CN112375399B - 单偶氮化合物、制备方法及其用途 - Google Patents
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Abstract
本发明公开了一种通式(1)的单偶氮化合物,其中D1指苯环上邻、间、或对位置被一个三氟甲基取代的重氮组份基团。D2指取代的苯系列或取代吡啶系列。其中R1为氢、甲氧基、乙氧基、丙氧基、丁氧基、2‑甲氧乙基、卤素;R2是氢、C1‑6直链或支链烷基、烯丙基、氰乙基、苄基、苯乙基;R3是氢、C1‑6直链或支链烷基、烯丙基、氰乙基、苄基、苯乙基;R4是氢、甲基、乙基、羟基、‑NHO2S‑C1‑4烷基或取代烷基、‑NHOC‑C1‑4烷基或取代烷基、卤素;R5为羟乙基,2‑乙氧基乙基,2甲氧基乙基,3‑甲氧基丙基,或是一种未被取代的或取代的芳基;R6为羟乙基,2‑乙氧基乙基,2甲氧基乙基,3‑甲氧基丙基,或是一种未被取代的或取代的芳基。本发明还涉及到他们的制备方法及它们在塑料着色中的用途。D1‑N=N‑D2(1)
Description
技术领域
本发明涉及溶剂染料技术领域,具体地说是一种邻、间、或对位被一个三氟甲基取代的被苯胺作为重氮组份的单偶氮化合物、制备方法及其用途。
背景技术
尼龙塑胶由于其化学结构的特殊性,普通的塑胶溶剂染料很难适用于尼龙塑胶的着色。尤其是尼龙6和尼龙66对染料的耐还原性要求极高,国内市场现有的溶剂染料基本都不能满足要求。发明系列尼龙用溶剂染料对满足市场的需求,具有很好的现实意义和经济意义。
发明内容
本发明的目的是提供一种以三氟甲基取代苯胺做为重氮组份,以取代苯系列或取代吡啶系列为偶合组份合成的单偶氮化合物、制备方法及其用途。
塑胶染料不仅能满足普通塑胶的着色要求,亦能满足尼龙6和尼龙66的着色要求,可应用于尼龙6和尼龙66的注塑着色和纺前着色领域。用于运动、休闲服装的弹性纤维增长较快,因此,增加用于着尼龙着色的染料品种就非常必要,为达到上述目的,本发明涉及的以三氟甲基苯胺为重氮组份,以取代苯系列或取代吡啶系列为偶合组份合成的新型结构单偶氮染料化合物,如式(1)所示,
D1-N=N-D2
(1)
式中,
D1是指苯环上邻、间、或对位被一个三氟甲基取代的重氮组份基团;
D2是指取代的苯系列或取代吡啶系列;
R1是指氢、甲氧基、乙氧基、丙氧基、丁氧基、2-甲氧乙基或卤素;
R2是指氢、C1-6直链或支链烷基、烯丙基、氰乙基、苄基或苯乙基;
R3是指氢、C1-6直链或支链烷基、烯丙基、氰乙基、苄基或苯乙基;
R4是指氢、甲基、乙基、羟基、-NHO2S-C1-4烷基或取代烷基、-NHOC-C1-4烷基或取代烷基或卤素;
R5是指羟乙基,2-乙氧基乙基,2甲氧基乙基,3-甲氧基丙基或2-甲基苯基;
R6是指羟乙基,2-乙氧基乙基,2甲氧基乙基,3-甲氧基丙基,3-甲基苯基或2-甲基苯基。
所述的单偶氮化合物,其特征在于R1是氢、甲氧基或乙氧基。
所述的单偶氮化合物,其特征在于R2是指氢、C1-6直链或支链烷基、烯丙基、氰乙基或苄基。
所述的单偶氮化合物,其特征在于R3是指氢、C1-6直链或支链烷基、烯丙基、氰乙基或苄基。
所述的单偶氮化合物,其特征在于R4是指氢、甲基、羟基、-NHO2S-C1-4烷基或取代烷基或-NHOC-C1-4烷基。
所述的单偶氮化合物,其特征在于R5是指羟乙基,2-甲氧基乙基,3-甲氧基丙基或2甲基苯基。
所述的单偶氮化合物,其特征在于R6是指羟乙基,2甲氧基乙基,3-甲氧基丙基或2-甲基苯基。
所述的单偶氮化合物,其特征在于(1a)所示,
所述的单偶氮化合物,其特征在于(1b)所示,
所述的单偶氮化合物,其特征在于(1c)所示,
所述的单偶氮化合物,其特征在于(1d)所示,
所述的单偶氮化合物,其特征在于(1e)所示,
所述的单偶氮化合物,其特征在于(1f)所示,
所述单偶氮化合物的制备方法,其特征在于包括如步骤,将式(2)所述的化合物所述的化合物溶于5%-10%的盐酸中,降温到-5℃~20℃,滴加30%亚硝酸钠溶液,进行重氮化,加完后在-5℃~20℃保温1-5
小时,得到重氮盐备用;
将式(D2)所示化合物的分散在硫酸或醋酸的酸性水介质中,
降温到0℃~25℃后,搅拌下滴加重氮液进行偶合反应,1-4小时加完,同样温度下保温2-6小时,经过滤,水洗,烘干得粗品染料;将粗品染料加入到重量3倍的DMF中105-110℃溶解后,降温到30℃物料析出,过滤,甲醇洗到无色,母液回收套用,滤饼烘干的同时回收甲醇,本发明所得产品;
其中式(2)为邻三氟甲基苯胺,间三氟甲基苯胺或对三氟甲基苯胺;
其中R1、R2、R3、R4、R5和R6具有上述式(1)的定义;
其中重氮化的温度为-5℃~20℃;
其中偶合的温度为0℃~25℃。
本发明还包括:所述反应中重氮化的优化温度为0℃-10℃。
本发明所述反应中偶合的优化温度为10℃-15℃。
本发明涉及一种以三氟甲基取代苯胺做为重氮组份,以取代苯系列或取代吡啶系列为偶合组份合成的新型结构单偶氮化合物,如式(1)所示,制备的单偶氮化合物,该类化合物作为着色染料,具有以下优势:
(1)高温色牢度好。高温稳定好,从260℃到300℃染色强度基本不变。
(2)制备工艺简单,成本低,“三废”排放量少。在染料合成过程中,重氮组份和偶合组份都为市场普通的产品,其合成方法简单,收率高,成本较低。
所述式(1)的单偶氮染料用于制备塑胶纺前染色或聚合物注塑着色。用具有通式(1)的偶氮染料对高分子有机物质进行着色,例如,通过使用轧制、混合装置或研磨装置将这种染料混合进那些基质中,染料被溶解或细微的分散在高分子量原料中,然后使用本身为我们知道的工艺,例如压延、压塑、挤出、纺丝或注塑的方法,来加工含有染料的高分子有机原料,这样来对塑料或聚合物染色。染料和聚合物或塑料的掺和也可以在实际操作步骤前,可以通过连续地将一固体染料(例如,一般粉末状染料),同时将粒状或粉末状的高分子有机原料,直接加入到一挤出机的进料区,一般优选地,预先将染料混合到高分子有机原料中,这样到高分子有机原料可以得到更好的着色。
本发明的偶氮化合物用于被着色的优选高分子有机物是介电常数≥2.5的非常普通的聚合物,特别是是聚酰胺,聚酯,聚甲基丙烯酸甲酯,聚碳酸脂,聚苯乙烯,聚丙烯,聚乙烯等。优化的是聚酰胺和聚酯。例如,尼龙-6,尼龙-66或线性的芳香聚酯。
下面的实施例起说明本发明的作用。在实施例中,除非另有说明,份数按重量份数计算,百分率按重量百分率计算,温度为摄氏度。按重量计算的分数和按体积计算的份数之间的关系与克和立方厘米之间的关系相同。
实施例1:
将32.2g的邻三氟甲基苯胺,100g的水,97g的30%盐酸加入到500ML的三口瓶内,冰水降温到0-5℃,1-2小时滴加30%亚硝酸钠溶液46g,加完后保持对碘化钾试纸显蓝色,在0-5℃保温2小时,1小时滴入有10ML浓硫酸,300G的冰水和32.5G的化合物(3a)的混合物中,
继续搅拌3小时,过滤,水洗,烘干得64G粗品染料,在192G的DMF中105-110℃溶解后,降温到30℃物料析出,过滤,甲醇洗到无色,母液回收套用,滤饼烘干的同时回收甲醇,得下式的染料,
用于尼龙66着色为黄色,吸收波长457nm。
实施例2:
将32.2g的邻三氟甲基苯胺,100g的水,97g的30%盐酸加入到500ML的三口瓶内,冰水降温到0-5℃,1-2小时滴加30%亚硝酸钠溶液46g,加完后保持对碘化钾试纸显蓝色,在0-5℃保温2小时,1小时滴入有10ML浓硫酸,300G的冰水和41.2g的化合物(3b)的混合物中,
继续搅拌3小时,过滤,水洗,烘干得73G粗品染料,在219G的DMF中105-110℃溶解后,降温到30℃物料析出,过滤,甲醇洗到无色,母液回收套用,滤饼烘干的同时回收甲醇得下式的染料,
用于尼龙66着色为橙色,吸收波长477nm。
实施例3:
将32.2g的邻三氟甲基苯胺,100g的水,97g的30%盐酸加入到500ML的三口瓶内,冰水降温到0-5℃,1-2小时滴加30%亚硝酸钠溶液46g,加完后保持对碘化钾试纸显蓝色,在0-5℃保温2小时,1小时滴入有10ML浓硫酸,300G的冰水和52.8g的化合物(3c)的混合物中,
继续搅拌3小时,过滤,水洗,烘干得84G粗品染料,在252G的DMF中100-105℃溶解后,降温到30℃物料析出,过滤,甲醇洗到无色,母液回收套用,滤饼烘干的同时回收甲醇得下式的染料,
用于尼龙66着色为红色,吸收波长499nm。
实施例4:
将32.2g的邻三氟甲基苯胺,100g的水,97g的30%盐酸加入到500ML的三口瓶内,冰水降温到0-5℃,1-2小时滴加30%亚硝酸钠溶液46g,加完后保持对碘化钾试纸显蓝色,在0-5℃保温2小时,1小时滴入有10ML浓硫酸,300G的冰水和46.6g的化合物(3d)的混合物中,
继续搅拌3小时,过滤,水洗,烘干得78G粗品染料,在234G的DMF中100-105℃溶解后,降温到40℃物料析出,过滤,甲醇洗到无色,母液回收套用,滤饼烘干的同时回收甲醇得下式的染料,
用于尼龙66着色为橙色,吸收波长479nm。
实施例5:
将32.2g的邻三氟甲基苯胺,100g的水,97g的30%盐酸加入到500ML的三口瓶内,冰水降温到0-5℃,1-2小时滴加30%亚硝酸钠溶液46g,加完后保持对碘化钾试纸显蓝色,在0-5℃保温2小时,1小时滴入有10ML浓硫酸,300G的冰水和64.6g的化合物(3e)的混合物中,
继续搅拌3小时,过滤,水洗,烘干得96G粗品染料,在288G的DMF中1115-120℃溶解后,降温到40℃物料析出,过滤,甲醇洗到无色,母液回收套用,滤饼烘干的同时回收甲醇得下式的染料,
用于尼龙66着色为黄色,吸收波长472nm。
实施例6:
将32.2g的邻三氟甲基苯胺,100g的水,97g的30%盐酸加入到500ML的三口瓶内,冰水降温到0-5℃,1-2小时滴加30%亚硝酸钠溶液46g,加完后保持对碘化钾试纸显蓝色,在0-5℃保温2小时,1小时滴入有10ML浓硫酸,300G的冰水和61.3g的化合物(3f)的混合物中,
继续搅拌3小时,过滤,水洗,烘干得93G粗品染料,在279G的DMF中110-115℃溶解后,降温到35℃物料析出,过滤,甲醇洗到无色,母液回收套用,滤饼烘干的同时回收甲醇得下式的染料,
用于尼龙66着色为嫩黄色,吸收波长450nm。
实施例7-38
下述染料同样适合于聚酯纤维材料的染色。他们类似于实施例制备
表一:
实施例39-70(表二)
下述染料同样适合于聚酯纤维材料的染色。他们类似于实施例制备
表二:
实施例71-102(表三)
下述染料同样适合于聚酯纤维材料的染色。他们类似于实施例制备
表三
实施例103-119(表四)
下述染料同样适合于聚酯纤维材料的染色。他们类似于实施例制备
表四:
实施例120-136(表五)
下述染料同样适合于聚酯纤维材料的染色。他们类似于实施例制备
表五
实施例137-153(表六)
下述染料同样适合于聚酯纤维材料的染色。他们类似于实施例制备
表六
应用例:
染料称取各实施例的样品0.034g,钛白1.0g,尼龙66 400g。设置注塑机温度260摄氏度,约40分钟达到温度,开始注塑打板取第8块,第9块,第10块留作样板。提升注塑机温度到280摄氏度,约20分钟到达温度,注塑打板同样取第8块,第9块,第10块留作样板。再次提升注塑机温度到300摄氏度,约20分钟到达温度,注塑打板同样取第8块,第9块,第10块留作样板。用测色仪检测260摄氏度的第8块,第9块,第10块样板色光强度,以其样板为标准,分别和280摄氏度样板,300摄氏度样板做对比,检测色光和强度变化。得到各实施例在不同高温下的强度。(表七)
表七
由表七可以得出本发明涉及一种以邻三氟甲基苯胺做为重氮组份,以特定的取代苯系列或取代吡啶系列为偶合组份合成的新型结构单偶氮染料化合物用于尼龙66着色,在高温下,实施例强度基本不变,色光近似,说明染料耐高温性好。特别优选的实施例1和实施例6。
Claims (8)
2.如权利要求1所述的单偶氮染料化合物,其特征在于R2是指乙基、丙基、烯丙基或氰乙基。
3.如权利要求1所述的单偶氮染料化合物,其特征在于R3是指乙基、丙基、烯丙基或氰乙基。
4.如权利要求1所述的单偶氮染料化合物,其特征在于R4是指-NHO2SCH3或-NHOCCH3。
5.一种制备如权利要求1所述单偶氮染料化合物的方法,其特征在于包括如步骤,将式(2)所述的化合物溶于5%-10%的盐酸中,
降温到-5℃~20℃,滴加30%亚硝酸钠溶液,进行重氮化,加完后在-5℃~20℃保温1-5小时,得到重氮盐备用;
将式(D2)所示化合物分散在硫酸或醋酸的酸性水介质中,降温到0℃~25℃后,搅拌下滴加重氮液进行偶合反应,1-4小时加完,同样温度下保温2-6小时,经过滤,水洗,烘干得粗品染料;将粗品染料加入到其重量3倍的DMF中105-110℃溶解后,降温到30℃物料析出,过滤,甲醇洗到无色,母液回收套用,滤饼烘干的同时回收
甲醇,得产品;
其中R1、R2、R3、R4为权利要求1的定义;
其中重氮化的温度为-5℃~20℃;
其中偶合的温度为0℃~25℃。
6.如权利要求5所述的单偶氮染料化合物制备方法,其特征在于,所述反应中重氮化的温度为0℃-10℃。
7.如权利要求5所述的单偶氮染料化合物制备方法,其特征在于,所述反应中偶合的温度为10℃-15℃。
8.如权利要求1-4中任一项所述的单偶氮染料化合物的应用,其特征在于,所述单偶氮染料化合物均适用于在制备塑胶纺前着色或聚合物注塑着色方面。
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