PL79967B1 - - Google Patents
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- PL79967B1 PL79967B1 PL1969132039A PL13203969A PL79967B1 PL 79967 B1 PL79967 B1 PL 79967B1 PL 1969132039 A PL1969132039 A PL 1969132039A PL 13203969 A PL13203969 A PL 13203969A PL 79967 B1 PL79967 B1 PL 79967B1
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- PL
- Poland
- Prior art keywords
- amino
- group
- acid
- hydroxy
- formula
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 93
- 239000000975 dye Substances 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 15
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 11
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000000985 reactive dye Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- HONMCSLFRKBQHG-UHFFFAOYSA-N 1,3-diamino-1,3-diphenylurea Chemical compound C=1C=CC=CC=1N(N)C(=O)N(N)C1=CC=CC=C1 HONMCSLFRKBQHG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 claims description 3
- 229910006069 SO3H Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- DQRLCTAGMVGVFH-UHFFFAOYSA-N cyanide;hydrochloride Chemical compound Cl.N#[C-] DQRLCTAGMVGVFH-UHFFFAOYSA-N 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 2
- 102220492497 ATP-dependent RNA helicase DDX54_W20R_mutation Human genes 0.000 claims 1
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000001007 phthalocyanine dye Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 28
- -1 cyanuric acid halides Chemical class 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- 150000004699 copper complex Chemical class 0.000 description 13
- 238000004043 dyeing Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 239000010979 ruby Substances 0.000 description 3
- 229910001750 ruby Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000021286 stilbenes Nutrition 0.000 description 3
- 125000001174 sulfone group Chemical group 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- ICIDZHMCYAIUIJ-UHFFFAOYSA-N dinaphthalen-1-yldiazene Chemical compound C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ICIDZHMCYAIUIJ-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- SSYKTZQYHQJVAJ-UHFFFAOYSA-N 1-(3-aminophenyl)-4-[(2-carboxy-4-sulfophenyl)diazenyl]-5-oxo-4H-pyrazole-3-carboxylic acid Chemical compound NC=1C=C(C=CC=1)N1N=C(C(C1=O)N=NC1=C(C=C(C=C1)S(=O)(=O)O)C(=O)O)C(=O)O SSYKTZQYHQJVAJ-UHFFFAOYSA-N 0.000 description 1
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
- OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical class ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 1
- XFAWFWZQPYCAPS-UHFFFAOYSA-N 2-[[1-(3-aminophenyl)-3-methyl-5-oxo-4H-pyrazol-4-yl]diazenyl]benzene-1,4-disulfonic acid Chemical compound NC=1C=C(C=CC=1)N1N=C(C(C1=O)N=NC1=C(C=CC(=C1)S(=O)(=O)O)S(=O)(=O)O)C XFAWFWZQPYCAPS-UHFFFAOYSA-N 0.000 description 1
- VMKHNXYWSCMKSS-UHFFFAOYSA-N 2-amino-5-hydroxy-6-[(2-hydroxy-5-sulfophenyl)diazenyl]naphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=C(S(O)(=O)=O)C(N)=CC=C2C(O)=C1N=NC1=CC(S(O)(=O)=O)=CC=C1O VMKHNXYWSCMKSS-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- XXZDPVOWJBCNQC-UHFFFAOYSA-N 3-[(4-amino-2-methylphenyl)diazenyl]naphthalene-1,5-disulfonic acid Chemical compound CC1=CC(N)=CC=C1N=NC1=CC(S(O)(=O)=O)=C(C=CC=C2S(O)(=O)=O)C2=C1 XXZDPVOWJBCNQC-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical class ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- XHHWJFFOFMYBHG-UHFFFAOYSA-N 4-hydroxy-3-[(4-methoxy-2-sulfophenyl)diazenyl]-6-(methylamino)naphthalene-2-sulfonic acid Chemical compound OC=1C2=CC(NC)=CC=C2C=C(S(O)(=O)=O)C=1N=NC1=CC=C(OC)C=C1S(O)(=O)=O XHHWJFFOFMYBHG-UHFFFAOYSA-N 0.000 description 1
- FPYLBERKEKTGLO-UHFFFAOYSA-N 4-hydroxy-6-(methylamino)-3-[(2-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OC=1C2=CC(NC)=CC=C2C=C(S(O)(=O)=O)C=1N=NC1=CC=CC=C1S(O)(=O)=O FPYLBERKEKTGLO-UHFFFAOYSA-N 0.000 description 1
- ACIJABUQDFAJDW-UHFFFAOYSA-N 4-phenyldiazenylpyrazol-3-one Chemical compound O=C1N=NC=C1N=NC1=CC=CC=C1 ACIJABUQDFAJDW-UHFFFAOYSA-N 0.000 description 1
- AFABYZDPBFSKLR-UHFFFAOYSA-N 5-[(6-amino-1-hydroxy-3,5-disulfonaphthalen-2-yl)diazenyl]-2-hydroxybenzoic acid Chemical compound Nc1ccc2c(O)c(N=Nc3ccc(O)c(c3)C(O)=O)c(cc2c1S(O)(=O)=O)S(O)(=O)=O AFABYZDPBFSKLR-UHFFFAOYSA-N 0.000 description 1
- YEZBOLDRJIAVBA-UHFFFAOYSA-N 5-[(8-amino-1-hydroxy-3,6-disulfonaphthalen-2-yl)diazenyl]-2-hydroxybenzoic acid Chemical compound OC1=C2C(N)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=C1N=NC1=CC=C(O)C(C(O)=O)=C1 YEZBOLDRJIAVBA-UHFFFAOYSA-N 0.000 description 1
- WZNRCYVMHBODTD-UHFFFAOYSA-N 5-acetamido-3-[(3-amino-4-sulfophenyl)diazenyl]-4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OC1=C2C(NC(=O)C)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=C1N=NC1=CC=C(S(O)(=O)=O)C(N)=C1 WZNRCYVMHBODTD-UHFFFAOYSA-N 0.000 description 1
- HAIMEEBRQYGMSM-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[(2-hydroxy-5-sulfophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OC1=C2C(N)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=C1N=NC1=CC(S(O)(=O)=O)=CC=C1O HAIMEEBRQYGMSM-UHFFFAOYSA-N 0.000 description 1
- ISTNBIUEOOWHHO-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[(2-sulfophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OC1=C2C(N)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=C1N=NC1=CC=CC=C1S(O)(=O)=O ISTNBIUEOOWHHO-UHFFFAOYSA-N 0.000 description 1
- TYCNXOAPQGVAQU-UHFFFAOYSA-N 5-oxo-1-(4-sulfophenyl)-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=C(S(O)(=O)=O)C=C1 TYCNXOAPQGVAQU-UHFFFAOYSA-N 0.000 description 1
- IRJIXEKAWHQKHK-UHFFFAOYSA-N 7-acetamido-3-[(5-amino-2-sulfophenyl)diazenyl]-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(NC(=O)C)=CC=C2C(O)=C1N=NC1=CC(N)=CC=C1S(O)(=O)=O IRJIXEKAWHQKHK-UHFFFAOYSA-N 0.000 description 1
- WJBNEMQYSHMDPS-UHFFFAOYSA-N 7-amino-4-hydroxy-3-[(2-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(N)=CC=C2C(O)=C1N=NC1=CC=CC=C1S(O)(=O)=O WJBNEMQYSHMDPS-UHFFFAOYSA-N 0.000 description 1
- ZPRUFNWBYQKDGT-UHFFFAOYSA-N 7-amino-4-hydroxy-3-[(4-methoxy-2-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(OC)=CC=C1N=NC1=C(O)C2=CC=C(N)C=C2C=C1S(O)(=O)=O ZPRUFNWBYQKDGT-UHFFFAOYSA-N 0.000 description 1
- CSEIGFQMUDCSEV-UHFFFAOYSA-N 8-amino-2-(naphthalen-2-yldiazenyl)naphthalen-1-ol Chemical compound NC=1C=CC=C2C=CC(=C(C12)O)N=NC1=CC2=CC=CC=C2C=C1 CSEIGFQMUDCSEV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- YFHUQOUYHLLPPY-UHFFFAOYSA-N [Cu].NC1=CC(=CC2=CC(=C(C(=C12)O)N=NC1=C(C(=CC(=C1)S(=O)(=O)O)Cl)O)S(=O)(=O)O)S(=O)(=O)O Chemical compound [Cu].NC1=CC(=CC2=CC(=C(C(=C12)O)N=NC1=C(C(=CC(=C1)S(=O)(=O)O)Cl)O)S(=O)(=O)O)S(=O)(=O)O YFHUQOUYHLLPPY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- QYUDDCLXBAJUNA-UHFFFAOYSA-L disodium;2-aminobenzene-1,4-disulfonate Chemical compound [Na+].[Na+].NC1=CC(S([O-])(=O)=O)=CC=C1S([O-])(=O)=O QYUDDCLXBAJUNA-UHFFFAOYSA-L 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 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 description 1
- 238000002156 mixing Methods 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- YYHJPNVCYHVPJK-UHFFFAOYSA-N naphthalen-1-yl-(2-phenylnaphthalen-1-yl)diazene Chemical group C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1N=NC1=CC=CC2=CC=CC=C12 YYHJPNVCYHVPJK-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 238000005303 weighing 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
- C09B62/043—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 containing two or more triazine rings linked together by a non-chromophoric link
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB01462/68A GB1243263A (en) | 1968-03-08 | 1968-03-08 | New water-soluble reactive dyestuffs containing chlorotriazine residues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL79967B1 true PL79967B1 (en, 2012) | 1975-08-30 |
Family
ID=9986701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1969132039A PL79967B1 (en, 2012) | 1968-03-08 | 1969-03-01 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3658782A (en, 2012) |
| BR (1) | BR6906961D0 (en, 2012) |
| CA (1) | CA931140A (en, 2012) |
| CH (3) | CH510726A (en, 2012) |
| CS (3) | CS164816B2 (en, 2012) |
| ES (3) | ES364539A1 (en, 2012) |
| FI (1) | FI47199C (en, 2012) |
| FR (1) | FR2003529A1 (en, 2012) |
| GB (1) | GB1243263A (en, 2012) |
| NL (1) | NL6903597A (en, 2012) |
| PL (1) | PL79967B1 (en, 2012) |
| SE (1) | SE342051B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936436A (en) * | 1969-12-22 | 1976-02-03 | Imperial Chemical Industries Limited | Water-soluble azo dyestuffs containing triazine and 3-azo-2,6-dihydroxypyrid-6-one radicals |
| US3966705A (en) * | 1974-01-04 | 1976-06-29 | Ciba-Geigy Corporation | Disulfo naphthalene containing fiber-reactive tetrazo dyes |
| CH606347A5 (en, 2012) * | 1975-01-15 | 1978-10-31 | Ciba Geigy Ag | |
| JPS5857464B2 (ja) * | 1975-12-29 | 1983-12-20 | 日本化薬株式会社 | ハンノウセイアゾセンリヨウノセイホウ |
| CH656629A5 (de) * | 1981-08-08 | 1986-07-15 | Sandoz Ag | Tetrakisazoverbindungen mit brueckenglied, verfahren zur herstellung und verwendung. |
| CH669305GA3 (en, 2012) * | 1981-12-11 | 1989-03-15 | ||
| EP0549529B1 (de) * | 1991-12-20 | 1996-09-11 | Ciba-Geigy Ag | Verfahren zum Färben oder Bedrucken von hydroxylgruppenhaltigen Fasermaterialien |
-
1968
- 1968-03-08 GB GB01462/68A patent/GB1243263A/en not_active Expired
-
1969
- 1969-02-27 CA CA044196A patent/CA931140A/en not_active Expired
- 1969-03-01 PL PL1969132039A patent/PL79967B1/pl unknown
- 1969-03-03 US US803977A patent/US3658782A/en not_active Expired - Lifetime
- 1969-03-03 FI FI690637A patent/FI47199C/fi active
- 1969-03-07 FR FR6906515A patent/FR2003529A1/fr not_active Withdrawn
- 1969-03-07 CH CH348769A patent/CH510726A/de not_active IP Right Cessation
- 1969-03-07 BR BR206961/69A patent/BR6906961D0/pt unknown
- 1969-03-07 NL NL6903597A patent/NL6903597A/xx unknown
- 1969-03-07 CH CH660471A patent/CH574995A5/xx not_active IP Right Cessation
- 1969-03-07 SE SE3194/69A patent/SE342051B/xx unknown
- 1969-03-07 CH CH660371A patent/CH574994A5/xx not_active IP Right Cessation
- 1969-03-08 ES ES364539A patent/ES364539A1/es not_active Expired
- 1969-03-08 ES ES364541A patent/ES364541A1/es not_active Expired
- 1969-03-08 ES ES364540A patent/ES364540A1/es not_active Expired
- 1969-03-10 CS CS2885*A patent/CS164816B2/cs unknown
- 1969-03-10 CS CS1722A patent/CS164814B2/cs unknown
- 1969-03-10 CS CS2886*A patent/CS164817B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES364541A1 (es) | 1970-12-16 |
| NL6903597A (en, 2012) | 1969-09-10 |
| BR6906961D0 (pt) | 1973-01-02 |
| DE1911738A1 (de) | 1969-10-09 |
| DE1911738B2 (de) | 1976-07-08 |
| CH574994A5 (en, 2012) | 1976-04-30 |
| CH510726A (de) | 1971-07-31 |
| GB1243263A (en) | 1971-08-18 |
| FI47199B (en, 2012) | 1973-07-02 |
| CS164814B2 (en, 2012) | 1975-11-28 |
| CS164816B2 (en, 2012) | 1975-11-28 |
| ES364539A1 (es) | 1970-12-16 |
| CA931140A (en) | 1973-07-31 |
| CS164817B2 (en, 2012) | 1975-11-28 |
| FI47199C (fi) | 1973-10-10 |
| ES364540A1 (es) | 1970-12-16 |
| CH574995A5 (en, 2012) | 1976-04-30 |
| SE342051B (en, 2012) | 1972-01-24 |
| FR2003529A1 (en, 2012) | 1969-11-07 |
| US3658782A (en) | 1972-04-25 |
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