CS224632B2 - Method for producing in water soluble azo-compounds - Google Patents

Method for producing in water soluble azo-compounds Download PDF

Info

Publication number: CS224632B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; beta; alkyl; compound
Prior art date: 1980-11-06

Application number

CS818102A

Other languages

Czech (cs)

English (en)

Inventor

Peter Dr Mischke

Herman Dr Fuchs

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1980-11-06

Filing date

1981-11-04

Publication date

1984-01-16

1981-11-04 Application filed by Hoechst Ag filed Critical Hoechst Ag

1984-01-16 Publication of CS224632B2 publication Critical patent/CS224632B2/cs

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 14
238000004519 manufacturing process Methods 0.000 title description 2
-1 chloro- Chemical class 0.000 claims description 81
150000001875 compounds Chemical class 0.000 claims description 53
238000005859 coupling reaction Methods 0.000 claims description 47
238000010168 coupling process Methods 0.000 claims description 44
230000008878 coupling Effects 0.000 claims description 42
238000000034 method Methods 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
125000001309 chloro group Chemical group Cl* 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000011734 sodium Chemical group 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
229910052736 halogen Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
125000004957 naphthylene group Chemical group 0.000 claims description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000005521 carbonamide group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
239000011591 potassium Chemical group 0.000 claims description 3
229910052700 potassium Chemical group 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
150000002431 hydrogen Chemical class 0.000 claims 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
125000001188 haloalkyl group Chemical group 0.000 claims 2
230000001180 sulfating effect Effects 0.000 claims 2
229920002554 vinyl polymer Polymers 0.000 claims 2
CYTCTRAEJYIZRX-UHFFFAOYSA-N (9a-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzofuran-6-yl) acetate Chemical compound C1CC2(C)C(OC(C)=O)CCC(=C)C2(O)C2C1C(C)C(=O)O2 CYTCTRAEJYIZRX-UHFFFAOYSA-N 0.000 claims 1
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
108010044467 Isoenzymes Proteins 0.000 claims 1
BKAYIFDRRZZKNF-VIFPVBQESA-N N-acetylcarnosine Chemical compound CC(=O)NCCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 BKAYIFDRRZZKNF-VIFPVBQESA-N 0.000 claims 1
241000569510 Spino Species 0.000 claims 1
150000001218 Thorium Chemical class 0.000 claims 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000000987 azo dye Substances 0.000 claims 1
125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
229940104869 fluorosilicate Drugs 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
125000000262 haloalkenyl group Chemical group 0.000 claims 1
150000002540 isothiocyanates Chemical class 0.000 claims 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
229910052726 zirconium Inorganic materials 0.000 claims 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 31
239000000975 dye Substances 0.000 description 22
238000004043 dyeing Methods 0.000 description 19
229920000742 Cotton Polymers 0.000 description 18
239000000243 solution Substances 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
235000002639 sodium chloride Nutrition 0.000 description 14
239000003792 electrolyte Substances 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
210000002268 wool Anatomy 0.000 description 12
239000000843 powder Substances 0.000 description 11
239000000985 reactive dye Substances 0.000 description 11
159000000000 sodium salts Chemical class 0.000 description 10
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical class [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 9
238000001694 spray drying Methods 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000006193 diazotization reaction Methods 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
239000000835 fiber Substances 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
IAVHKMVGTPXJIC-UHFFFAOYSA-N 2-phenylamino-ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1=CC=CC=C1 IAVHKMVGTPXJIC-UHFFFAOYSA-N 0.000 description 5
AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 5
238000004040 coloring Methods 0.000 description 5
239000002657 fibrous material Substances 0.000 description 5
235000011007 phosphoric acid Nutrition 0.000 description 5
235000011164 potassium chloride Nutrition 0.000 description 5
239000004952 Polyamide Substances 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229920002647 polyamide Polymers 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
239000001103 potassium chloride Substances 0.000 description 4
STZCRXQWRGQSJD-UHFFFAOYSA-M sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-M 0.000 description 4
229920003043 Cellulose fiber Polymers 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
238000010025 steaming Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
150000003457 sulfones Chemical class 0.000 description 3
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
KYQSQCLRQWXHLX-UHFFFAOYSA-N 2-(n-methylanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(C)C1=CC=CC=C1 KYQSQCLRQWXHLX-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
125000005518 carboxamido group Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000010985 leather Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 description 1
QLRBNEZOQPLERN-UHFFFAOYSA-N (sulfonylamino)benzene Chemical compound O=S(=O)=NC1=CC=CC=C1 QLRBNEZOQPLERN-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
TZBSXNLGYKTVHJ-UHFFFAOYSA-N 1-sulfonyl-2h-naphthalen-2-amine Chemical compound C1=CC=C2C(=S(=O)=O)C(N)C=CC2=C1 TZBSXNLGYKTVHJ-UHFFFAOYSA-N 0.000 description 1
ZBQIMMIPACUIIO-UHFFFAOYSA-N 2-(5-chloro-2-methoxyanilino)ethanesulfonic acid Chemical compound COC1=CC=C(Cl)C=C1NCCS(O)(=O)=O ZBQIMMIPACUIIO-UHFFFAOYSA-N 0.000 description 1
SVDAGORERCSAIV-UHFFFAOYSA-N 2-(n-ethyl-3-methylanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CC)C1=CC=CC(C)=C1 SVDAGORERCSAIV-UHFFFAOYSA-N 0.000 description 1
SARHGESRKAMMJB-UHFFFAOYSA-N 2-[3-chloro-n-(2-hydroxyethyl)anilino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCO)C1=CC=CC(Cl)=C1 SARHGESRKAMMJB-UHFFFAOYSA-N 0.000 description 1
GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
OTTPFCJTQXRWHO-UHFFFAOYSA-N 3-(2,3-dichloroanilino)cyclohex-2-en-1-one Chemical class ClC1=CC=CC(NC=2CCCC(=O)C=2)=C1Cl OTTPFCJTQXRWHO-UHFFFAOYSA-N 0.000 description 1
JTPLQOAZXUQHCI-UHFFFAOYSA-N 3-[3-chloro-n-(2-sulfoethyl)anilino]propanoic acid Chemical compound OC(=O)CCN(CCS(O)(=O)=O)C1=CC=CC(Cl)=C1 JTPLQOAZXUQHCI-UHFFFAOYSA-N 0.000 description 1
USPVTJCHQHJFBQ-UHFFFAOYSA-N 3-chloro-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC(Cl)=C1 USPVTJCHQHJFBQ-UHFFFAOYSA-N 0.000 description 1
LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
LTDLDKOTRWNWCY-UHFFFAOYSA-N 4-chlorobutane-2-sulfonic acid Chemical compound OS(=O)(=O)C(C)CCCl LTDLDKOTRWNWCY-UHFFFAOYSA-N 0.000 description 1
MZQBTOQTTSJPBT-UHFFFAOYSA-N 6-ethenylsulfonyl-1,3-benzothiazol-2-amine Chemical compound C1=C(S(=O)(=O)C=C)C=C2SC(N)=NC2=C1 MZQBTOQTTSJPBT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
240000004153 Hibiscus sabdariffa Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
240000006240 Linum usitatissimum Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
101100022176 Mus musculus Gstz1 gene Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229920000571 Nylon 11 Polymers 0.000 description 1
229920001007 Nylon 4 Polymers 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
229920002302 Nylon 6,6 Polymers 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical group C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000005236 alkanoylamino group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
235000009120 camo Nutrition 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
235000005607 chanvre indien Nutrition 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
BYPHZHGVWNKAFC-UHFFFAOYSA-N ethenesulfonyl fluoride Chemical class FS(=O)(=O)C=C BYPHZHGVWNKAFC-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical group OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
210000004209 hair Anatomy 0.000 description 1
239000011487 hemp Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000010409 ironing Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000001048 orange dye Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940005657 pyrophosphoric acid Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
239000013535 sea water Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
OESSQZSTPKCQOE-UHFFFAOYSA-M sodium;2,4-dinitronaphthalen-1-olate Chemical compound [Na+].C1=CC=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 OESSQZSTPKCQOE-UHFFFAOYSA-M 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
XWNXEWLCHSLQOI-UHFFFAOYSA-K trisodium;triacetate Chemical compound [Na+].[Na+].[Na+].CC([O-])=O.CC([O-])=O.CC([O-])=O XWNXEWLCHSLQOI-UHFFFAOYSA-K 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
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/513—Disazo or polyazo dyes
- 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
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo dyes
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- 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
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
- C09B62/447—Azo dyes
- C09B62/45—Monoazo dyes
- 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
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
- C09B62/447—Azo dyes
- C09B62/453—Disazo or polyazo dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS818102A 1980-11-06 1981-11-04 Method for producing in water soluble azo-compounds CS224632B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3041891		1980-11-06
DE19813113001 DE3113001A1 (de)	1980-11-06	1981-04-01	Wasserloesliche monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe

Publications (1)

Publication Number	Publication Date
CS224632B2 true CS224632B2 (en)	1984-01-16

Family

ID=25788960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS818102A CS224632B2 (en)	1980-11-06	1981-11-04	Method for producing in water soluble azo-compounds

Country Status (7)

Country	Link
US (1)	US4652634A (fr)
EP (1)	EP0051808B1 (fr)
KR (1)	KR880002248B1 (fr)
AR (1)	AR241250A1 (fr)
BR (1)	BR8107192A (fr)
CS (1)	CS224632B2 (fr)
DE (2)	DE3113001A1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3441272A1 (de) *	1984-11-12	1986-05-15	Hoechst Ag, 6230 Frankfurt	Faserreaktive monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
DE3537260A1 (de) *	1985-10-12	1987-04-16	Hoechst Ag	Mischungen wasserloeslicher reaktivfarbstoffe
DE3614045A1 (de) *	1986-04-25	1987-11-05	Hoechst Ag	Wasserloesliche monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
DE3710176A1 (de) *	1987-03-27	1988-10-13	Hoechst Ag	Verfahren zur herstellung des lithiumsalzes eines faserreaktiven azofarbstoffes
DE3717814A1 (de) *	1987-05-27	1988-12-08	Bayer Ag	Reaktivfarbstoffe
DE3828849A1 (de) *	1988-08-25	1990-03-01	Hoechst Ag	Wasserloesliche azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
DE3927790A1 (de) *	1989-08-23	1991-02-28	Bayer Ag	Reaktivfarbstoffe
US5432266A (en) *	1991-06-22	1995-07-11	Bayer Aktiengesellschaft	Fiber-reactive monoazo and disazo dyes
DE4226374A1 (de) *	1992-08-10	1994-02-17	Bayer Ag	Verfahren zum Färben von Polyurethankunststoffen mit Monoazoeinbaufarbstoffen sowie neue Monoazofarbstoffe
AU653086B2 (en) *	1991-12-26	1994-09-15	Sumitomo Chemical Company, Limited	Bisazo compounds and method for dyeing or printing fiber materials using the same
DE59307910D1 (de) *	1992-03-05	1998-02-12	Ciba Geigy Ag	Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
EP0586331B1 (fr) *	1992-07-31	1999-01-07	Ciba SC Holding AG	Procédé de teinture de matériaux en fibres synthétiques à base de polyamide
WO2002057370A1 (fr) *	2001-01-17	2002-07-25	Korea Research Institute Of Chemical Technology	Colorants reactifs disperses contenant de l'acetoxymethylsulfone ou du vinylsulfone
CN102292399A (zh) *	2008-11-20	2011-12-21	德司达染料德国有限责任公司	环氟化活性染料

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE500513A (fr) *	1950-01-09
DE2159216A1 (de) *	1971-11-30	1973-06-14	Hoechst Ag	Neue wasserloesliche disazofarbstoffe und verfahren zu ihrer herstellung
CH586739A5 (fr) *	1973-10-17	1977-04-15	Hoechst Ag
DE2653478C3 (de) *	1976-11-25	1980-03-06	Hoechst Ag, 6000 Frankfurt	Wasserlösliche Farbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben und Bedrucken von Cellulose- und Polyamidfasermaterialien

1981
- 1981-04-01 DE DE19813113001 patent/DE3113001A1/de not_active Withdrawn
- 1981-10-28 DE DE8181109104T patent/DE3164603D1/de not_active Expired
- 1981-10-28 EP EP81109104A patent/EP0051808B1/fr not_active Expired
- 1981-11-04 AR AR81287341A patent/AR241250A1/es active
- 1981-11-04 KR KR1019810004284A patent/KR880002248B1/ko not_active Expired
- 1981-11-04 CS CS818102A patent/CS224632B2/cs unknown
- 1981-11-05 BR BR8107192A patent/BR8107192A/pt unknown
1986
- 1986-01-15 US US06/819,988 patent/US4652634A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE3113001A1 (de)	1982-06-09
EP0051808B1 (fr)	1984-07-04
DE3164603D1 (en)	1984-08-09
BR8107192A (pt)	1982-07-27
KR880002248B1 (ko)	1988-10-20
EP0051808A2 (fr)	1982-05-19
KR830007768A (ko)	1983-11-07
US4652634A (en)	1987-03-24
AR241250A1 (es)	1992-03-31
EP0051808A3 (en)	1983-01-19

Publication	Publication Date	Title
KR910001687B1 (ko)	1991-03-18	트리펜디옥사진 비닐 설폰의 제조방법
KR850001475B1 (ko)	1985-10-10	셀룰로스 섬유용 아조 염료의 제조방법
EP0020161A2 (fr)	1980-12-10	Colorants azoiques dérivés d'amines hétérocycliques pentagonales et de copulants aromatiques contenant des groupes sulfo ou leurs sels et leur utilisation pour la teinture de fibres en polyamide
EP0022575A1 (fr)	1981-01-21	Colorants réactifs monoazo, procédé pour leur préparation et leur utilisation pour teindre les fibres et les textiles cellulosiques
KR890002642B1 (ko)	1989-07-21	반응성 단일 관능형 비스 아조 블루-블랙 염료의 제조방법
JPS5855987B2 (ja)	1983-12-13	シンキナスイヨウセイアゾセンリヨウノセイホウ
KR880002248B1 (ko)	1988-10-20	수용성 아조 화합물의 제조방법
JP4024296B2 (ja)	2007-12-19	アミノナフタリン列からのカップリング成分を有する反応性アゾ染料
US4283196A (en)	1981-08-11	Process for coloring fiber materials with azo dyestuff containing --SO2 CH2 CH2 OSO3 H and --N(CH2 CH2 OSO.sub. H)2 groups
KR880002250B1 (ko)	1988-10-20	수용성 디스아조 화합물의 제조방법
US4271072A (en)	1981-06-02	Azo dyestuffs containing -SO2 CH2 CH2 OSO3 H and -N(CH2 CH2 OSO3 H)2 groups
CA1097622A (fr)	1981-03-17	Colorants solubles dans l'eau, leur preparation et leur emploi pour la teinture et l'impression sur fibres de polyamides et de cellulose
ITRM960342A1 (it)	1997-11-17	Coloranti per dispersione monoazo (caso 150-5866).
KR900004223B1 (ko)	1990-06-18	반응성 디스아조 염료의 제조방법
US3519616A (en)	1970-07-07	Water-soluble monoazo dyestuffs
EP0503385B1 (fr)	1995-08-09	Doubles phénylazo- ou naphthylazobenzènes ayant plusieurs groupes réactifs, ainsi que leurs produits intermédiaires
US2623884A (en)	1952-12-30	Condensation products of alkenyl
EP0071035A1 (fr)	1983-02-09	Colorant bleu-noir disazoique réactif monofonctionnel
CH395397A (de)	1965-07-15	Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe
JPH07316452A (ja)	1995-12-05	繊維反応性アゾ染料
KR100352808B1 (ko)	2002-12-18	섬유반응성디스아조염료
DE2161553C3 (de)	1981-12-17	Wasserlösliche, faserreaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Leder, Wolle, Seide und Materialien aus Polyamid- oder Polyurethanfasern oder negativen oder regenerierten Cellulosefasern
DE3843135A1 (de)	1990-06-28	Kupferkomplex-formazan-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
US3636064A (en)	1972-01-18	Anthraquinone reactive dyes
EP0433764A1 (fr)	1991-06-26	Colorants réactifs avec groupements d'ancrage triazinyle et chlorobutinyle