CN106433182A - 8‑羟基喹啉基杂环偶氮分散染料及其制备方法 - Google Patents
8‑羟基喹啉基杂环偶氮分散染料及其制备方法 Download PDFInfo
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- CN106433182A CN106433182A CN201610805297.8A CN201610805297A CN106433182A CN 106433182 A CN106433182 A CN 106433182A CN 201610805297 A CN201610805297 A CN 201610805297A CN 106433182 A CN106433182 A CN 106433182A
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Abstract
本发明涉及一种8‑羟基喹啉基杂环偶氮分散染料及其制备方法,所述8‑羟基喹啉基杂环偶氮分散染料由重氮组分与偶合组分两部分组成,其中所述的偶合组分为在碱性条件下偶合的杂环活泼亚甲基化合物或杂环酚类化合物,所述的重氮组分弱碱性杂环芳胺或弱碱性苯胺衍生物。所述制备方法是在稳定剂存在下,在有机溶剂中对弱碱性杂环芳胺或弱碱性苯胺衍生物进行重氮化,析出稳定的重氮盐固体,过滤得到固体后,将之应用于碱性偶合,获得目标染料。该染料可应用于聚酯纤维、聚酰胺纤维、聚乳酸纤维、聚丙烯纤维、醋酸纤维染色,具有优异的染色亮度。
Description
技术领域
本发明涉及一种杂环偶氮分散染料及其制备方法。
背景技术
合成纤维结构紧密,结晶度高,染色较困难,一般采用分散染料进行染色,以提高染料与疏水性纤维的结合力。
分散染料结构中不含有磺酸基或羧基等水溶性基团,难溶于水。其商品化时需与分散剂一起研磨,应用时借助分散剂以不溶性微细粒子分散于水中,用于合成纤维的高温高压或高温热熔染色。合成纤维用分散染料按结构分主要包括偶氮、蒽醌、硝基二苯胺等类型,而偶氮型分散染料由于结构简单,覆盖红、黄、蓝全色谱体系,在分散染料中占有极其重要的地位。含杂环基团的分散染料,具有色光鲜艳、发色强度高,具有较好的深色效应和较高的摩尔消光系数等特性,是分散染料中重要的染料品种。
偶氮型杂环分散染料由重氮组分与偶合组分两部分组成。当重氮组分能够在盐酸中进行重氮化时(此时重氮组分为苯胺、氯取代苯胺、1-硝基取代苯胺),其偶合组分可以是杂环芳胺、酚或杂环活泼亚甲基化合物,当重氮组分只能够在浓硫酸中进行重氮化时(此时重氮组分为弱碱性芳胺,如:氨基噻吩、氨基噻唑、氨基苯并噻唑、2,4-二硝基苯胺、4-硝基-2-氰基苯胺、4-硝基-2,6-二氯苯胺等),其偶合组分只能是在酸性条件下偶合的苯胺衍生物或杂环芳胺。而杂环活泼亚甲基化合物、杂环酚类化合物需要在碱性条件下偶合,弱碱性芳胺在浓硫酸中进行重氮化,将体系调到碱性时,将产生大量无机盐,难以获得相应染料。
因此,本发明的目的是开发一类新的杂环偶氮分散染料及其制备技术,此种染料的偶合组分是在碱性条件下偶合的杂环活泼亚甲基化合物、杂环酚类化合物;重氮组分是弱碱性芳胺;其制备方法是在有机溶剂中对弱碱性芳胺进行重氮化,析出稳定的重氮盐固体,过滤得到固体后,将之应用于碱性偶合,获得目标染料。
发明内容
本发明的第一方面,提供一种新的杂环偶氮分散染料,该染料由重氮组分与偶合组分两部分组成,其中所述的偶合组分为在碱性条件下偶合的杂环活泼亚甲基化合物或杂环酚类化合物,所述的重氮组分为在浓硫酸中可进行重氮化的杂环芳胺或弱碱性苯胺衍生物。
一种杂环偶氮型分散染料,具有通式(Ⅰ)的结构:
A-N=N-B
(Ⅰ)
式Ⅰ中A为重氮组分经重氮化得到的重氮组分的重氮盐与偶合组分偶合后的残基,所述重氮组分选自通式(Ⅱ-1)、(Ⅱ-2)、(Ⅱ-3)、(Ⅱ-4)、(Ⅱ-5)、(Ⅱ-6)、(Ⅱ-7)、(Ⅱ-8)、(Ⅱ-9)和(Ⅱ-10)的结构:
式(Ⅱ-1)中:
Ra 1为-H、-CN、-NO2、-COR、-COAr、-CONH2、-CONHR、-SO2、-COOR或-COAr;
Ra 2为-H、-R、-OR、-NO2、-Cl或-Br;
Ra 3为-H、-CN、-NO2、-Ar、-COR、-COAr、-COOR、-COOAr、-CONH2、-CONHR、-SCN、-OCOR、-CONHAr或-CHO;
式(Ⅱ-2)中:
Rb 1为-H、-R、-Ar、-CF3、-CN、-COOR、-CONH2或-CH2OH;
Rb 2为-H、-NO2、-R、-ROH、-Ar、-COOR、-CONH2、-SO2R、-SO2Ar或-CN;
式(Ⅱ-3)中:
RC 1和RC 2各自独立地选自-H、-Cl、-Br、-NO2、-R、-OR、-CN、-SO2R、-SO2NR和-CF3;
RC 2为在1、2或3位的取代基;
式(Ⅱ-4)中:
Rd 1为-NO2、-Cl、-Br或-H;
Rd 2为-H、-Cl或-Br;
式(Ⅱ-5)中:
Re为-H、-R、-Ar、-OR、-CN、-SCN、-Cl或-CCl3;
式(Ⅱ-6)中:
Rf为-H、-R、-Ar、-OR、-CN、-SCN、-Cl或-CCl3;
式(Ⅱ-7)中:
Rg为-H、-R、-Ar、-OR、-CN、-SCN、-NO2、CN、-Cl或-CCl3;
式(Ⅱ-8)中:
Rh 1为-CN、-H、-COOH或-COOCH3;
Rh 2为-SCH、-H、-CONH2或-CH2CN;
Rh 3为-H、苯基或环己基;
式(Ⅱ-9)中:
Ri 1为-CN、-NO2、-Cl、-Br或-I;
Ri 2为-H、-CN、-NO2、-Cl,-Br或-I,且当Ri 1为-Cl、-Br或-I时,Ri 2不能为-H;
式(Ⅱ-10)中:
Rj为-H、-CN、-NO2、-Cl、-Br或-I;
式(Ⅰ)中B为偶合组分与重氮组分的重氮盐偶合后的残基,所述的偶合组分选自通式(Ⅲ-1)、(Ⅲ-2)、(Ⅲ-3)、(Ⅲ-4)、(Ⅲ-5)、(Ⅲ-6)、(Ⅲ-7)和(Ⅲ-8)所示的结构:
式(Ⅲ-1)中:
Rj 1为-H、-CH3、-Ar、-CF3、-CN、-COOR或-CONHR;
Rj 2为-H、-Ar、-ArCl、或-ArSO2NHR;
式(Ⅲ-2)中:
Rk 1为-R、-OR、-NHR、COOR、-Ar或-CN;
Rk 2为-H、R、-Ar、-CN、-COOR、-SO2NHR或-CONHR;
Rk 3为-R、-Ar或环己基;
式(Ⅲ-3)中:
RL为-R、-OR、-NO2、-CN、-Cl、-Br、-COOR或-Ar;
式(Ⅲ-4)中:
Rm 1为-R、-OR、COOR、-Ar或-CN;
Rm 2为-H、R、-Ar、-CN、-COOR、-SO2NHR或-CONHR;
式(Ⅲ-5)中:
Rn 1为-R、-OR、COOR、-Ar或-CN;
Rn 2为-H、R、-Ar、-CN、-COOR、-SO2NHR或-CONHR;
式(Ⅲ-6)中:
Ro 1为-R、-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN或-Ar;
Ro 2为-H、R、-Ar、-CN、-COOR、-SO2NHR或-CONHR;
式(Ⅲ-7)中:
Rp 1为-R、环己基、-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN或-Ar;
Rp 2为-H、-NO2、-CN、-Cl、-Br、-COOR、-SO2NHR或-CONHR;
式(Ⅲ-8)中:
Rq 1为-R、环己基、-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN或-Ar;
Rq 2为-R、环己基、-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN或-Ar;
在式(Ⅱ-1)至式(Ⅱ-7)和式(Ⅲ-1)至式(Ⅲ-8)中:
R为氢、C1-4烷基或C1-4烷氧基;
Ar为苯基。
本发明的第二方面提供本发明所述的由通式(Ⅰ)所示的杂环偶氮型分散染料的制备方法,该方法包括如下步骤:
(1)将权利要求1所述的重氮组分、浓硫酸、有机溶剂和稳定剂加入反应容器A中,降温至0010℃后,分批加入重氮化试剂,反应0.1010h,过滤得到重氮组分的重氮盐固体;
(2)将权利要求1所述的偶合组分和水加入反应容器B中,用10%氢氧化钠调pH值至8012,使偶合组分溶解,冷却至0010℃,搅拌下加入步骤(1)得到的重氮组分的重氮盐固体,同时用10%碳酸钠溶液控制反应的pH值在8010范围内,在0010℃下反应1010h,得式(Ⅰ)的化合物;
其中所述重氮化试剂为亚硝酰硫酸、亚硝酸丁酯、亚硝酸叔丁酯、亚硝酸异戊酯、亚硝酸戊酯、亚硝酸异丁酯、亚硝酸异丙酯、质量浓度为30%的亚硝酸钠溶液、亚酸钠固体中的一种或两种。
进一步地,在步骤(1)中所述的重氮化试剂与重氮组分的投料摩尔比为101.05:1。
进一步地,在步骤(1)中所述的重氮组分、浓硫酸和稳定剂的投料摩尔比为1:103:103
进一步地,在步骤(1)中所述的重氮组分、浓硫酸和稳定剂相加的总量占反应体系总重量的5030%。
进一步地,,在步骤(2)中所述的偶合组分与重氮组分的重氮盐固体的投料摩尔比为0.801:0.801.05。
进一步地,在步骤(1)中,重氮化试剂的加入时间为0.101h。
进一步地,在步骤(2)中,搅拌下加入重氮组分的重氮盐固体的时间为5060min。
进一步地,所述的有机溶剂为乙酸乙酯、乙醚、乙二醇单甲醚、乙二醇二甲醚、乙二醇二乙醚、二乙二醇二甲醚、二乙二醇二乙醚、四氢呋喃、乙醇、异丙醇、二氧六环中的一种、两种或三种。
进一步地,所述的稳定剂为氟硼酸、氟硼酸钠、醋酸锌、氯化锌、苯磺酸、1-萘磺酸、2-萘磺酸、1,5-二萘磺酸、2,6-二萘磺酸、亚甲基二萘磺酸、亚甲基双甲基萘磺酸中的一种或两种。
本发明的第三方面提供本发明所述的杂环偶氮型染料在聚酯纤维、聚酰胺纤维、聚乳酸纤维、聚丙烯纤维、醋酸纤维染色中的应用。
相对于现有技术,本发明的有益效果:
1.本发明的化合物的结构上其偶合组分为杂环活泼亚甲基化合物、杂环酚类化合物,重氮组分是弱碱性芳胺,获得的染料染色亮度高。
2.本发明的化合物的制备方法上是在有机溶剂中对弱碱性芳胺进行重氮化,析出稳定的重氮盐固体,过滤得到固体后,将之应用于碱性偶合,获得目标染料,该方法与在硫酸中进行重氮化的传统方法相比,硫酸用量降至2摩尔倍量以下,减少硫酸8摩尔倍量以上;并且该方法获得的重氮盐为稳定的固体,可用于碱性偶合,获得新型分散染料。
3.本发明化合物可以用于聚酯纤维、聚酰胺纤维、聚乳酸纤维、聚丙烯纤维、醋酸纤维的染色,部分化合物还可用于pH敏感检测领域。
附图说明
图1为染料化合物1#的质谱图;
图2为染料化合物1#的FT-IR图;
图3为染料化合物1#的核磁谱图;
图4为染料化合物2#的质谱图;
图5为染料化合物2#的FT-IR图;
图6为染料化合物2#的核磁谱图;
图7为染料化合物3#的质谱图;
图8为染料化合物3#的FT-IR图;
图9为染料化合物3#的核磁谱图;
图10为染料化合物3#在不同pH下的紫外-可见吸收光谱;
图11为染料化合物4#的质谱图;
图12为染料化合物4#的FT-IR图;
图13为染料化合物4#的核磁谱图。
具体实施方式
为了使本发明的目的、方案、流程和优点更加清楚明晰,结合附图和实施例对本发明做进一步的详细说明,值得注意的是,此处具体实施例仅作为解释说明本发明,并不用于限定本发明。下述实施例中,如无特殊说明,所使用的实验方法均为常规方法,所用材料、试剂等均可从化学公司购买。
除另有说明外,本发明中使用的技术术语有如下含义。
本发明中使用的术语“烷基”包括直链烷基和支链烷基。如提及单个烷基如“丙基”,则只特指直链烷基,如提及单个支链烷基如“异丙基”,则只特指支链烷基。又如“C1-4烷基”包括C1-3烷基、甲基、乙基、正丙基、异丙基和叔丁基。类似的规则也适用于本说明书中使用的其它基团。
式(Ⅱ-1)中:Ra 1优选为-H、-CN、-NO2、-COR、-COAr、-CONH2;更优选为-H、-CN、-NO2;最优选为-H、-NO2;Ra 2优选为-H、-R、-OR、-NO2、-Cl;更优选为-H、-R、-OR、-NO2;最优选为-H、-NO2;Ra 3优选为-H、-CN、-NO2、-Ar、-COR、-COAr,更优选为-H、-CN、-NO2、-Ar、-COAr;最优选为-H、-NO2、-Ar。
式(Ⅱ-2)中:Rb 1优选为-H、-R、-Ar、-CF3、-CN、-COOR;更优选为-H、-R、-Ar、-CF3、-CN;最优选为-H、-Ar、-CF3、-CN;Rb 2优选为-H、-NO2、-R、-ROH、-Ar、-COOR、-SO2Ar或-CN;更优选为-H、-NO2、-Ar、-COOR、-SO2Ar或-CN;最优选为-H、-NO2、-Ar、-SO2Ar。
式(Ⅱ-3)中:优选RC 1和RC 2各自独立地选自-H、-Cl、-Br、-NO2、-R、-OR;更优选为-H、-Cl、-NO2、-OR;最优选为-H、-Cl、-NO2;RC 2优选定位在1、2位置上;更优选定位在1位。
式(Ⅱ-4)中:Rd 1优选为-NO2、-Cl或-H;更优选为-NO2或-H;最优选为-NO2;Rd 2优选为-H、-Cl;更优选为-H。
式(Ⅱ-5)中:Re优选为-H、-Ar、-OR、-CN、-Cl或-CCl3;更优选为-H、-Ar、-CN或-CCl3;最优选为-H、-CN或-CCl3。
式(Ⅱ-6)中:Rf优选为-H、-R、-Ar、-OR、-CN、;更优选为-H、-Ar、-OR、-CN;最优选为-H、-Ar、-CN。
式(Ⅱ-7)中:Rg优选为-H、-R、-Ar、-OR、-CN、-SCN、-Cl;更优选为-H、-R、-Ar、-CN、-Cl;最优选为-H、-Ar、-CN。
式(Ⅱ-8)中:Rh 1优选为-CN、-H、-COOCH3;更优选为-CN、-H;Rh 2优选为-CONH2、-H、或-CH2CN;更优选为-H、或-CH2CN;Rh 3优选为-H、苯基;更优选为苯基。
式(Ⅱ-9)中:Ri 1优选为-CN、-NO2、-Br或-Cl;更优选为-CN、-NO2或-Cl;最优选为-NO2或-Cl;Ri 2优选为-H、-CN、-NO2、-Br或-Cl,更优选为-H、-NO2、-Cl;最优选为-H、-Cl;且当Ri 1为Cl、Br或I时,Ri 2不能为H。
式(Ⅱ-10)中:Rj优选为-H、-CN、-NO2、-Br;更优选为-H、-NO2;最优选为-H。
式(Ⅲ-1)中:Rj 1优选为-H、-CH3、-Ar、-COOR或-CONHR;更优选为-H、-CH3、-Ar或-CONHR;最优选为-H、-Ar;Rj 2优选为-H、-Ar或-ArSO2NHR;更优选为-H、-Ar;最优选为-Ar。
式(Ⅲ-2)中:Rk 1优选为-R、-OR、-NHR、COOR或-CN;更优选为-R、-NHR、COOR或-CN;最优选为-R、COOR或-CN;Rk 2优选为R、-Ar、-CN或-CONHR;更优选为R、-Ar、-CN;最优选为R、-Ar;Rk 3优选为-R、-Ar;更优选为-R。
式(Ⅲ-3)中:RL优选为-R、-OR、-NO2、-COOR或-Ar;更优选为-R、-NO2、-COOR或-Ar;最优选为-R、-NO2、-COOR。
式(Ⅲ-4)中:Rm 1优选为-R、-OR、COOR;更优选为-R、COOR;最优选为-R;Rm 2为-H、R、-Ar、-CN、-COOR;更优选为-H、-Ar、-CN、-COOR;最优选为-H、-Ar。
式(Ⅲ-5)中:Rn 1优选为-R、-OR、COOR、-Ar;更优选为-R、-OR、COOR;最优选为-R、-OR;Rn 2优选为-H、R、-Ar、-SO2NHR或-CONHR;更优选为-H、R、-Ar或-CONHR;最优选为-H、R。
式Ⅲ-6中:Ro 1优选为-R、-CH2CH2CH2OH、-CH2CH2OH;更优选为-R、-CH2CH2OH;Ro 2优选为-H、R、-Ar、-SO2NHR或-CONHR;更优选为-H、R、-Ar、-CONHR;最优选为-H、-Ar。
式(Ⅲ-7)中:Rp 1优选为-R、环己基、-CH2CH2CH2OH、CH2CH2CN;更优选为-R、-CH2CH2CH2OH、CH2CH2CN;最优选为-R、CH2CH2CN;Rp 2优选为-H、-NO2、-CN、-Cl、-Br;更优选为-H、-NO2、-CN、-Cl;最优选为-H、-NO2。
式(Ⅲ-8)中:Rq 1优选为-R、-CH2CH2CH2OH、-CH2CH2OH;更优选为-R、-CH2CH2OH;Rq 2优选为-R、-CH2CH2CH2OH、-CH2CH2OH;更优选为-R、-CH2CH2OH。
在式(Ⅱ-1)至式(Ⅱ-7)和式(Ⅲ-1)至式(Ⅲ-8)中:R优选为-H、C1-4烷基或C1-4烷氧基;更优选为氢、C1-2烷基或C1-2烷氧基;进一步优选为-H、乙基、甲氧基。
Ar为苯基。
在另一方面,本发明还提供了上述所述化合物的制备方法,该制备方法是在浓硫酸存在下,在有机溶剂中对重氮组分进行重氮化,析出稳定的重氮盐固体,过滤得到该固体后,在碱性条件下与偶合组分进行偶合反应,获得目标染料。具体包括如下步骤:
(1)将本发明所述的重氮组分、浓硫酸、有机溶剂和稳定剂加入反应容器A中,降温至0010℃后,分批加入重氮化试剂,反应0.1010h,过滤得到重氮组分的重氮盐固体;
(2)将权利要求1所述的偶合组分和水加入反应容器B中,用10%氢氧化钠调pH值至8012,使偶合组分溶解,冷却至0010℃,搅拌下加入步骤(1)得到的重氮组分的重氮盐固体,用10%碳酸钠溶解控制反应pH值至8010范围内,在0010℃下反应1010h,得式(Ⅰ)的化合物;
其中所述重氮化试剂为亚硝酰硫酸、亚硝酸丁酯、亚硝酸叔丁酯、亚硝酸异戊酯、亚硝酸戊酯、亚硝酸异丁酯、亚硝酸异丙酯、质量浓度为30%的亚硝酸钠溶液、亚酸钠固体中的一种或两种。
在优选的技术方案中,所述的重氮化试剂为亚硝酰硫酸、亚硝酸丁酯、亚硝酸叔丁酯、亚硝酸异戊酯、亚硝酸戊酯、亚硝酸异丁酯中的一种或两种;更优选为亚硝酰硫酸、亚硝酸叔丁酯、亚硝酸异戊酯、亚硝酸异丁酯;最优选为亚硝酰硫酸、亚硝酸叔丁酯。
在优选的技术方案中,在步骤(1)中所述的重氮化试剂与重氮组分的投料摩尔比为1.0501:1,更优选为1.0201:1,最优选为1:1;重氮组分与浓硫酸的投料摩尔比为1:103,更优选为1:102.5,最优选为1:102。
在优选的技术方案中,在步骤(1)中所述的重氮组分、浓硫酸和稳定剂的投料摩尔比为1:103:103,更优选为1:102.5:102.5,最优选为1:102:102。
在优选的技术方案中,在步骤(1)中所述的重氮组分、浓硫酸和稳定剂相加的总量占反应体系总重量的5030%,更优选为5020%,最优选为5015%。
在优选的技术方案中,在步骤(2)中所述的偶合组分与重氮组分的重氮盐固体的投料摩尔比为1:101.05;更优选为1:101.03,最优选为1:1。
在优选的技术方案中,在步骤(1)中,滴加重氮化试剂的时间为0.101h,更优选为0.100.5h。
在优选的技术方案中,在步骤(2)中,搅拌下加入重氮组分的重氮盐固体的时间为5060min,更优选为10040min。
在优选的技术方案中,所述的有机溶剂为乙酸乙酯、乙醚、乙二醇单甲醚、乙二醇二甲醚、乙二醇二乙醚、二乙二醇二甲醚、二乙二醇二乙醚、四氢呋喃、乙醇、异丙醇、二氧六环中的一种、两种或三种,更优选为乙酸乙酯、乙二醇单甲醚、乙二醇二甲醚、乙二醇二乙醚、二乙二醇二甲醚、二乙二醇二乙醚、四氢呋喃、二氧六环中的一种、两种或三种,最优选为乙酸乙酯、乙二醇单甲醚、乙二醇二甲醚、二乙二醇二甲醚、二乙二醇二乙醚、乙二醇二乙醚中的一种、两种或三种。
在优选的技术方案中,所述的稳定剂为氟硼酸、氟硼酸钠、醋酸锌、氯化锌、苯磺酸、1-萘磺酸、2-萘磺酸、1,5-二萘磺酸、2,6-二萘磺酸、NNO、MF中的一种或两种,更优选为氟硼酸、氯化锌、1-萘磺酸、2-萘磺酸、1,5-二萘磺酸、2,6-二萘磺酸、亚甲基二萘磺酸、亚甲基双甲基萘磺酸一种或两种,最优选为氟硼酸、1,5-二萘磺酸、2,6-二萘磺酸、亚甲基二萘磺酸、亚甲基双甲基萘磺酸一种或两种。
实施例1化合物1#的制备
(1)将1.5g 5-氨基苯并咪唑酮,1g浓硫酸,80ml乙二醇二乙醚,5g 1,5-萘二磺酸加入三口瓶中,冰水浴中降温至5℃,滴加3g亚硝酸叔丁酯,滴加时间为0.5h,滴加完毕后反应2小时;过滤后得到重氮盐固体;(2)将1.34g 3-甲基-1-苯基-5吡唑啉酮、100ml水加入反应器中,用10%氢氧化钠溶液调pH值至10,冷却至5℃,搅拌下加入步骤(1)得到的5-氨基苯并咪唑酮重氮盐,并用10%碳酸钠溶液控制pH值在9,半小时内加完,并在5℃反应2hr;反应完毕,过滤,利用冰水洗至滤液为中性,干燥后得到杂环偶氮分散染料(化合物1#),偶合得率为95%。
质谱(图1)中在m/z 333.1处出现了化合物1#的[M-H]-离子峰,红外光谱(图2)中在1700cm-1为羰基特征峰,H-NMR核磁谱图(图3)中8.5-10ppm为芳环上氢质子峰。
实施例2化合物2#的制备
(1)将1.83g 2,4-二硝基苯胺,2g浓硫酸,40ml乙二醇二甲醚,4g 1,5-萘二磺酸加入三口瓶中,冰水浴中降温至3℃,滴加3g亚硝酰硫酸,滴加时间为0.5h,滴加完毕后反应2小时;过滤后得到重氮盐固体;(2)将0.81g 3-甲基-5-吡唑酮、80ml水加入反应器中,用10%氢氧化钠溶液调pH值至11,冷却至4℃,搅拌下加入步骤(1)得到的2,4-二硝基苯胺重氮盐,并用10%碳酸钠溶液控制pH值在9,半小时内加完,并在5℃反应2hr;反应完毕,过滤,利用冰水洗至滤液为中性,干燥后得到杂环偶氮分散染料(化合物2#),偶合得率为99%。
质谱(图4)中在m/z 291处出现了化合物2#的[M-H]-离子峰,红外光谱(图5)中在1690cm-1为羰基特征峰,H-NMR核磁谱图(图6)中8.2-9.5ppm为芳环上氢质子峰。
实施例3化合物3#的制备
(1)将1.45g 2-氨基-5-硝基噻唑,60ml乙酸乙酯,5g浓硫酸,5g醋酸锌(30%水溶液)加入三口瓶中,冰水浴中降温至005摄氏度,加入2g亚硝酰硫酸,完毕后反应2小时;过滤后得到重氮盐固体;(2)将0.97g 8-羟基喹啉、80ml水加入反应器中,用10%氢氧化钠溶液调pH值至10,冷却至5℃,搅拌下加入在步骤(1)得到的2-氨基-5-硝基噻唑重氮盐,并用10%碳酸钠溶液控制pH值在9,半小时内加完,并在5℃反应2hr;反应完毕,过滤,利用冰水洗至滤液为中性,干燥后得到杂环偶氮分散染料(化合物3#),偶合得率为80%。
质谱(图7)中在m/z 300处出现了化合物3#的[M-H]-离子峰,红外光谱(图8)中在1550cm-1与1350cm-1为硝基特征峰,H-NMR核磁谱图(图9)中8.2-9.5ppm为芳环上氢质子峰。在其紫外-可见吸收光谱(图10)中可以看出,当溶液pH值为6时,为紫色,当溶液pH值为8时,最大吸收波长为626nm,为蓝色,颜色变化显著,具有pH敏感变色特性,可用于pH的裸眼检测。
实施例4化合物4#的制备
(1)将2.07g 4-硝基-2,6-二氯苯胺,3g浓硫酸,50ml乙二醇二甲醚,3g 1,5-萘二磺酸加入三口瓶中,冰水浴中降温至4摄氏度,滴加亚硝酸钠溶液(30%,所滴加量与重氮组分的摩尔比为1.05:1),滴加时间为0.5h,滴加完毕后反应1小时;过滤后得到重氮盐固体;(2)将1.24g 3-甲基-1-苯基-5吡唑啉酮、50ml水加入反应器中,用10%氢氧化钠溶液调pH值至11,冷却至6℃,搅拌下加入4-硝基-2,6-二氯苯胺重氮盐,并用10%碳酸钠溶液控制pH值在10,半小时内加完,并在8℃反应2h;反应完毕,过滤,利用冰水洗至滤液为中性,干燥后得到杂环偶氮分散染料(化合物4#),偶合得率为92%。
质谱(图11)中在m/z 390处出现了化合物3#的[M-H]-离子峰,红外光谱(图12)中在1660为羰基特征峰,核磁谱图(图13)中7-8.6ppm为芳环上氢质子峰。
实施例5
(1)将1.96g 2-氨基-3,5-二硝基噻吩,1g浓硫酸,60ml乙二醇二甲醚,5g 2,6-萘二磺酸加入三口瓶中,冰水浴中降温至3℃,滴加4g亚硝酸异戊酯,滴加时间为0.5h,滴加完毕后反应2小时;过滤后得到重氮盐固体;(2)将1.74g N-乙基-3-氰基-4-甲基-6-羟基-2-吡啶酮、100ml水加入反应器中,用10%氢氧化钠溶液调pH值至11,冷却至5℃,搅拌下加入在步骤(1)得到的2-氨基-3,5-二硝基噻吩重氮盐,并用10%碳酸钠溶液控制pH值在9,半小时内加完,并在5℃反应2hr;反应完毕,过滤,利用冰水洗至滤液为中性,干燥后得到杂环偶氮分散染料。
实施例6
(1)将1.0g 2-氨基噻唑,60ml乙酸乙酯,5g浓硫酸,5g氟硼酸(40%水溶液)加入三口瓶中,冰水浴中降温至5℃,加入0.7g亚硝酸钠,完毕后反应2小时;过滤后得到重氮盐固体;(2)将1.62g 4-羟基香豆素、80ml水加入反应器中,用10%氢氧化钠溶液调pH值至11,冷却至8℃,搅拌下加入步骤(1)得到的2-氨基噻唑重氮盐,并用10%碳酸钠溶液控制pH值在9,半小时内加完,并在5℃反应2hr;反应完毕,过滤,利用冰水洗至滤液为中性,干燥后得到杂环偶氮分散染料。
实施例7-22
利用3-氰基-6-羟基-4-甲基-2-吡啶酮、N-乙基-3-氰基-4-甲基-6-羟基-2-吡啶酮、六羟基吡啶酮、3-甲酰氨基-4-甲基-6-羟基-N-乙基吡啶酮、4-羟基香豆素、7-硝基-4-羟基香豆素、7-甲基-4-羟基香豆素、4-羟基喹啉、2,4-二羟基喹啉、7-氯-4-羟基喹啉、N-甲基-4-羟基-2-喹啉酮、4-羟基-1,8-萘二甲酰亚胺、N-甲基-4-羟基-1,8-萘二甲酰亚胺、1-(4-氯苯基)-3-甲基-5-吡唑啉酮、1-苯基-3-甲基-4-苯甲酰基-5-吡唑啉酮、3-甲基-5-吡唑酮代替实施例1中的3-甲基-1-苯基-5吡唑啉酮,在碱性条件下分别与5-氨基苯并咪唑酮的重氮盐固体偶合,得到相应杂环偶氮分散染料。
实施例23-30
利用2,4-二硝基苯胺、4-硝基-2,6-二溴苯胺、4-硝基-2-氰基苯胺、2-氨基苯并噻唑、6-硝基噻唑、5-氨基苯并-1,2,3-噻二唑、2-氨基噻吩、1-苯基-3-甲基-4-氰基-5-氨基吡唑代替实施例1中的5-氨基苯并咪唑酮,进行重氮化,获得相应重氮盐固体,在碱性条件下分别与3-甲基-1-苯基-5吡唑啉酮,得到相应杂环偶氮分散染料。
实施例31-38
利用乙酸乙酯、乙醚、乙二醇单甲醚、乙二醇二甲醚、四氢呋喃、乙醇、异丙醇、二氧六环代替实施例1中的乙二醇二乙醚作为5-氨基苯并咪唑酮重氮化的溶剂,获得相应重氮盐固体,在碱性条件下分别与3-甲基-1-苯基-5吡唑啉酮偶合,得到相应杂环偶氮分散染料。
实施例39-46
利用氟硼酸、氟硼酸钠、醋酸锌、苯磺酸、1-萘磺酸、2-萘磺酸、2,6-二萘磺酸、NNO、MF代替实施例1中的1,5-萘二磺酸作为5-氨基苯并咪唑酮的稳定剂,获得相应重氮盐固体,在碱性条件下分别与3-甲基-1-苯基-5吡唑啉酮偶合,得到相应杂环偶氮分散染料。
实施例47-54
利用亚硝酰硫酸、亚硝酸丁酯、亚硝酸异戊酯、亚硝酸戊酯、亚硝酸异丁酯、亚硝酸异丙酯代替实施例1中的亚硝酸叔丁酯作为5-氨基苯并咪唑酮的重氮化试剂,获得相应重氮盐固体,在碱性条件下分别与3-甲基-1-苯基-5吡唑啉酮,得到相应杂环偶氮分散染料。
实施例55-70
利用3-氰基-6-羟基-4-甲基-2-吡啶酮、六羟基吡啶酮、3-甲酰氨基-4-甲基-6-羟基-N-乙基吡啶酮、4-羟基香豆素、7-硝基-4-羟基香豆素、7-甲基-4-羟基香豆素、4-羟基喹啉、2,4-二羟基喹啉、7-氯-4-羟基喹啉、N-甲基-4-羟基-2-喹啉酮、4-羟基-1,8-萘二甲酰亚胺、N-甲基-4-羟基-1,8-萘二甲酰亚胺、1-(4-氯苯基)-3-甲基-5-吡唑啉酮、1-苯基-3-甲基-4-苯甲酰基-5-吡唑啉酮、3-甲基-5-吡唑酮代替实施例2中的3-甲基-5-吡唑酮,在碱性条件下分别与2,4-二硝基苯胺的重氮盐固体偶合,得到相应杂环偶氮分散染料。
实施例71-78
利用2-氨基-3,5-二硝基噻吩、4-硝基-2,6-二溴苯胺、4-硝基-2-氰基苯胺、2-氨基苯并噻唑、6-硝基噻唑、5-氨基苯并-1,2,3-噻二唑、2-氨基噻吩、1-苯基-3-甲基-4-氰基-5-氨基吡唑代替实施例2中的2,4-二硝基苯胺,进行重氮化,获得相应重氮盐固体,在碱性条件下分别与3-甲基-5-吡唑酮偶合,得到相应杂环偶氮分散染料。
实施例79-86
利用乙酸乙酯、乙醚、乙二醇单甲醚、乙二醇二乙醚、四氢呋喃、乙醇、异丙醇、二氧六环代替实施例2中的乙二醇二甲醚作为2,4-二硝基苯胺重氮化的溶剂,获得相应重氮盐固体,在碱性条件下分别与3-甲基-5-吡唑酮偶合,得到相应杂环偶氮分散染料。
实施例87-94
利用氟硼酸、氟硼酸钠、醋酸锌、苯磺酸、1-萘磺酸、2-萘磺酸、2,6-二萘磺酸、亚甲基二萘磺酸、亚甲基双甲基萘磺酸代替实施例2中的1,5-萘二磺酸作为2,4-二硝基苯胺重氮盐的稳定剂,获得相应重氮盐固体,在碱性条件下分别与3-甲基-5-吡唑酮偶合,得到相应杂环偶氮分散染料。
实施例95-102
利用亚硝酸异戊酯、亚硝酸丁酯、亚硝酸叔丁酯、亚硝酸戊酯、亚硝酸异丁酯、亚硝酸异丙酯代替实施例2中的亚硝酰硫酸作为2,4-二硝基苯胺的重氮化试剂,获得相应重氮盐固体,在碱性条件下分别与3-甲基-5-吡唑酮偶合,得到相应杂环偶氮分散染料。
实施例103-118
利用3-氰基-6-羟基-4-甲基-2-吡啶酮、六羟基吡啶酮、3-甲酰氨基-4-甲基-6-羟基-N-乙基吡啶酮、7-硝基-4-羟基香豆素、7-甲基-4-羟基香豆素、4-羟基喹啉、2,4-二羟基喹啉、7-氯-4-羟基喹啉、N-甲基-4-羟基-2-喹啉酮、4-羟基-1,8-萘二甲酰亚胺、N-甲基-4-羟基-1,8-萘二甲酰亚胺、1-(4-氯苯基)-3-甲基-5-吡唑啉酮、1-苯基-3-甲基-4-苯甲酰基-5-吡唑啉酮、3-甲基-5-吡唑酮代替实施例3中的8-羟基喹啉,在碱性条件下分别与2-氨基-5-硝基噻唑的重氮盐固体偶合,得到相应杂环偶氮分散染料。
实施例119-126
利用2,4-二硝基苯胺、4-硝基-2,6-二溴苯胺、4-硝基-2-氰基苯胺、2-氨基苯并噻唑、6-硝基噻唑、5-氨基苯并-1,2,3-噻二唑、2-氨基噻吩、1-苯基-3-甲基-4-氰基-5-氨基吡唑代替实施例3中的2-氨基-5-硝基噻唑,进行重氮化,获得相应重氮盐固体,在碱性条件下分别与8-羟基喹啉偶合,得到相应杂环偶氮分散染料。
实施例127-134
利用乙二醇二甲醚、乙醚、乙二醇单甲醚、乙二醇二乙醚、四氢呋喃、乙醇、异丙醇、二氧六环代替实施例3中乙酸乙酯的作为2-氨基-5-硝基噻唑重氮化的溶剂,获得相应重氮盐固体,在碱性条件下分别与8-羟基喹啉偶合,得到相应杂环偶氮分散染料。
实施例135-142
利用1,5-萘二磺酸、氟硼酸钠、氟硼酸、苯磺酸、1-萘磺酸、2-萘磺酸、2,6-二萘磺酸、亚甲基二萘磺酸、亚甲基双甲基萘磺酸代替实施例3中的醋酸锌作为2-氨基-5-硝基噻唑重氮盐的稳定剂,获得相应重氮盐固体,在碱性条件下分别与8-羟基喹啉偶合,得到相应杂环偶氮分散染料。
实施例143-150
利用亚硝酸异戊酯、亚硝酸钠、亚硝酸丁酯、亚硝酸叔丁酯、亚硝酸戊酯、亚硝酸异丁酯、亚硝酸异丙酯代替实施例3中的亚硝酰硫酸作为2-氨基-5-硝基噻唑的重氮化试剂,获得相应重氮盐固体,在碱性条件下分别与8-羟基喹啉偶合,得到相应杂环偶氮分散染料。
实施例151-166
利用3-氰基-6-羟基-4-甲基-2-吡啶酮、六羟基吡啶酮、3-甲酰氨基-4-甲基-6-羟基-N-乙基吡啶酮、7-硝基-4-羟基香豆素、7-甲基-4-羟基香豆素、4-羟基喹啉、2,4-二羟基喹啉、7-氯-4-羟基喹啉、N-甲基-4-羟基-2-喹啉酮、4-羟基-1,8-萘二甲酰亚胺、N-甲基-4-羟基-1,8-萘二甲酰亚胺、1-(4-氯苯基)-3-甲基-5-吡唑啉酮、1-苯基-3-甲基-4-苯甲酰基-5-吡唑啉酮、3-甲基-5-吡唑酮代替实施例4中的3-甲基-1-苯基-5吡唑啉酮,在碱性条件下分别与4-硝基-2,6-二氯苯胺的重氮盐固体偶合,得到相应杂环偶氮分散染料。
实施例167-174
利用2,4-二硝基苯胺、2-氨基噻唑、4-硝基-2,6-二溴苯胺、4-硝基-2-氰基苯胺、2-氨基苯并噻唑、6-硝基噻唑、5-氨基苯并-1,2,3-噻二唑、2-氨基噻吩、1-苯基-3-甲基-4-氰基-5-氨基吡唑代替实施例4中的4-硝基-2,6-二氯苯胺,进行重氮化,获得相应重氮盐固体,在碱性条件下分别与3-甲基-1-苯基-5吡唑啉酮偶合,得到相应杂环偶氮分散染料。
应用例1
实施例1得到的染料砂磨试验:将0.50g的实施例1得到的染料、1.00g的分散剂NNO与2.80g的水置于装有砂磨珠和砂磨棒的砂磨管中,搅拌砂磨1h,实施例1得到的染料扩散性能达到HGT3399-2001规定的5级。
应用例2
实施例2得到的染料砂磨试验:将0.50g的实施例2得到的染料、1.00g的分散剂NNO与2.80g的水置于装有砂磨珠和砂磨棒的砂磨管中,搅拌砂磨1h,实施例2得到的染料扩散性能达到HGT3399-2001规定的5级。
应用例3
实施例4得到的染料砂磨试验:将0.50g的实施例4得到的染料、1.00g的分散剂NNO与2.80g的水置于装有砂磨珠和砂磨棒的砂磨管中,搅拌砂磨1h,实施例4得到的染料扩散性能达到HGT3399-2001规定的5级。
应用例4
实施例1得到的染料用于涤纶染色试验:按GBT9337-2009对涤纶进行染色,浴比1:20,色度1.5%,pH=5~6,270.02╳103Pa、130℃下进行高温高压染色,竭染率≥98%,染色纤维经电子测色配色仪测定染色后布样的亮度为71.65。
实施例2得到的染料用于涤纶染色试验:按GBT9337-2009对涤纶进行染色,浴比1:20,色度1.5%,pH=5~6,270.02╳103Pa、130℃下进行高温高压染色,竭染率≥98%,染色纤维经电子测色配色仪测定染色后布样的亮度为80.51。
实施例4得到的染料用于涤纶染色试验:按GBT9337-2009对涤纶进行染色,浴比1:20,色度1.5%,pH=5~6,270.02╳103Pa、130℃下进行高温高压染色,竭染率98.2%,染色纤维经电子测色配色仪测定染色后布样的亮度为80.88。此染色纤维的亮度明显高于以N,N-二乙基苯胺为偶合组分的染料(应用对比实施例1)染色后的亮度;此染色纤维的亮度明显高于以N-乙基-N-氰乙基苯胺为偶合组分的染料(应用对比实施例2)染色后的亮度,表明以弱碱性芳胺为重氮组分、以杂环活泼亚甲基化合物或杂环酚类为偶合组分,获得杂环偶氮分散染料具有优异的染色亮度。
应用对比实施例1
采用如下结构A的染料进行砂磨试验:将0.50g染料、1.00g的分散剂NNO与2.80g的水置于装有砂磨珠和砂磨棒的砂磨管中,搅拌砂磨1h,染料扩散性能达到HGT3399-2001规定的5级。上述染料用于涤纶染色试验:按GBT9337-2009对涤纶进行染色,浴比1:20,色度1.5%,pH=5~6,270.02╳103Pa、130℃下进行高温高压染色,竭染率97.9%,染色纤维经电子测色配色仪测定染色后布样的亮度为38.24。
应用对比实施例2
采用如下结构B的染料进行砂磨试验:将0.50g染料、1.00g的分散剂NNO与2.80g的水置于装有砂磨珠和砂磨棒的砂磨管中,搅拌砂磨1h,染料扩散性能达到HGT3399-2001规定的5级。上述染料用于涤纶染色试验:按GBT9337-2009对涤纶进行染色,浴比1:20,色度1.5%,pH=5~6,270.02╳103Pa、130℃下高温高压染色,竭染率98.5%,染色纤维经电子测色配色仪测定染色后布样的亮度为40.91。
Claims (10)
1.一种8-羟基喹啉基杂环偶氮分散染料,具有通式Ⅰ的结构:
A-N=N-B (Ⅰ)
式(Ⅰ)中A为重氮组分经重氮化得到的重氮组分的重氮盐与偶合组分偶合后的残基,所述重氮组分选自通式(Ⅱ-1)、(Ⅱ-2)、(Ⅱ-3)、(Ⅱ-4)、(Ⅱ-5)、(Ⅱ-6)、(Ⅱ-7)、(Ⅱ-8)、(Ⅱ-9)和(Ⅱ-10)的结构:
式(Ⅱ-1)中:
Ra 1为-H、-CN、-NO2、-COR、-CONHR、-SO2、-COOR或-COAr;
Ra 2为-R、-OR、-NO2、-Cl或-Br;
Ra 3为-H、-CN、-NO2、-Ar、-COR、-COAr、-COOR、-COOAr、-CONHR、-SCN、-OCOR、-CONHAr或-CHO;
式(Ⅱ-2)中:
Rb 1为-R、-Ar、-CF3、-CN、-COOR、-CONH2或-CH2OH;
Rb 2为-NO2、-R、-Ar、-COOR、-CONH2、-SO2R、-SO2Ar或-CN;
式(Ⅱ-3)中:
RC 1和RC 2各自独立地选自-Cl、-Br、-NO2、-R、-OR、-CN、-SO2R、-SO2N或-CF3;
RC 2为在1、2或3位的取代基;
式(Ⅱ-4)中:
Rd 1为-NO2、-Cl、-Br或-H;
Rd 2为-H、-Cl或-Br;
式(Ⅱ-5)中:
Re为-R、-Ar、-OR、-CN、-SCN、-Cl或-CCl3;
式(Ⅱ-6)中:
Rf为-R、-Ar、-OR、-CN、-SCN、-Cl或-CCl3;
式(Ⅱ-7)中:
Rg为-R、-Ar、-OR、-CN、-SCN、-NO2、CN、-Cl或-CCl3;
式(Ⅱ-8)中:
Rh 1为-CN、-H、-COOH或-COOCH3;
Rh 2为-SCH、-H、-CONH2或-CH2CN;
Rh 3为-H、苯基或环己基;
式(Ⅱ-9)中:
Ri 1为-CN、-NO2、-Cl、-Br或-I;
Ri 2为-H、-CN、-NO2、-Cl,-Br或-I,且当Ri 1为-Cl、-Br或-I时,Ri 2不能为-H;
式(Ⅱ-10)中:
Rj为-H、-CN、-NO2、-Cl、-Br或-I;
式(Ⅰ)中B为偶合组分与重氮组分的重氮盐偶合后的残基,所述的偶合组分选自通式(Ⅲ-5)所示的结构:
式(Ⅲ-5)中:
Rn 1为-R、-OR、COOR、-Ar或CN;
Rn 2为R、-Ar、-CN、-COOR、-SO2NHR或-CONHR;
在式(Ⅱ-1)至式(Ⅱ-7)和式(Ⅲ-5)中:
R为氢、C1-4烷基或C1-4烷氧基;
Ar为苯基。
2.如权利要求1所述的8-羟基喹啉基杂环偶氮分散染料的制备方法,其特征在于,该方法包括如下步骤:
(1)将权利要求1所述的重氮组分、浓硫酸、有机溶剂和稳定剂加入反应容器A中,降温至0~10℃后,分批加入重氮化试剂,反应0.1~10h,过滤得到重氮组分的重氮盐固体;
(2)将权利要求1所述的偶合组分和水加入反应容器B中,用10%氢氧化钠调pH值至8~12,使偶合组分溶解,冷却至0~10℃,搅拌下加入步骤(1)得到的重氮组分的重氮盐固体,同时用10%碳酸钠溶液控制反应的pH值在8~10范围内,在0~10℃下反应1~10h,得式(Ⅰ)的化合物;
其中所述重氮化试剂为亚硝酰硫酸、亚硝酸丁酯、亚硝酸叔丁酯、亚硝酸异戊酯、亚硝酸戊酯、亚硝酸异丁酯、亚硝酸异丙酯、质量浓度为30%的亚硝酸钠溶液、亚酸钠固体中的一种或两种。
3.根据权利要求2所述的制备方法,其特征在于,在步骤(1)中所述的重氮化试剂与重氮组分的投料摩尔比为1~1.05:1。
4.根据权利要求2所述的制备方法,其特征在于,在步骤(1)中所述的重氮组分、浓硫酸和稳定剂的投料摩尔比为1:1~3:103。
5.根据权利要求2所述的制备方法,其特征在于,在步骤(1)中所述的重氮组分、浓硫酸和稳定剂相加的总量占反应体系总重量的5~30%。
6.根据权利要求2所述的制备方法,其特征在于,在步骤(2)中所述的偶合组分与重氮组分的重氮盐固体的投料摩尔比为0.8~1:0.8~1.05。
7.根据权利要求2所述的制备方法,其特征在于,在步骤(1)中,重氮化试剂的加入时间为0.1~1h。
8.根据权利要求2所述的制备方法,其特征在于,在步骤(2)中,搅拌下加入重氮组分的重氮盐固体的时间为5~60min。
9.根据权利要求2~8的任一项所述的制备方法,其特征在于,所述的有机溶剂为乙酸乙酯、乙醚、乙二醇单甲醚、乙二醇二甲醚、乙二醇二乙醚、二乙二醇二甲醚、二乙二醇二乙醚、四氢呋喃、乙醇、异丙醇、二氧六环中的一种、两种或三种;所述的稳定剂为氟硼酸、氟硼酸钠、醋酸锌、氯化锌、苯磺酸、1-萘磺酸、2-萘磺酸、1,5-二萘磺酸、2,6-二萘磺酸、亚甲基二萘磺酸、亚甲基双甲基萘磺酸中的一种或两种。
10.如权利要求1所述的8-羟基喹啉基杂环偶氮分散染料在聚酯纤维、聚酰胺纤维、聚乳酸纤维、聚丙烯纤维或醋酸纤维染色中的应用。
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CN106380892A (zh) * | 2016-08-16 | 2017-02-08 | 上海贝通色彩科技有限公司 | 一种用于三醋纤的分散染料组合物 |
CN107501988B (zh) * | 2017-08-26 | 2020-09-25 | 宁波德欣科技有限公司 | 一种溶剂红195的制备方法 |
CN108034278A (zh) * | 2017-12-27 | 2018-05-15 | 沈阳化工研究院有限公司 | 一种偶合制备偶氮染料的方法 |
CN113683903B (zh) * | 2021-07-10 | 2024-03-15 | 青岛理工大学 | 一种噻唑杂环偶氮型活性染料及其制备方法 |
CN115612309B (zh) * | 2022-10-14 | 2023-07-21 | 浙江博澳新材料股份有限公司 | 一种双杂环双酯基偶氮分散染料及其制备方法 |
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CN114933818B (zh) * | 2022-06-28 | 2024-01-16 | 绍兴文理学院 | 一种吲哚啉分散染料及其制备方法 |
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