CN1149265C - 新的双偶氮染料 - Google Patents
新的双偶氮染料 Download PDFInfo
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- CN1149265C CN1149265C CNB98804790XA CN98804790A CN1149265C CN 1149265 C CN1149265 C CN 1149265C CN B98804790X A CNB98804790X A CN B98804790XA CN 98804790 A CN98804790 A CN 98804790A CN 1149265 C CN1149265 C CN 1149265C
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 238000004043 dyeing Methods 0.000 claims abstract description 24
- 238000007639 printing Methods 0.000 claims abstract description 12
- 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 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims abstract 3
- 239000000975 dye Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 23
- 229920000742 Cotton Polymers 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000007641 inkjet printing Methods 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000976 ink Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- -1 alkali metal cation Chemical class 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000176 photostabilization Effects 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 description 1
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-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
- 241000196324 Embryophyta Species 0.000 description 1
- 235000001018 Hibiscus sabdariffa Nutrition 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000005291 Rumex acetosa Nutrition 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
- 230000000743 anti-peroxide Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by 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
- C09B62/02—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
- C09B62/20—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 pyrimidine ring
- C09B62/24—Azo dyes
- C09B62/25—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
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
- D06P1/382—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group directly attached to heterocyclic group
-
- 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
- D06P3/14—Wool
- D06P3/148—Wool 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/248—Polyamides; Polyurethanes using reactive dyes
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- 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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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及按照式(I)的化合物和它们的盐,其中X代表氢或氯,R1和R3代表氢或甲基,R2和R4代表氢,甲基或甲氧基,和R5代表氢或C1-4烷基,它们在染色或印染含有羟基以及含有氮的有机基质中用作纤维活性染料,和用于制备适于喷墨工艺的印刷油墨。
Description
本发明涉及双偶氮染料及其制备方法和它们在染色和印染工艺中作为纤维活性染料的方法。
本发明提供了按照式(I)的化合物及其盐,
其中
R1和R3代表氢或甲基,
R2和R4代表氢,甲基或甲氧基,和
R5代表氢或C1-4烷基
优选萘基A具有2至3个磺基。在环B中磺基连接在6,7,8位上。优选用至少一个甲基或甲氧基取代环C。取代的环C的具体例子是通过用间-甲苯胺,2,5-二甲基苯胺,2-甲氧基-5-甲基-苯胺,5-甲氧基-2-甲基苯胺和3,6-二甲基-苯胺偶联得到的苯残基。
用式(Ia)表示式(I)的更优选化合物,
可以将式(I)的化合物形成为游离酸或盐的形式。
当式(I)的化合物是盐的形式时,在相应的盐是水溶性的前提条件下,对与磺基连接的阳离子要求不高,并且阳离子可以是在纤维活性染料领域中常用的任何一个不发色的阳离子。
这类阳离子的例子可以是碱金属阳离子和未取代的铵阳离子,例如锂,钠,钾,铵,单,二-,三-和四甲基铵,三乙基铵,和单,二-和三乙醇铵。优选的阳离子是碱金属阳离子和铵阳离子,最优选钠阳离子。
在式(I)的化合物中磺基阳离子可以相同也可以不同,例如它们可以是上述提到的阳离子的混合物,也就是式(I)的化合物可以是混盐的形式。
本发明的另一目的是提供一种形成式(I)的化合物,它们的盐或其混合物的方法,该方法包括将按照式(II)的化合物与通式(III)的化合物反应,
其中R1,R2,R3,R4和R5具有上述所给的含义。
按照已知的方法进行该缩合反应,并且优选在温度20-50℃,更优选30-40℃和pH值4-5的条件下进行反应。
起始原料既容易买到又可以从普通市售原料合成。
可以按照已知的方法离析式(I)的化合物,例如通过常规的方法用碱金属盐盐析,过滤,和可以选择在真空和稍提高温度的条件下进行干燥。
根据反应条件和分离条件可将式(I)的化合物形成为游离酸或优选的盐的形式或甚至含有例如一种或更多种上述提到的阳离子的混盐的形式。
可以将式(I)的化合物从游离酸转化成盐的形式或盐的混合物,反之亦然,或用常规的方法将式(I)的化合物从一种盐的形式转化成其它的形式。
式(I)的化合物,它们的盐及其混合物是活性染料。它们适于染色和印染含有羟基或含有氮的基质。它们可以生产褐色染色物或印花布(prints)。
本发明的另一目的是提供一种染色或印染含有羟基或含有氮的基质的方法,其中用如上文所描述的式(I)的化合物,它们的盐及其混合物进行染色或印染。
可以提到的优选的基质是皮革或纤维材料,其由天然的或合成的聚酰胺类和特别是天然的或再生的纤维素如棉,粘胶纤维或粘胶短纤维组成或含有这些物质。通常优选的基质是由棉组成或含有棉的纺织材料。
按照在活性染色领域中所有通常的染色和印染方法,以染浴或印染浆的形式使用式(I)的化合物,它们的盐或其混合物。优选通过从含水介质的尽染法实现染色,并且温度范围为30-80℃,更优选50-60℃,和盐的含量从10-80g/l,优选10-50g/l,更优选10-30g/l。优选液体与物品的比(这里指,液体与基质的比)从4∶1至30∶1,更优选6∶1至20∶1。
本发明的再一目的是提供上文所定义的化合物,它们的盐或其混合物在染色或印染如上所述基质方面的用途。
本发明的化合物及其盐与已知的纤维活性染料具有良好的混溶性。因此,本发明的化合物,它们的盐或其混合物可以单独用于染色或印染方法中,或在包括其它同类活性染料的染色或印染组合物的混合物中作为一个组份,也就是,该方法的活性染料具有类似的染色性能,例如牢度性和从染浴到基质上的尽染能力程度。特别是本发明的染料可以以适当比例与具有相同或其它相当的活性基团的某些合适的黄色和兰色染料一起用于三色染浴,以产生宽范围的色调。得到的拼色染色物或印花布所具有的牢度性能与那些使用本发明的单个染料制成的染色物或印花布相差不大。
当用作染料时,式(I)的化合物,它们的盐或其混合物提供良好的尽染率和固色率。另外,容易从基质上洗掉任何不固定的染料。形成的染色物和印花布显示良好的耐光性和耐湿性如耐洗,耐水,耐海水和耐汗性。它们还显示良好的耐氧化剂的性能如耐氯化的水、耐次氯酸盐漂白剂、耐过氧化物漂白剂和耐含过硼酸盐洗涤剂。
式(I)的化合物,它们的盐或其混合物还可以用于制备尤其适于喷墨工艺的印刷油墨。
下面的各实施例将说明本发明。在各实施例中,除相反地指明外,所有的份和百分含量都用重量表示,所有的温度用摄氏度。
实施例1
将96份2-氨基萘-3,6,8-三磺酸放入500份水中,并用盐酸调节pH值为0.5。在用冰冷却的条件下,加入亚硝酸钠并得到重氮盐溶液。加入56份2-氨基萘-7-磺酸,并在偶联过程中用碳酸钠溶液保持pH值在3-4。在第一次偶联反应结束后,往得到的溶液中加入20份亚硝酸钠,然后将该溶液加入到冰水混合物中,用100份30%的盐酸将其酸化。在重氮反应结束后,加入27份间-甲苯胺用于偶联,并用碳酸钠溶液保持pH值在3-4。把pH值提高到5-6后,加入36份2,4,6-三氟嘧啶,并在温度50-60℃用碳酸钠溶液保持pH值在该值不变。在反应结束,将所得到的染料盐析、过滤并在50℃真空下干燥。在其游离酸的形式中,染料相应的结构式如下
并且将棉染成具有良好耐湿性的红褐色。特别要提到的是在用氙灯照射后的耐光性。
实施例2-30
表1公开了按照类似于实施例1所描述的方法并使用相应起始原料形成的几种染料。就一切情况而论,所得到的染料将棉布染色或印染成褐色,并且所得到的染色物和印花布显示良好的耐光性和耐湿性,和氧化稳定性。
表1
应用实施例A
将0.3份实施例1的染料溶解在100份软化水中并加入3g芒硝(煅烧的)。将染浴加热到50℃,然后加入100份棉织物(漂白的)。在50℃30分钟后,将0.4份碳酸钠(煅烧的)加入到浴中。在加入碳酸钠的过程中保持温度50℃。接着将染浴加热到60℃,在60℃进一步染色1小时。然后用流动的冷水漂洗染色的织物3分钟,然后,用流动的热水进一步漂洗3分钟。在有0.25份橄榄油皂的500份沸腾的软化水中,将染色物煮洗15分钟。当用流动的热水漂洗(3分钟)和离心后,在约70℃的干燥柜中干燥染色物。所得到的褐色棉染色物显示良好的牢度性能,特别是高度的耐湿性,它具有氧化稳定性。
应用实施例B
将10份棉织物(漂白的)加入到含有100份软化水和3g芒硝(煅烧的)的染浴中。在10分钟内将染浴加热到50℃,并加入0.5份实施例1染料。在50℃30分钟后,将1份碳酸钠(煅烧的)加入到浴中。然后将染浴加热到60℃,并且在60℃继续进一步染色45分钟。按照应用实施例A的方法用流动的冷水漂洗和然后用流动的热水漂洗,和在沸水中煮洗染色织物。漂洗和干燥后所得到的褐色棉染色物的牢度性能与应用实施例A中所显示的相同。
类似地,按照应用实施例A或B中描述的方法,使用实施例2-30的染料或各例示染料的混合物染棉品。因此得到的棉染色物是褐色的并显示良好的牢度性能。
应用实施例C
按照常规的印染方法将由下列成份组成的印染浆印到棉织物
40份 实施例1的染料
100份 尿素
350份 水
500份 4%藻酸钠增稠剂和
10份 碳酸氢钠
1000份 总计上。将印染的织物在102-104℃的蒸汽中干燥和固定4-8分钟。按照应用实施例A的方法,用冷水漂洗和然后用热水漂洗,在沸水中煮洗织物并干燥。所得到的褐色印花布通常具有良好的牢度性能。
类似地,按照应用实施例C中所给的方法,使用实施例2-30的染料或各例示染料的混合物印染棉制品。得到的所有印花布是褐色的并显示良好的牢度性能。
应用实施例D
于60℃,将3份实施例1的染料溶解在83份软化水和15份二甘醇中。冷却到室温后可以得到褐色的印刷油墨,按照喷墨工艺该油墨尤其适于印刷纸或由棉组成的纺织材料。
类似地,按照应用实施例D所给的方法,可将实施例2-30的染料或各例示染料的混合物用于制备印刷油墨。
Claims (6)
1.按照式(I)的化合物或它们的盐,
其中
R1和R3代表氢或甲基,
R2和R4代表氢,甲基或甲氧基,和
R5代表氢或C1-4烷基。
2.按照权利要求1具有式(Ia)的化合物,
4.一种染色和印染含有羟基或含有氮的有机基质的方法,其中可以用权利要求1所描述的式(I)的化合物,它们的盐或其混合物进行染色或印染。
5.权利要求1的式(I)的化合物、它们的盐或其混合物的用途,用于染色或印染由棉组成或含有棉的纺织材料。
6.权利要求1的式(I)的化合物、它们的盐或其混合物的用途,用于染色或印染含有羟基或含有氮的有机基质或制备适于喷墨工艺的印刷油墨。
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GB9710611.6 | 1997-05-23 | ||
GBGB9710611.6A GB9710611D0 (en) | 1997-05-23 | 1997-05-23 | New disazo dyestuffs |
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JP (1) | JP2002500688A (zh) |
KR (1) | KR100539284B1 (zh) |
CN (1) | CN1149265C (zh) |
BR (1) | BR9809675A (zh) |
DE (1) | DE69810765T2 (zh) |
ES (1) | ES2189162T3 (zh) |
GB (1) | GB9710611D0 (zh) |
HK (1) | HK1026221A1 (zh) |
ID (1) | ID22680A (zh) |
TR (1) | TR199902699T2 (zh) |
TW (1) | TW459021B (zh) |
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ZA (1) | ZA984331B (zh) |
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US6084077A (en) * | 1997-05-23 | 2000-07-04 | Clariant Fianance (Bvi) Limited | Disazo dyestuffs |
US20030060608A1 (en) * | 2000-03-28 | 2003-03-27 | Ludwig Hasemann | Composition for printing recording materials |
JP2005513189A (ja) | 2001-12-19 | 2005-05-12 | クラリアント インターナショナル リミティド | 記録材料印刷のための色素の使用 |
JP5153436B2 (ja) | 2008-02-13 | 2013-02-27 | 日東電工株式会社 | 耐水性偏光膜の製造方法 |
ES2695152T3 (es) * | 2012-06-18 | 2019-01-02 | Dystar Colours Distrib Gmbh | Tintes reactivos, proceso para la producción de los mismos y su uso |
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DE3122425A1 (de) * | 1981-06-05 | 1982-12-23 | Bayer Ag, 5090 Leverkusen | Faserreaktive disazofarbstoffe, ihre herstellung und verwendung |
DE3426008A1 (de) * | 1984-07-14 | 1986-01-23 | Bayer Ag, 5090 Leverkusen | Reaktivfarbstoffe |
BR9303266A (pt) * | 1992-08-14 | 1994-03-08 | Sandoz Ag | Compostos e seus sais ou misturas de fais compostos ou sais,processos para sua preparacao,e processo para tingimento ou estampagem de um substrato organico |
GB9509159D0 (en) * | 1995-05-05 | 1995-06-28 | Sandoz Ltd | Organic compounds |
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1997
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- 1998-05-22 DE DE69810765T patent/DE69810765T2/de not_active Expired - Fee Related
- 1998-05-22 CN CNB98804790XA patent/CN1149265C/zh not_active Expired - Fee Related
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ES2189162T3 (es) | 2003-07-01 |
KR100539284B1 (ko) | 2005-12-28 |
KR20010012853A (ko) | 2001-02-26 |
DE69810765D1 (de) | 2003-02-20 |
TW459021B (en) | 2001-10-11 |
HK1026221A1 (en) | 2000-12-08 |
EP0983321A1 (en) | 2000-03-08 |
TR199902699T2 (xx) | 2000-09-21 |
JP2002500688A (ja) | 2002-01-08 |
EP0983321B1 (en) | 2003-01-15 |
CN1255153A (zh) | 2000-05-31 |
DE69810765T2 (de) | 2003-09-25 |
ID22680A (id) | 1999-12-09 |
WO1998053009A1 (en) | 1998-11-26 |
GB9710611D0 (en) | 1997-07-16 |
BR9809675A (pt) | 2000-07-11 |
ZA984331B (en) | 1999-11-22 |
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