CN105130885B - 一种含有联吡啶结构的芳香二胺及其合成方法 - Google Patents

一种含有联吡啶结构的芳香二胺及其合成方法 Download PDF

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CN105130885B
CN105130885B CN201510527878.5A CN201510527878A CN105130885B CN 105130885 B CN105130885 B CN 105130885B CN 201510527878 A CN201510527878 A CN 201510527878A CN 105130885 B CN105130885 B CN 105130885B
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彭信文
侯豪情
许文慧
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Abstract

本发明公开了一种含有联吡啶结构的芳香二胺及其合成方法，其化学结构式如式(1)所示，本发明所制备的含联吡啶单元的芳香二胺是一类新型的含联吡啶单元的二胺单体，作为含氮杂环的单体，相比类似的含苯环的单体，为聚合得到的PI带来了更加显著的性能的改善，包括显著提高了聚合物的热稳定性和玻璃化转变温度，显著改善了聚合物的介电性，总之，本发明的芳香二胺更加有益于改善聚酰亚胺和聚酰胺的应用加工性能及拓展其应用领域。

Description

一种含有联吡啶结构的芳香二胺及其合成方法
技术领域
本发明属于有机化合物及其制备方法的技术领域，具体涉及到一种含有联吡啶结构的芳香二胺及其合成方法。
背景技术
聚酰亚胺是一类具有优异的热稳定性、机械性能及电性能的高性能高分子材料，广泛应用于汽车、航空航天、微电子等高科技领域。联吡啶及其衍生物对过渡金属以及稀土金属具有很强的亲和性，能与很多的过渡金属以及稀土金属形成络合物，配合物中存在较强的dπ-pπ反馈键。联吡啶单元的氮杂环引入聚酰亚胺分子中，不仅能提高其玻璃化转变温度、热稳定性以及力学性能，还能赋予其络合功能，形成PI/金属络合交联的功能性高分子材料，在保持其较高热稳定性、优异介电性的同时，且具有低膨胀系数，以期将PI材料的应用领域大幅度拓展。
发明内容
本发明的目的之一在于：提供一种含联吡啶啶结构的芳香二胺，它作为单体，能够为聚合得到的PI带来更加显著的性能改善。
本发明的另一个目的在于：提供一种含联吡啶结构的芳香二胺的合成方法，该方法具有步骤简单，反应产率高，环境友好等优点。
为实现此目的，本发明的技术方案如下：
提供一种含联吡啶结构的芳香二胺，其化学结构式如式(1)所示：
本发明一种优选的方案中，式(1)所示的含联吡啶结构的芳香二胺的氨基在苯氧基苯环上的取代位为4位置。
本发明的另一种优选方案中，式(1)所示的含联吡啶结构的芳香二胺的两端苯环上的氨基取代位置相同。
本发明还提供所述的含联吡啶结构的芳香二胺的制备方法，包括以下步骤：
1)将2,2′-联吡啶与溴发生取代反应得到5,5′-二溴-2,2′-联吡啶；
2)将步骤1)得到的5,5′-二溴-2,2′-联吡啶再与4-氨基苯酚发生亲核取代反应，得到5,5′-双[(4-氨基)苯氧基]-2,2′-联吡啶。
步骤1)所述的取代反应优选2,2′-联吡啶与液溴在反应釜中1.5～2.0大气压下加热反应。
步骤2)所述的反应溶剂为N-甲基吡咯烷酮或者二甲基亚砜。
本发明优选的制备方法如下：
第一步反应：2,2'-联吡啶与液溴物质量比为1:1.5～1:2.5放入反应釜140～160℃下及1.5～2.0大气压反应8～15小时，反应后冷却至室温，把固体粉碎，加入到Na2SO3溶液中搅拌，除去未反应的溴，过滤，再用5％NaOH的溶液碱化除酸，过滤，得到粗产品，用乙酸乙酯/石油醚来进行柱层分离，得到白色5,5'-二溴-2,2'-联吡啶。
第二步反应：5,5'-二溴-2,2'-联吡啶与4-氨基苯酚物质量比为1:2.4～1:3.0加入三颈烧瓶中，再加入除水的N-甲基吡咯烷酮或者二甲基亚砜，加入无水碳酸钾或者氢氧化钠或者氢氧化钾，反应物在170～200℃反应8～12小时，冷却至室温，倒入5％NaOH溶液搅拌1小时，过滤出固体，用蒸馏水反复洗涤几次，用水和乙醇重结晶，得到白色的2,6-双[(4-氨基)苯氧基]-2,2'-联吡啶。
本发明所制备的含联吡啶单元的芳香二胺是一类新型的含联吡啶单元的二胺单体，作为含氮杂环的单体，相比类似的含苯环的单体，为聚合得到的PI带来了更加显著的性能的改善，包括显著提高了聚合物的热稳定性和玻璃化转变温度，显著改善了聚合物的介电性，总之，本发明的芳香二胺更加有益于改善聚酰亚胺和聚酰胺的应用加工性能及拓展其应用领域。
附图说明
图1：5,5′-双[(4-氨基)苯氧基]-2,2′-联吡啶的红外光谱图IR(KBr)。
图2：5,5′-双[(4-氨基)苯氧基]-2,2′-联吡啶的核磁谱图1HMR(DMSO-d6)。
图3：5,5′-双[(4-氨基)苯氧基]-2,2′-联吡啶的核磁谱图13CMR(DMSO-d6)。
具体实施方式
下面将结合附图实施例详细说明本发明所具有的有益效果，旨在帮助阅读者更好地理解本发明的实质，但不能对本发明的实施和保护范围构成任何限定。
实施例1
2,2'-联吡啶(4.99g,0.032mol)和液溴(10.24g,0.064mol)放入反应釜中1.5大气压下150℃反应15小时，反应后冷却至室温，把固体粉碎，加入到Na2SO3溶液中搅拌，除去未反应的溴，过滤，再用5％NaOH的溶液碱化除酸，过滤，得到粗产品，用乙酸乙酯/石油醚来进行柱层分离，得到白色5,5'-二溴-2,2'-联吡啶8.64g,产率86％,m.p.221.6-222.1℃.1H-NMR(400MHz,CDCl3,d):7.95(d,2H),8.28(s,2H),8.71(d,2H)；13C-NMR(100MHz,CDCl3,d):121.47(C5),122.25(C3),139.64(C4)；150.28(C6),153.64(C2),IR(KBr):3049(C-H,stretching),1562,1453,1356(Ar,stretching),636(C-Br,stretch).Anal.calcd forC10H6N2Br2:C 38.22,H 1.91,N 8.92,Br 50.95；found:C 38.23,H 1.92,N 8.91,Br 50.94。
5,5'-二溴-2,2'-联吡啶(6.28g，0.02mol)，4-氨基苯酚(5.23g，0.048mol)加入三颈烧瓶中，再加入100ml除水的N-甲基吡咯烷酮，加入无水碳酸钾K2CO3(2.73g，0.02mol,)，反应物在175℃反应12小时，冷却至室温，倒入5％NaOH溶液搅拌1小时，过滤出固体，用蒸馏水反复洗涤几次，用水和乙醇重结晶，得到白色的2,6-双[(4-氨基)苯氧基]-2,2'-联吡啶6.44g，产率87％，m.p.204.0-204.6℃.1H-NMR(400MHz,DMSO-d6,d):5.06(s,4H),6.61(d,4H),6.85(d,4H),7.29(d,2H),8.21(s,2H),8.29(d,2H).13C-NMR(100MHz,DMSO-d6,d):114.89(C3'),120.82(C2’),123.92(C3,C4),138.43(C6),144.75(C4'),146.04(C1'),148.84(C2),155.36(C5).FTIR(KBr):3396,3302(N-H,stretching),1633,1558,1503,1455(Ar,stretching).Anal.calcd for C22H18N4O2:C 71.35,H 4.86,N 15.14,O 8.65；found:C71.33,H 4.87,N15.13,O 8.67。
实施例2
2,2'-联吡啶(4.99g,0.032mol)和液溴(10.24g,0.064mol)放入反应釜中2.0大气压下150℃反应15小时，反应后冷却至室温，把固体粉碎，加入到Na2SO3溶液中搅拌，除去未反应的溴，过滤，再用5％NaOH的溶液碱化除酸，过滤，得到粗产品，用乙酸乙酯/石油醚来进行柱层分离，得到白色5,5'-二溴-2,2'-联吡啶8.64g,产率91％,m.p.221.6-222.1℃.1H-NMR(400MHz,CDCl3,d):7.95(d,2H),8.28(s,2H),8.71(d,2H)；13C-NMR(100MHz,CDCl3,d):121.47(C5),122.25(C3),139.64(C4)；150.28(C6),153.64(C2),IR(KBr):3049(C-H,stretching),1562,1453,1356(Ar,stretching),636(C-Br,stretch).Anal.calcd forC10H6N2Br2:C 38.22,H 1.91,N 8.92,Br 50.95；found:C 38.23,H 1.92,N 8.91,Br 50.94。
5,5'-二溴-2,2'-联吡啶(6.28g，0.02mol)，4-氨基苯酚(5.23g，0.048mol)加入三颈烧瓶中，再加入100ml除水的N-甲基吡咯烷酮，加入无水碳酸钾K2CO3(2.73g，0.02mol,)，反应物在175℃反应12小时，冷却至室温，倒入5％NaOH溶液搅拌1小时，过滤出固体，用蒸馏水反复洗涤几次，用水和乙醇重结晶，得到白色的2,6-双[(4-氨基)苯氧基]-2,2'-联吡啶6.44g，产率87％，m.p.204.0-204.6℃.1H-NMR(400MHz,DMSO-d6,d):5.06(s,4H),6.61(d,4H),6.85(d,4H),7.29(d,2H),8.21(s,2H),8.29(d,2H).13C-NMR(100MHz,DMSO-d6,d):114.89(C3'),120.82(C2’),123.92(C3,C4),138.43(C6),144.75(C4'),146.04(C1'),148.84(C2),155.36(C5).FTIR(KBr):3396,3302(N-H,stretching),1633,1558,1503,1455(Ar,stretching).Anal.calcd for C22H18N4O2:C 71.35,H 4.86,N 15.14,O 8.65；found:C71.33,H 4.87,N 15.13,O 8.67。
实施例3
2,2'-联吡啶(4.99g,0.032mol)和液溴(10.24g,0.064mol)放入反应釜中1.5大气压下150℃反应15小时，反应后冷却至室温，把固体粉碎，加入到Na2SO3溶液中搅拌，除去未反应的溴，过滤，再用5％NaOH的溶液碱化除酸，过滤，得到粗产品，用乙酸乙酯/石油醚来进行柱层分离，得到白色5,5'-二溴-2,2'-联吡啶8.64g,产率86％,m.p.221.6-222.1℃.1H-NMR(400MHz,CDCl3,d):7.95(d,2H),8.28(s,2H),8.71(d,2H)；13C-NMR(100MHz,CDCl3,d):121.47(C5),122.25(C3),139.64(C4)；150.28(C6),153.64(C2),IR(KBr):3049(C-H,stretching),1562,1453,1356(Ar,stretching),636(C-Br,stretch).Anal.calcd forC10H6N2Br2:C 38.22,H 1.91,N 8.92,Br 50.95；found:C 38.23,H 1.92,N 8.91,Br 50.94。
5,5'-二溴-2,2'-联吡啶(6.28g，0.02mol)，4-氨基苯酚(5.23g，0.048mol)加入三颈烧瓶中，再加入100ml除水的N-甲基吡咯烷酮，加入无水碳酸钾K2CO3(2.73g，0.02mol,)，反应物在195℃反应12小时，冷却至室温，倒入5％NaOH溶液搅拌1小时，过滤出固体，用蒸馏水反复洗涤几次，用水和乙醇重结晶，得到白色的2,6-双[(4-氨基)苯氧基]-2,2'-联吡啶6.44g，产率92％，m.p.204.0-204.6℃.1H-NMR(400MHz,DMSO-d6,d):5.06(s,4H),6.61(d,4H),6.85(d,4H),7.29(d,2H),8.21(s,2H),8.29(d,2H).13C-NMR(100MHz,DMSO-d6,d):114.89(C3'),120.82(C2’),123.92(C3,C4),138.43(C6),144.75(C4'),146.04(C1'),148.84(C2),155.36(C5).FTIR(KBr):3396,3302(N-H,stretching),1633,1558,1503,1455(Ar,stretching).Anal.calcd for C22H18N4O2:C 71.35,H 4.86,N 15.14,O 8.65；found:C71.33,H 4.87,N 15.13,O 8.67。
实施例4
2,2'-联吡啶(4.99g,0.032mol)和液溴(10.24g,0.064mol)放入反应釜中1.5大气压下150℃反应15小时，反应后冷却至室温，把固体粉碎，加入到Na2SO3溶液中搅拌，除去未反应的溴，过滤，再用5％NaOH的溶液碱化除酸，过滤，得到粗产品，用乙酸乙酯/石油醚来进行柱层分离，得到白色5,5'-二溴-2,2'-联吡啶8.64g,产率86％,m.p.221.6-222.1℃.1H-NMR(400MHz,CDCl3,d):7.95(d,2H),8.28(s,2H),8.71(d,2H)；13C-NMR(100MHz,CDCl3,d):121.47(C5),122.25(C3),139.64(C4)；150.28(C6),153.64(C2),IR(KBr):3049(C-H,stretching),1562,1453,1356(Ar,stretching),636(C-Br,stretch).Anal.calcd forC10H6N2Br2:C 38.22,H 1.91,N 8.92,Br 50.95；found:C 38.23,H 1.92,N 8.91,Br 50.94。
5,5'-二溴-2,2'-联吡啶(6.28g，0.02mol)，4-氨基苯酚(5.23g，0.048mol)加入三颈烧瓶中，再加入100ml除水的二甲基亚砜(DMSO)，加入无水碳酸钾K2CO3(2.73g，0.02mol,)，反应物在185℃反应12小时，冷却至室温，倒入5％NaOH溶液搅拌1小时，过滤出固体，用蒸馏水反复洗涤几次，用水和乙醇重结晶，得到白色的2,6-双[(4-氨基)苯氧基]-2,2'-联吡啶6.44g，产率88％，m.p.204.0-204.6℃.1H-NMR(400MHz,DMSO-d6,d):5.06(s,4H),6.61(d,4H),6.85(d,4H),7.29(d,2H),8.21(s,2H),8.29(d,2H).13C-NMR(100MHz,DMSO-d6,d):114.89(C3'),120.82(C2’),123.92(C3,C4),138.43(C6),144.75(C4'),146.04(C1'),148.84(C2),155.36(C5).FTIR(KBr):3396,3302(N-H,stretching),1633,1558,1503,1455(Ar,stretching).Anal.calcd for C22H18N4O2:C 71.35,H 4.86,N 15.14,O 8.65；found:C 71.33,H 4.87,N 15.13,O 8.67。
实施例5
2,2'-联吡啶(4.99g,0.032mol)和液溴(10.24g,0.064mol)放入反应釜中1.5大气压下150℃反应15小时，反应后冷却至室温，把固体粉碎，加入到Na2SO3溶液中搅拌，除去未反应的溴，过滤，再用5％NaOH的溶液碱化除酸，过滤，得到粗产品，用乙酸乙酯/石油醚来进行柱层分离，得到白色5,5'-二溴-2,2'-联吡啶8.64g,产率86％,m.p.221.6-222.1℃.1H-NMR(400MHz,CDCl3,d):7.95(d,2H),8.28(s,2H),8.71(d,2H)；13C-NMR(100MHz,CDCl3,d):121.47(C5),122.25(C3),139.64(C4)；150.28(C6),153.64(C2),IR(KBr):3049(C-H,stretching),1562,1453,1356(Ar,stretching),636(C-Br,stretch).Anal.calcd forC10H6N2Br2:C 38.22,H 1.91,N 8.92,Br 50.95；found:C 38.23,H 1.92,N 8.91,Br 50.94。
5,5'-二溴-2,2'-联吡啶(6.28g，0.02mol)，4-氨基苯酚(5.23g，0.048mol)加入三颈烧瓶中，再加入100ml除水的二甲基亚砜(DMSO)，加入无水碳酸钾K2CO3(2.73g，0.02mol,)，反应物在170℃反应12小时，冷却至室温，倒入5％NaOH溶液搅拌1小时，过滤出固体，用蒸馏水反复洗涤几次，用水和乙醇重结晶，得到白色的2,6-双[(4-氨基)苯氧基]-2,2'-联吡啶6.44g，产率82％，m.p.204.0-204.6℃.1H-NMR(400MHz,DMSO-d6,d):5.06(s,4H),6.61(d,4H),6.85(d,4H),7.29(d,2H),8.21(s,2H),8.29(d,2H).13C-NMR(100MHz,DMSO-d6,d):114.89(C3'),120.82(C2’),123.92(C3,C4),138.43(C6),144.75(C4'),146.04(C1'),148.84(C2),155.36(C5).FTIR(KBr):3396,3302(N-H,stretching),1633,1558,1503,1455(Ar,stretching).Anal.calcd for C22H18N4O2:C 71.35,H 4.86,N 15.14,O 8.65；found:C 71.33,H 4.87,N 15.13,O 8.67。
以上所述的实施例仅仅是对本发明的优选实施方式进行描述，并非对本发明的范围进行限定，在不脱离本发明设计精神的前提下，本领域普通技术人员对本发明的技术方案作出的各种变形和改进，均应落入本发明权利要求书确定的保护范围内。

Claims (1)

1.一种5,5'-双[(4-氨基)苯氧基]-2,2'-联吡啶的合成方法，包括以下步骤：
第一步反应：2,2'-联吡啶与液溴物质量比为1:1.5～1:2.5放入反应釜140～160℃下及1.5～2.0大气压反应8～15小时，反应后冷却至室温，把固体粉碎，加入到Na2SO3溶液中搅拌，除去未反应的溴，过滤，再用5％的NaOH溶液碱化除酸，过滤，得到粗产品，用乙酸乙酯/石油醚来进行柱层分离，得到白色5,5'-二溴-2,2'-联吡啶；
第二步反应：5,5'-二溴-2,2'-联吡啶与4-氨基苯酚物质量比为1:2.4～1:3.0加入三颈烧瓶中，再加入除水的N-甲基吡咯烷酮或者二甲基亚砜，加入无水碳酸钾或者氢氧化钠或者氢氧化钾，反应物在170～200℃反应8～12小时，冷却至室温，倒入5％的NaOH溶液搅拌1小时，过滤出固体，用蒸馏水反复洗涤几次，用水和乙醇重结晶，得到白色的5,5'-双[(4-氨基)苯氧基]-2,2'-联吡啶。
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