CN1066475C - 耐酸、碱变色的吡啶酮系黄色偶氮分散染料 - Google Patents
耐酸、碱变色的吡啶酮系黄色偶氮分散染料 Download PDFInfo
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- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
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Abstract
本发明提出一种新型耐酸、碱变色的吡啶酮分散染料,其结构式为:
X1为-Cl、-Br、-NO2、-OCH3,X2为-Cl、-Br、-NO2、-OCH3、-CN、R为-CH3、-C2H5、-C4H9、-CH2CH2CH2OCH3。该染料在酸、碱变色方面要优于其它吡啶酮染料。本发明同时还提出该染料的相关中间体N-烷基-脱氰基吡啶酮合成的改进方法。
Description
本发明提出一种新型吡啶酮分散染料及其相关中间体合成的改进方法。
本发明经过研究,发现了造成氰基吡啶酮染料酸、碱变色现象的原因在于:吡啶酮系染料存在腙体与偶氮体互变异构的平衡,而解离质酸、碱性增强,分别有利于腙式或偶氮式阴离子稳定造成的。并且色变点对应的PH值,随着3-位上的取代基R由-CN、-CONH2、H变化而增大。
本发明在此基础上提出了耐酸,碱变色的新型吡啶酮分散染料及其相应的合成方法。
式中X1为-Cl、-Br、-NO2、-OCH3,X2为-Cl、-Br、-NO2、-OCH3、-CN,R为-CH3、-C2H5、-C4H9、-CH2CH2CH2OCH3。染料的合成方法与传统的偶氮型分散染料的合成方法相类似。即先将重氮组份(Ⅱ)经重氮化反应合成重氮盐,再将重氮盐与偶合组份(Ⅲ),偶合反应而获得染料(Ⅰ)。
本发明所提出的染料,经检验,当PH值小于11时,其λmax值不发生改变,具有优秀的耐酸、碱变色性能,并且其各项性能指标均达到或超过对应的含氰基吡啶酮染料的各项性能指标。(见所附染料性能表)
本发明在提出新型吡啶酮分散染料的同时,也研究了其相关中间体N-烷基-脱氰基吡啶酮(Ⅲ)的合成路线及各步工艺条件。
N-烷基-氰基吡啶酮的合成原理为:Guareshi Thrope反应
AlKyl=烷基 R=甲基 z=烷基其反应原理是用乙酰乙酸乙酯、乙酰乙酰苯胺等和含有氰基的活性亚甲基化合物(如氰乙酸甲酯、氰乙酸乙酯、氰乙酰胺),在哌啶或醇钠存在下环构成N-取代的吡啶酮衍生物。最近的研究工作表明:氰乙酸乙酯、乙酰乙酸乙酯,在氨水中可直接环构成吡啶酮衍生物,这无疑简化了吡啶酮衍生物的合成工艺。对于N-烷基-脱氰基吡啶酮,有文献记载其合成可通过类似Guareshi-Thrope反应直接得到。但当R是H或CONH2时,由于H及CONH2使亚甲基活化能力远较-CN差,所以直接获取N-烷基-脱氰基吡啶酮的产率低得多。因此,直接获取N-烷基-脱氰基吡啶酮的方法在实际中不能采用。
R=甲基R'=CN Z=烷基
本发明经过研究,提出采用先合成N-烷基-氰基吡啶酮,再经脱氰反应合成N-烷基-脱氰基吡啶酮的工艺路线。该工艺路线和直接合成脱氰基吡啶酮路线相比,虽然多了脱氰基步骤,但最终收率较高,能在实际中应用。
N-烷基-氰基吡啶酮的合成,有文献与专利对其合成原理及方法作了具体的研究。美国专利U.S 4,284,752运用Guareshi Thrope反应原理,提出N-烷基氰基吡啶酮的合成方法:反应原料为胺、氰乙酸甲酯、乙酰乙酸甲酯。操作过程为:先将氰乙酸甲酯加入到胺中,常温搅拌后补加乙酰乙酸甲酯和水,升温到120℃,加压为5~20bar,反应到终点后,经稀释,中和,过滤,洗涤得产品。产品的收率为85.0%,这种合成方法的优点是:采用胺的水溶液进行反应,未用醇钠或哌啶等,简化了吡啶酮的合成工艺。缺点是:反应时间长,设备要求耐压。
本发明经过研究,认为N-烷基-氰基吡啶酮的合成历程为:首先,氰乙酸甲酯与胺反应生成氰胺,然后,氰胺再与乙酰乙酸甲酯合成N-烷基-氰基吡啶酮。在合成过程中,生成氰胺的时间可缩短,而加压过程的实质,是通过加压提高反应物的沸点,缩短反应时间。
本发明在此基础上提出N-烷基-氰基吡啶酮的两种改进方法:
加压分次投料方案:投料摩尔比(胺∶氰乙酸乙酯∶乙酰乙酸乙酯)不低于1.0∶1.0∶1.0,一般情况下为1.0~4.0∶1∶1.0~4.0。操作过程:先将氰乙酸乙酯加入到胺中,常温搅拌0.5~8hr,补加乙酰乙酸乙酯和水,升温到100℃以上,压力为反应物自身产生的压力,反应时间不少于5hr,反应物冷却后,经稀释、中和、过滤、洗涤得产品,产品收率为85.0%。
常压分次投料方案:投料摩尔比(胺∶氰乙酸乙酯∶乙酰乙酸乙酯)不低于1.0∶1.0∶1.0,一般情况下为1.0~4.0∶1∶1.0~4.0。操作过程:先将氰乙酸乙酯加入到胺中,常温搅拌0.5~8hr,补加乙酰乙酸乙酯和水,升温回流不少于12hr,一般为14~20hr。反应物冷却后,经稀释、中和、过滤、洗涤得产品,产品收率为85.0%。
加压分次投料方案、常压分次投料方案两种方法,和已有文献、专利中提到的合成方法相比,具有反应时间少、设备要求低的优点。
N-烷基-氰基吡啶酮脱氰反应,反应原理是-CN基团的水解,英国专利B.P1,288,671提出N-烷基-氰基吡啶酮脱氰反应合成N-烷基-吡啶酮的具体方法为:投料摩尔比(N-烷基-氰基吡啶酮∶硫酸)为1∶8,反应温度为100~110℃,反应时间为16~18小时,收率为95%。这种方法的优点在于保证了较高的收率,但硫酸的用量太大,在工业化过程中会增加成本。
本发明经过研究认为脱氰反应中硫酸的作用是溶剂与催化剂,其用量可以降低,并且可通过提高反应温度缩短反应时间。
本发明在此基础上提出了脱氰反应的改进方法为:投料摩尔比(烷基-氰基吡啶酮∶硫酸)为1∶3~6,反应温度可提高到120℃以上,一般为120℃~160℃,反应时间12~16小时,收率为95%,改进后的合成方法具有硫酸用量少,反应时间短的优点。
综上所述,本发明提出了一种新型吡啶酮分散染料,该种染料在酸、碱变色性能方面要优于现有的吡啶酮分散染料。并且本发明还就该种染料的相关中间体的合成,提出了改进方法。
本发明通过以下例子,对提出的新型耐酸、碱变色染料及相关中间体,作进一步的说明。
实例1:N-乙基-氰基-吡啶酮的合成(加压分次投料方案)
将11.3g的氰乙酸乙酯与10.4g的乙胺在常温下混合搅拌3小时,然后补加乙酰乙酸乙酯14.3g,水10ml,密封反应,升温到140℃,反应6小时,然后将反应混合物冷却,再用200ml水稀释,用10%盐酸调PH值为5~6,过滤、干燥得产品,熔点为184~185℃,收率为85.0%。
实例2:N-乙基-氰基吡啶酮的合成(常压分次投料方案)
将11.3g的氰乙酸乙酯与10.4g的乙胺在常温下混合搅拌3小时,然后,补加乙酰乙酸乙酯14.3g,水10ml,回流反应18小时,反应混合物冷却后,用200ml水稀释,用10%盐酸调PH值为5~6,过滤、干燥得产品。熔点为:184~185℃,收率为85.0%。
实例3:N-(γ-甲氧基丙基)-氰基吡啶酮的合成(加压分次投料方案)
将11.3g的氰乙酸乙酯与20.5g的γ-甲氧基丙胺在常温下混合,搅拌3小时,然后,补加乙酰乙酸乙酯14.3g,水100ml,加压反应6小时,反应混合物冷却后,用200.0ml水稀释,用10%盐酸调PH值为5~6,过滤、干燥得产品,熔点为:200~201℃,收率为85.0%。
实例4:N-(γ-甲氧基丙基)-氰基吡啶酮的合成(常压分次投料方案)
将11.3g的氰乙酸乙酯与20.5g的γ-甲氧基丙胺在常温下混合搅拌1小时,然后,补加乙酰乙酸乙酯14.3g,水10ml回流反应14小时,反应混合物冷却后,用200.0ml水稀释,用10%盐酸调PH值为5~6,过滤、干燥得产品,熔点为200~201℃,收率为85.0%。
实例5:N-乙基-脱氰基吡啶酮的合成
将9.19g的N-乙基-氰基吡啶酮与29.5ml 78%的硫酸混合,升温到100~130℃,反应16小时,将反应混合物冷却,用200.0g冰水混合物稀释,用30%NaOH溶液中和至PH值为5~6,过滤、干燥、洗涤得产品,熔点为:134~136℃,收率为95.0%。
实例6:N-(γ-甲氧基丙基)-脱氰基吡啶酮的合成
合成方法与实例5相似,熔点为102~103℃,收率为95.0%。
实例7:N-异丙基-脱氰基吡啶酮的合成
合成法与实例5相似,熔点为104~105℃,收率为95.0%。
实例8:N-丁基-脱氰基吡啶酮的合成
合成方法与实例5相似,熔点为:101~102℃,收率为95.0%。
实例9:染料(1)的合成
将干燥的亚硝酸钠粉末3.5g加入到40ml的浓硫酸中,并于70℃反应30min制成亚硝酰硫酸,再将8.9g对氯邻硝基苯胺逐渐加入到已制备好的亚硝酰硫酸中,保持此温度反应1hr,反应液变澄清,得到重氮盐溶液。将7.7(g)N-乙基-吡啶酮溶于20ml的10%Na2CO3水溶液中,得到偶合组份的水溶液。在0~2℃,搅拌的条件下,30分钟内将重氮盐溶液加入到偶合组份中,调整反应混合物的PH值为5~6,反应2小时,经过滤、洗涤得到染料,收率为95.0%,结构式如(1)。
实例10染料(2)的合成
将干燥的亚硝酸钠粉末3.5g加入到15ml水浴液中溶解,置于冰水浴中备用,再将8.9g邻氯对硝基苯胺的重氮组份加热溶于98%的浓硫酸中,然后加入冰水中析出。用亚硝酸钠溶液将芳胺悬浮液重氮化,随着反应进行,反应液变澄清,透明,搅拌1.5hr,得到重氮盐溶液。将9.1gN-乙基-吡啶酮溶于20ml的10%Na2CO3水溶液中,得到偶合组份的水溶液。在0~2℃,搅拌的条件下,30分钟内将重氮盐溶液加入到偶合组份中,调整反应混合物的PH值为5~6,反应2小时,经过滤、洗涤得到染料,收率为95.0%,结构式如(2)。
实例11:染料(3)的合成
实例12,染料(4)的合成
合成方法与实例9同,收率为95.0%
染料性能表
编号 | 项目染料编号 | 砂磨比例 | 耐温率度 | 摩擦率度 | 升华率度(180°,30°) | 皂洗率度(60±2℃,30°) | 汗渍率度(37±2℃,60°) | |||||||||
干度 | 湿度 | 原样变色 | 棉布沾色 | 涤沾色 | 原样变色 | 棉布沾色 | 不沾色 | 原样变色 | 棉布沾色 | 涤沾色 | ||||||
1 | ○ | 1∶1 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
2 | A | 1∶1 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3-4 | 5 | 5 | 5 | 5 | 5 | 5 | ||
3 | a | 1∶1 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
4 | B | 1∶1 | 6~7 | 4 | 4 | 4-5 | 4-5 | 2 | 5 | 5 | 5 | 5 | 5 | 5 | ||
5 | b | 1∶1 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3-4 | 5 | 5 | 5 | 5 | 5 | 5 | ||
6 | ○ | 1∶2 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
7 | A | 1∶2 | 6~7 | 4-5 | 4-5 | 4-5 | 4-5 | 3-4 | 5 | 5 | 5 | 5 | 5 | 5 | ||
8 | a | 1∶2 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3-4 | 5 | 5 | 5 | 5 | 5 | 5 | ||
9 | B | 1∶2 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
10 | b | 1∶2 | 6~7 | 4 | 4 | 4-5 | 4-5 | 2 | 5 | 5 | 5 | 5 | 5 | 5 | ||
11 | A∶a | 2∶8 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
12 | A∶a | 3∶7 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
13 | A∶a | 4∶6 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
14 | A∶a | 5∶5 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
15 | A∶a | 6∶4 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
16 | A∶a | 7∶3 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
17 | A∶a | 8∶2 | 6~7 | 4 | 4 | 4-5 | 4-5 | 3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
18 | B∶b | 2∶8 | 6~7 | 4 | 4 | 3-4 | 3-4 | 2-3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
19 | B∶b | 3∶7 | 6~7 | 4 | 4 | 3-4 | 3-4 | 2-3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
20 | B∶b | 4∶6 | 6~7 | 4 | 4 | 3-4 | 3-4 | 2-3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
21 | B∶b | 5∶5 | 6~7 | 4 | 4 | 3-4 | 3-4 | 2-3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
22 | B∶b | 6∶4 | 6~7 | 4 | 4 | 3-4 | 3-4 | 2-3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
23 | B∶b | 7∶3 | 6~7 | 4 | 4 | 3-4 | 3-4 | 2-3 | 5 | 5 | 5 | 5 | 5 | 5 | ||
24 | B∶b | 8∶2 | 6~7 | 4 | 4 | 3-4 | 3-4 | 2-3 | 5 | 5 | 5 | 5 | 5 | 5 |
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CN100371393C (zh) * | 2005-12-03 | 2008-02-27 | 青岛大学 | 一种耐光黄色单偶氮有机颜料及其制备方法 |
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CA2445022A1 (en) * | 2001-05-07 | 2002-11-14 | Ciba Specialty Chemicals Holding Inc. | Pyridone dyes, a process for their preparation and their use in the production of coloured plastics or polymeric colour particles |
CN103881412A (zh) * | 2014-03-22 | 2014-06-25 | 浙江山峪染料化工有限公司 | 一种单偶氮分散染料化合物及其制备方法 |
CN108250788B (zh) * | 2018-01-25 | 2021-11-16 | 江苏迪安化工有限公司 | 含磺酸酯基的吡啶酮类偶氮分散染料及其合成方法 |
CN108587229B (zh) * | 2018-06-05 | 2021-01-12 | 杭州吉华江东化工有限公司 | 一种含有吡啶酮结构分散染料的制备工艺与应用 |
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GB2201962A (en) * | 1987-02-16 | 1988-09-14 | Sumitomo Chemical Co | Monoazo pyridone disperse dyes |
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GB2201962A (en) * | 1987-02-16 | 1988-09-14 | Sumitomo Chemical Co | Monoazo pyridone disperse dyes |
US4826505A (en) * | 1987-02-16 | 1989-05-02 | Sumitomo Chemical Company, Limited | Monoazo pyridone compounds and application thereof for dyeing of hydrophobic fiber materials |
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