CN105130885A - 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

Info

Publication number
CN105130885A
CN105130885A CN201510527878.5A CN201510527878A CN105130885A CN 105130885 A CN105130885 A CN 105130885A CN 201510527878 A CN201510527878 A CN 201510527878A CN 105130885 A CN105130885 A CN 105130885A
Authority
CN
China
Prior art keywords
dipyridyl
aromatic diamines
diamines containing
bromo
synthetic method
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201510527878.5A
Other languages
English (en)
Other versions
CN105130885B (zh
Inventor
彭信文
侯豪情
许文慧
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangxi Normal University
Original Assignee
Jiangxi Normal University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangxi Normal University filed Critical Jiangxi Normal University
Priority to CN201510527878.5A priority Critical patent/CN105130885B/zh
Publication of CN105130885A publication Critical patent/CN105130885A/zh
Application granted granted Critical
Publication of CN105130885B publication Critical patent/CN105130885B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1085—Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Pyridine Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

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.calcdforC10H6N2Br2:C38.22,H1.91,N8.92,Br50.95；found:C38.23,H1.92,N8.91,Br50.94。
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.calcdforC22H18N4O2:C71.35,H4.86,N15.14,O8.65；found:C71.33,H4.87,N15.13,O8.67。
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.calcdforC10H6N2Br2:C38.22,H1.91,N8.92,Br50.95；found:C38.23,H1.92,N8.91,Br50.94。
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.calcdforC22H18N4O2:C71.35,H4.86,N15.14,O8.65；found:C71.33,H4.87,N15.13,O8.67。
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.calcdforC10H6N2Br2:C38.22,H1.91,N8.92,Br50.95；found:C38.23,H1.92,N8.91,Br50.94。
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.calcdforC22H18N4O2:C71.35,H4.86,N15.14,O8.65；found:C71.33,H4.87,N15.13,O8.67。
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.calcdforC10H6N2Br2:C38.22,H1.91,N8.92,Br50.95；found:C38.23,H1.92,N8.91,Br50.94。
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.calcdforC22H18N4O2:C71.35,H4.86,N15.14,O8.65；found:C71.33,H4.87,N15.13,O8.67。
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.calcdforC10H6N2Br2:C38.22,H1.91,N8.92,Br50.95；found:C38.23,H1.92,N8.91,Br50.94。
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.calcdforC22H18N4O2:C71.35,H4.86,N15.14,O8.65；found:C71.33,H4.87,N15.13,O8.67。
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 (7)

1.一种含联吡啶结构的芳香二胺，其化学结构式如式如式所示：
2.根据权利要求1所述的一种含联吡啶结构的芳香二胺，其特征在于，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。
3.根据权利要求1所述的一种含联吡啶结构的芳香二胺，其特征在于，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。
4.合成权利要求1所述的一种含联吡啶结构的芳香二胺的方法，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。
5.根据权利要求4所述的一种含联吡啶结构的芳香二胺的合成方法，其特征在于，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。
6.根据权利要求4所述的一种含联吡啶结构的芳香二胺的合成方法，其特征在于，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。
7.根据权利要求4所述的一种含联吡啶结构的芳香二胺的合成方法，其特征在于，具体包括以下步骤：
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％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。
CN201510527878.5A 2015-08-25 2015-08-25 一种含有联吡啶结构的芳香二胺及其合成方法 Expired - Fee Related CN105130885B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510527878.5A CN105130885B (zh) 2015-08-25 2015-08-25 一种含有联吡啶结构的芳香二胺及其合成方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510527878.5A CN105130885B (zh) 2015-08-25 2015-08-25 一种含有联吡啶结构的芳香二胺及其合成方法

Publications (2)

Publication Number Publication Date
CN105130885A true CN105130885A (zh) 2015-12-09
CN105130885B CN105130885B (zh) 2018-08-24

Family

ID=54716520

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510527878.5A Expired - Fee Related CN105130885B (zh) 2015-08-25 2015-08-25 一种含有联吡啶结构的芳香二胺及其合成方法

Country Status (1)

Country Link
CN (1) CN105130885B (zh)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107383372A (zh) * 2017-07-31 2017-11-24 江汉大学 具有嘧啶侧基的聚酰亚胺膜及其制备方法
CN107445944A (zh) * 2017-07-31 2017-12-08 江汉大学 含n‑嘧啶吲哚结构的二胺单体及其制备方法
CN107446133A (zh) * 2016-06-01 2017-12-08 台虹科技股份有限公司 聚酰胺酸组合物、聚酰亚胺及积层板
CN108659220A (zh) * 2018-05-30 2018-10-16 江西师范大学 一种含联三吡啶结构的聚酰亚胺及其制备方法
CN115417809A (zh) * 2022-09-05 2022-12-02 天津药明康德新药开发有限公司 一种4,4-二吡咯-2,2-联吡啶的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013036232A2 (en) * 2011-09-08 2013-03-14 Deciphera Pharmaceuticals, Llc Methods and compositions for the treatment of myeloproliferative diseases and other proliferative diseases
CN103102488A (zh) * 2013-02-07 2013-05-15 江西师范大学 含联嘧啶结构的高介电常数聚酰亚胺及其制备方法
CN103113309A (zh) * 2013-02-07 2013-05-22 江西师范大学 联嘧啶二苯二醚二胺及其合成方法
CN103113583A (zh) * 2013-02-07 2013-05-22 江西师范大学 高介电常数的聚酰亚胺金属络合物及其制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013036232A2 (en) * 2011-09-08 2013-03-14 Deciphera Pharmaceuticals, Llc Methods and compositions for the treatment of myeloproliferative diseases and other proliferative diseases
CN103102488A (zh) * 2013-02-07 2013-05-15 江西师范大学 含联嘧啶结构的高介电常数聚酰亚胺及其制备方法
CN103113309A (zh) * 2013-02-07 2013-05-22 江西师范大学 联嘧啶二苯二醚二胺及其合成方法
CN103113583A (zh) * 2013-02-07 2013-05-22 江西师范大学 高介电常数的聚酰亚胺金属络合物及其制备方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KAZUHISA ISHIMOTO ET AL.: "Development of a Scalable Synthesis of a Vascular Endothelial Growth Factor Receptor‑2 Kinase Inhibitor: Efficient Construction of a 6‑Etherified [1,2,4]Triazolo[1,5‑a]pyridine-2-amine Core", 《ORGANIC PROCESS RESEARCH & DEVELOPMENT》 *
王艳荣: "可溶性含钌配合物和空穴传输基团聚酰亚胺光伏材料的合成与表征", 《中国博士学位论文全文数据库 工程科技II辑》 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107446133A (zh) * 2016-06-01 2017-12-08 台虹科技股份有限公司 聚酰胺酸组合物、聚酰亚胺及积层板
CN107383372A (zh) * 2017-07-31 2017-11-24 江汉大学 具有嘧啶侧基的聚酰亚胺膜及其制备方法
CN107445944A (zh) * 2017-07-31 2017-12-08 江汉大学 含n‑嘧啶吲哚结构的二胺单体及其制备方法
CN107445944B (zh) * 2017-07-31 2018-07-10 江汉大学 含n-嘧啶吲哚结构的二胺单体及其制备方法
CN108659220A (zh) * 2018-05-30 2018-10-16 江西师范大学 一种含联三吡啶结构的聚酰亚胺及其制备方法
CN108659220B (zh) * 2018-05-30 2021-05-04 江西师范大学 一种含联三吡啶结构的聚酰亚胺及其制备方法
CN115417809A (zh) * 2022-09-05 2022-12-02 天津药明康德新药开发有限公司 一种4,4-二吡咯-2,2-联吡啶的制备方法

Also Published As

Publication number Publication date
CN105130885B (zh) 2018-08-24

Similar Documents

Publication Publication Date Title
CN105130885A (zh) 一种含有联吡啶结构的芳香二胺及其合成方法
Zeng et al. Studies on self-promoted cure behaviors of hydroxy-containing phthalonitrile model compounds
CN105085281B (zh) 含二苯胺‑芴的二胺单体、制备方法及其在制备聚酰亚胺中的应用
Kim et al. Syntheses and thermal properties of poly (hydroxy) urethanes by polyaddition reaction of bis (cyclic carbonate) and diamines
CN105237462B (zh) 一种含咔唑结构的具有高平面性二胺单体及其合成方法和应用
CN104016870B (zh) 一种含间三联苯结构二胺化合物及其合成方法和应用
Wang et al. New fluorinated poly (ether sulfone imide) s with high thermal stability and low dielectric constant
CN107056711B (zh) 含哒嗪基团的二胺单体及其制备方法与应用
US20230242707A1 (en) Biomass benzoxazine-based shape memory resin, preparation method therefor, and application thereof
Yi et al. Soluble aromatic polyimides with high glass transition temperature from benzidine containing tert-butyl groups
CN103483206A (zh) 一种含不对称非共平面结构的二胺单体及其制备方法
Zeng et al. Synthesis and curing of a novel amino-containing phthalonitrile derivative
CN113480442A (zh) 一种可交联二胺单体、制备方法及其在制备聚酰亚胺中的应用
Faghihi et al. New polyamides based on 2, 5‐bis [(4‐carboxyanilino) carbonyl] pyridine and aromatic diamines: Synthesis and characterization
Huang et al. Synthesis and characterization of novel highly soluble and optical transparent polyimides containing tert-butyl and morpholinyl moieties
Zhao et al. Synthesis of a new pyridine-containing diamine and related polyimide
CN101870693B (zh) 含1,3,4-噁二唑结构双马来酰亚胺及其制备方法
CN111909122A (zh) 一种含有2,5-呋喃二甲醇结构的二胺单体及其制备方法、聚酰亚胺薄膜及其制备方法
CN106543174A (zh) 一种含醚及二氮芴结构二酸单体及其聚苯并咪唑的合成
CN116730845A (zh) 一种高含氟联苯二胺、一种无色聚酰亚胺光学薄膜及其制备方法与应用
CN102796015A (zh) 一种含双三氟甲基取代不对称芳香二胺单体及其制备方法
Mallakpour et al. Ionic liquid catalyzed synthesis of organosoluble wholly aromatic optically active polyamides
Kim et al. DBU-catalyzed CO2 fixation in polypropargylamines under solvent-free conditions
CN103467353B (zh) 含芴基及芳醚键结构的双马来酰亚胺及其制备方法
Banihashemi et al. Synthesis and properties of novel aromatic polyamides derived from benzofuro [2, 3-b] benzofuran-2, 9-dicarboxylic acid and aromatic diamines

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20180824

Termination date: 20190825

CF01 Termination of patent right due to non-payment of annual fee