GB2037795A - Fibre-reactive monoazo compounds - Google Patents
Fibre-reactive monoazo compounds Download PDFInfo
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- GB2037795A GB2037795A GB7938818A GB7938818A GB2037795A GB 2037795 A GB2037795 A GB 2037795A GB 7938818 A GB7938818 A GB 7938818A GB 7938818 A GB7938818 A GB 7938818A GB 2037795 A GB2037795 A GB 2037795A
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- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 238000004043 dyeing Methods 0.000 claims abstract description 13
- 150000003839 salts Chemical group 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 230000008878 coupling Effects 0.000 claims abstract description 9
- 238000010168 coupling process Methods 0.000 claims abstract description 9
- 238000005859 coupling reaction Methods 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims abstract description 8
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 5
- 230000003381 solubilizing effect Effects 0.000 claims abstract description 5
- 150000001448 anilines Chemical class 0.000 claims abstract description 4
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical class OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 41
- -1 monoazo compound Chemical class 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 239000000975 dye Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910006069 SO3H Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004627 regenerated cellulose Substances 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical group 0.000 description 3
- NQRLWRODNCDUHY-UHFFFAOYSA-N 6-n,6-n,2-trimethylacridine-3,6-diamine Chemical compound C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 NQRLWRODNCDUHY-UHFFFAOYSA-N 0.000 description 2
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The present invention relates to monoazo compounds having a diazo component of the sulphoaniline series and a coupling component of the aniline series, such components being free from substituents in ortho position to the azo group, the amine group of which coupling component bearing a fibre-reactive group of the 2,4,6,trihalogen-1,3,5-triazinyl series in which one halogen is replaced by an aliphatic- or aromatic carbocyclic substituted amino group which contains at least one water solubilizing group and mixtures of such compounds, which compounds or mixtures are in free acid or salt form and are useful for dyeing and printing hydroxyl-group or amino-group- containing organic substrates.
Description
SPECIFICATION
Fibre-reactive monoazo compounds
The present invention relates to fibre-reactive monoazo compounds.
More particularly, the present invention provides monoazo compounds having a diazo component of the sulpho-aniline series and a coupling component of the aniline series, such components being free from substituents in ortho position to the azo group, the amine group of the coupling component bearing a fibre-reactive group of the 2,4,6-trihalogen-1 3,5-triazinyl series in which one halogen is replaced by an aliphatic- or aromatic carbocyclic substituted amino group which contains at least one water solubilizing group and mixtures of such compounds, which compounds or mixtures are in free acid or salt form.
Preferred compounds according to the invention are those of formula I,
in which R1 is hydrogen, halogen, (C1~4)alkyl or (C1~4)alkoxy, X is hydrogen, (C14)alkyl, (C1~4)alkoxy or carboxy, each of R2 and R3 independently, is hydrogen or (C,,)-alkyl, Hal is fluorine, chlorine or bromine, and Z is an aliphatic or aromatic-carbocyclic group containing at least one water-solubilizing group, and mixtures thereof, which compounds and mixtures are in free acid or salt form.
Any halogen as R1 is fluorine, chlorine or bromine. The preferred halogens are chlorine and bromine, especially chlorine. Preferred alkyl and alkoxy groups as R1 contain 1 or 2 carbon atoms, with methyl and methoxy being most preferred.
Preferably R1 is R;, where R1 is hydrogen, methyl, methoxy or ethoxy. More preferably, RX is R' where R'1 is hydrogen, methyl or methoxy. Most preferably R1 is R,", where R1" is hydrogen or methyl, especially hydrogen.
When R1 is hydrogen the sulpho group is preferably in the 3-position to the azo group. When R1 is a substituent such is preferably ortho to the sulpho group.
Any alkoxy as X is preferaby methoxy or ethoxy, especially methoxy. Any alkyl is preferably methyl.
X is preferably X', where X' is hydrogen, methyl, methoxy, ethoxy or carboxy. More preferably X is
X", where X" is hydrogen, methoxy or ethoxy. Most preferably X is X"', where X"' is methoxy or ethoxy, with methoxy being especially preferred.
R2 is preferably Fl2,, where Fl2, is hydrogen or methyl. Most preferably R2 is hydrogen.
R3 is preferably R3, where R3 is hydrogen, methyl or ethyl. More preferably R3 is hydrogen or methyl, with hydrogen being especially preferred.
Suitable water-solubilizing groups in the group Z are carboxy and sulpho. When Z is an aromatic carbocyclic group it preferably contains at least one sulpho group.
Preferred aromatic groups as Z are phenyl groups which contain one or two substituents selected from carboxy and sulpho and are optionally further substituted by up to two substituents selected from the groups consisting of fluorine, chlorine, bromine, C,, (preferably C12)alkyl and C14 (preferably C1~2)alkoxy.
Preferred aliphatic groups as Z are (C2~4)alkyl-SO3H or (C2~4)alkyl-COOH. More preferred are such in which the alkyl groups contain 2 or 3 carbon atoms, with sulphoethyl and carboxyethyl being most preferred,
Preferably, Z is Z', where Z' is a group of formula (a)
in which R4 is hydrogen, sulpho orcarboxy, R5 is hydrogen, chlorine, methyl, ethyl, methoxy or ethoxy, or Z' is (C2~4)alkyl-SO3H or (C2~4)a I kyl-COOH .
More preferably Z is Z", where Z" is a group of formula (a). Even more preferably Z is Z"', where
Z"' is a group of formula (a) wherein R5 is hydrogen, methyl or methoxy. Yet even more preferably Z is ziv, where Ziv is a group of formula (a) wherein R5 is hydrogen or methyl. Most preferably Z is ZY, where ZV is a group of formula (a) wherein R4 is sulpho or carboxy and R5 is hydrogen or methyl, especially hydrogen, with disulphophenyl being especially preferred.
When Z is a group of formula (a) and both R4 and R5 are hydrogen the sulpho group is preferably in
the 3- or 4-position. When R4 is carboxy and R5 is hydrogen, the preferred positions are 2-carboxy-4- or
5-sulpho. When R4 is sulpho and R5 is hydrogen the sulpho groups are preferably in the 2,4-or 2,5
positions, especially the 2,5-positions.When R4 is hydrogen and R5 is other than hydrogen the preferred
positions are 2-R5- 4- or 5-sulpho especially 2-Fl5-4-sulpho. When R4 is sulpho or carboxy and R5 is
other than hydrogen the three substituents are preferably in the 2,4,5-positions, most preferably with a
carboxy or sulpho group in the 2-position.
Hal is preferably fluorine or chlorine, more preferably chlorine.
Preferred compounds of formula I are
(1) those where R2 and R3 are both hydrogen; (2) those where Z is Z'; (3) those where Z is Z", more preferably Z"', especially Zlv; (4) those where Z is Zv; (5) those of(l) where Z is Z'; (6) those of (2) where R1 is R1'; especially R1"; (7) those where X is X'; (8) those of (1) where Z is Z"; (9) those of(i) where Z isZV; (10) those of (1) to (9) where Hal is fluorine or chlorine, especially those where Hal is chlorine; (11) compounds of formula lar
in which Hal' is fluorine or chlorine, especially chlorine, especially those where R1" is hydrogen and the sulpho group is in the 3-position and where R1 is methyl the two groups are in ortho position to one another.
(12) those of (11) where R1" is hydrogen especially where the sulpho group is in the 3-position; (13) those of (11) where X' is X"; (14) those of (11) where X' is X"', especially methoxy; (15) those of (11) to (14) where Z"' is Ziv; and
(16) those of (11) to (14) where Z"' is Zv, especially disulphophenyl.
The salt form of the carboxy and sulpho groups in the compounds according to the present invention is not critical. The cation may be any one of the usual non-chromophoric cations for anionic dyestuffs. Examples of such cations are alkalimetal cations and cations of the ammonium type e.g.
sodium, lithium, potasium, ammonium, mono-, di-, tri- and tetramethylammonium, triethylammonium, mono-, di- and triethanolammonium and mono-,-di and tri-isopropylammonium. The preferred cations are sodium, lithium, potassium and ammonium, with sodium being the most preferred.
The present invention further provides a process for the preparation of monoazo compounds having a diazo component of the sulphoaniline series and a coupling component of the aniline series, the ortho positions to the azo groups of such components being free from substituents and the amino group of said coupling component bearing a fibre reactive group of the 2,4,6-trihalogen-1 ,3,5-tri-azinyi series in which one halogen is replaced with an aliphatic or aromatic carbocylic-substituted amino group which contains at least one water-solubilizing substituent comprising condensing cyanurotrihalogenide with a corresponding fibre-reactive group free monoazo dyestuff, or a mixture thereof, and with an aliphatic- or aromatic-substituted amine which contains at least one water solubilizing group, or a mixture thereof, in any desired order, and optionally converting the product to a salt form.
Thus, the process for preparing the preferred dyes of formula I comprises
condensing cyanurotrihalogenide with a compound of formula Il
and a compound of formula Ill, or a mixture thereof, HNR3Z Ill in any desired order, and optionally converting the product to the salt form.
The condensation reactions are carried out in accordance with known methods. The replacement of the halogen atoms of the cyanurotrihalogenide is preferably effected in a weakly acid to weakly alkaiine medium. The replacement of the first halogen atom is suitably effected at temperatures from 0 to 50C and the second at a higher temperature, preferably between room temperature and 650C.
Suitably an acid binding agent such as sodium carbonate, sodium bicarbonate or sodium hydroxide is employed. The isolation of the compounds according to the invention is effected in accordance with known methods, for example by salting out, filtering and drying in vacuo.
The starting materials are either known or may be prepared by known methods from available starting materials.
The compounds according to the present invention and mixtures thereof in free acid or salt form are useful as reactive dyestuffs for dyeing or printing hydroxyl-group or amino-group-containing organic substrates. Preferred substrates are leather and textiles for example those comprising or consisting of neutral or synthetic polyamides such as wool, silk and nylon and epeciallythose comprising or consisting of natural or regenerated cellulose such as cotton, viscose and spun rayon. The dyestuffs according to the invention give deep dyeings and have a good fixation yield as well as a short fixation time.
Dyeing and printing with the dyes of the invention may be carried out in accordance with known methods.
The dyeings and prints obtained exhibit notable light-fastness in conjunction with good general fastness properties such as wet-fastness, wash-fastness especially repeated washing at the boil, sweat-fastness, and fastness to chlorine and hypochlorine beach.
The dyestuffs and mixtures of the invention are suitable for combination dyeings employing dyestuffs of the same class and such combination dyeings do not exhibit catalytic fading.
The dyestuffs and mixtures of the invention form notably stable padding liquors and printing pastes and unbound dyestuff is easily washed off the substrate.
The following Examples further serve to illustrate the invention. In the Examples all parts are by weight and all temperatures are in degrees Centigrade.
EXAMPLE 1
92.3 Parts of finely-powdered 2,4,6-trichl6ro-1 ,3,5-triazine are stirred to homogeneity in 500 parts ice water. With ice cooling, a solution of 126.5 parts 1 -aminobenzene-2,5-disulphonic acid in 500 parts water and the necessary amount of a sodium hydroxide solution are added over a period of approximately 5 minutes and the whole is subsequently stirred for ca. 3 hours at 0--50C. The pH is maintained at approximately 6 by the addition of a 3N sodium carbonate solution whereupon the condensation products goes into solution.
1 53.5 Parts of 4-amino-3-methoxy-1 ,1 '-azobenzene-3'-sulphonic acid (prepared by coupling diazotized 1-a minobenzene-3-su Iphonic acid with 1 -amino-2-methoxy-benzene-N-o- methanesulphonic acid and splitting off the co-methanesulphonic acid group) are stirred in 1000 parts water and the pH is adjusted to 7 by the addition of aqueous sodium hydroxide. Approximately 75 parts sodium bicarbonate are added thereto and the mixture is added over the course of 1 5 minutes to the solution of the condensation product obtained as described above. The temperature is raised over an hour to approximately 35--400 and the whole is stirred for 3-4 hours until the reaction is complete.
The dyestuff is salted out by the addition of sodium chloride, filtered and dried in vacuo at 1000.
The dyestuff which corresponds to the formula
gives wool and regenerated cellulose dyeings of a slightly greenish yellow shade having good light- and wash-fastness.
In the following Table further dyestuffs are given which are prepared in analogy with the procedure described in Example 1 and owing to the isolation step are obtained in the sodium salt form.
However, they may also be isolated in the free acid form employing conventional methods. In the table the symbol y denotes the dyeshade on cotton where a is yellow and b is reddish yellow. The dyestuffs correspond to the general formula
TABLE 1
g Example No. D X R2 Hal R3 Z y 2 3-sulphophenyl OCH3 H F H 2,5-disulphophenyl a 3 do. H H Cl H do. a 4 do. OC2H5 H Cl H do. a 5 do. CH3 H Cl H do. a 6 4-sulphophenyl OCH3 H Cl H do. b 7 do. do. H F H do. b 8 do. H H Cl H do. b 9 do. OC2Hs H CI H do. b 10 3-sulphophenyl OCH3 H Cl H 2,5-disulpho-4- a methylphenyl 11 do. OC2H5 H Cl H do. a 12 4-sulphophenyl OCH3 H Cl H do. b 13 do. do. H Cl H 4-suiphophenyl b 14 3-su I phopheny I do. H CI H 2-carboxy-4- a sulphophenyl 15 do. do. H CI H -CH2CH2SO3Na a 16 do. do. H Cl CH3 do. a 17 do. do. H F H do.- a 18 do. do. CH3 Cl H 2,5-disulphophenyl a 19 4-methoxy-3- H H Cl H do. b sulphophenyl 20 4-ethoxy-3- H H Cl H do.- b sulphophenyl 21 3-methyl-4- OCH3 H CI H do. b sulphophenyl 22 do. OC2H5 H Cl H do. b 23 3-methoxy-4- H H Cl H do. b su I phophenyl 24 do. OCH3 H Cl H do. b 25 4-suiphophenyl COONa H Cl H 4-sulphophenyl b 26 do. do. H F H do. b 27 do. do. H Cl H 3-sulphophenyl b TABLE 1 (Continued)
Example No. D X R2 Hal R3 Z y 28 4-sulphophenyl COONa H Cl H 2-methyl-4-sulpho- b phenyl 29 3,sulphophenyl do. H Cl H do. a 30 do. do. H Cl H 2-carboxy-Ssulpho- a phenyl 31 4-sulphophenyl do. H Cl H do. b 32 do. do. H Cl H 2-carboxy-5-sulpho- b phenyl 33 do. do. H Cl H 2,5-disuiphophenyl b 34 3-sulphophenyl do. H Cl H do. a 35 do. do. H F H do. a EXAMPLE A
2 Parts of the dye of Example 1 are dissolved in 100 parts warm water (ca. 400) to which 10 parts urea have been added. 30 Parts 10% sodium hydroxide and 0.5 parts sodium salt of 1-nitrobenzene-3sulphonic acid are added thereto. Spun rayon fabric is impregnated with this solution (take-up 75% of dry weight). After drying, the fabric is steamed for 5 to 10 minutes at 1 020, rinsed and soaped at the boil for 1 5 minutes After drying, a neutral yellow dyeing with good light- and wet-fastness is obtained.
EXAMPLE B
2 Parts of the dyestuff of Example 6 are dissolved in 50 parts water and 20 parts urea at 200.
After the addition of 15 parts 10% sodium carbonate the solution is made up to 100 parts by volume.
The solution is padded onto 20 parts cotton fabric (take-up 80% of the dry weight) After intermediate drying the fabric is steamed at 1030 for 10 minutes, rinsed, soaped at the boil, rinsed again and dried. A reddish-yellow dyeing with good fastnesses is obtained.
EXAMPLE C
Mercurised cotton satin is printed in accordance with known methods with a printing paste containing: 25 parts dye of Example 1
100 parts urea 440 parts water 400 parts 4% sodium alginate
10 parts sodium salt of 1 -nitrobenzene-3-sulphonate
25 parts sodium bicarbonate.
The printed textile is steamed for 48 minutes at 1 02--1 040 C and then cold- and hot-rinsed.
After hot-soaping followed by rinsing and drying, a neutral yellow print with good light- and wetfastness is obtained.
The dyestuffs of Example 2 to 5 and 7 to 35 may be employed for dyeing or printing in analogy with the procedure described in the above Examples A to C.
Claims (28)
1. A monoazo compound having a diazo component of the sulphoaniline series and a coupling component of the aniline series, such components being free from substituents in ortho position to the azo group, the amine group of the coupling component bearing a fibre-reactive group of the 2,4,6,trihalogen-1 ,3,5-triazinyl series in which one halogen is replaced by an aliphatic- or aromatic carbocyclic substituted amino group which contains at least one water solubilizing group, or a mixture thereof, which compound or mixture is in free acid or salt form.
2. A compound or mixture according to Claim 1, in which the monoazo compound is of formula I,
in which R1 is hydrogen, halogen, (C,~4)alkyl or (C14)alkoxy, X is hydrogen, (C,~4)alkyl, (C1-4)alkoxy or carboxy, each of R2 and R3 independently, is hydrogen or (C1-4)-alkyl,
Hal is fluorine, chlorine or bromine, and Z is an aliphatic or aromatic-carbocyclic group containing at least one water-solubilizing group.
3. A compound or mixture according to Claim 2, in which Z is Z', where Z' is a group of formula (a)
in which R4 is hydrogen, sulpho or carboxy, R5 is hydrogen, chlorine, methyl, ethyl, methoxy or ethoxy, or
Z' is (C2~4)alkyl-SO3H or (C2~4)alkyl-COOH.
4. A compound or mixture according to Claim 2 or Claim 3, in which R, is R1', where R1' is hydrogen, methyl, methoxy or ethoxy.
5. A compound or mixture according to Claim 4, in which R, is R'1', where R't is hydrogen, methyl or methoxy.
6. A compound or mixture according to Claim 5, in which R, is RIN, where Rt" is hydrogen or methyl.
7. A compound or mixture according to any one of Claims 2 to 6, in which R2 and R3 are both hydrogen.
8. A compound or mixture according to any one of Claims 2 to 7, in which Z is Z", where Z" is a group of formula (a).
9. A compound or mixture according to any one of Claims 2 to 8, in which Z is Z"', where Z"' is a group offormula (a) wherein R5 is hydrogen, methyl or methoxy.
10. A compound or mixture according to any one of Claims 2 to 9, in which X is X', where X' is hydrogen, methyl, methoxy, ethoxy or carboxy.
11. A compound or mixture according to any one of Claims 2 to 10, in which Z is zv, where zlv is group of formula (a) wherein R5 is hydrogen or methyl.
12. A compound or mixture according to any one of Claims 2 to 11, in which Z is ZV, where ZV is a group of formula (a) wherein R4 is sulpho or carboxy and R5 is hydrogen or methyl.
13, A compound or mixture according to any one of Claims 2 to 12, in which Hal is Hal' where Hal' is fluorine or chlorine.
14. A compound or mixture according to anyone of Claims 2 to 13, of formula l
and where R1" is hydrogen the sulpho group is in the 3-position and where R1" is methyl, the two groups are in ortho position to one another.
1 5. A compound or mixture according to any one of Claims 2 to 4, in which X is X", where X" is hydrogen, methoxy or ethoxy.
16. A compound or mixture according to any one of Claims 2 to 1 5, in which X is X"', where X"' is methoxy or ethoxy.
17. A compound or mixture according to any one of Claims 2 to 16, in which Z is disulphophenyl.
18. A compound of formula
or a salt thereof.
19. A compound of formula
or a salt thereof.
20. A compound of formula
or a salt thereof.
21. A compound offormula
or a salt thereof
22. A process'for the production of a monoazo compound as claimed in Claim 1, or a mixture thereof, comprising condensing cyanurotrihalogenide with a corresponding fibre-reactive freecontaining monoazo dyestuff, or a mixture thereof, and with an aliphatic- or aromatic-substituted amine which contains at least one water solubilizing group or a mixture thereof, in any desired order, and optionally converting the product to a salt form.
23. A process for the production of a monoazo dye as claimed in Claim 1, substantially as
hereinbefore described with reference to any one of Examples 1 to 35.
24. A monoazo dye or mixture thereof, whenever prepared by a process according to Claim 22 or 'Claim 23.
25. A process for dyeing or printing hydroxyl-group or amino-group containing organic substrates
comprising applying a compound or mixture according to any one of Claims 1 to 21 or 24, thereto.
26. A process according to Claim 25, in which the substrate consists of or comprises natural or
synthetic polyamides or natural or regenerated cellulose.
27. A process for dyeing or printing hydroxy-group or amino-group containing organic substrates
substantially as hereinbefore described with reference to any one of Examples A to C.
28. Dyed or printed substrates whenever obtained by a process according to any one of Claims 25
to 27.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1173678A CH640876A5 (en) | 1978-11-15 | 1978-11-15 | MONOAZO COMPOUNDS WITH FIBER REACTIVE REMAIN, METHOD FOR THE PRODUCTION AND USE. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2037795A true GB2037795A (en) | 1980-07-16 |
| GB2037795B GB2037795B (en) | 1982-12-22 |
Family
ID=4376408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7938818A Expired GB2037795B (en) | 1978-11-15 | 1979-11-09 | Fibre-reactive monoazo compounds |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5925825B2 (en) |
| BR (1) | BR7907401A (en) |
| CH (1) | CH640876A5 (en) |
| DE (1) | DE2944624A1 (en) |
| ES (1) | ES485965A0 (en) |
| FR (1) | FR2441645A1 (en) |
| GB (1) | GB2037795B (en) |
| HK (1) | HK98385A (en) |
| IT (1) | IT1126823B (en) |
| KE (1) | KE3575A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2945058A1 (en) * | 1979-11-08 | 1981-06-04 | Bayer Ag, 5090 Leverkusen | FIBER REACTIVE MONOAZO DYES, THEIR PRODUCTION AND USE |
| JPS57183478A (en) * | 1981-05-06 | 1982-11-11 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
| DE3045789A1 (en) * | 1980-12-04 | 1982-07-22 | Bayer Ag, 5090 Leverkusen | FIBER ACTIVE AZO DYES, METHOD FOR THEIR PRODUCTION AND THEIR USE FOR COLORING AND PRINTING FIBER MATERIALS CONTAINING HYDROXYL GROUPS AND / OR NITROGEN |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2945022A (en) * | 1956-09-14 | 1960-07-12 | Ciba Ltd | Monoazo and disazo triazine dyes |
| US3565882A (en) * | 1967-12-18 | 1971-02-23 | Gaf Corp | Halotriazinylmonoazo dyestuffs |
| US3708259A (en) * | 1967-12-18 | 1973-01-02 | Gaf Corp | Method for dyeing polyamide fibers with halotriazinylmonoazo dyestuffs |
| AU497288B2 (en) * | 1975-04-15 | 1978-12-07 | Imperial Chemical Industries Limited | Dyestuffs |
| DE2840380C2 (en) * | 1978-09-16 | 1985-05-30 | Bayer Ag, 5090 Leverkusen | Fiber-reactive azo dyes |
-
1978
- 1978-11-15 CH CH1173678A patent/CH640876A5/en not_active IP Right Cessation
-
1979
- 1979-11-05 DE DE19792944624 patent/DE2944624A1/en active Granted
- 1979-11-06 IT IT50754/79A patent/IT1126823B/en active
- 1979-11-09 GB GB7938818A patent/GB2037795B/en not_active Expired
- 1979-11-12 FR FR7927804A patent/FR2441645A1/en active Granted
- 1979-11-13 JP JP54146139A patent/JPS5925825B2/en not_active Expired
- 1979-11-14 BR BR7907401A patent/BR7907401A/en unknown
- 1979-11-14 ES ES485965A patent/ES485965A0/en active Granted
-
1985
- 1985-10-30 KE KE3575A patent/KE3575A/en unknown
- 1985-12-05 HK HK983/85A patent/HK98385A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8100330A1 (en) | 1980-11-01 |
| FR2441645B1 (en) | 1983-05-20 |
| IT7950754A0 (en) | 1979-11-06 |
| ES485965A0 (en) | 1980-11-01 |
| JPS5580465A (en) | 1980-06-17 |
| BR7907401A (en) | 1980-10-07 |
| IT1126823B (en) | 1986-05-21 |
| JPS5925825B2 (en) | 1984-06-21 |
| HK98385A (en) | 1985-12-13 |
| DE2944624A1 (en) | 1980-05-29 |
| GB2037795B (en) | 1982-12-22 |
| KE3575A (en) | 1985-11-22 |
| DE2944624C2 (en) | 1987-07-02 |
| FR2441645A1 (en) | 1980-06-13 |
| CH640876A5 (en) | 1984-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |