CN107056975A - 一种吩噁嗪类化合物为光引发剂的原子转移自由基聚合制备聚合物的方法 - Google Patents
一种吩噁嗪类化合物为光引发剂的原子转移自由基聚合制备聚合物的方法 Download PDFInfo
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- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- QHTRBQBPXGFDDO-UHFFFAOYSA-N 2-bromo-2-methylpropanedioic acid Chemical class OC(=O)C(Br)(C)C(O)=O QHTRBQBPXGFDDO-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
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- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
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- 229920002521 macromolecule Polymers 0.000 description 1
- NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 description 1
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
- C08F120/14—Methyl esters, e.g. methyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F112/02—Monomers containing only one unsaturated aliphatic radical
- C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F112/06—Hydrocarbons
- C08F112/08—Styrene
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- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
- C08F120/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F120/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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- C08F120/52—Amides or imides
- C08F120/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
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- C08F2/00—Processes of polymerisation
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- C08F2438/00—Living radical polymerisation
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Abstract
本发明公开了一种吩噁嗪类化合物为光引发剂的原子转移自由基聚合制备聚合物的方法，主要步骤如下：(1)将可进行自由基聚合的单体、原子转移自由基聚合引发剂、吩噁嗪类光引发剂、溶剂组成聚合反应体系；(2)在光照射下进行原子转移自由基聚合，得到具有活性特征的聚合物。本发明条件温和，且在聚合过程不适用金属催化剂，得到的聚合物没有金属离子污染，具有良好的工业前景。
Description
技术领域
本发明涉及高分子化学领域，具体是一种吩噁嗪类化合物为光引发剂的原子转移自由基聚合制备聚合物的方法。
背景技术
原子转移自由基聚合(ATRP)(Wang JS, Matyjaszewski K. Controlled/"living" radical polymerization. Atom transfer radical polymerization in thepresence of transition-metal complexes. J Am Chem Soc, 1995, 117, 5614-5615;Kato M, Kamigaito M, Sawamoto M, Higashimura T. Polymerization of methylmethacrylate with the carbon tetrachloride/dichlorotris-(triphenylphosphine)ruthenium(II)/methylaluminum bis (2, 6-di-tert-butylphenoxide) initiatingsystem: possibility of living radical polymerization. Macromolecules, 1995,28, 1721-1723.)提供了一种合成分子量可控，分子量分布窄的聚合物的方法。然而，在ATRP过程不可避免要用到的过渡金属催化剂导致得到的最终产物中会出现大量催化剂的残留。这不仅影响了ATRP在生物医药方面的应用，对环境资源而言都是不利的。到目前为止，已经有很多关于ATRP中催化剂分离技术的报道，但大多需要通过复杂的后处理反应并且大多是非均相反应。且冗长的后处理过程和不可避免地催化剂流失使得这些技术复杂化而不利于工业运用。
发明内容
由于吩噁嗪类化合物优良的光电特性以及强的给电子性，其应用于光敏染料得了良好的光电转化效率。N-苯基吩噁嗪(一种合成N-芳基-吩噁嗪类化合物的方法，专利号CN103819423A)、N-(4-腈基苯基)吩噁嗪(一种合成N-芳基-吩噁嗪类化合物的方法，专利号CN103819423A)、N-(3-噻吩基)吩噁嗪(一种合成N-芳基-吩噁嗪类化合物的方法，专利号CN103819423A)是三种吩噁嗪类化合物。
本发明的目的是提供一种以N-苯基吩噁嗪、N-(4-腈基苯基)吩噁嗪、N-(3-噻吩基)吩噁嗪化合物为光引发剂，在没有金属催化剂存在的前提下通过原子转移自由基聚合制备了分子量及分子量分布可控的聚合物。
具体实施方案：
实施例1：
称取10.00 g（100 mmol）甲基丙烯酸甲酯单体、0.2431g （1mmol）α-溴代苯乙酸乙酯、0.0003 g（0.001 mmol）N-(3-噻吩基)吩噁嗪加入到装有20 ml N,N-二甲基甲酰胺的三口瓶中，超声分散，氮气置换，室温下光照射10小时。反应完成后，将反应混合溶液倒入甲醇中析出，得到聚合产物，即聚甲基丙烯酸甲酯。采用重量法测其转化率为36.8%，用凝胶渗透色谱分析其分子量为Mn,GPC=6200 g/mol，聚合分散度PDI=1.25。
实施例2：
称取10.04 g （100 mmol）苯乙烯单体、0.2431g （1mmol）α-溴代苯乙酸乙酯、0.0003 g（0.001 mmol）N-(3-噻吩基)吩噁嗪加入到装有20 ml N,N-二甲基甲酰胺的三口瓶中，超声分散，氮气置换，室温下光照射10小时。反应完成后，将反应混合溶液倒入甲醇中析出，得到聚合产物，即聚苯乙烯。采用重量法测其转化率为26.7%，用凝胶渗透色谱分析其分子量为Mn,GPC=4800 g/mol，聚合分散度PDI=1.32。
实施例3：
称取7.108 g（100 mmol）丙烯酰胺单体、0.2431g（1mmol）α-溴代苯乙酸乙酯、0.0003 g（0.001 mmol）N-(3-噻吩基)吩噁嗪加入到装有20 ml N,N-二甲基甲酰胺的三口瓶中，超声分散，氮气置换，室温下光照射10小时。反应完成后，将反应混合溶液倒入甲醇中析出，得到聚合产物，即聚甲基丙烯酸甲酯。采用重量法测其转化率为31.8%，用凝胶渗透色谱分析其分子量为Mn,GPC=5800 g/mol，聚合分散度PDI=1.29。
实施例4：
称取10.00 g（100 mmol）甲基丙烯酸甲酯单体、0.2531 g（1 mmol）2-溴-2-甲基丙二酸二乙基酯、0.0003 g（0.001 mmol）N-苯基吩噁嗪加入到装有20 ml N,N-二甲基甲酰胺的三口瓶中，超声分散，氮气置换，室温下光照射12小时。反应完成后，将反应混合溶液倒入甲醇中析出，得到聚合产物，即聚甲基丙烯酸甲酯。采用重量法测其转化率为38.5%，用凝胶渗透色谱分析其分子量为Mn,GPC=5800 g/mol，聚合分散度PDI=1.18。
实施例5：
称取12.81 g（100 mmol）丙烯酸丁酯单体、0.2531 g（1 mmol）2-溴-2-甲基丙二酸二乙基酯、0.0003 g（0.001 mmol）N-(4-腈基苯基)吩噁嗪加入到装有20 ml N,N-二甲基甲酰胺的三口瓶中，超声分散，氮气置换，室温下光照射24小时。反应完成后，将反应混合溶液倒入甲醇中析出，得到聚合产物，即聚甲基丙烯酸甲酯。采用重量法测其转化率为51.3%，用凝胶渗透色谱分析其分子量为Mn,GPC=7700 g/mol，聚合分散度PDI=1.35。
Claims (6)
1.一种光诱导原子转移自由基聚合的方法，有以下步骤组成：在光照射条件下，将可进行自由基聚合的单体、原子转移自由基聚合引发剂、吩噁嗪类化合物光引发剂、溶剂组成聚合反应体系，在光照射下室温进行原子转移自由基聚合反应，得到分子及分子量分布可控的聚合物。
2.根据权利要求1所述的方法，其特征在于，所述的单体是丙烯酸酯类、苯乙烯、丙烯酰胺。
3.根据权利要求1所述的方法，其特征在于，所述的原子转移自由基聚合引发剂是α-溴代苯乙酸乙酯、2-溴-2-甲基丙二酸二乙基酯。
4.根据权利要求1所述的方法，其特征在于，所述的吩噁嗪类化合物光引发剂是N-苯基吩噁嗪、N-(4-腈基苯基)吩噁嗪、N-(3-噻吩基)吩噁嗪。
5.根据权利要求1所述的方法，其特征在于，所述的可进行自由基聚合的单体、原子转移自由基聚合引发剂、吩噁嗪类化合物光引发剂的摩尔比是(50-1000):(1-2):(0.001-0.01)。
6.根据权利要求1所述的方法，其特征在于，所述的溶剂为N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、甲醇、乙醇、乙二醇、二氯甲烷、水。
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