CN102076779A - 酸性染料的用途 - Google Patents

酸性染料的用途 Download PDF

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CN102076779A
CN102076779A CN2009801247511A CN200980124751A CN102076779A CN 102076779 A CN102076779 A CN 102076779A CN 2009801247511 A CN2009801247511 A CN 2009801247511A CN 200980124751 A CN200980124751 A CN 200980124751A CN 102076779 A CN102076779 A CN 102076779A
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CN102076779B (zh
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R·努赛
U·盖吉尔
L·哈塞曼
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Abstract

通式(I)的酸性染料用于染色有机基底，其中各取代基具有权利要求所述的含义。

Description

酸性染料的用途
本发明涉及酸性染料的新用途，其制备方法及其用于染色有机基底的用途。
酸性染料是已知的，带有桥联结构单元的染料也是已知的。令人惊讶地发现，用于本体染色聚合物纤维，特别是聚酰胺纤维的特定酸性染料，能够用于在水性介质中染色纺织品纤维。这些聚酰胺纤维可以是人造聚酰胺纤维(所有的尼龙类型)或天然的聚酰胺纤维，如羊毛或真丝。
本发明涉及通式(I)化合物的用途，
Figure BDA0000041295440000011
其中
R0表示取代的C1-C4烷基或未取代的C1-C4烷基；
R1表示H，取代的C1-C4烷基或未取代的C1-C4烷基，磺酸基，-CO-NH-(C1-C4烷基)或CN；
R2表示H，或未取代的C1-C4烷基；
R3表示H，磺酸基，取代的C1-C4烷基或未取代的C1-C4烷基，取代的C1-C4烷氧基或未取代的C1-C4烷氧基；
R4表示H，取代的C1-C4烷基或未取代的C1-C4烷基，取代的C1-C4烷氧基或未取代的C1-C4烷氧基；
用于在水性介质中染色或印刷由天然或合成聚酰胺构成的纤维材料。
优选的式(I)化合物具有至少一个阴离子型取代基，更优选1或2或3个阴离子型取代基，其中2个阴离子型取代基是特别优选的。
式(I)化合物的至少一个阴离子型取代基优选位于取代基R1和/或R3之一中。优选位于取代基之一中也可以意味着该取代基是阴离子基团。
优选的阴离子型取代基是羧基和/或磺酸基，并且磺酸基是特别优选的。
取代的C1-C4烷基的优选的取代基选自以下取代基：-OH，-O(C1-C4烷基)，-SO3H，-COOH，-NH(C1-C4烷基)。取代的C1-C4烷基的更优选的取代基选自以下取代基：-OH，-O(C1-C4烷基)，-SO3H，-COOH，-NH(C1-C4烷基)。烷基基团是支链或直链的。最优选的烷基是甲基、乙基、丙基、异丙基、丁基、异丁基(2-甲基丙基)、戊基、异戊基(3-甲基丁基)、己基、庚基、辛基、或壬基。
取代的C1-C4烷氧基的优选的取代基选自以下取代基：-OH，-O(C1-C4烷基)，-SO3H，-COOH，-NH(C1-C4烷基)。烷氧基基团是支链或直链的。
取代的芳基的优选的取代基选自以下取代基：-OH，-O(C1-C4烷基)，-SO3H，取代的C1-C4烷基，未取代的烷基，取代的C1-C4烷氧基和未取代的C1-C4烷氧基。
在优选的通式(I)化合物中，
R0表示未取代的C1-C2烷基；
R1表示取代的C1-C2烷基或未取代的C1-C2烷基，磺酸基，
-CO-NH-(C1-C2烷基)或CN；
R2表示未取代的C1-C3烷基；
R3表示H，磺酸基，未取代的C1-C2烷基，未取代的C1-C2烷氧基；
R4表示H，未取代的C1-C2烷基，未取代的C1-C2烷氧基。
在更优选的通式(I)化合物中，
R0表示甲基；
R1表示-CH2-SO3H或-CN；
R2表示乙基；
R3表示H，甲基，甲氧基或磺酸基；
R4表示H，甲基或甲氧基。
在最优选的通式(I)化合物中，
R0表示甲基；
R1表示-CH2-SO3H；
R2表示乙基；
R3表示H，甲基；
R4表示H，甲基或甲氧基，优选H。
优选地，通式(I)化合物具有式(I’)
Figure BDA0000041295440000031
其中各取代基具有如上所述的含义。
本发明还提供了制备式(I)化合物的方法。根据本发明的式(I)化合物可在常规条件下通过常规方法制得。
在这些方法中，使由文献已知的式(II)化合物的两个胺官能团以常规方式重氮化，
Figure BDA0000041295440000032
并偶联到共两当量的式(III)化合物上，
其中各取代基如上定义。
在这些方法中，将特定的二胺冷却至0-10℃或优选0-5℃，并通过加入亚硝基硫酸或亚硝酸钠重氮化。随后，可以使双重氮化的二胺与化合物(III)反应，优选在水溶液中。
式(I)的染料可通过常规方法从反应介质中分离，例如通过用碱金属盐盐析，过滤并干燥，适当的话，在降低的压力下并在升高的温度下。
取决于反应和/或分离条件，式(I)的染料可以游离酸、盐或复盐的形式获得，其包含例如一种或多种阳离子，所述阳离子选自碱金属离子(例如钠离子)，或铵离子或烷基铵阳离子(例如单、二或三甲基或乙基铵阳离子)。染料可通过常规技术由游离酸转化为盐或复盐，反之亦然，或者由一种盐形式转化为另一种。如果需要的话，染料可通过渗滤进一步纯化，在该情况下，将不期望的盐和合成副产物从粗制阴离子染料中分离。
借助半透膜通过施加压力来去除不期望的盐和合成副产物，并且从粗制染料溶液中部分去除水，由此得到不含不期望的盐和合成副产物的溶液形式的染料，如果必要，以常规手段得到固体形式的染料。
式(I)的染料及其盐特别适用于将由天然或合成聚酰胺构成的纤维材料染色或印刷成黄色至绿黄色调。式(I)的染料及其盐适于生产喷墨印刷油墨，并适于使用这些喷墨印刷油墨印刷由天然或合成聚酰胺或纤维素(例如纸张)构成的纤维材料。
因此，本发明另一方面提供了式(I)的染料、其盐和混合物的用途，用于染色和/或印刷由天然或合成聚酰胺构成的纤维材料。另一方面是生产喷墨印刷油墨及其用于印刷由天然或合成聚酰胺构成的纤维材料的用途。
按照已知的方法实施在水性介质中或来自水性介质的染色，参见例如Ullmanns
Figure BDA0000041295440000051
der technischen Chemie，第4版，1982，22卷，658-673页或者M.Peter与H.K.Rouette的著作Grundlagen derTextilveredlung，第13版，1989，535-556和566-574页中描述的染色方法。优选的是用吸尽法，在30-140℃，更优选80-120℃，最优选80-100℃温度下，并且在3∶1至40∶1的范围内的液体比例下进行染色。
因此本发明还提供了在水性介质中染色或印刷由天然或合成聚酰胺构成的纤维材料的方法，该方法包括以下步骤：提供一个由天然或合成聚酰胺构成的基底，提供一种或多种全部取代基如上定义的式(I)化合物、其盐或它们的混合物，用所述一种或多种化合物、其盐或它们的混合物染色或印刷或喷墨印刷所述基底。
要染色的基底可以例如以纱线、纺织品、成圈编织品或地毯的形式存在。在纤细基底上的成衣染色甚至有永固的可能性，基底的例子为羔羊毛、开司米、羊驼绒和马海毛。本发明的染料特别适用于染色细旦尼尔纤维(微纤维)。
根据本发明的染料及其盐与已知的酸性染料高度相容。因而，式(I)的染料及其盐或混合物可以单独用于染色或印刷工艺，或另外地与其它同类酸性染料，即与具有类似染色性质(如例如色牢度和从染色浴到基底上的吸尽速率)的染料一起用作拼色染色或印刷组合物中的组分。本发明的染料尤其可以与具有合适发色团的特定的其它染料共同使用。染料在拼色染色或印刷组合物中的比例由要得到的色度决定。
上述式(I)的染料，非常适用于将从水性介质中得到的天然或合成聚酰胺染色，例如羊毛、真丝和所有的尼龙类型，在其上的染色具有高色牢度水平，尤其是良好的耐光色牢度和良好的耐湿色牢度(洗涤，碱性汗蚀)。式(I)的染料及其盐具有高吸尽速率。式(I)的染料及其盐的积聚能力同样很好。在确定基底上的同色染色具有优良品质。所有染色在人造光下还具有恒定的色度。此外，对汽蒸和沸煮的色牢度也很好。
式(I)染料的一个重要优点是不含金属，并提供均匀染色。
根据本发明的化合物可用作单独的染料，或者另外地，由于其良好的相容性，用作与其它具有类似染色性质(例如在通用色牢度，吸尽值等方面)的同类染料的组合元素。所得的拼色染色与使用单独染料的染色具有相似的色牢度。
本发明式(I)的染料还可以用作三原色染色或印刷中的黄色组分。三原色染色或印刷可以使用所有常规的和公知的染色和印刷方法，例如连续法、吸尽法、泡沫染色法和喷墨法。
在本发明方法中所用的三原色染料组合物中，单个染料成分的组成取决于想要的色彩。例如棕色优选使用20-40％重量的黄色组分，40-60％重量的本发明橙色或红色组分，和10-20％重量的蓝色组分。
如上所述的黄色组分，可由单一组分或依照式(I)的不同橙色的单独成分混合物组成。优选使用二重和三重组合。
特别优选的红色和/或蓝色成分分别描述于WO2002/46318或WO99/51681中。
在以下实施例中，份数和百分数以重量计，温度为摄氏度。
实施例1
将24.8份(0.1mol)3，3’-二氨基-二苯砜，在0-5℃下，在200份水和60份盐酸(约30％)中，用13.8份(0.2mol)亚硝酸钠，按照常规方法双偶氮化。将溶于250份水中的49.4份(0.2mol)下式化合物
Figure BDA0000041295440000061
在30分钟期间内加入冰冷的双偶氮化溶液。通过添加30％NaOH溶液
将pH调至3-4.5，得到下式的染料
Figure BDA0000041295440000071
该染料可通过用氯化钠盐析而分离，过滤并在50℃下减压干燥，或者反应混合物可直接用于染色，而无需分离产品。在羊毛上和特别是在聚酰胺纤维上，其产生具有非常好的耐光色牢度和耐湿色牢度的黄色染色品(λmax＝445nm)。
实施例2-4
下表1包含类似于实施例1所述的方法通过使用相应的原料可制备的染料。这些染料提供在聚酰胺纤维和羊毛上具有非常好的耐光色牢度和耐湿色牢度的黄色染色品。λmax以nm表示(纳米，在1％乙酸溶液中测得)。
表1
Figure BDA0000041295440000081
Figure BDA0000041295440000082
应用实施例A
向由2000份水、1份弱阳离子活性匀染剂(基于乙氧基化的氨基丙基脂肪酸酰胺且对染料有亲和性)、0.25份制备实施例2的染料组成的并用1-2份40％乙酸调节至pH 5的40℃的染料浴投入100份尼龙-6织物。在40℃下10分钟后，将染料浴以每分钟1℃的速率加热至98℃，然后保持沸腾45-60分钟。之后在15分钟期间内将其冷却至70℃。将染色品从浴中取出，先用热水后用冷水漂洗并干燥。得到的结果是具有良好耐光色牢度和耐湿色牢度的黄色聚酰胺染色品。
应用实施例B
向由2000份水、1份弱阳离子活性匀染剂(基于乙氧基化的氨基丙基脂肪酸酰胺且对染料有亲和性)、0.3份制备实施例2的染料组成的并用1-2份40％乙酸调至pH 5.5的40℃的染料浴投100份尼龙-6，6织物。在40℃下10分钟后，将染料浴以每分钟1.5℃的速率加热至120℃，然后在该温度下保持15-25分钟。之后在25分钟期间内将其冷却至70℃。将染色品从染料浴中取出，先用热水后用冷水漂洗并干燥。得到的结果是匀染性良好并具有良好耐光色牢度和耐湿色牢度的黄色聚酰胺染色品。
应用实施例C
向由4000份水、1份弱两性匀染剂(基于硫酸化、乙氧基化的脂肪酸酰胺且对染料有亲和性)、0.4份制备实施例2的染料组成的并用1-2份40％乙酸调至pH 5的40℃的染料浴投入100份羊毛织物。在40℃下10分钟后，将染料浴以每分钟1℃的速率加热至沸腾，之后保持沸腾40-60分钟。之后在20分钟期间内将其冷却至70℃。将染色品从染料浴中取出，先用热水后用冷水漂洗并干燥。得到的结果是具有良好耐光色牢度和耐湿色牢度的黄色羊毛染色品。
应用实施例D
将100份尼龙-6纺织材料用50℃的液体轧染，该液体组成为
40份制备实施例2的染料，
100份脲，
20份基于丁基二乙二醇的非离子增溶剂，
15-20份乙酸(以调节pH至4)，
10份基于乙氧基化的氨基丙基脂肪酸酰胺的弱阳离子
活性匀染剂，且对染料有亲和性，
810-815份水(以组成1000份轧染液)。
将这样浸渍的材料卷起并在饱和蒸汽条件下在85-98℃下置于汽蒸室中固色3-6小时。然后将染色品用热水和冷水漂洗并干燥。得到的结果是具有良好的本体匀染性和良好的耐光色牢度和耐湿色牢度的黄色尼龙染色品。
应用实施例E
将由尼龙-6构成的且具有合成纤维基布的纺织割绒片材用液体轧染，该液体含有每1000份
1份制备实施例2的染料，
4份基于角豆粉醚的可商购的增稠剂
2份高级烷基酚的非离子环氧乙烷加合物，
1份60％乙酸。
随后用浆料印刷，该浆料每1000份包含以下组分：
20份可商购的烷氧基化的脂肪烷基胺(置换产品)，
20份基于角豆粉醚的可商购的增稠剂。
将印刷品在100℃下在饱和蒸汽中固色6分钟，漂洗并干燥。得到的结果是具有黄白图案的均匀着色的覆盖材料。
应用实施例F
向由2000份水、1份弱阳离子活性匀染剂(基于乙氧基化的氨基丙基脂肪酸酰胺且对染料有亲和性)、1.5份实施例2的染料、0.2份专利申请WO2002/46318的制备实施例8的红色染料：
Figure BDA0000041295440000101
和0.5份专利申请WO99/51681和EP1066340B1的制备实施例46的蓝色染料：
Figure BDA0000041295440000111
组成的并用1-2份40％乙酸调至pH 5的40℃的染料浴投入100份尼龙-6，6织物。在40℃下10分钟后，将染料浴以每分钟1℃的速率加热至98℃，然后保持沸腾45-60分钟。之后在15分钟期间内冷却至70℃。将染色品从染料浴中取出，先用热水后用冷水漂洗并干燥。得到的结果是具有良好耐光色牢度和耐湿色牢度的均匀灰色的聚酰胺染色品。
应用实施例G
将100份经铬鞣的且经综合复鞣的湿刮粒面皮革，在300份水和2份制备实施例2的染料的浴中在55℃下染色30分钟。在加入4份60％的亚硫酸化鱼油乳液后，将皮革加脂45分钟。然后用8.5％的甲酸酸化并研磨10分钟(浴中最终pH为3.5-4.0)。然后将皮革漂洗、滴干并以常规方式整理。得到的结果是以良好色牢度染色为均匀亮橙色的皮革。
应用实施例A至G也可用染料1，3和4实施，得到相似的结果。
应用实施例H
将3份制备实施例3的染料在60℃下溶于82份去离子水和15份二甘醇。冷却至室温得到橙色印刷油墨，其非常适用于在纸张或聚酰胺和羊毛纺织品上进行喷墨印刷。
应用实施例H也可用染料1，3和4实施，得到相似的结果。
应用实施例I
将由1000份水，80份煅烧芒硝，1份硝基苯-3-磺酸钠和1份实施例2的染料组成的染料浴在10分钟内加热至80℃。然后，加入100份丝光棉。之后，在80℃染色5分钟，然后在15分钟内加热至95℃。在95℃下10分钟后，在95℃下加入3份碳酸钠，接着在20分钟后再加入7份碳酸钠，并且在30分钟后加入另外10份碳酸钠。随后，在95℃下继续染色60分钟。然后，从染料浴中取出染色品并在流动的去离子水中漂洗3分钟。之后洗涤两次：每次用5000份沸腾的去离子水洗涤10分钟，随后在60℃下在流动的去离子水中漂洗3分钟，并用冷自来水漂洗1分钟。干燥后得到具有良好色牢度的亮黄色棉染色品。
应用实施例J
将0.2份制备实施例2的染料溶于100份热水，将溶液冷却至室温。将该溶液加入100份化学漂白亚硫酸盐纸浆中，该纸浆在荷兰式打浆机中在2000份水中打浆。混合15分钟后，以常规方式用树脂胶料和硫酸铝对浆料上胶。由该浆料得到的纸张具有色牢度良好的黄色。
应用实施例I和J也可用染料1，3和4实施，得到相似的结果。

Claims (5)

1.通式(I)化合物的用途，
Figure FDA0000041295430000011
其中
R0表示取代的C1-C4烷基或未取代的C1-C4烷基；
R1表示H，取代的C1-C4烷基或未取代的C1-C4烷基，磺酸基，-CO-NH-(C1-C4烷基)或CN；
R2表示H，或未取代的C1-C4烷基；
R3表示H，磺酸基，取代的C1-C4烷基或未取代的C1-C4烷基，取代的C1-C4烷氧基或未取代的C1-C4烷氧基；
R4表示H，取代的C1-C4烷基或未取代的C1-C4烷基，取代的C1-C4烷氧基或未取代的C1-C4烷氧基；
用于在水性介质中染色或印刷由天然或合成聚酰胺构成的纤维材料。
2.权利要求1所述的化合物，其特征在于，式(I)化合物具有至少一个阴离子型取代基。
3.权利要求2所述的用途，其特征在于，
R0表示未取代的C1-C2烷基；
R1表示取代的C1-C2烷基或未取代的C1-C2烷基，磺酸基，-CO-NH-(C1-C2烷基)或CN；
R2表示未取代的C1-C3烷基；
R3表示H，磺酸基，未取代的C1-C2烷基，未取代的C1-C2烷氧基；
R4表示H，未取代的C1-C2烷基，未取代的C1-C2烷氧基。
4.权利要求3所述的化合物，其特征在于，
R0表示甲基；
R1表示-CH2-SO3H或-CN；
R2表示乙基；
R3表示H，甲基，甲氧基或磺酸基；
R4表示H，甲基或甲氧基。
5.可通过如下反应得到的权利要求1所述式(I)的用途：
使式(II)化合物的两个胺官能团重氮化，
Figure FDA0000041295430000021
并偶联到共两当量的式(III)化合物上，
其中各取代基如上定义。
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CN104629401A (zh) * 2014-12-30 2015-05-20 南京工业大学 一种双偶氮分散染料及其制备方法和用途
CN104629401B (zh) * 2014-12-30 2017-03-29 南京工业大学 一种双偶氮分散染料及其制备方法和用途
CN116023795A (zh) * 2022-12-22 2023-04-28 苏州科法曼化学有限公司 一种染料化合物及其制备方法

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JP2015038264A (ja) 2015-02-26
BRPI0914939B1 (pt) 2018-06-19
KR101760661B1 (ko) 2017-07-24
JP2011526636A (ja) 2011-10-13
EP2307509A1 (en) 2011-04-13
KR101649484B1 (ko) 2016-08-19
BRPI0913833B1 (pt) 2018-06-12
ES2383580T3 (es) 2012-06-22
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EP2307509B1 (en) 2012-02-29
BRPI0913833A2 (pt) 2015-10-20
KR20110039542A (ko) 2011-04-19
WO2010000779A1 (en) 2010-01-07
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