CN108929558B - 一种分散大红染料化合物及其制备方法和应用 - Google Patents
一种分散大红染料化合物及其制备方法和应用 Download PDFInfo
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
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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
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
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- 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
- D06P3/28—Preparing azo dyes on the material
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- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/56—Preparing azo dyes on the material
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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
- D06P3/82—Textiles which contain different kinds of fibres
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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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
Abstract
Description
一、技术领域
本发明涉及一种分散大红染料化合物及其制备方法及其在疏水性纤维材料印染中的应用。
二、背景技术
现有的分散红染料中,很少有色光特别鲜艳的品种。尽管C.I.分散红153被行业内普遍认为其鲜艳度较好,但随着涤纶纤维及其混纺织物的发展,有必要拓展艳丽色光染料品种的多样性和丰富性。同时,除了满足常规聚酯织物染色的牢度要求外,还应适用于混纺织物特别是近年来快速发展的涤纶/氨纶混纺织物的印染需求,从而扩大染料的应用范围。
三、发明内容
本发明要解决的技术问题是提供一种分散大红染料化合物及其制备方法和在疏水性纤维材料印染中的应用,其色光艳丽且具有优异的耐水洗牢度和耐升华牢度。
下面对本发明所采用的技术方案做具体说明。
一方面,本发明提供了一种分散大红染料化合物,其结构如式(Ⅰ)所示:
上式中:
进一步,所述的烷基优选为C1-C4的烷基,如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基;更优选为甲基。
进一步,所述的烷氧基优选C1-C4的烷氧基,如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基;更优选为甲氧基或乙氧基。
进一步,所述的卤素优选为Cl或Br,更优选为Cl。
优选的,所述化合物为下列之一:
另一方面,本发明提供了一种所述分散大红染料化合物的制备方法,所述方法如下:
(1)将式(II)所示的化合物经重氮化反应,获得重氮盐;
(2)将步骤(1)得到的重氮盐与2-萘酚进行偶合反应,即得式(I)所示的分散大红染料化合物;
式(II)中,R的定义同式(I)。
本发明将式(II)所示的化合物用本领域人员所熟知的方式进行重氮化反应得到重氮盐,再与2-萘酚用本领域人员所熟知的方式进行偶合反应合成。
所述重氮化反应和偶合反应为本领域中常见反应,其常规反应条件亦适用于本发明化合物的制备,本发明中优选采用以下反应条件:
步骤(1)中,重氮化试剂为亚硝酰硫酸溶液,或者为盐酸或硫酸与亚硝酸钠的混合溶液;重氮化反应在0~15℃下进行,优选0~10℃;步骤(2)中偶合反应在0~15℃下进行,优选0~10℃。
由于染料行业的特殊性,很难也没有必要制成纯品,通常会带有一些制备过程中的杂质,本发明的分散染料制成成品时也允许含有少量的水份及微量的物理杂质。
对于行业内本领域普通技术人员,式(Ⅱ)的化合物是已知的,可通过已知方法由已知化合物制备,也可采用市售商品。
第三方面,本发明提供了所述分散大红染料化合物在疏水性纺织材料印染中的应用。
本发明所述分散大红染料化合物在应用时通常先制成分散染料制剂。本发明提供了一种分散染料制剂,包括一种以上式(Ⅰ)所示的分散大红染料化合物和助剂,分散大红染料化合物与助剂质量之比为1:0.2~5。所述的助剂为分散染料复配时常用的分散剂、扩散剂等,优选下列之一或其任意几种的混合物:萘磺酸甲醛缩合物、烷基萘磺酸甲醛缩合物、苄基萘磺酸甲醛缩合物、木质素磺酸盐等阴离子分散剂。具体地,萘磺酸甲醛缩合物如扩散剂NNO,烷基萘磺酸甲醛缩合物如分散剂MF(甲基萘磺酸甲醛缩合物),苄基萘磺酸甲醛缩合物如扩散剂CNF等,木质素磺酸盐如木质素磺酸钠(如市售分散剂Reax 83A、Reax 85A)等。所述分散染料制剂的配制方法为:分散大红染料化合物在助剂、水的存在下用砂磨机或研磨机等粉碎机进行微粒子化。本发明制得的分散染料制剂,可以微粒子化后的液态、乳膏态或者用喷雾干燥法等进行干燥后的粉状、颗粒状态供给染色。
根据本发明制成的分散染料制剂,可采用普通浸染法、轧染法进行染色,也可用于直接印花。其中,普通浸染法如将聚酯或其混纺织物进行预处理,放入染缸中进行浸染,染毕,冷水清洗至中性,绞干,再进行还原清洗,烘干;直接印花如将织物进行染前处理,烘干,定形,在印花机上印分散染料色浆,再进行蒸化,利用汽蒸方式使织物上的染料固色,最后水洗,拉幅定型。
本发明所述的分散大红染料化合物,也可与其它染料如分散红、分散橙、分散紫、分散黄、分散蓝等染料复配后应用于染色。
本发明的有益效果在于:本发明所述分散大红染料化合物特别适用于疏水性纺织材料的印染,包括半合成或合成的疏水性纤维混纺的纺织材料的染色和印花,尤其适用于聚酯材料及其混纺织物的浅色染色,相较于C.I.分散红153,色光更鲜艳,水洗沾色牢度和升华沾色牢度尤其是水洗沾色牢度更优异。
四、附图说明
图1为实施例1的质谱图;
图2为实施例4的质谱图。
五、具体实施方式
下面结合具体实施例对本发明进行进一步描述,但本发明的保护范围并不仅限于此:
实施例1:
重氮原料的制备:
向1000ml容器里投入120.9g对乙酰氨基苯酚(含量99%),20克催化剂碳酸钠,100g 无水乙醇,121g氯化苄(含量99%),通入氢气,升温到75℃,回流10h,降温,在0-5℃保温搅拌12h,结晶过滤,用50g无水乙醇洗涤。洗好后烘干,得产物A。
向500ml容器里投入240g的63%的硝酸,降温到0-5℃,耗时5h缓慢加入144.7g产物A,搅拌12h,加水100g,结晶过滤,得粗品B,重新投入250ml烧杯中,加入100g甲醇,在 10℃保温搅拌15h,结晶过滤,得产品B。
向500ml容器里投入30%的液碱160g,171g产物B,升温至90℃,搅拌8h,结晶过滤,洗涤到中性,烘干得重氮原料2-硝基-4-苄氧基苯胺。
重氮化:向150ml容器中加入含量98%浓硫酸30g,加入34.1g含量40%亚硝酰硫酸,降温到0-5℃,控制3-4h加完2-硝基-4-苄氧基苯胺干粉24.9g(0.1mol),加完后保温3h,得到重氮盐。
偶合:向2L容器里投入1000g水,0.1mol偶合组分2-萘酚,打浆半小时。将上述重氮盐在2h内滴加到偶合组分打浆液里。控制温度0-5℃。充分反应5-6h,pH控制在7-9。用渗圈实验检测反应。终点到后,将物料升温到75℃,保温3h,抽滤,洗涤到中性。烘干,可制得下式(Ⅰ-1)的红色染料化合物,波长λmax=515nm:
实施例2~8
按照实施例1所述的制备方法或类似的方法,重氮组分用表1中所示的组分进行等摩尔量替换,可制得符合本发明的红色染料化合物。
表1
实施例9:
将82克式(I-1)化合物,150克的分散剂MF,加400克水混拼后,研磨分散并干燥,即得成品,该成品能提供织物大红色色调,相较于C.I.分散红153,色光更鲜艳。
实施例10:
将100克式(I-2)化合物,200克的分散剂MF,加500克水混拼后,研磨分散并干燥,即得成品,该成品能提供织物大红色色调,相较于C.I.分散红153,色光更鲜艳。
染色实施例:
选取上述实施例1~8制得的分散红染料和C.I.分散红153,按照实施例9所述的方法进行商品化,采用常规高温高压染色法和热定型处理涤纶/氨纶织物,处理过程中,控制染色深度(o.w.f)2.0%,浴比1∶25,调染浴pH值4~5,室温入染,以1℃/min升温至125℃,保温45min,按常法还原净洗、水洗、干燥,180℃热定型60秒,得到大红色染织物。按照 ISO105-X12、AATCC 61-2A、ISO 105-P01分别测试其耐摩擦、耐水洗、耐升华色牢度,结果见下表2:
表2
本发明提供的分散红染料化合物,当染色深度为2%时,为目前市场上最艳的大红色染料,同时相较于现有的C.I.分散红153,耐水洗沾色牢度有显著改善。
Claims (7)
3.如权利要求2所述的制备方法,其特征在于:所述制备方法采用以下反应条件:
步骤(1)中,重氮化试剂为亚硝酰硫酸溶液,或者为盐酸或硫酸与亚硝酸钠的混合溶液,重氮化反应在0~15℃下进行;步骤(2)中偶合反应在0~15℃下进行。
4.如权利要求3所述的制备方法,其特征在于:重氮化反应和偶合反应分别在0~10℃下进行。
5.如权利要求1所述的分散大红染料化合物在疏水性纺织材料印染中的应用。
7.如权利要求6所述的分散染料制剂,其特征在于:所述的助剂选自下列之一或其任意几种的混合物:萘磺酸甲醛缩合物、烷基萘磺酸甲醛缩合物、苄基萘磺酸甲醛缩合物、木质素磺酸盐。
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