CN1315785C - β－羟烷基酰胺、其制备方法和用途 - Google Patents

β－羟烷基酰胺、其制备方法和用途 Download PDF

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CN1315785C
CN1315785C CNB011375140A CN01137514A CN1315785C CN 1315785 C CN1315785 C CN 1315785C CN B011375140 A CNB011375140 A CN B011375140A CN 01137514 A CN01137514 A CN 01137514A CN 1315785 C CN1315785 C CN 1315785C
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beta
hydroxy alkylamide
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hydroxy
alkylamide
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CN1351008A (zh
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A·卡普兰
R·吉斯勒
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EMS Chemie AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers

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Abstract

本发明涉及通式I的β-羟烷基酰胺，其中R1是H或直链或支链的C1-C10烷基，R2是直链或支链C1-C5烷基。

Description

β-羟烷基酰胺、其制备方法和用途
技术领域
本发明涉及新的β-羟烷基酰胺、其制备方法和用途。
背景技术
β-羟烷基酰胺作为中间体产物和用作聚合物的交联剂是非常重要的。β-羟烷基酰胺通常通过烷基酯和β-烷醇胺在碱性催化剂存在下的氨解制备。β-羟烷基酰胺或者通过在溶剂中结晶分离和提纯，或者，特别是对于固体β-羟烷基酰胺，采用不使用溶剂的淤浆处理方法。在US 5 101 073和EP 0 473 380 B1中描述了上述类型的方法。淤浆处理方法基于这样的事实，即，在β-羟烷基酰胺生产期间发生的平衡反应向需要的最终产物方向移动，这是在定义的温度范围内回火从熔化物沉淀所要的β-羟烷基酰胺并且随后结晶熔化物的结果。这种方法的缺点是使用等摩尔量的烷基酯和β-羟烷基酰胺。
在DE 198 23 925中描述了另一种用于制备β-羟烷基酰胺的方法。在该方法中，不使用溶剂，在碱性催化剂存在下，酯和醇胺一起转化。
EP-A-322 834描述了一种粉末涂料，其含有聚酯和β-羟烷基酰胺作为交联剂(固化剂)。相应的性质优良的涂料可用所述文献中描述的配方生产。
由于β-羟烷基酰胺作为中间体产物的主要重要性，特别是如EP-A-322 834中描述的作为用于聚酯粉末涂料的交联剂，人们近来对于新的β-羟烷基酰胺产生了很大的兴趣。
发明内容
基于上述现有技术，本发明的目的是提供一种新的、先前未知的β-羟烷基酰胺及其相应的制备方法。
本发明教导，该目的可通过如下文中通式I所定义，且R1表示氢或直链或支链的C1-C10烷基，R2是直链或支链的C1-C5烷基的β-羟烷基酰胺和如下文所述的通过将通式II的羧酸衍生物与通式III的烷醇胺反应的方法实现；其中通式II中R3为卤素或OR4，R4表示直链C1-C5烷基；而通式III中R1和R2定义同前文。从属权利要求描述了本发明的有利的发展。本发明要求保护的β-羟烷基酰胺的用途包括其作为聚合物的交联剂、粉末涂料的交联剂、聚酯粉末涂料的交联剂以及和另一种选自β-羟烷基酰胺和/或环氧化物的交联剂的混合物用作交联剂的用途。
本发明的β-羟烷基酰胺如通式I所定义：
Figure C0113751400051
式I中，R1表示氢或直链或支链的C1-C10烷基。R2是直链或支链的C1-C5烷基。本发明的新的β-羟烷基酰胺特征特别在于OH基团旁边的取代的碳原子。在本发明的β-羟烷基酰胺中，R2基团位于此处。
β-羟烷基酰胺优选的结构是其中R1基团为H、叔丁基、异丙基或戊基并位于CO基团的对位。
本发明的一个非常特别优选的实施方案的特征在于，R1基团是氢而R2基团是甲基。
这些β-羟烷基酰胺的制备是通过将通式II的羧酸衍生物用通式III的烷醇胺转化，
R1和R2基团定义如上。R3基团可以是卤素，优选氯，或是OR4基团。如果是OR4基团，则R4是直链的C1-C5烷基，优选CH3基团。
羧酸衍生物和烷醇胺的转化反应优选在溶液中进行。优选的溶剂非限制性地包括：芳烃类，诸如苯、甲苯或二甲苯。醚类诸如乙醚或上述溶剂的混合物也适用。
本发明方法的基本特征在于通式II的羧酸衍生物和通式III的烷醇胺在剧烈搅拌下反应。因此，烷醇胺优选先存在，然后在剧烈搅拌下滴加羧酸衍生物。
在羧酸卤化物的情况下，转化在-10-25℃、优选0-10℃进行。反应时间通常为0.5-5小时。反应时间为2小时是最有利的。
如果在方法中包括酯(R3＝OR4)，则反应温度为室温至150℃。
本发明的β-羟烷基酰胺特别适用于作为聚合物的交联剂。β-羟烷基酰胺特别优选作为用于用聚酯或聚丙烯酸酯作为聚合物的粉末涂料的交联剂。
基本上，与如EP-A-322 A34中引用的β-羟烷基酰胺相似，所述β-羟烷基酰胺可用作交联剂(固化剂)。本发明的β-羟烷基酰胺还可与其它固化剂一起使用。这种用法的一个例子是EMS-CHEMIE AG，Domat/Ems以PRIMID名称出售的固化剂。PRIMID是N，N，N’，N’2-羟基乙基己二酰二胺。
具体实施方式
参考作为本发明优选实施方案的一个制备实施例更详细地说明本发明，其中R1是H，R2是CH3。
制备实施例：
将44.16g(0.32mol)无水K2CO3、42.56g(0.32mol)二异丙醇胺、160ml水和160ml乙醚置于装有搅拌器、漏斗、温度计和回流冷凝器的1升的四颈圆底烧瓶中。用漏斗将44.96g(0.32mol)苯甲酰氯加入并溶于160ml甲苯。该溶液随后在剧烈搅拌下用2小时滴加到反应烧瓶中。在加料期间，反应混合物的温度保持在0-5℃。加料完毕后，在0-5℃再继续搅拌30分钟。然后移去冰浴，在室温将混合物再搅拌50分钟。
滤出在反应期间形成的沉淀，用35ml甲苯洗涤2次，然后用30ml乙醚洗涤3次，再在50℃真空下干燥。干燥的粗产物(74.28g)在苯中沸腾(25％溶液)，滤出不溶的部分，在室温下结晶产物。过滤并干燥后，得到51.80g(68％)N，N-二(2-羟基异丙基)苯甲酰胺，熔点103℃。元素分析：C13H19NO3计算值：C＝65.82％，H＝8.02％，N＝5.91％，0＝20.25％。实验值：C＝66.25％，H＝8.09％，N＝5.83％，0＝19.83％。

Claims (3)

1.制备式I的β-羟烷基酰胺的方法：
Figure C011375140002C1
其特征在于，使二异丙醇胺与苯甲酰氯在溶剂中于剧烈搅拌或搅动下在0-5℃反应。
2.权利要求1的方法，其特征在于，使用芳烃和/或醚作为溶剂。
3.权利要求2的方法，其特征在于，所述芳烃是苯、甲苯或二甲苯。
CNB011375140A 2000-10-26 2001-10-26 β－羟烷基酰胺、其制备方法和用途 Expired - Fee Related CN1315785C (zh)

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ATE555904T1 (de) 2009-08-10 2012-05-15 Eastman Kodak Co Lithografische druckplattenvorläufer mit betahydroxy-alkylamid-vernetzern
CN101704762B (zh) * 2009-11-13 2013-01-09 六安市捷通达化工有限责任公司 一种β-羟烷基酰胺的生产工艺
JP6283477B2 (ja) * 2012-06-25 2018-02-21 ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ アミド成分を含むフォトレジスト
CN103641737B (zh) * 2013-11-29 2016-04-20 六安市捷通达化工有限责任公司 一种羧酸改性的羟烷基酰胺固化剂的制备方法
CN106986786A (zh) * 2017-02-27 2017-07-28 沈阳化工大学 一种合成β‑羟烷基酰胺的工艺方法
EP4025617A1 (en) 2019-09-03 2022-07-13 Poliresin S.r.l. Hydroxyalkylamide functionalized acrylic polymers and process for manufacturing them
EP4299656A1 (de) 2022-07-01 2024-01-03 Evonik Operations GmbH Herstellung von propoxylierten benzoldicarbonsäureamiden und dem entsprechenden polyurethanschaum

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DE19823925A1 (de) * 1998-05-28 1999-12-02 Inventa Ag Verfahren zur Herstellung von beta-Hydroxyalkylamiden
CN1057519C (zh) * 1992-02-28 2000-10-18 罗姆和哈斯公司 β－羟酰胺的制备

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