CN115322223A - 一种新型磷酸酯类阻燃防老化助剂及其制备方法 - Google Patents
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Abstract
本发明的目的在于提供一种新型磷酸酯类阻燃防老化助剂及其制备方法,是通过甲基膦酸二甲酯或乙基膦酸二乙酯和四甲基哌啶醇进行酯交换反应得到目标产物(低分子量光稳定剂),该产物可作为一种同时具有阻燃和防老化效果的新型助剂,可以作为同时需要阻燃和耐候要求产品的添加助剂;容易制备、合成工艺相对简单,该方法制得的产品产率高,反应条件温和,易于工业化生产。
Description
技术领域
本发明属于高分子材料助剂领域,具体为一种新型磷酸酯类阻燃防老化助剂及其制备方法。
背景技术
阻燃剂是塑料助剂中发展最快的品种之一。有资料显示,全世界阻燃剂需求量已超过120万吨/年,包括卤系阻燃剂、磷系阻燃剂、无机阻燃剂等数百个品种。由于众所周知的环境与毒理学方面的原因,欧盟在十多年前就开始对大量生产的化学品对环境以及人类健康的潜在影响进行评估。阻燃剂也不例外,已经开始评估的有溴系阻燃剂和磷系阻燃剂。其中对五溴二苯醚、八溴二苯醚以及十溴二苯醚评估已经结束。欧盟于2004年8月15日开始禁用五溴二苯醚和八溴二苯醚;对十溴二苯醚所进行的风险评估结论是对人类健康或环境’没有显见的风险’,不必采取风险降低措施。
阻燃剂主要有有机和无机,卤素和非卤。有机是以溴系、氮系和红磷及化合物为代表的一些阻燃剂,无机主要是三氧化二锑、氢氧化镁、氢氧化铝,硅系等阻燃体系。一般来讲有机阻燃具有很好的亲和力在塑料中,溴系阻燃剂在有机阻燃体系中占据绝对优势,虽然在环保问题上“非议”多端但一直难以有其他阻燃剂体系取代。
高分子防老化是高分子化学中的一个重要课题。高分子老化主要是热氧老化和光氧老化;对于不饱和的高分子,臭氧老化也占一定的地位。主要的防老化措施有:①在高分子中添加各种稳定剂(高分子防老剂);②用物理方法进行防护;③改进聚合和加工工艺;④进行聚合物的改性。其中,添加稳定剂是防老化常用的方法。
光稳定剂是高分子制品(例如塑料、橡胶、涂料、合成纤维)的一种添加剂,它能屏蔽或吸收紫外线的能量,猝灭单线态氧及将氢过氧化物分解成非活性物质等功能,使高分子聚合物在光的辐射下,能排除或减缓光化学反应可能性,阻止或延迟光老化的过程,从而达到延长高分子聚合物制品使用寿命的目的。
酯化反应为可逆反应,在酯的溶液中,是有少量的游离醇和酸存在的。酯交换反应正是基于酯化反应的可逆性而进行的,反应中的醇能够与酯溶液中少量游离的酸进行酯化反应,新的酯化反应就生成了新的酯和新的醇。由于酯化反应的可逆性,若想酯交换反应能够进行,至少满足下面两种情况的一种:一、生成的新酯稳定性强于之前的酯。二、生成的新酯能够在反应过程中不断蒸出。
发明内容
为解决上述问题,本发明公开了一种容易制备、合成工艺相对简单,同时具备光稳定功能和阻燃功能的新型助剂制备方法,通过甲基膦酸二甲酯或乙基膦酸二乙酯和四甲基哌啶醇进行酯交换反应得到目标产物(低分子量光稳定剂),该方法制得的产品产率高,反应条件温和,易于工业化生产。
为达到上述目的,本发明的技术方案如下:
一种新型磷酸酯类阻燃防老化助剂,结构式如式(Ⅰ)所示:
式(Ⅰ)
一种新型磷酸酯类阻燃防老化助剂的制备方法,包括以下步骤:将甲基膦酸二甲酯或乙基膦酸二乙酯加入溶剂中,加热搅拌,降温,加入四甲基哌啶醇和催化剂,反应得到新型磷酸酯类阻燃防老化助剂,反应方程式如下所示。
作为本发明的进一步改进,所述甲基膦酸二甲酯或乙基膦酸二乙酯与溶剂的摩尔比为1:5-1:3。
作为本发明的进一步改进,所述甲基膦酸二甲酯或乙基膦酸二乙酯与四甲基哌啶醇的摩尔比为1:1.12。
作为本发明的进一步改进,所述催化剂质量为磷酸酯用量1%。
作为本发明的进一步改进,所述加热搅拌的转速为50-200r/min,加热搅拌的时间为5-30min,加热搅拌的温度为60-100℃。
作为本发明的进一步改进,所述反应的温度为80-130℃,反应的时间为6-12h。
作为本发明的进一步改进,所述溶剂为甲苯、正辛烷、石油醚中的一种。
作为本发明的进一步改进,所述催化剂为异丙醇铝。
作为本发明的进一步改进,所述降温为降温至50℃。
本发明的有益效果为:
本发明一种新型磷酸酯类阻燃防老化助剂的制备方法,合成步骤较少,反应条件温和,产物同时具备磷酸酯和受阻胺两种官能团,具有一定的阻燃效果和光稳定效果,可以作为同时需要阻燃和耐候要求产品的添加助剂。
附图说明
图1为实施例6产物的气相色谱图。
具体实施方式
下面结合具体实施方式,进一步阐明本发明,应理解下述具体实施方式仅用于说明本发明而不用于限制本发明的范围。
实施例1
在有冷凝器、分水器、扑沫器、回流管、温度计和搅拌器组装而成后的1000ml的四口瓶中加入460g甲苯做溶剂,124g甲基膦酸二甲酯,1.24g异丙醇铝开启搅拌,80℃,100r/min下搅拌30min。降温至30℃后加入176g四甲基哌啶醇,开启搅拌,90℃下反应8h后降温至室温,然后水洗、脱色、过滤得到目标产物235.9g。
实施例2
在有冷凝器、分水器、扑沫器、回流管、温度计和搅拌器组装而成后的1000ml的四口瓶中加入460g甲苯做溶剂,166g乙基磷酸二乙酯,1.66g异丙醇铝开启搅拌,80℃,100r/min下搅拌30min。降温至30℃后加入176g四甲基哌啶醇,开启搅拌,100℃下反应8h后降温至室温,然后水洗、脱色、过滤得到目标产物243.7g。
实施例3
在有冷凝器、分水器、扑沫器、回流管、温度计和搅拌器组装而成后的1000ml的四口瓶中加入460g甲苯做溶剂,166g乙基磷酸二乙酯,开启搅拌,80℃,100r/min下搅拌30min。降温至30℃后加入176g四甲基哌啶醇,1.66g异丙醇铝开启搅拌,110℃下反应8h后降温至室温,然后水洗、脱色、过滤得到目标产物249.0g。
实施例4
在有冷凝器、分水器、扑沫器、回流管、温度计和搅拌器组装而成后的1000ml的四口瓶中加入460g甲苯做溶剂,166g乙基磷酸二乙酯,1.66g异丙醇铝开启搅拌,80℃,100r/min下搅拌30min。降温至30℃后加入176g四甲基哌啶醇,开启搅拌,120℃下反应8h后降温至室温,然后水洗、脱色、过滤得到目标产物258.6g。
实施例5
在有冷凝器、分水器、扑沫器、回流管、温度计和搅拌器组装而成后的1000ml的四口瓶中加入460g甲苯做溶剂,166g乙基磷酸二乙酯,1.66g异丙醇铝开启搅拌,80℃,100r/min下搅拌30min。降温至30℃后加入176g四甲基哌啶醇,开启搅拌,120℃下反应10h后降温至室温,然后水洗、脱色、过滤得到目标产物267.6g。
实施例6
在有冷凝器、分水器、扑沫器、回流管、温度计和搅拌器组装而成后的1000ml的四口瓶中加入460g甲苯做溶剂,166g乙基磷酸二乙酯,1.66g异丙醇铝开启搅拌,80℃,100r/min下搅拌30min。降温至30℃后加入176g四甲基哌啶醇,开启搅拌,120℃下反应12h后降温至室温,然后水洗、脱色、过滤得到目标产物271.1g。其气相色谱图如图1所示。
将实施例1-6制备产物分别以3‰添加量添加至聚丙烯T30s中经拉丝机制备成扁丝样品,空白组指未添加光稳定剂的扁丝产品,进行老化试验和阻燃试验,老化试验方法:紫外灯313 老化标准参照ASTM G154。阻燃试验方法:添加5%不同样品阻燃剂注塑阻燃试片,通过测试阻燃试片阻燃等级(UL94)对比不同助剂的阻燃效果。以下是实施例产物的测试结果:
表1 老化和阻燃性能检测数据表
需要说明的是,以上内容仅仅说明了本发明的技术思想,不能以此限定本发明的保护范围,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰均落入本发明权利要求书的保护范围之内。
Claims (10)
2.一种如权利要求1所述的新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,包括以下步骤:将磷酸酯加入溶剂中,加热搅拌,降温,加入四甲基哌啶醇和催化剂,反应得到新型磷酸酯类阻燃防老化助剂;所述磷酸酯为甲基膦酸二甲酯或乙基膦酸二乙酯。
3.根据权利要求2所述的一种新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,所述甲基膦酸二甲酯或乙基膦酸二乙酯与溶剂的摩尔比为1:5-1:3。
4.根据权利要求2所述的一种新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,所述甲基膦酸二甲酯或乙基膦酸二乙酯与四甲基哌啶醇的摩尔比为1:1.12。
5.根据权利要求2所述的一种新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,所述催化剂质量为磷酸酯用量1%。
6.根据权利要求2所述的一种新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,所述加热搅拌的转速为50-200r/min,加热搅拌的时间为5-30min,加热搅拌的温度为60-100℃。
7.根据权利要求2所述的一种新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,所述反应的温度为80-130℃,反应的时间为6-12h。
8.根据权利要求3所述的一种新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,所述溶剂为甲苯、正辛烷、石油醚中的一种。
9.根据权利要求5所述的一种新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,所述催化剂为异丙醇铝。
10.根据权利要求2所述的一种新型磷酸酯类阻燃防老化助剂的制备方法,其特征在于,所述降温为降温至30-50℃。
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