichloro - s - triazin of the formula
and a naphthylamine of the formula
H-Z (7) wherein Z has its previous significance,
by (diazotisation), coupling and condensation to
produce a reactive dye of the formula (1).
If necessary or desired, instead of using a diaminobenzenesulfonic acid of the formula (5) there is used the corresponding aminoacetylaminobenzenesulfonic acid and the acetyl radical is removed again by saponification after the diazotisation and coupling.
If W is carbamoyl in the 6-hydroxypyridone-(2) of the formula (4), the carbamoyl radical W is removed during the coupling.
In a preferred embodiment of the process of the invention, the starting materials are a 6-hydroxypyridone-(2) of the formula (4), wherein X is sulfomethyl, cyano or carbamoyl, each of R1 and
R2 independently is hydrogen of alkyl of 1 to 4 carbon atoms, and a naphthylamine of the formula (7), wherein Z is a mono-, di- or trisulfonaphthylamino group.
The valuable reactive dyes of the formula (2) may be obtained by coupling and condensing, in any order, a 6-hydroxypyridone-(2) of the formula
wherein R1 is hydrogen or alkyl of 1 to 4 carbon atoms and W is hydrogen or carbamoyl, 1,3 diaminobenzene - 4 - sulfonic acid, 2,4,6 - trichloro s - triazine and an aminonaphthalenesulfonic acid of the formula
As the individual process steps described above can be carried out in varying sequence, and, if desired, also in some cases simultaneously, different variants of the process are possible. The starting materials to be used for each partial reaction follow from formula (1). In general, the sequence of the simple reactions between the individual reaction components of the formula (4) to (7) can be freely chosen.
Important process varients comprise:
1) condensing 2,4,6 - trichloro - s - triazine of the formula (6) with a diaminobenzenesulfonic acid of the formula (5), diazotising the primary condensation product and coupling the diazo compound to a 6-hydroxypyridone-(2) of the formula (4), and finally replacing a chlorine atom in the s-triazine radical by condensation with a naphthylamine of the formula (7);;
2) diazotising a diaminobenzenesulfonic acid of the formula (5) or a corresponding aminoacetylaminobenzenesulfonic acid and coupling the diazo compound to a 6-hydroxypyridone-(2) of the formula (4) (and, if desired, removing the acetyl radical by saponification), condensing the azo
compound with 2,4,6 - trichloro - s - triazine of the formula (6), and condensing the mono-condensation
product with a naphthylamine of the formula (7);
3) condensing a diaminobenzensulfonic acid of the formula (5) with 2, 4, 6 - trichloro - s - triazine of the formula (6), condensing the primary condensation product with a naphthylamine of the formula (7), diazotising the secondary condensation product and coupling the diazo compound to a 6-hydroxypyridone-(2) of the formula (4);;
4) diazotising a diaminobenzenesulfonic acid of the formula (5) our a corresponding aminoacetylaminobenzenesulfonic acid and coupling the diazo compound to a 6-hydroxypyridone-(2) of the formula (4) (and, if desired, removing the acetyl radical by saponification), in addition condensing 2, 4, 6 - trichloro - s - triazine of the formula (6) and a naphthylamine of the formula (7) and condensing both intermediates with each other;
5) condensing 2,4,6 - trichloro - s - triazine of the formula (6) with a naphthylamine of the formula (7), condensing the monocondensation product with a diaminobenzenesulfonic acid of the formula (5), diazotising the secondary condensation product and coupling the diazo compound to a 6-hydroxypyridone-(2) of the formula (4).
In the following Examples, the manufacture of the intermediates is not described in every case; however, any undisclosed manufacture is clearly evident from what has been stated above.
As starting materials which can be used for the production of the fibre-reactive azo dyes of the formula (1) the following compounds may be men tioned: 6-Hydroxyp yridones- (2) of the formula (4): 1 - ethyl - 3 - carbamoyl - 4 - methyl - 6 - hydroxypyridone- (2), 1,4 - dimethyl - 3 - carbamoyl - 6 - hydroxypyridone (2), 1 - ethyl -3 - sulfomethyl -4-methyl - 6- hydroxypyridone- (2), 3 - sulphomethyl - 4 - methyl - 2,6 dihydroxypyridine, 3 - cyano - 4 - methyl - 2,6 - dihydroxypyridine, 1 - ethyl - 3 - cyano - 4 - methyl - 6 - hydroxypyridone -(2), 3 - carbamoyl - 4 - methyl - 2,6 - dihydroxypyridine, 1 - ethyl - 3 - sulfomethyl - 4 - methyl - 5 - carbamoyl 6 - hydroxypyridone - (2), 3 - sulfomethyl - 4 - methyl - 5 - carbamoyl - 2,6 dihydroxypyridine, 1 -ethyl-3-cyano-4-methyl-5-carbamoyl-6- hydroxypyridone- (2).
Diaminobenzensulfonic acids ofthe formula (5): 1,3 - diaminobenzene - 4 - sulfonic acid, 1,4- diaminobenzene - 2 - sulfonic acid.
1 - amino - 3 - acetylaminobenzene - 4 - sulfonic acid (subsequently saponified), 1 - amino - 4 - acetayaminobenzene - 2 - sulfonic acid (subsequently saponified), 1 - amino - 3 - acetylamino - 6 - methylbenzene - 4 sulfonic acid (subsequently saponified), 1 - amino - 3 - acetylamino - 6 - methoxybenzene - 4 sulfonic acid (subsequently saponified), 1,3 - diamino - 6 - methylbenzene - 4 - sulfonic acid,
1,4 - diamino - 6 - chlorobenzene - 2 - sulfonic acid.
2, 4, 6- Trichloro - s - triazine of the formula (6), cyanuric chloride
Naphthylamines of the formula (7) 1-naphthylamine, 2-naphthylamine, 1-naphthylamine-2-, -3-, -4-, -5-, -6-, -7-and -8- sulfonic acid, 2-naphthylamine-1-, -3-, -4-, -5-, -6-, -7
and 8-sulfonic acid, 1-naphthylamine-2,4-, -2,5-, -2,7-, -2,8-, -3,5-, -3,6-, -3,7-, -3,8-, -4,6-, -4,7-, -4,8- and -5,8-disulfonic acid, 2-naphthylamine-1,5-, -1,6-, -1,7-, -3,6-, -3,7-, -4,7-, -4,8-, -5,7-and -6,8-disulfonic acid, 1 -naphthylamine-2,4,6-, -2,4,7-, -2,5,7-, -3,5,7-, -3,6,8- and -4,6,8-trisulfonic acid, 2-naphthylamine-1 3,7-, -1,5,7-, -3,5,7-, -3,6,7-, -3,6,8and -4,6,8-trisulfonic acid.
The diazotisation of the diaminobenzenesulfonic acids of the formula (5) is normally carried out by treatment with nitrous acid in an aqueous mineral acid solution at low temperature, and the coupling to the 6-hydroxypyridone-(2) of the formula (4) is carried out at weakly acid or neutral to weakly alkaline pH values.
The condensation reactions of the 2,4,6-trifluoros-triazine with the diaminobenzenesulfonic acids of the formula (5) and the naphthylamines of the formula (7) are carried out preferably in aqueous solution or suspension, at low temperature and at a weakly acid or neutral to weakly alkaline pH value.
Advantageously, hydrogen chloride which is set free during the condensation is neutralised continuously by the addition of aqueous alkali hyroxides, carbonates or bicarbonates.
The fibre-reactive azo dyes of the formula (1 ) are distinguished by a pronounced reactivity and a high degree of fixation. They are suitable for dyeing and printing a very wide variety of materials, such as silk, leather, wool, polyamide and polyurethane fibres, and especially cellulosic materials of fibrous structure, such as linen, cellulose, regenerated cellulose,
and in particular cotton. They are suitable both for the exhaust process and for dyeing by the paddyeing process, in which the goods are impregnated with aqeous and, if appropriate, also with saltcontaining dye solutions, and the dyes are fixed after treatment with alkali or in the presence of alkali, with or without the application of heat.
They are also suitable for printing, in particular on cotton, and also for printing nitrogen-containing fibres, for example wool, silk, or blends containing wool.
It is advisable to rinse the dyeings and prints thoroughly with cold and hot water, if appropriate with the addition of an agent which acts as a dispersant and promotes the diffusion of non-fixed dye.
In the following Examples, the parts and percentages are by weight.
Example 1: 39.5 parts of 1 - ethyl - 3 - carbamoyl - 4 methyl - 5 - (5' - amino - 2' - sulfophenylazo) - 6 hydroxypyridone - (2) (obtained by coupling 3 amino - acetanilide- 4 - sulfonic acid to 1 - ethyl - 3 carbamoyl - 4 - methyl -6 - hydroxypyridone - (2) and subsequent saponification) are dissolved at pH 7 in 500 parts of water with sodium hydroxide and the solution is cooled to 0450C by addition of ice. Then 18.4 parts of cyanuric chloride are tipped in and the pH is subsequently kept at 4-5 with sodium hydroxide solution.After 20 to 30 minutes, a neutral solution of 22.2 parts of 2 - naphthylamine - 6 - sulfonic acid in 150 parts of water are poured in and the pH is kept at 7.5 by further addition of sodium hydroxide while simultaneously raising the temperature to 40"C. After stirring for about 30 minutes, the dye is precipitated with 150 parts of potassium chloride.
The batch is stirred again, then the precepitate is collected by filtration and dried. The dye of the formula
is a yellow powder. It dyes cotton in brilliant, slightly greenish yellow shades of very good fastness properties.
Dyes of the same shade and with similar fastness properties are obtained by using, instead of the 2-naphthylamine-6-sulfonic acid of this Example, one of the following naphthylamine-mono-, di- or trisulfonic acids: 1 - naphthylamine - 4 - sulfonic acid, 1 - naphthylamine - 5 - sulfonic acid, 1 - naphthylamine - 6 - sulfonic acid, 1 - naphthylamine - 7 - sulfonic acid, 1 - naphthylamine - 8 - sulfonic acid, 2 - naphthylamine - 5 - sulfonic acid, 2 - naphthylamine - 6 - sulfonic acid, 2 - naphthylamine - 7 - sulfonic acid, 2 - naphthylamine - 8 - sulfonic acid, 1 - naphthylamine - 3,6 - disulfonic acid, 1 - naphthylamine - 3, 7 - disulfonic acid, 2 - naphthylamine - 1, 5 - disulfonic acid, 2 - naphthylamine - 3, 5 - disulfonic acid, 2 - naphthylamine - 4,8 - disulfonic acid, 2 - naphthylamine - 5,7 - disulfonic acid, 2 - naphthylamine - 6, 8 - disulfonic acid, 1 - naphthylamine - 2, 5, 7 - trisulfonic acid, 1 - naphthylamine - 3, 6,8 - trisulfonic acid, 1 - naphthylamine - 4, 6, 8 - trisulfonic acid, 2 - naphthylamine - 1, 5, 7 - trisulfonic acid, 2 - naphthylamine - 4,6,8 - trisulfonic acid.
Examples2to 10
18.8 parts of 1,3 - phenylenediamine - 4 - sulfonic acid are dissolved at pH 7 and 0 C in 250 parts of water and 18.4 parts of cyanuric chloride are tipped into the solution. The mixture is stirred at 0"-5"C while keeping the pH at 7 to 8 by the dropwise addition of 2N sodium hydroxide solution. As soon as no more alkali is taken up, 20 parts of 2-naphthylamine-6-sulfonic acid and 2.2 parts of 2-naphthylamine-5-su Ifonic acid are dissolved neutral in 150 parts of water. This solution is added to the reaction mixture, which is warmed to 40"C while keeping the pH at 7 to 8 by the further addition of sodium hydroxide solution.When the condensation is complete, the reaction mixture is cooled to 0 C, then acidified with 25 parts of concentrated hydrochloric acid and diazotisation is carried out with 25 parts of 4N sodium nitrite solution. The diazo solution is stirred briefly and any excess nitrite is destroyed. A neutral solution of 19.6 parts of 1 - ethyl - 3 - carbamoyl - 4 - methyl -6 - hydroxypyridone - (2) in 100 parts of water is then run in. The pH is adjusted initially to 4.5 by addition of sodium hydroxide solution, then raised to 7 when the coupling is complete.
The dye is precipitated with 70 parts of potassium chloride, yieiding a dyestuff mixture which dyes cotton in very fast greenish yellow shades.
Table I lists dyes of similar properties which are obtained by repeating the procedure of this example, but condensing the 1,3 - phenylenediamine - 4 sulfonic acid with cyanuric chloride, reacting the condensate with the naphthylaminesulfonic acids of column II and, after diazotisation, coupling to the pyridones of column 111. The shade of the resulting dyes on cotton is indicated in column IV.
Table 1
n iii I 111 lv 2 H2RXSo3H H035-C" greenish yellow CH2L yellow H3 3 mS n greenish o3 yellow 4 NA2 Hj ~ 503H CH3 5 90 E | , or yellow SO H 0 cH .3 H2N l Il greenish i I'ellow OH v H cH2Cd3 3
Iii Ill 77 ~~~~~~~~~ yellcw H2 SO3H HO3ECH.lOH 7 mixture of 8 Hh HH-0c"3 greenish i 503H ; yellow and ccH3 u2N - 9 " greenish 9 4 42- CX green i sh SO3H cH2 10 ar t or 9 2ee grse.ish d H2N.c yellcw 503H cH2CH3 and 50311 ~ H2N X ~ Example 111 equivalent of 2naphthylamine-6-sulfonic acid is condensed initially with 1 equivalent of cyanuric chloride, the primary condensation product is then condensed with 1 equivalent of 1 ,3-phenylenediamine-4-sulfonic acid and the further procedure described in Example 2 is repeated, affording the same dye in the same quality.
Examples 12 to 24
The procedure of Example 11 is repeated, except that 1 equivalent of the naphthylamine of column of Table 2 is condensed with 1 equivalent of cyanuric chloride, the primary condensation product is condensed with a further equivalent of the phenylenediamine of column II, and the intermediate obtained is diazotised and coupled to 1 equivalent of the pyridone of column IV. The resulting dye colours cotton in the respective shade indicated in column V.
TABLE II
lx: I I IV V 12 503H HzNtNN2 .. B2N-0c rydedliSw I O3N ryei1ow ;03H 23 I t 3 N2N3li503 do. do. do.
ao. ao. do.
I / N2N A NN2 3 cN3 03N CH2CH3 HO3SCNO2N yellow CN2CN3 11 II III IV V so ii SOjlt O CN3 15 H2N X do. N2NoCON do.
ZOO 6 CH2C83 I CN3 N H2N-C greenish 'SOgH t2 OAH yellow CN 2CN3 /C1 17 do. N2Nii2 do. yellow NO3S " II III IV I V ~~ H2N 3 \ fi 3 N3 18 t03N H2N tNH2 CH 2cm3 yellow 3 CN2CH3 NN2 NN HLNi H2 3 112N - O3N N2N- greemish 503N CN3 oloii O* CN2CN3 U SO3N /NH2 N2N1% N N / \ -SO N 2 3 NCH yellow l 503H SO3N CN2CH31 CN2CN3
IX: II ITT TV V N 2N NN NI'2 ?. l{3 2 1 21N N2N-C @ greenish yellow 61(3 2,2 do. CH3 do. do. H2 do. mixture of 1 mjx'ure uf 23 H2NirNH2 0 CN so,n yellow N2N-O" 3 greenish and S03N 20311 ON, ON yellow H2Nmt CH2CH3 - S03H II IIr | it I it IV V SO N CN 24 { H2Nt H2N < NN2 D035 CH2ffi) yellow C'N2CN3
Example 25 18.8 parts of 1,3 - phenylenediamine - 4 - sulfonic acid are dissolved at pH 7 and 0 C in 250 parts of water and 18.4 parts of cyanuric chloride are tipped into the solution. The mixture is stirred at 0"-5"C while keeping the pH at 4 to 5 by the dropwise addition of 52 parts of 2N sodium hydroxide solution. When the condensation is complete, the pH is adjusted to 7.5, 25 parts of 4N sodium nitrite solution are added and the diazo solution is added to a mixture of 25 parts of concentrated hydrochloric acid and 100 parts of ice. After the diazotisation the batch is briefly stirred, any excess nitrite is destroyed, and a neutral solution of 19.6 parts of 1 - ethyl - 3 - carbamoyl - 4 - methyl - 6 - hydroxypyridone 2 in 100 parts of water is run in.The pH is initially adjusted with sodium hydroxide to 4.5 and then to 7 when the coupling is complete. After addition of a neutral solution of 22.2 parts of 2-naphthylami ne-6-su Ifonic acid in 150 parts of water, the mixture is slowly warmed to 40"C while keeping the pH at 7 to 8 by the dropwise addition of sodium hydroxide. When the condensation is complete, the dye is salted out with 70 parts of potassium chloride and worked up. The resulting dye is identical with that obtained in Example 1.
Example 26
Dyeing Procedure 1 2 parts of the dye obtained in Example 1 are dissolved at 20 to 50"C in 100 parts of water with the addition of 5 to 20 parts of urea and 2 parts of calcined sodium carbonate. A cotton fabric is impregnated with this solution to a pick-up of 60 to 80% and then dried. The fabric is then thermofixed for 30 seconds to 5 minutes at 1400 to 210"C, subsequently soaped for a quarter of an hour in a 0.1% boiling solution of a non-ionic detergent, rinsed and dried.
Example 27
Dyeing Procedure 2 2 parts of the dye obtained in Example 1 are dissolved at 75"C in 2000 parts of water with the addition of 2 to 10 parts of sodium chloride or calcined
Glauber's salt. Then 100 parts of a cotton fabric are put into this dyebath and the temper < .ture is kept constant for 30 to 60 minutes. Ten parts of calcined sodium carbonate and 4 ml of sodium hydroxide solution (36 se) are then added. The temperature is kept for a further45 to 60 minutes at 75" to 80"C and the fabric is then soaped for 15 minutes in a 0.1% boiling solution of a non-ionic detergent, rinsed and dried.
Example 28
Dyeing Procedure 3 2 parts of the dye obtained in Example 1 are dissolved in 100 parts of water while adding 0.5 part of sodium m-nitrobenzenesulfonate. A cotton fabric is impregnated with the resulting solution to a liquor pick-up of 75% and then dried.
The fabric is then impregnated with a warm solution of 20"C which contains, per litre, 5 g of sodium hydroxide and 300 g of sodium chloride, and squeezed out to a pickup of 75%. The dyeing is steamed for 30 seconds at 100" to 101 C, rinsed, soaped for a quarter of an hour in a 0.3% boiling solution of a non-ionic detergent, rinsed and dried.
Example 29
Dyeing Procedure 4 2 parts of the dye obtained in Example 1 are dissolved in 100 parts of water. The solution is added to 1900 parts of cold water, 60 parts of sodium chloride are added and 100 parts of a cotton fabric are put into this dyebath. The temperature is raised to 60"C and 40 parts of calcined sodium carbonate and another 60 parts of sodium chloride are added after 30 minutes. The temperature is kept for 30 minutes at 60"C. The dyeing is rinsed and then soaped for 15 minutes in a 0.3% boiling solution of a non-ionic detergent, rinsed and dried.
Example 30
Printing Procedure 2 parts of the dye obtained according to Example 1 are sprinkled, with rapid stirring, into 100 parts of a stock thickening which contains 45 parts of 5% sodium alginate thickening, 32 parts of water, 20 partsofurea, 1 of sodium m-nitrobenzenesulfonate and 2 parts of sodium carbonate.
A cotton fabric is printed with this printing paste on a roller printing machine. The printed fabric is steamed 4to 8 minutes at 100"C in saturated steam, then thoroughly rinsed in cold and hot water, in the process of which non-fixed dye can be very easily removed from the fabric, and then dried.
Claims (17)
1. A reactive dye of the formula
wherein X is sulfomethyl, cyano or carbamoyl, each of R1 and R2 independently is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, and Z is a sulfonaphthylamino group, and the benzene radical can contain further substituents in addition to the HO3S group.
2. A reactive dye according to claim 1, wherein X is sulfomethyl, cyano or carbamoyl, each of R, and
R2 independently is hydrogen or alkyl of 1 to 4 carbon atoms, and Z is a mono-, di- or trisulfonaphthylamino group.
3. A reactive dye according to claim 2 of the formula
wherein R1 is hydrogen or alkyl of 1 to 4 carbon atoms.
4. The reactive dye according to claim 3 of the formula
5. A reactive dye of formula I substantially as described with reference to any of Examples 1 to 25.
6. A process for the manufacture of a reactive dye of the formula (1) as defined in claim 1 which comprises reacting, in any order, a 6-hydroxypyridone-(2) of the formula
wherein R1, R2 and X are as defined in claim 1 and W is hydrogen or carbamoyl, a diaminobenzenesul tonic acid of the formula
2,4,6-trich loro-s-triazine of the formula
and a naphthylamine of the formula
H-Z (7) wherein Z is as defined in claim 1, by (diazotisation), coupling and condensation, to produce a reactive dye of the formula (1).
7. A process according to claim 6, wherein the starting materials are a 6-hydroxypyridone-(2) of the formula (4), wherein X is sulfomethyl, cyano or carbamoyl, each of R1 and R2 independently is hydrogen or alkyl of 1 to 4 carbon atoms, and a naphthylamine of the formula (7), wherein Z is a mono-, di- ortrisulfonaphthylamino group.
8. A process according to claim 7, which comprises reacting, in any order, a 6hydroxypyridone-(2) of the formula
wherein R1 is hydrogen or alkyl of 1 to 4 carbon atoms and W is hydrogen or carbamoyl, 1,3 diaminobenzene - 4 - sulfonic acid, 2,4, 6 - trichloro s - triazine and an aminonaphthalenesulfonic acid of the formula
by coupling and condensation, to produce a reactive dye of the formula
9.A process according to claim 8 which comprises diazotising 1 - amino - 3 - acetylamino - 6 sulfonic acid and coupling the diazo compound to 1 ethyl - 4 - methyl - 5 - carbamoyl - 6 - hydroxypyridone - (2), removing the acetyl group by saponification, condensing the resulting aminomonoazo compound with cyanuric chloride, and condensing the primary condensation product with 2 - aminonaphthalene - 6 - sulfonic acid, to produce the azo dye of the formula
10. A process for the production of a reactive dye of formula (1) substantially as described in any of the
Examples 1 to 25.
11. A reactive dye of formula (1) when produced by a process claimed in any of claims 6 to 10.
12. A method of dyeing or printing organic material wherein there is used, as dyestuff, a reactive dye as claimed in any of claims 1 to 5.
13. A method as claimed in claim 12 wherein the organic material is a cellulosic material of fibrous structure.
14. A method as claimed in claim 12 substantially as described with reference to any of Examples 26 to 30.
15. Organic material when produced bya method claimed in any of claims 12 to 14.
16. Adyeing orprinting preparation which contains a fibre-reactive azo dye as claimed in any of claims 1 to 5.
17. A dyeing or printing preparation substantially as described with reference to any of Examples 26 to 30.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH752278A CH635858A5 (en) | 1978-07-11 | 1978-07-11 | FIBER REACTIVE AZO DYES AND THEIR PRODUCTION. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2028360A true GB2028360A (en) | 1980-03-05 |
| GB2028360B GB2028360B (en) | 1983-02-02 |
Family
ID=4326455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7923812A Expired GB2028360B (en) | 1978-07-11 | 1979-07-09 | Fibre-reactive azo dyes processes for their manufacture and use thereof |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5513790A (en) |
| BE (1) | BE877594A (en) |
| CH (1) | CH635858A5 (en) |
| DE (1) | DE2927718A1 (en) |
| FR (1) | FR2430964A1 (en) |
| GB (1) | GB2028360B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504273A (en) * | 1982-08-25 | 1985-03-12 | Ciba-Geigy Corporation | Reactive dyes, process for their preparation and use thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5891767A (en) * | 1981-11-25 | 1983-05-31 | Sumitomo Chem Co Ltd | Monoazo compound and method for dyeing cellulose fiber by using the same |
| DE3542001A1 (en) * | 1985-11-28 | 1987-06-04 | Bayer Ag | REACTIVE DYES |
| CN102504579B (en) * | 2011-09-28 | 2017-03-29 | 天津德凯化工股份有限公司 | A kind of yellow reaction dyestuff and its preparation method and application |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936436A (en) * | 1969-12-22 | 1976-02-03 | Imperial Chemical Industries Limited | Water-soluble azo dyestuffs containing triazine and 3-azo-2,6-dihydroxypyrid-6-one radicals |
| GB1353474A (en) * | 1970-11-25 | 1974-05-15 | Ici Ltd | Azo dyestuffs |
| CA972353A (en) * | 1970-12-22 | 1975-08-05 | Ciba-Geigy Ag | Azo compounds, their manufacture and use |
-
1978
- 1978-07-11 CH CH752278A patent/CH635858A5/en not_active IP Right Cessation
-
1979
- 1979-07-09 FR FR7917746A patent/FR2430964A1/en active Granted
- 1979-07-09 GB GB7923812A patent/GB2028360B/en not_active Expired
- 1979-07-09 DE DE19792927718 patent/DE2927718A1/en not_active Withdrawn
- 1979-07-10 BE BE0/196215A patent/BE877594A/en unknown
- 1979-07-11 JP JP8699679A patent/JPS5513790A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504273A (en) * | 1982-08-25 | 1985-03-12 | Ciba-Geigy Corporation | Reactive dyes, process for their preparation and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2430964A1 (en) | 1980-02-08 |
| JPS5513790A (en) | 1980-01-30 |
| CH635858A5 (en) | 1983-04-29 |
| GB2028360B (en) | 1983-02-02 |
| FR2430964B1 (en) | 1983-06-10 |
| BE877594A (en) | 1980-01-10 |
| DE2927718A1 (en) | 1980-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |