GB2030168A - Azo reactive dyestuffs - Google Patents
Azo reactive dyestuffs Download PDFInfo
- Publication number
- GB2030168A GB2030168A GB7930437A GB7930437A GB2030168A GB 2030168 A GB2030168 A GB 2030168A GB 7930437 A GB7930437 A GB 7930437A GB 7930437 A GB7930437 A GB 7930437A GB 2030168 A GB2030168 A GB 2030168A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyestuff
- denotes
- sulpho
- general formula
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 4-sulphophenylazo Chemical group 0.000 claims abstract description 25
- 238000004043 dyeing Methods 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000003368 amide group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 239000000975 dye Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 12
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000006482 condensation reaction Methods 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000835 fiber Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical group 0.000 abstract description 4
- 229910006069 SO3H Inorganic materials 0.000 abstract 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 31
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 12
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 8
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 4
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 241000219422 Urtica Species 0.000 description 2
- 235000009108 Urtica dioica Nutrition 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000005406 washing Methods 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
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- JJXVFBWXSFQBLA-UHFFFAOYSA-N 2-acetamido-5-aminobenzene-1,4-disulfonic acid Chemical compound CC(=O)NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O JJXVFBWXSFQBLA-UHFFFAOYSA-N 0.000 description 1
- DCYBHNIOTZBCFS-UHFFFAOYSA-N 2-amino-5-[(4-sulfophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 DCYBHNIOTZBCFS-UHFFFAOYSA-N 0.000 description 1
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 1
- KTFUNVBAGAPLLC-UHFFFAOYSA-N 2-amino-5-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=C(N)C(S(O)(=O)=O)=C1 KTFUNVBAGAPLLC-UHFFFAOYSA-N 0.000 description 1
- CAFUHBWYTBNBEY-UHFFFAOYSA-N 2-amino-5-ethylbenzenesulfonic acid Chemical compound CCC1=CC=C(N)C(S(O)(=O)=O)=C1 CAFUHBWYTBNBEY-UHFFFAOYSA-N 0.000 description 1
- YYRVBCBZQPTVEO-UHFFFAOYSA-N 2-amino-5-methylbenzene-1,4-disulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O YYRVBCBZQPTVEO-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- CDZWHCZLBLCDFR-UHFFFAOYSA-N 3-methoxybenzenesulfonic acid Chemical compound COC1=CC=CC(S(O)(=O)=O)=C1 CDZWHCZLBLCDFR-UHFFFAOYSA-N 0.000 description 1
- LEPWEWNWYDOBKQ-UHFFFAOYSA-N 4-(3-amino-2,6-difluoro-2H-1,3,5-triazin-4-yl)benzenesulfonic acid Chemical compound NN1C(F)N=C(F)N=C1C1=CC=C(S(O)(=O)=O)C=C1 LEPWEWNWYDOBKQ-UHFFFAOYSA-N 0.000 description 1
- MPRNZGSLMIZZRE-UHFFFAOYSA-N 4-amino-3-sulfobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1S(O)(=O)=O MPRNZGSLMIZZRE-UHFFFAOYSA-N 0.000 description 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- JFXDIXYFXDOZIT-UHFFFAOYSA-N 4-methoxy-n-methylaniline Chemical compound CNC1=CC=C(OC)C=C1 JFXDIXYFXDOZIT-UHFFFAOYSA-N 0.000 description 1
- MLNFMFAMNBGAQT-UHFFFAOYSA-N 4-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=C(N)C=C1 MLNFMFAMNBGAQT-UHFFFAOYSA-N 0.000 description 1
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 1
- WFYPPSFMLNZNRB-UHFFFAOYSA-N 6,6-diaminocyclohexa-2,4-diene-1-sulfonic acid Chemical compound NC1(N)C=CC=CC1S(O)(=O)=O WFYPPSFMLNZNRB-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- XIKDGQPYAJHKKY-UHFFFAOYSA-N C1=CC=CC=C1.S(=O)(=O)(O)C1=CC=C(C2=CC(=CC=C12)N)C Chemical compound C1=CC=CC=C1.S(=O)(=O)(O)C1=CC=C(C2=CC(=CC=C12)N)C XIKDGQPYAJHKKY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CWDDWYDRCDWCBW-UHFFFAOYSA-N NC1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C Chemical compound NC1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C CWDDWYDRCDWCBW-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- OKPVJLADHVDOQW-UHFFFAOYSA-N benzenesulfonic acid naphthalen-2-amine Chemical compound OS(=O)(=O)C1=CC=CC=C1.C1=CC=CC2=CC(N)=CC=C21 OKPVJLADHVDOQW-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- QCIFLGSATTWUQJ-UHFFFAOYSA-N n,4-dimethylaniline Chemical compound CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- IJNQJQRKLLCLMC-UHFFFAOYSA-N n-methylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NC)=CC=C21 IJNQJQRKLLCLMC-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 210000002268 wool Anatomy 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
Dyestuffs for use for dyeing and printing materials containing hydroxyl and amide groups have the formula <IMAGE> wherein D is a radical of the formula <IMAGE> in which R2 is halogen, alkyl (C1-4), alkoxy (C1-4), -SO3H, -COOH, acylamino or 4-sulphophenylazo or D is a radical of the formula <IMAGE> in which R3 is H, alkyl (C1-4) or acylamino, R is hydrogen or methyl, X is H, halogen, alkyl (C1-4), alkoxy (C1-4), -SO3H, -COOH or acylamino, and R is hydrogen, methyl or ethyl.i
Description
SPECIFICATION
Fibre-reactive azo dyestuffs
wherein
wherein
R2 represents halogen, such as fluorine, chlorine or bromine, C1-C4-alkyl, C1-C4-alkoxy or a sulpho, carboxyl, acylamino or 4-sulphophenylazo group, or
wherein
R3 represents hydrogen, C,-C4-alkyl or an acylamino group.
R = hydrogen, methyl or ethyl,
R1 = hydrogen or methyl and
X = hydrogen, C1-C4-alkyl, C1-C4-alkoxy, halogen, such as fluorine, chlorine or bromine, a carboxyl or sulpho group or an acylamino group (in particular acetyl-, formyl-, oxalylamino- or ureido).
Examples of amines of the formula
D-NH2
(II) are the following: -amino-2-sulpho-4-methylbenzene, 1-amino-2-sulpho-4-ethylbenzene, 1-amino-2- sulpho-4-chloro-benzene, 1 -amino-2-sulpho-4-methoxy-benzene, 1 -amino-2-sulpho-4-ethoxy-benzene, 1amino-2-sulpho-4-carboxy-benzene, 1-amino-2,4-disulpho-benzene, 1-amino-2-sulpho-4-(4'sulphophenylazo)-benzene, 1-amino-2-sulpho-4-acetylamino-benzene, 1-amino-2,5-disulpho-benzene, 1amino-2,5-disulpho-4-methyl-benzene and 1-amino-2,5-disulpho-4-acetylamino-benzene.
Preferred dyestuffs correspond to the
formulae so3H formulae 5o5H OH H035 N oSN/ > s (III) ff wherein
X and R1 have the meaning indicated above and R4 = chlorine, methyl, methoxy, ethoxy, sulpho, carboxyl, acetylamino or 4-sulphophenylazo. and
wherein R1 and X have the meaning indicated above and P5 = hydrogen, methyl or acetylamino.
Dyestuffs of the formulae Ill and IV in which
R1 = hydrogen, and dyestuffs of the formulae Ill and IV in which
Xand R1 = hydrogen, are also preferred.
The invention furthermore relates to a process for the preparation of the compounds of the formula (I). It consists of a procedure in which dyestuffs of the formula wherein
D and R has the meaning indicated above, are subjected to condensation reactions with 2,4,6-trifluoro-1 ,3,5-triazine, hydrofluoric acid being split off, and the resulting difluoro compounds are reacted with an amine of the formula
hydrofluoric acid being split off, to give (I).
The condensation of the dyestuffs (V) with s-trifluorotriazine is preferably carried out in aqueous solution or suspension, at low temperature and at a weakly acid, neutral to weakly alkaline pH value.
The condensation reaction is advantageously carried out in the pH range of 3-5. The hydrogen fluoride liberated is buffered by adding aqueous alkali metal hydroxides, carbonates or bicyrbonates. The reaction of the difluoro compound with the amines (VI) is likewise preferably carried out in aqueous solution or suspension, at low temperature and at a weakly acid to neutral to weakly alkaline pH value. The hydrogen fluoride liberated during the condensation reaction is neutralised by adding aqueous alkali metal hydroxides, carbonates or bicarbonates. In general, isolation of the difluoro compound is dispensed with.
The dyestuffs (V) are obtained by coupling the diazotised amines (11) with I-acid under such conditions that the coupling preferably takes place in the o-position relative to the hydroxyl group of the I-acid. However, coupling with a N-acylated I-acid is in general preferred, the acyl radical subsequently being split off by warming in an acid or alkaline medium. Possible acyl radicals are, in particular, acetyl, carbamoyl, methoxycarbonyl, ethoxy-carbonyl or -CO-(l-acid urea by reaction with phosgene).
Examples of amines (VI) are the following: aniline, N-methyl-aniline, 4-methyl-aniline, 4-iso-propyl-aniline, 4-ethylaniline, 4-chloroaniline, 4-suipho-aniline, 4-carboxy-aniline, 4-acetylamino-aniline, 4-methoxyaniline, 4-ethoxy-aniline, 4-iso-propoxy-aniline, N-methyl-4-methyl-aniline and N-methyl-4-methoxy-aniline.
In the case where X = sulpho or carboxyl, the dyestuffs (I) can also be prepared by a process in which p-sulphanilic acid or 4-carboxy-aniline is first reacted with s-trifluorotriazine and the condensation with the dyestuff (V) is then carried out.
Afurther possibility for the preparation of (I) is a process in which diazotised amines (II) are combined with coupling components oftheformula
OH (VIZ) " HIYINNHX above, Ir wherein
X and R have the meaning indicated in a weakly acid, neutral to weakly alkaline range.
The new dyestuffs are suitable for dyeing and printing materials containing hydr6xyl groups or amide groups, such as textile fibres-, filaments and fabrics of wool, silk or synthetic polyamide, and polyurethane fibres, and for dyeing and printing natural or regenerated cellulose in dyeings and prints which are fast to washing, the treatment of cellulose materials appropriately being carried out, by the processes disclosed for reactive dyestuffs, in the presence of acid-binding agents and if appropriate by the action of heat.
The formulae indicated for the dyestuffs are those of the corresponding free acids. In general, the dyestuffs were isolated and employed for dyeing in the form of the alkali metal salts, in particular the Na salts.
Example 1
50.3 g of the aminoazo dyestuff2,5-disulpho-benzene < 1 azo 2 > 1-hydroxy-3-sulpho-6-aminonaphthalene are dissolved in a mixture of 300 ml of water and 200 g of ice. 13.5 g of 2,4,6-trifluorotriazine are then added dropwise and the pH value is kept between 3.5 and 4.5 by simultaneously adding dilute sodium hydroxide solution. When the condensation reaction has ended, 9.3 g of aniline are added to the clear solution and the pH is kept between 5 and 6 with dilute sodium hydroxide solution. During the second condensation stage, the temperature is between 0 and 10 . After the end of the acylation has been confirmed by a thin layer chromatogram, the dyestuff is salted out with sodium chloride, filtered off, dried and ground.
An orange-coloured dyestuff powder which dissolves readily in water is obtained. The dyestuff corresponds to the formula
The dyestuff used as the starting material is obtained by diazotising 1-amino-2,5-disulpho-benzene, coupling the diazotisation product with N-acetyl-l-acid, subsequently saponifying the acetyl group with dilute sodium hydroxide solution at 80-90 and isolating the product by salting out in a weakly alkaline range.
Dyeing Examples
Printing Instructions
When cotton nettle is printed with a printing paste which contains, per kilogram, 20 g of the dyestuff prepared according to Example 1, 100 g of urea, 300 ml of water, 500 g of alginate thickener (60 g of sodium alginate/kg of thickener) and 10 g of sodium carbonate and which has been made up to 1 kg with water, and the cotton nettle is dried, steamed at 103"C for 1 minute, rinsed with hot water and soaped at the boil, a clear orange-coloured print of good fastness to wet processing and light is obtained.
Padding Instructions
30 parts of the dyestuff prepared according to Example 1 are dissolved in 1,000 parts of water. A cotton fabric is padded with this solution and pressed off to a weight decrease of 90%. The still moist cotton is treated for 30 minutes at 700 in a bath which contains 300 parts of calcined sodium sulphate and 10 parts of calcined sodium carbonate dissolved in 1,000 parts of water. The dyeing is then finished in the customary manner. A briiliant orange dyeing with outstanding fastness to wet processing and light is obtained.
Dyeing instructions 168 my of water of 20-25" are initially introduced into a dyeing beaker which has a capacity of 300 ml and is in a water bath which can be heated.0.3 of the dyestuff obtained according to Example 1 is mixed thoroughly with 2 ml of cold water to form a paste and 30 ml of hot water (700) are added; the dyestuff thereby dissolves. The dyestuff solution is added to the initially introduced water and 10 g of cotton yarn are kept continuously in motion in this dye liquor. The temperature of the dye liquor is increased to 40-50" in the course of 10 minutes, 10g of anhydrous sodium sulphate are added and dyeing is continued for 30 minutes.
4 g of anhydrous sodium carbonate are then added to the dye liquor and dyeing is carried out at 40-50" for 60 minutes. The dyed material is then taken out of the dye liquor, the adhering liquor is removed by wringing out or pressing off and the material is rinsed first with cold water and then with hot water until the rinsing liquor is no longer stained. The dyed material is then soaped at the boiling point for 20 minutes in 200 ml of a liquor which contains 0.2 g of a sodium alkyl-sulphate, rinsed again and dried at 60-70" in a drying cabinet. A brilliant orange dyeing of good fastness to washing and light is obtained.
If the procedure followed is as according to the statements of Example 1, but instead of the aminoazo dyestuff used in that example compounds which are obtainable by diazotisation of the diazo components listed in column 1, coupling of the diazotisation products with the acetyl compounds of the coupling components mentioned in column 2 and saponification of the acetyl group are employed, and instead of aniline one of the amines described in column 3 is used, equally valuable dyestuffs which dye cotton in one of the shades listed in column 4 by one of the dyeing processes mentioned result.
Example Column 1 Column2 Column 3 Column4 2 1-Amino-2,5-di- 1-Hydroxy-3-sulpho- N-Methylaniline Orange sulpho-benzene 6-amino-naphthalene 3 " " p-Toluidine " 4 " " p-Chloroaniline " 5 " " p-Anisidine " 6 " " p-Phenetidine " 7 1-Amino-2,4-di- " Aniline " sulpho-benzne 8 " " N-Methylaniline " 9 " " p-Toluidine " 10 " " p-Chloroaniline " 11 " " p-Anisidine " 12 " " p-Phenetidine " 13 1-Amino-2-sulpho- " Aniline " 4-carboxy-benzene 14 " " N-Methylaniline " 15 " " p-Toluidine " 16 1-Amino-2,5-disul- " Aniline " pho-4-methyl-benzene 17 " " N-Methylaniline " 18 " " p-Toluidine " 19 1-Amino-2,5-di- 1-Hydroxy-3-sulpho- p-Chloroaniline Orange sulpho-4-methyl- 6-amino-naphthalene benzene 20 " " p-Anisidine " 21 1-Amino-2,5-di- " Aniline Scarlet sulpho-4-acetylamino-benzne 22 1-Amino-2-sulpho- " p-Sulphanilic acid " 4-methoxy-benzne 23 " " " " Example Column 1 Column 2 Column 3 Column 4 24 " "4-Carboxy-aniline " 25 " " p-Anisidine " 26 " " p-Phenetidine O 27 1-Amino-2-sulpho- " Aniline Orange benzne 28 " " N-Methylaniline " 29 " " p-Sulphanilic acid " 30 " " 4-Carboxy-aniline " 31 " " p-Anisidine " 32 1-Amino-2-sulpho- " ANILINE " -METHYL-BENZENE 3/83/8 " " N-Methylaniline Reddish-tinged orange 34 1-Amino-2-sulpho- 1-Hydroxy-3-sulpho-6- p-Anisidine Reddish-tinged 4-methyl-benzene amino-naphthalene orange 35 " " p-Sulphanilic acid " 36 " " 4-Carboxy-aniline " 37 1-Amino-2-sulpho- " Aniline Orange 4-chloro-benzne 38 " " N-Methylaniline " 39 " " p-Anisidine " 40 " " p-Sulphanilic acid " 41 " " 4-Carboxy-aniline " 42 1-Amino-2-sulpho- " Aniline Scarlet 4-acetylaminobenzne 43 " " N-Methylaniline " 44 " " p-Sulphanilic acid " 45 " " 4-Carboxy-aniline " 46 " 1-Hydroxy-3-sulpho- Aniline " 6-methylaminonaphthalene 47 " " N-Methylaniline " 48 " " 4-Carboxy-aniline " 49 " " 4-Sulpho-aniline " Example Column 1 Column 2 Column 3 Column 4 50 1-Amino-2-sulpho- 1-Hydroxy-3-sulpho- Aniline Scarlet (4'-sulpho- 6-methylamino phenylamino)-ben- naphthalene zene 51 " " N-Methylaniline " 52 " " p-Toluidine " 53 " " p-Chloroaniline " 54 " 1-Hydroxy-3-sulpho Aniline " 6-amino-naphthalene 55 " " p-Toluidine " 56 " " p-Sulphanilic acid " 57 1-Amino-2-sulpho- Aniline " 4-methoxy-benzene 58 " " N-Methylaniline " 59 " " p-Sulphanilic acid " 60 " " 4-Carboxy-aniline " 61 " " p-Anisidine " 62 " " p-Toluidine " 63 1-Amino-2-sulpho- " Aniline " 4-ethoxy-benzne 64 " " p-Sulphanilic acid " 65 " " 4-Carboxy-aniline " 66 " " N-Methylaniline " Example 67
45.3 g of the dyestuff 2-sulpho-4-methoxy-benzene < 1 azo 2 > 1 -hydroxy-3-sulpho-6-amino-naphthalene are stirred in a mixture of 400 ml of water and 100 g of ice. An ice-cold solution of 28.8 g of 2,4-difluoro-6-(4'-sulphophenyl)-amino-1,3,5triazine is then added and a pH of 5-6 is maintained during the condensation reaction by adding dilute sodium carbonate solution. The temperature is 5-10". When the acylation reaction has ended, the dyestuff is salted out, filtered off, dried and ground. The dyestuff is identical to the product prepared according to Example 59.
Example 68
An aqueous suspension of the diazo compound which is obtained from 20.3 g of 1-amino-2-sulpho-4methoxy-benzene is added in portions to a solution of 50.7 g of the secondary condensation product of 1 mol each of p-sulphanilic acid, 1-hydroxy-3-sulpho-6-amino-naphthalene and 2,4,6-trifluorotriazine in 600 ml of water, and during this addition a pH of 5-6 is maintained by simultaneously adding dilute sodium carbonate solution. When the coupling reaction has ended, the dyestuff is salted out, filtered off, dried and ground. The dyestuff is identical to the product prepared according to Example 59.
The dyestuff of Example 60 is likewise obtained when the procedure followed is as according to the statements of Example 67 or 68 but the starting materials used are products which, instead of the p-sulphanilic acid used in that example, employs an equivalent amount of4-carboxy-aniline.
Claims (1)
1. Adyestsuffofthe general formula
in which D denotes a radical of the general formula
in which
R2 denotes a halogen atom or a C1 to C4 alkyl,
C1 to C4 alkoxy, sulpho, carboxyl, acylamino or
4-sulphophenylazo group, or
D denotes a radical of the general formula in which
R3 denotes a hydrogen atom or a C1 to C4 alkyl
or acylamino group,
R1 denotes a hydrogen atom or a methyl group,
X denotes a hydrogen or halogen atom or a C1
to C4 alkyl, C1 to C4 alkoxy, sulpho, carboxyl
or acylamino group, and
R denotes a hydrogen atom or a methyl or ethyl group.
3. A dyestuff according to claim 1 of the general formula
in which
X and R1 have the same meanings as in claim 1 and
R4 denotes a chlorine atom or a methyl, methoxy, ethoxy, sulpho, carboxyl, acetylamino or 4-sulpho phenylazo group.
4. A dyestuff according to claim 1 of the general formula
in which
X and R1 have the same meanings as in claim 1 and
R5 denotes a hydrogen atom or a methyl or acety-amino group.
5. A dyestuff according to claim 3 or 4, in which R1 denotes a hydrogen atom.
6. A dyestuff according to claim 3 or 4 in which
R1 and X denotes hydrogen atoms
7. A dyestuff according to claim 1 as herein before specifically identified.
8. A process for the production of a dyestuff as claimed in claim 1, in which a dyestuff of the general formula
in which D and R have the same meanings as in claim 1, is reacted with 2,4,6-trifluorotriazine, 1 mol of hydrofluoric acid being split off, and the resulting difluoro compound is subjected to a condensation reaction with an amine of the general formula
in which X and R1 have the same meanings as in claim 1, 1 mol of hydrofluoric acid being split off.
9. A process for the production of a dyestuff as claimed in claim 1, in which an amine of the general formula D-NH2 (II) in which D has the same meaning as in claim 1, is diazotised and coupled with a coupling component of the general formula.
in which X and R have the same meanings as in claim 1, in a weakly acid, neutral to weakly alkaline range
10. A process for the production of a dyestuff as claimed in claim 1 when carried out substantially as described in any one of the Examples.
11. A dyestuff as claimed in claim 1 when produced by the process of any of claims 8 to 10.
12. A process for dyeing or printing a fibre material containing hydroxyl groups or amide groups comprising treating the material with a dyestuff as claimed in any of claims 1 to 7 and 11.
13. A process according to claim 12 when carried out substantially as described in the "Printing
Instructions", "Padding Instructions" or "Dyeing Instructions" of Example 1.
14. A fibre material containing hydroxyl groups or amide groups when dyed or printed by the process of claim 12 or 13.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782838616 DE2838616A1 (en) | 1978-09-05 | 1978-09-05 | FIBER REACTIVE AZO DYES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2030168A true GB2030168A (en) | 1980-04-02 |
| GB2030168B GB2030168B (en) | 1982-11-10 |
Family
ID=6048690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7930437A Expired GB2030168B (en) | 1978-09-05 | 1979-09-03 | Azo reactive dyestuffs |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5536290A (en) |
| DE (1) | DE2838616A1 (en) |
| FR (1) | FR2435510A1 (en) |
| GB (1) | GB2030168B (en) |
| IT (1) | IT7925446A0 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074557A2 (en) * | 1981-09-10 | 1983-03-23 | Bayer Ag | Reactive azo dyestuffs |
| GB2128200A (en) * | 1982-09-17 | 1984-04-26 | Sandoz Ltd | Chloro-triazinyl mondazo compounds |
| EP0426618A1 (en) * | 1989-11-01 | 1991-05-08 | Ciba-Geigy Ag | Reactive dyes, their preparation and their use |
| US5268457A (en) * | 1990-09-25 | 1993-12-07 | Ciba-Geigy Corporation | Reactive dyes containing a chloro or fluorotriazine group |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1101657B (en) * | 1956-09-14 | 1961-03-09 | Ciba Geigy | Process for the preparation of metal-free monoazo dyes |
| CH350390A (en) * | 1956-09-14 | 1960-11-30 | Ciba Geigy | Process for the production of new azo dyes |
| CH364059A (en) * | 1957-06-07 | 1962-08-31 | Ciba Geigy | Process for the production of new azo dyes |
| DE1113050B (en) * | 1958-03-26 | 1961-08-24 | Ici Ltd | Process for the preparation of monoazo dyes |
| GB859989A (en) * | 1958-03-26 | 1961-01-25 | Ici Ltd | New monoazo triazine dyestuffs |
| DE1544542A1 (en) * | 1965-09-13 | 1970-04-02 | Bayer Ag | Reactive dyes and processes for their preparation |
| DE1644208C3 (en) * | 1967-04-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Reactive dyes |
| CH626650A5 (en) * | 1974-12-18 | 1981-11-30 | Ciba Geigy Ag |
-
1978
- 1978-09-05 DE DE19782838616 patent/DE2838616A1/en not_active Withdrawn
-
1979
- 1979-09-03 JP JP11181579A patent/JPS5536290A/en active Pending
- 1979-09-03 IT IT7925446A patent/IT7925446A0/en unknown
- 1979-09-03 GB GB7930437A patent/GB2030168B/en not_active Expired
- 1979-09-04 FR FR7922097A patent/FR2435510A1/en active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074557A2 (en) * | 1981-09-10 | 1983-03-23 | Bayer Ag | Reactive azo dyestuffs |
| EP0074557A3 (en) * | 1981-09-10 | 1983-06-22 | Bayer Ag | Reactive azo dyestuffs |
| GB2128200A (en) * | 1982-09-17 | 1984-04-26 | Sandoz Ltd | Chloro-triazinyl mondazo compounds |
| EP0426618A1 (en) * | 1989-11-01 | 1991-05-08 | Ciba-Geigy Ag | Reactive dyes, their preparation and their use |
| US5149791A (en) * | 1989-11-01 | 1992-09-22 | Ciba-Geigy Corporation | Chlorotriazine reactive dyes having a 4-methoxy-2-sulfoaniline diazo component and 2-amino-5-naphthol-7-sulfonic acid coupling component |
| US5268457A (en) * | 1990-09-25 | 1993-12-07 | Ciba-Geigy Corporation | Reactive dyes containing a chloro or fluorotriazine group |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2030168B (en) | 1982-11-10 |
| FR2435510A1 (en) | 1980-04-04 |
| FR2435510B1 (en) | 1984-06-29 |
| DE2838616A1 (en) | 1980-03-13 |
| IT7925446A0 (en) | 1979-09-03 |
| JPS5536290A (en) | 1980-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |