CN1121097A - 有纤维活性基团的偶氮染料 - Google Patents
有纤维活性基团的偶氮染料 Download PDFInfo
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- 239000000987 azo dye Substances 0.000 title 1
- 238000004043 dyeing Methods 0.000 claims abstract description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- -1 Methoxyl group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 238000004045 reactive dyeing Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 54
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 2
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- 239000000985 reactive dye Substances 0.000 abstract 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UERKTBSAPLOJRQ-UHFFFAOYSA-N 1-amino-1-phenylurea Chemical compound NC(=O)N(N)C1=CC=CC=C1 UERKTBSAPLOJRQ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 150000004992 toluidines Chemical class 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000012928 buffer substance Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- HIMMCCJEMMCUJS-UHFFFAOYSA-N 4-fluorotriazine Chemical class FC1=CC=NN=N1 HIMMCCJEMMCUJS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 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
- 239000003595 mist Substances 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000000176 photostabilization Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- IZUPJOYPPLEPGM-UHFFFAOYSA-M sodium;hydron;phthalate Chemical compound [Na+].OC(=O)C1=CC=CC=C1C([O-])=O IZUPJOYPPLEPGM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 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
- C09B62/44—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
- C09B62/4401—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
- C09B62/4415—Disazo or polyazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/248—Polyamides; Polyurethanes using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
- D06P3/663—Natural or regenerated cellulose using reactive dyes reactive group directly attached to heterocyclic group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
本发明涉及下式(1)的偶氮活性染料，其中D代表苯或萘系的重氮成分的基团，X代表CH＝CH2或CH2CH2-Z，其中Z代表在染色条件下可被脱除的基团，和其中其余的取代基如说明书中所定义。所述染料具有改善的与应用有关的性质。
Description
本发明涉及新的偶氮活性染料、它们的制备方法及用途。
偶氮活性染料已经在许多出版物中公开，例如，DE-A-3940266、EP-A-581729、EP-A-559617和EP-A-567036。然而，这些已知的染料仍有某些有关于应用的缺点。本发明涉及下式(1)的活性染料：
其中A代表一个任意取代的亚苯基或亚萘基，R1和R2是相同的或不同的，并彼此独立地代表氢、甲基、乙基、
甲氧基、乙氧基或NHCOE、其中，E＝NH2、CH3、C2H5、
n-C3H7、iSO-C3H7、CH2OH或CH2SO3H，T1和T2是相同的或不同的，并彼此独立地代表氢、甲基、乙基、
甲氧基或乙氧基，D代表苯或萘系的重氮成分的基团，R3和R4是相同的或不同的，并彼此独立地代表氢、甲基、乙基、
甲氧基或乙氧基，Y代表氟、氯或任意取代的吡啶鎓基，和X代表CH＝CH2或CH2CH2-Z，其中Z代表在染色条件下可被脱
除的基团。
基团D可含有另一个有基团SO2X的活性基团。因此，在如下通式(2)和(3)表示的两种不同种类的重氮基部分之间构成区别：
H2ND1 (2)
H2ND2-SO2X1 (3)其中D1代表一个苯基或萘基，它没有活性基团，并被任意地取代，D2代表一个任意取代的亚苯基或亚萘基，和X1有如上文中对X所给的定义之一。
基团A和D1或D2的取代基的实例如下：甲基、乙基、甲氧基、乙氧基、氯、羧基和磺酸基。
对于Z，如下基团可以举例的方式提到：-OSO3H、-OPO3H2、-OCOCH3、-Cl、-OSO2CH3、-S2O3H。Z优选地表示-OSO3H。
吡啶鎓基Y的取代基是：甲基、乙基、羧基、羧酰胺、磺酰胺和磺酸基。Y的优选定义是氯。
在式(1)的范围中，优选的染料是如下染料，其中X代表CH＝CH2或CH2CH2OSO3H，R代表氢，Y代表氯或氟，尤其是氯，R1和R2彼此独立地表示甲基、氢基羰基氨基、乙酰氨基或丙酰氨
基，和T1和T2代表氢。
更优选的是如下给出的式(1)的染料，其中D1的定义中的基团D表示如下结构：
和如下式(1)的染料，其中在-D2-SO2X1和A-SO2X定义中的基团D彼此独立地表示如下结构之一：
式(1)中-A-SO2X或-D2-SO2X1的优选定义为：
在式(1)的范围中，尤其优选的是如下染料2-4：
其中R5在每种情况下独立地为CH3、NHCOCH3、NHCONH2。
用于制备过程的反应条件与酰化、重氮化和偶合领域常用的条件相一致，因此，本发明的染料中间体的制备过程优选地在含水介质中进行。
例如，如下式(5)的单偶氮染料：其中A、R1、T1和R3如上文所定义，与如下式(6)的卤代三嗪反应，以得到如下式(7)的染料。
其中Y1代表氯或氟，
该染料随后与如下式(8)的单偶氮染料缩合：
其中D、R2、T2和R4如上文所定义，得到式(1)的染料，其中Y＝氯或氟。
染料也可以相反的顺序合成，单偶氮染料(8)首先与卤代三嗪(6)缩合以形成下式(9)的染料：
该染料随后与单偶氮染料(5)缩合得到式(1)的染料。
在其中Y代表一个任意取代的吡啶鎓基的情况下，其中Y＝氯或氟的式(1)的染料可以与下式的吡啶化合物反应：其中G代表甲基、乙基、羟酰胺、磺酸或磺酰胺，并且，如果G代表甲
基或乙基时，n＝0-3，如果G代表羧基、羧酰胺、磺酸或磺
酰胺时，n＝0-1。
卤素取代基Y转化成吡啶鎓取代基的过程通过在含水介质中，在40-90℃和在3-9，尤其为5-7的pH范围内加热而进行。
由上述方法得到的活性染料以常规的方法分离，例如，通过用氯化钠或氯化钾进行盐析，或通过浓缩中性的含水染料溶液，优选在稍高的温度及减压下进行浓缩，或通过喷雾干燥。染料可作为固体制剂使用，要不则作为浓缩溶液使用。
在一优选的具体实施方式中，染料作为颗粒使用，染料颗粒可经如下步骤得到；混合造粒
在本方法中，染料粉末用按粉末混合物计为15-55％的水增湿，然后在混合成粒机中形成混合物，随后混合物被干燥和除尘，除尘剂作为气雾剂混合物被喷雾在颗粒上。喷雾造粒
在本方法中，合成的溶液或悬浮液在流化喷雾-干燥器中同时被干燥和造粒。
染料粉末或染料颗粒通常含有(以％重量计)30-80％的式(1)活性染料，和5-15％的水，在各种情况下均以基于全部组合物重量计。此外，它们还可含有无机盐，如碱金属氯化物或碱金属硫酸盐、分散剂和除尘剂。
优选的固体混合物附加地含有缓冲物质，当其溶解于20倍量的水(基于染料制剂的重量)中时，得到的pH值为3.5-7.5，尤其为4.5-6.5。这些缓冲混合物的加入量以总重量计为3-50％(重量)，尤其为5-15％(重量)。
含水活性染料溶液通常含有5-50％的式(1)的染料(以溶液的总重量计)。
优选的含水活性染料溶液附加地含有缓冲物质，并且其pH值为3.5-7.5，尤其为4.5-6.5。以总重量计，这些缓冲物质的添加量优选为0.1-50％，尤其为1-20％(重量)。
所用的缓冲物对活性基团是惰性的。缓冲物的实例为：磷酸二氢钠、磷酸氢二钠、磷酸二氢钾、磷酸氢二钾、乙酸钠、乙酸钾、硼酸钠、硼酸钾、草酸钠、草酸钾和邻苯二甲酸氢钠。这些缓冲物可单独地或作为混合物使用。
偶氮化合物(1)具有有价值的染色性能。由于存在纤维活性基团SO2X和卤代三嗪基，所以它们有纤维活性。
式(1)的活性染料得到具有好的耐湿性和耐光性性能的染色。尤其应强调的是，所述染料具有好的溶解性和电解质溶解性，从而有好的上染性能和高的染色固色性，并且染料的未固色部分可容易地被除去。
式(1)的新染料适用于染色和印花含羟基或酰胺基的材料，如纺织纤维、纱线和羊毛、丝、合成聚酰胺和聚氨基甲酸乙酯纤维的织物，适用于天然或再生纤维素的耐洗染色和印花，纤维素材料的处理有利的是在酸结合剂存在下进行，并且，如果需要的话，根据已知的用于活性染料的方法，通过加热作用进行。
给出的结构式是染料的相应的游离酸。染料通常以碱金属盐，尤其是Na盐的形式被分离得到和用于染色。实施例1a)重氮化
将28ml浓度为30％的盐酸加入到在500ml冰水中的36.1g 4-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸中。然后向其中滴加70ml浓度为10％的亚硝酸钠溶液，搅拌混合物，直到仅稍过量的亚硝酸盐仍可被检测到。过量的盐随后用氨基磺酸破坏掉。b)偶合
将13.5g 3-氨基苯脲在加热条件下溶解于400ml水中得到中性溶液，将该溶液加入a)中得到的重氮化溶液中，混合物的pH通过加入碳酸氢钠调节至3-4，搅拌混合物直到偶合完全。c)缩合
将a)中得到的下式的单偶氮染料的溶液：冷却到5-8℃，向其中加入9.5g氰尿酰氯。在反应过程中，通过加入碳酸氢钠使pH维持在5.0-5.5，持续搅拌，直到不再消耗碳酸氢钠。此时约50％所用的单偶氮染料被酰化。随后将温度上升至40-50℃，经进一步加入碳酸氢钠使pH维持在5-6范围内。在缩合完成后，使用氯化钾从澄清溶液中盐析出染料，抽滤出，在循环空气干燥箱中在70℃下干燥并研磨，得到橙色粉末，其易溶于水中得到黄色溶液。
该染料相应于如下的结构式：
用该染料，采用对于有这些活性基团的活性染料常用的染色方法之一，在棉布上得到鲜明的红黄色。
重复该实施例，但在步骤a中使用第2栏所列的重氮成分，在步骤b中使用第3栏所示的偶合成分，同样得到有价值的染料，其将棉布染色成红黄色。
反应后，染料的λmax值为
| 实施例 | 重氮成分 | 偶合成分 |
| 2345678910111213141516171819 | 4-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸4-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸4-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸4-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸4-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸4-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸5-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸5-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸5-(β-硫酸根合乙基磺酰基)-苯胺-2-磺酸5-(β-硫酸根合乙基磺酰基)-苯胺-2，4-二磺酸5-(β-硫酸根合乙基磺酰基)-苯胺-2，4-二磺酸5-(β-硫酸根合乙基磺酰基)-苯胺-2，4-二磺酸8-(β-硫酸根合乙基磺酰基)-萘-6-磺酸8-(β-硫酸根合乙基磺酰基)-萘-6-磺酸8-(β-硫酸根合乙基磺酰基)-萘-6-磺酸6-(β-硫酸根合乙基磺酰基)-萘-8-磺酸6-(β-硫酸根合乙基磺酰基)-萘-8-磺酸6-(β-硫酸根合乙基磺酰基)-萘-8-磺酸 | 间-甲苯胺3-氨基-N-乙酰苯胺3-丙酰氨基苯胺3-氢乙酰氨基苯胺3-硫酸根合乙酰氨基苯胺3-苯甲酰氨基苯胺间-甲苯胺3-氨基苯脲3-氨基-N-乙酰苯胺间-甲苯胺3-氨基苯脲3-氨基-N-乙酰苯胺间-甲苯胺3-氨基苯脲3-氨基-N-乙酰苯胺间-甲苯胺3-氨基苯脲3-氨基-N-乙酰苯胺 |
实施例 nm
2 400
3 400实施例20-26
如果步骤a)和b)根据实施例1方法进行，但使用19g而不是9.5g氰尿酰氯，得到二氯代三嗪染料的缩合过程以上述方式进行，如下所示的0.09mol单偶氮染料用于取代第二个氯原子，染料经盐析、抽滤、干燥和研磨而分离得到，于是同样得到将棉布染成红黄色的有价值的活性染料。实施例27
如果步骤a)和b)根据实施例1方法进行，但在缩合阶段使用7g三氟代三嗪代替9.5g氰尿酰氯，酰化过程在0℃和pH＝5-6范围下进行，pH值通过滴加稀氢氧化钠溶液而维持，将混合物随后加热至20℃以取代第二个氟原子，同样通过滴加稀氢氧化钠溶液而维持pH值，于是得到透明的黄色溶液，由该溶液经盐析、抽滤、干燥和研磨以黄红色粉末的形式得到染料。染料易溶于水得到黄色溶液，经常规的用于含这些活性基团的活性染料的染色方法之一将棉布染色成鲜明的红黄色泽。该染料相应于如下结构式：
实施例28-45
按照实施例27，如果使用用于实施例2-19中的氨基单偶氮染料，得到其它有价值的活性染料，它们将棉布染成红黄色泽。实施例46
将14g吡啶-3-羧酸加入按实施例1方法得到的染料溶液中，并将该混合物在pH5-6下在90℃加热5小时。在氯原子被吡啶鎓基团取代后，用氯化钾盐析出染料，并抽滤、干燥和研磨。得到橙色染料粉末，其易溶于水得到黄色溶液。采用常规的用于活性染料的染色方法之一对棉布进行染色，在棉布上得到红黄色。该染料相应于
Claims (9)
1.如下式(1)的活性染料：
其中A代表一个任意取代的亚苯基或亚萘基，R1和R2是相同的或不同的，并彼此独立地代表氢、甲基、乙基、
甲氧基、乙氧基或NHCOE、其中，E＝NH2、CH3、C2H5、
n-C3H7、iSO-C3H7、CH2OH或CH2SO3H，T1和T2是相同的或不同的，并彼此独立地代表氢、甲基、乙基、
甲氧基或乙氧基，D代表苯或萘系的重氮成分的基团，R3和R4是相同的或不同的，并彼此独立地代表氢、甲基、乙基、
甲氧基或乙氧基，Y代表氟、氯或任意取代的吡啶鎓基，和X代表CH＝CH2或CH2CH2-Z，其中Z代表在染色条件下可被脱
除的基团。
2.根据权利要求1所述的活性染料，其中基团D包含基团SO2X，其中，X代表CH＝CH2或CH2CH2-Z，其中Z代表在染色条件下可被脱除的基团。
3.根据权利要求1所述的活性染料，其中基团A和D是未取代的或被甲基、乙基、甲氧基、乙氧基、氯、羧基或被至少一个磺酰基取代。
4.根据权利要求1所述的活性染料，其中当Z多于一次出现时，在每种情况下Z独立地代表-OSO3H、-OPO3H2、-OCOCH3、-Cl、-OSO2CH3或-S2O3H。
5.根据权利要求1所述的活性染料，其中D代表
6.根据权利要求1所述的活性染料，其中D和基团A-SO2X彼此独立地具有如下的定义：
7.根据权利要求1所述的活性染料，其相应于如下结构式(2)、(3)或(4)中的一种结构式：
其中，取代基R5彼此独立地代表CH3、NHCOCH3、NHCONH2。
8.一种用活性染料染色或印花含羟基或酰胺基材料的方法，其中所述材料用权利要求1所述的染料染色或印花。
9.一种尤其基于纤维素或聚酰胺的被染色的材料，其已被权利要求1所述的染料染色或印花。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4423650A DE4423650A1 (de) | 1994-07-06 | 1994-07-06 | Azofarbstoffe mit einer faserreaktiven Gruppe |
| DEP4423650.6 | 1994-07-06 |
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| Publication Number | Publication Date |
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| CN1121097A true CN1121097A (zh) | 1996-04-24 |
| CN1069332C CN1069332C (zh) | 2001-08-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN95108157A Expired - Fee Related CN1069332C (zh) | 1994-07-06 | 1995-07-06 | 有纤维活性基团的偶氮染料 |
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| Country | Link |
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| US (1) | US5623061A (zh) |
| EP (1) | EP0691383B1 (zh) |
| JP (1) | JPH0827389A (zh) |
| KR (1) | KR960004452A (zh) |
| CN (1) | CN1069332C (zh) |
| DE (2) | DE4423650A1 (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1313542C (zh) * | 2001-11-07 | 2007-05-02 | 西巴特殊化学品控股有限公司 | 纤维活性染料,它们的制备和它们的用途 |
| CN112876875A (zh) * | 2020-12-31 | 2021-06-01 | 湖北丽源科技股份有限公司 | 双偶氮活性黄染料及其制备方法和应用 |
| CN116144195A (zh) * | 2022-12-12 | 2023-05-23 | 江苏德美科化工有限公司 | 一种高性能耐碱性黄色活性染料及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7093239B1 (en) * | 2000-07-14 | 2006-08-15 | Internet Security Systems, Inc. | Computer immune system and method for detecting unwanted code in a computer system |
| US6793869B2 (en) * | 2000-12-11 | 2004-09-21 | Lear Corporation | Method of manufacturing a vehicle pull handle assembly |
| DE102004062080A1 (de) | 2004-12-23 | 2006-07-06 | Zf Friedrichshafen Ag | Hydrodynamischer Drehmomentwandler |
| DE102005013960A1 (de) * | 2005-03-26 | 2006-09-28 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Reaktivfarbstoffe, Verfahren zur deren Herstellung und ihre Verwendung |
| CN1847324A (zh) * | 2005-04-13 | 2006-10-18 | 明德国际仓储贸易(上海)有限公司 | 纤维反应性染料 |
| CN100368481C (zh) * | 2005-12-27 | 2008-02-13 | 姜堰市东风染料化工厂 | 一种嫩黄色活性染料k-6g的制备方法 |
| ES2634543T3 (es) | 2010-02-18 | 2017-09-28 | Huntsman Advanced Materials (Switzerland) Gmbh | Mezcla de tintes reactivos con fibras y su uso en un método para la tinción o impresión di o tricromática |
| CN103031000A (zh) * | 2010-08-16 | 2013-04-10 | 天津德凯化工股份有限公司 | 黄色尼龙活性染料及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0348344B1 (de) * | 1988-06-21 | 1993-12-29 | Ciba-Geigy Ag | Azofarbstoffe |
| DE3940266A1 (de) | 1989-12-06 | 1991-06-13 | Bayer Ag | Azofarbstoffe und deren verwendung |
| ES2095925T3 (es) * | 1990-07-02 | 1997-03-01 | Ciba Geigy Ag | Azocolorante. |
| ES2111731T3 (es) | 1992-03-05 | 1998-03-16 | Ciba Geigy Ag | Colorantes reactivos, procedimiento para su preparacion y su empleo. |
| TW225549B (zh) * | 1992-04-14 | 1994-06-21 | Bayer Ag | |
| JP3649749B2 (ja) * | 1992-04-20 | 2005-05-18 | ダイスタージャパン株式会社 | 水溶性モノアゾ色素 |
| ES2118213T3 (es) | 1992-07-23 | 1998-09-16 | Ciba Geigy Ag | Colorantes reactivos, procedimiento para su obtencion y utilizacion de los mismos. |
-
1994
- 1994-07-06 DE DE4423650A patent/DE4423650A1/de not_active Withdrawn
-
1995
- 1995-06-23 EP EP95109785A patent/EP0691383B1/de not_active Expired - Lifetime
- 1995-06-23 DE DE59503509T patent/DE59503509D1/de not_active Expired - Fee Related
- 1995-06-29 US US08/496,750 patent/US5623061A/en not_active Expired - Fee Related
- 1995-06-30 JP JP7186521A patent/JPH0827389A/ja active Pending
- 1995-07-05 KR KR1019950019608A patent/KR960004452A/ko not_active Application Discontinuation
- 1995-07-06 CN CN95108157A patent/CN1069332C/zh not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1313542C (zh) * | 2001-11-07 | 2007-05-02 | 西巴特殊化学品控股有限公司 | 纤维活性染料,它们的制备和它们的用途 |
| CN112876875A (zh) * | 2020-12-31 | 2021-06-01 | 湖北丽源科技股份有限公司 | 双偶氮活性黄染料及其制备方法和应用 |
| CN112876875B (zh) * | 2020-12-31 | 2022-05-20 | 湖北丽源科技股份有限公司 | 双偶氮活性黄染料及其制备方法和应用 |
| CN116144195A (zh) * | 2022-12-12 | 2023-05-23 | 江苏德美科化工有限公司 | 一种高性能耐碱性黄色活性染料及其制备方法 |
| CN116144195B (zh) * | 2022-12-12 | 2024-04-02 | 江苏德美科化工有限公司 | 一种高性能耐碱性黄色活性染料及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59503509D1 (de) | 1998-10-15 |
| JPH0827389A (ja) | 1996-01-30 |
| EP0691383B1 (de) | 1998-09-09 |
| CN1069332C (zh) | 2001-08-08 |
| EP0691383A1 (de) | 1996-01-10 |
| DE4423650A1 (de) | 1996-01-11 |
| US5623061A (en) | 1997-04-22 |
| KR960004452A (ko) | 1996-02-23 |
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Effective date of registration: 20050930 Address after: Frankfurt, Germany Patentee after: Dystar Textilfarben GmbH & Co Dutschland K G Address before: The Federal Republic of Germany Leverkusen Patentee before: Bayer Aktiengesellschaft |
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