CN101287803B - 铬络合物染料 - Google Patents
铬络合物染料 Download PDFInfo
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- CN101287803B CN101287803B CN2006800266494A CN200680026649A CN101287803B CN 101287803 B CN101287803 B CN 101287803B CN 2006800266494 A CN2006800266494 A CN 2006800266494A CN 200680026649 A CN200680026649 A CN 200680026649A CN 101287803 B CN101287803 B CN 101287803B
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- 239000000975 dye Substances 0.000 title claims abstract description 32
- 229910052804 chromium Inorganic materials 0.000 title claims abstract description 17
- 239000011651 chromium Substances 0.000 title claims abstract description 17
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 17
- 238000004043 dyeing Methods 0.000 claims abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000007639 printing Methods 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052728 basic metal Inorganic materials 0.000 claims description 3
- 150000003818 basic metals Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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- 238000002360 preparation method Methods 0.000 abstract description 3
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- 125000001424 substituent group Chemical group 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 alkali metal acetate Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
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- 210000002268 wool Anatomy 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
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- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 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 2
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- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 2
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 230000000176 photostabilization Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000006424 Flood reaction Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical group [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
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- 239000004753 textile Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
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- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
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- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
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- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
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- 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
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Abstract
本发明涉及新型1∶2铬络合物染料、其制备方法及其在染色或印刷包含羟基或包含氮的纤维材料中的用途。本发明涉及一种式(I)的1∶2铬络合物染料、其制备及其在染色或印刷包含羟基或包含氮的纤维材料中的用途，其中所有的取代基如权利要求书所定义。
Description
本发明涉及新型1∶2铬络合物染料、其制备方法及其在染色或印刷包含羟基或包含氮的纤维材料中的用途。
本发明涉及一种式(I)的1∶2铬络合物染料及其混合物和/或其盐：
其中
R1为H、Cl、Br或-NO2；
R2为H、Cl、Br、-NO2、-SO2NH2或-SO3H；
R3为O(CH2)nOR4或(CH2)nOR4；
R4为H、直链C1-4烷基、支链C3-4烷基或-SO3H；
n为1、2、3或4；和
Ka+为阳离子。
所述直链或支链烷基可被取代或未被取代。合适的取代基可例如为羟基、卤素例如Cl或Br或磺基。
在优选的式(I)化合物中，R4为H、C1-3烷基或-SO3H，n为1、2、3或4，优选R4为H或C1-3烷基，n为1、2、3或4。
在优选的式(I)化合物中，R3在氮原子的对位。
在优选的式(I)化合物中，R1独立表示H或NO2，优选R1表示NO2。
在优选的式(I)化合物中，R2独立表示NO2或SO2NH2，优选R2表示NO2。
在更优选的式(I)化合物中，R4为H、CH3或CH2CH3，n为2、3或4。
在更优选的式(I)化合物中，R4为H，n为2。
合适的阳离子K为碱金属、碱土金属、铵、链烷醇铵或烷基铵阳离子。例如在一价阳离子的情况下，K还可为多于一种阳离子。相应的阳离子的实例有钠、锂或铵阳离子或单-、二-或三乙醇铵阳离子。
本发明的其他实施方案为一种制备式(I)化合物的方法，所述方法包括使式(II)的偶氮化合物
与式(III)的1∶1铬络合物反应，
其中R1、R2、R3和R4如上定义。
式(II)的偶氮化合物与式(III)的1∶1铬络合物的反应例如在含水介质中，在例如40℃-130℃，特别是70℃-100℃下，在pH例如为8-14，特别是pH为10-13下进行。所述反应最好在中和无机酸的试剂或碱性试剂存在下，例如在碱金属碳酸盐、碱金属乙酸盐或碱金属氢氧化物存在下进行，优选钠作为碱金属。
式(II)和(III)的化合物为已知的或可通过与已知方法类似的方法制得。
式(II)化合物可通过常规的重氮化和偶合反应制得。重氮化通常通过亚硝酸在无机酸水溶液中，于低温，例如0℃-20℃下进行，偶合最好进行在碱性pH，例如pH为8-12下进行。
式(III)的1∶1铬络合物可因此根据常规的镀铬方法制得，其中所述反应可使用铬盐例如在含水介质中、适当的情况下在加压下、在例如90℃-130℃下进行。铬盐例如为乙酸铬(III)、硝酸铬(III)、氯化铬(III)、水杨酸铬(III)或特别是硫酸铬(III)。
本发明的其他实施方案为一种染色或印刷包含羟基或包含氮的纤维材料的方法。
纤维材料优选为天然存在的聚酰胺纤维材料(例如丝或特别是羊毛)或合成的聚酰胺纤维材料(例如聚酰胺6或聚酰胺6，6或含羊毛或含聚酰胺的混纺织物)。合成的聚酰胺纤维材料为本文特别感兴趣的。
上述纤维材料可为多种加工形式，例如为纤维、纱、织造织物或针织织物形式，特别是地毯形式。
染色或印刷可在常规的染色或印刷设备中进行。染液或印浆可包含其他添加剂，例如润湿剂、消泡剂、流平剂或影响纺织品性能的试剂例如软化剂、提供阻燃整饰或防污、防水和防油试剂的添加剂以及水-软化剂和天然存在或合成的增稠剂例如藻酸盐和纤维素醚。
在优选的印刷法中，使用扎染法，例如扎染-汽蒸、扎染-热固化、扎染-干燥、扎染-分批、扎染-筛分和扎染-辊卷。或者可使用喷墨法进行印刷。
本发明的式(I)的1∶2铬络合物染料得到具有良好综合性能的均匀染色。本发明的式(I)的1∶2铬络合物染料还适合用作染色混合物的组分。
以下实施例用于说明本发明。除非另外说明，否则百分比为重量百分比，温度为摄氏度。
实施例1a
将195份4-羟基-7-[(4-(2′-羟基乙氧基)苯基)氨基]-萘-2-磺酸溶解于600份水和45份30％的氢氧化钠溶液中。随后在25℃下加入50份脲。在30分钟内加入由99.5份2-氨基-4，6-二硝基-1-羟基苯和125体积份4N的亚硝酸钠溶液的混合物形成的重氮盐溶液(0-5℃，pH为1)。在偶合反应过程中，通过连续加入30％的氢氧化钠溶液使pH保持为9-10。反应结束时，将制得的产物盐析，吸滤。这样制得的化合物具有式1的结构。
将吸滤后仍潮湿的残余物加至4000份水、65份甲酸和125份硫酸铬(III)的混合物中，随后在130℃和2巴压力下搅拌5小时。反应完成后，通过常规的方法分离形成的1∶1-铬络合物，随后过滤。产物具有式2的结构。
实施例1b
于75-80℃和pH为8-9下，将149.3份通过常规的方法制得的具有式3结构的单偶氮化合物悬浮于3000份水中。
搅拌下，向该混合物中加入318份通过实施例1a的方法制得的具有式(2)结构的1∶1铬络合物。
这时通过加入30％的氢氧化钠溶液使pH保持为10。反应完成后，使用常规的方法将所得到的1∶2铬络合物盐析，过滤，随后于60℃下真空干燥。终产物与式(4)一致，
将羊毛和合成聚酰胺染成蓝色色调。这样得到的染色具有优异的耐光性和耐湿性。
实施例2-15
表1公开了根据与实施例1a-1b类似的方法，使用相应的原料形成的几种染料(式(5)的取代基)。在所有的情况下，制得的染料将羊毛和合成聚酰胺染成蓝色色调，且这样得到的染色具有优异的耐光性和耐湿性。
表1
| 实施例 | R1 | R2 | R3 |
| 2 | -NO2 | -NO2 | -CH2CH2OH |
| 3 | -NO2 | -SO2NH2 | -CH2OH |
| 4 | -H | -NO2 | -CH2CH2CH2OH |
| 5 | -H | -NO2 | -CH2CH2CH2CH2OH |
| 6 | -NO2 | -NO2 | -OCH2CH2OCH3 |
| 7 | -NO2 | -NO2 | -OCH2CH2OCH2CH3 |
| 8 | -NO2 | -SO2NH2 | -OCH2CH2OCH3 |
| 9 | -NO2 | -SO2NH2 | -OCH2CH2OCH2CH3 |
| 10 | -NO2 | -NO2 | -OCH2CH2OSO3H |
| 11 | -NO2 | -SO2NH2 | -OCH2CH2OH |
| 12 | -Cl | -NO2 | -OCH2CH2OH |
| 13 | -NO2 | -Cl | -OCH2CH2OH |
| 14 | -H | -Cl | -OCH2CH2OCH3 |
| 15 | -H | -NO2 | -OCH2CH2OCH2CH3 |
应用实施例A
于40℃下，将由2000份水、1份基于乙氧基化的氨基丙基脂肪酰胺且对染料具有亲和力的弱阳离子活性流平剂、1.5份实施例1的染料组成，并用0.5份40％的乙酸将pH调节至6的染浴加至100份尼龙-6织物中。于40℃下10分钟后，以1℃/分钟的速率将染浴加热至98℃，随后沸腾45-60分钟。接着在15分钟内冷却至70℃。将染色物从染浴中移开，依次用热水和冷水漂洗，随后干燥。结果是得到具有非常高耐光性的灰色聚酰胺。
应用实施例B
于40℃下，将由4000份水，1份基于硫酸化的乙氧基化的氨基丙基脂肪酰胺且对染料具有亲和力的弱两性流平剂、2份实施例1的染料组成，并用0.5份40％的乙酸将pH调节至6的染浴加至100份羊毛织物中。于40℃下10分钟后，以1℃/分钟的速率将染浴加热至沸腾，持续沸腾45-60分钟。接着在20分钟内冷却至70℃。将染色物从染浴中移开，依次用热水和冷水漂洗，随后干燥。结果是得到具有非常高耐光性的灰色羊毛。
应用实施例C
使用50℃的由以下物质组成的染浴扎染100份织造尼龙-6材料：
40份实施例1的染料，
100份脲，
20份基于丁二醇的非离子增溶剂，
15-20份乙酸(将pH调节至4)，
10份基于乙氧基化的氨基丙基脂肪酰胺且对染料具有亲和力的弱阳离子活性流平剂，和
810-815份水(组成1000份扎染液)。
将这样浸渍的材料卷起，随后在蒸汽室中在85-98℃饱和蒸汽条件下停留3-6小时以固色。接着依次用热水和冷水漂洗染色物，随后干燥。结果是得到具有良好均匀性和良好耐光性的灰色尼龙。
应用实施例D
用每1000份包含以下物质的染液扎染由尼龙-6组成且具有合成基础织物的纺织短切长毛绒片材料：
2份 实施例1的染料；
4份 市售的基于角豆粉醚的增稠剂；
2份 高级烷基酚的非离子环氧乙烷加成物；
1份 60％的乙酸。
随后使用每1000份包含以下组分的印浆印刷：
20份 市售的烷氧基化的脂肪烷基胺(置换产物)；
20份 市售的基于角豆粉醚的增稠剂。
在100℃饱和蒸汽中固定印刷6分钟，漂洗，随后干燥。结果是得到具有灰色和白色图案的均色覆盖材料。
Claims (7)
1.一种式(I)的1∶2铬络合物染料及其混合物和/或其盐
其中
R1为H、Cl、Br或-NO2；
R2为H、Cl、Br、-NO2、-SO2NH2或-SO3H；
R3为O(CH2)nOR4或(CH2)nOR4；
R4为H、直链C1-4烷基、支链C3-4烷基或-SO3H；
n为1、2、3或4；和
Ka+选自碱金属、碱土金属、铵、链烷醇铵和烷基铵阳离子。
2.权利要求1的式(I)的1∶2铬络合物染料及其混合物和/或其盐，其中R3在氮原子的对位，R4为H、CH3或CH2CH3，n为2、3或4。
3.权利要求1的式(I)的1∶2铬络合物染料，其中R1表示H或NO2，R2表示NO2或SO2NH2。
4.一种制备权利要求1、2或3的式(I)化合物的方法，其特征在于使式(II)的偶氮化合物
与式(III)的1∶1铬络合物反应，
其中R1、R2、R3和R4如上定义。
5.一种制备喷墨油墨的方法，所述方法包括使用权利要求1、2或3的染料或染料的混合物。
6.一种染色或印刷包含羟基或包含氮的纤维材料的方法，其中使用式(I)化合物、其盐或其混合物进行染色或印刷。
7.一种包含羟基或包含氮的纤维材料，其特征在于使用权利要求1、2或3中定义的化合物、其盐或其混合物染色或印刷所述纤维材料。
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| PCT/EP2006/064313 WO2007009966A2 (en) | 2005-07-21 | 2006-07-17 | Chromium complex dyes |
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| CN102516795B (zh) * | 2011-12-09 | 2014-04-02 | 青岛双桃精细化工（集团）有限公司 | 一种蓝色染料的制备方法 |
| US11905424B2 (en) | 2019-04-01 | 2024-02-20 | General Electric Company | Fabrication of chromium metal mixtures in the form of core-shell nanoparticles |
| KR20230049541A (ko) | 2021-10-06 | 2023-04-13 | 이승주 | 자동 차량 방향 전환장치 |
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| US4663441A (en) * | 1984-09-15 | 1987-05-05 | Basf Aktiengesellschaft | Asymmetric 1:2 chrome complex dye of a phenylazosulphonaphtholamine and a naphtholazosulphonaphthol |
| US6764524B1 (en) * | 1998-08-14 | 2004-07-20 | Clariant Finance (Bvi) Limited | 1:2 chromium complex dyes, their production and use |
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| CH452747A (de) * | 1965-07-09 | 1968-03-15 | Sandoz Ag | Verfahren zur Herstellung von 1:2-Metallkomplexfarbstoffen |
| FR1486227A (fr) * | 1965-07-09 | 1967-06-23 | Sandoz Sa | Colorants à complexe métallifère 1:2, leurs procédés de fabrication et leurs applications |
| CH573949A5 (zh) | 1972-06-28 | 1976-03-31 | Sandoz Ag | |
| CH616953A5 (zh) | 1975-08-27 | 1980-04-30 | Sandoz Ag | |
| CH649775A5 (de) | 1979-09-25 | 1985-06-14 | Sandoz Ag | Wasserloesliche, anionische chromkomplexe, deren herstellung und verwendung. |
| JPS59159855A (ja) * | 1983-03-03 | 1984-09-10 | バスフ アクチェン ゲゼルシャフト | スルホンアミド基及びアミノ基を含有しない金属錯化合物染料 |
| US5283325A (en) | 1984-04-27 | 1994-02-01 | Sandoz Ltd. | 1:2 chromium and cobalt complexes of monoazo compounds having further unsubstituted or substituted nitro-2-hydroxyphenyl diazo component radicals and 6- or 7-acyl-amino-1-hydroxy-3-sulfonaphthalene coupling component radicals |
| DE3514387C2 (de) | 1984-04-27 | 2003-12-24 | Clariant Finance Bvi Ltd | 1:2-Metallkomplex-azoverbindungen, ihre Herstellung und Verwendung |
| DE3805746C2 (de) | 1987-03-05 | 2003-04-10 | Clariant Finance Bvi Ltd | 1:2-Chromkomplexfarbstoffe |
| CH685119A5 (de) | 1992-06-24 | 1995-03-31 | Sandoz Ag | Asymmetrische 1:2-Metallkomplex-azoverbindungen. |
| EP0718374B1 (de) * | 1994-12-21 | 2002-03-06 | Ciba SC Holding AG | 1:2-Chromkomplexfarbstoffe enthaltende Farbstoffmischungen und 1:2 Chromkomplexfarbstoffe |
| GB9604816D0 (en) | 1996-03-07 | 1996-05-08 | Clariant Finance Bvi Ltd | Organic compounds |
| US5738013A (en) * | 1996-05-14 | 1998-04-14 | New England Science & Specialty Products, Inc. | Method of making a lithographic printing plate with an ink jet fluid material |
| WO1998054264A1 (de) | 1997-05-29 | 1998-12-03 | Clariant Finance (Bvi) Limited | 1:2-chromkomplexfarbstoffe, deren herstellung und verwendung |
| DE60214747T2 (de) * | 2001-10-17 | 2007-09-13 | Clariant Finance (Bvi) Ltd., Road Town | 1:2 metallkomplexfarbstoffe, deren zusammensetzungen, deren herstellung und deren verwendung |
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| US4663441A (en) * | 1984-09-15 | 1987-05-05 | Basf Aktiengesellschaft | Asymmetric 1:2 chrome complex dye of a phenylazosulphonaphtholamine and a naphtholazosulphonaphthol |
| US6764524B1 (en) * | 1998-08-14 | 2004-07-20 | Clariant Finance (Bvi) Limited | 1:2 chromium complex dyes, their production and use |
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| EP1910473A2 (en) | 2008-04-16 |
| KR101275439B1 (ko) | 2013-06-14 |
| CN101287803A (zh) | 2008-10-15 |
| BRPI0613688B8 (pt) | 2017-03-21 |
| KR20080028944A (ko) | 2008-04-02 |
| BRPI0613688B1 (pt) | 2016-10-18 |
| ATE431383T1 (de) | 2009-05-15 |
| TW200720367A (en) | 2007-06-01 |
| JP2009501823A (ja) | 2009-01-22 |
| JP5091134B2 (ja) | 2012-12-05 |
| US20090263630A1 (en) | 2009-10-22 |
| ES2326693T3 (es) | 2009-10-16 |
| WO2007009966A2 (en) | 2007-01-25 |
| WO2007009966A3 (en) | 2007-04-05 |
| MX2008000783A (es) | 2008-02-21 |
| ZA200710412B (en) | 2009-08-26 |
| PT1910473E (pt) | 2009-08-05 |
| BRPI0613688A2 (pt) | 2011-01-25 |
| DE602006006837D1 (en) | 2009-06-25 |
| US7906632B2 (en) | 2011-03-15 |
| EP1910473B1 (en) | 2009-05-13 |
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