CN1222501C - 新型化合物 - Google Patents

新型化合物 Download PDF

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CN1222501C
CN1222501C CNB008013446A CN00801344A CN1222501C CN 1222501 C CN1222501 C CN 1222501C CN B008013446 A CNB008013446 A CN B008013446A CN 00801344 A CN00801344 A CN 00801344A CN 1222501 C CN1222501 C CN 1222501C
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上野隆三
北山雅也
南宪次
若森浩之
森直子
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Ueno Seiyaku Oyo Kenkyujo KK
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Abstract

提供通式〔1〕表示的化合物或其盐类这一新型化合物。本发明化合物作为聚酯或聚酰胺等的结构成分是有用的，当Y1、Y2、Y3和/或Y4为羧基时，特别是用作液晶聚合物的结构成分时，能够期待大大改善熔接强度和各向异性。

Description

新型化合物
技术领域
本发明涉及作为聚酯或聚酰胺等的结构成分有用的新型化合物。
背景技术
液晶聚酯由于分子刚直即使在熔融状态也不发生络合，而形成具有结晶状态的聚合区域(polydomain)，由于低剪切分子链显著沿流向取向，一般称为熔融型液晶(热致性液晶)聚合物。由于这种特异性行为，熔融流动性非常优良，能够容易地得到0.2～0.5mm左右的薄壁成形品，而且该成形品具有高强度、高刚性这种优点，但是也存在各向异性非常大，熔接强度显著低的缺点。
发明公开
本发明的目的在于提供一种期待作为聚酯或聚酰胺等结构成分更有用的新型化合物。
也就是说，本发明提供以2-羟基萘-3，6-二羧酸为原料得到的新型化合物。该化合物作为提供网状或梯状的聚酯和聚酰胺的多官能单体是非常重要的，例如用该化合物作为聚酯或聚酰胺等的结构成分时可以期待大幅度改善熔接强度和异向性。
也就是说，本发明涉及通式〔1〕表示的化合物或其盐类这一新型化合物。
〔式中，Y1、Y2、Y3、Y4可以相同，也可以不同，表示羧基、酯化的羧基或式-(CONH)n-X(式中X表示可以具有支链、可以具有取代基、可以具有不饱和键的烃基，或可以具有取代基的芳香基或具有共轭双键的杂环基团)，
n表示1或2的整数，
Q和Q’表示碳原子数1～6的可以具有支链的烷基或烷氧基、卤素原子、硝基或亚硝基，
m和m’表示0～3的整数，
A为碳原子数1～20的可以具有支链、可以具有不饱和键、可以具有取代基的2价烃基，分子中也可以包括可具有取代基的芳香族基或具有共轭双键的杂环基团。〕
上述式中，Y1、Y2、Y3、Y4中酯化的羧基优选碳原子数1～6的烷氧基羰基，特别是甲氧基羰基、乙氧基羰基、苯氧基羰基或苯甲酰甲基羰基，这些基团中含有的芳香基也可以具有取代基。另外，基团X例如可以具有支链、可以具有取代基、可以具有不饱和键的烃基，优选碳原子数1～20的烷基，可以具有取代基的芳香基，例如苯基、萘基、蒽醌基，或可以具有取代基的具有共轭双键的杂环基团，例如苯并咪唑啉酮基、咔唑基、吡啶基、噻唑基、苯并噻唑基、咪唑基、吲哚基、噻吩基、吩噻嗪基、吖啶基、喹啉基等。
这些基团的取代基例如卤素、硝基、低级烷基、低级烷氧基(例如甲氧基)、氰基、苯氧基、酰胺化的羧基(例如苯基氨基甲酰基)、酯化的羧基(例如甲氧基羰基、苯氧基羰基)。二烷基氨基磺酰基(例如二乙基氨基磺酰基)等。
这些取代基带有芳环时，该环上也可以具有1个以上的其它取代基，例如卤素、低级烷基、低级烷氧基、苯基、腈基(ニトリル)等。另外，本申请中“低级”表示碳原子数为1～6。
通式〔1〕表示的化合物的2个萘核也可以分别具有Q或Q’作为取代基、Q或Q’分别表示任意地碳原子数1～6可以具有支链的烷基或烷氧基(优选碳原子数1～4)、卤素原子、硝基、亚硝基等。表示取代基数的m和m’通常为0，也可以为3以下。
A中碳原子数为1～20可以具有支链、可以具有不饱和键、可以具有取代基的2价烃基例如亚烷基(优选直链碳原子数1～12的亚烷基)、亚烯基(优选直链的2-亚丁烯基等碳原子数1～12的亚烯基)以及可以具有氧代基等取代基的亚烷基{优选羰基、草酰基、亚甲基羰基、2，6-二氧代八亚甲基等)。这些基团在分子中可以进一步含有可以具有取代基的芳香基或具有共轭双键的杂环基团，亚烷基在分子中含有芳香基或具有共轭双键的杂环基团的物质例如式〔2〕、〔3〕表示的基团。另外，A的两端或一端具有氧代基的基团也适用，例如式〔4〕表示的基团。
Figure C0080134400061
Figure C0080134400063
作为通式〔1〕所示化合物的盐，例如Y1、Y2、Y3和Y4中任意一个为羧基时，其钠盐、钾盐等。
通式〔1〕表示的化合物可以按照下述方法制备。
Figure C0080134400064
〔式中，Y1、Y2、Y3、Y4、Q、Q’、m、m’和A与上述相同。〕
该反应通常多在溶剂(例如二甲基甲酰胺)中，在碱(例如碳酸钾)存在下进行。另外，可以根据需要进行水解，得到羧酸体。另外，上述化学反应式中使用二溴体〔6〕作为例子，也可以使用二氯体等其它二卤体代替二溴体。
其次，通式〔1〕表示的化合物中Y1、Y2、Y3、Y4分别不同或分子内为非对称的二醚体可以按照下述方法制备。
Figure C0080134400071
〔式中，Y1、Y2、Y3、Y4、Q、Q’、m、m’和A与上述相同。〕
使用例如溴氯体〔9〕代替上述方法中使用的二溴体〔6〕，在溶剂(例如二甲基甲酰胺)中，使碱(例如碳酸钾)作用得到单醚体〔10〕。然后与具有能形成非对称型的基团的〔11〕反应，得到非对称型二醚体〔12〕。另外，也可以与上述对称型二醚体同样水解，得到羧酸。
A的两端或一端的碳原子具有氧代基时，可以采用使用其二溴体、二氯体的上述方法，合成通式〔1〕的化合物。另外，也可以通过A的羧酸或其酯衍生物与2-羟基萘-3，6-二羧酸衍生物〔8〕的脱水缩合反应或酯交换反应等众所周知的反应合成。
在这一系列制备方法的例子中，首先进行酯化或酰胺化之后进行二醚化，也可以二醚化之后进行酯化或酰胺化，反应的顺序并没有限定。
本发明化合物作为聚酯、聚酰胺等聚合物的结构成分是非常有用的。
附图的简单说明
图1表示实施例1所得化合物的红外吸收图谱(KBr法)。
图2表示实施例10所得化合物的红外吸收图谱(KBr法)。
图3表示实施例30所得化合物的红外吸收图谱(KBr法)。
下面结合实施例进一步详细说明本发明。以下的实施例仅用于说明，并不限定本申请。
实施例1
将2-羟基-3，6-二甲氧基羰基萘2.6g悬浊在N，N-二甲基甲酰胺30g中，向其中加入1，2-二溴乙烷0.85g、碳酸钾2.1g和聚乙二醇(平均分子量3000)0.1g，100℃下反应15小时。然后将反应悬浊液注入到水400g和甲醇100g组成的混合液中，约1小时后，过滤回收析出物。用甲醇和水充分洗涤该物质，干燥，得到灰白色粉末1.52g(熔点：217℃)。
该物质的红外吸收图谱(KBr法)如图1所示。
实施例2～9
除用表1所示的Br-A-Br化合物代替实施例1中的1，2-二溴乙烷，以及用表1所示的萘酚化合物代替2-羟基-3，6-二甲氧基羰基萘以外，与实施例1同样合成酯体的本发明化合物。合成的各化合物的融点如表1所示。
〔表1中，Me表示甲基，Et表示乙基。〕
                         表1
Figure C0080134400101
                        续表1
Figure C0080134400111
实施例10
将实施例1得到的2，2’-亚乙基二氧-二(3，6-二甲氧基羰基萘)1.37g悬浊在1，4-二氧六环20g中，向其中加入氢氧化钠1.0g和水20g，一边回流一边反应2小时。冷却至室温，向反应溶液中加入水40g和Carboraffin 0.5g，约1小时后过滤。将滤液加热至50～60℃，用10％盐酸调节pH至2。放冷后，过滤回收析出物，用10％甲醇水溶液充分洗涤后，干燥，得到灰白色粉末1.05g(分解点：318℃)。
该物质的红外吸收图谱(KBr法)如图2所示。
实施例11～18
除用表2所示的酯化合物代替实施例10中的2，2’-亚乙基二氧-二(3，6-二甲氧基羰基萘)外，与实施例10同样合成四羧酸体的本发明化合物。合成的各化合物的分解点如表2所示。
                      表2
                       续表2
实施例19～29
除用表3所示的二溴亚烷基代替实施例1中的1，2-二溴乙烷，以及用表3所示的萘酚化合物代替2-羟基-3，6-二甲氧基羰基萘外，与实施例1同样合成各实施例的化合物。合成的各化合物的分解点如表3所示。
[表3中，Me表示甲基，Et表示乙基。]
                        表3
                       续表3
                       续表3
Figure C0080134400161
                       续表3
实施例30
除用1，4-二溴-2-丁烯代替实施例1中的1，2-二溴乙烷外，按照与实施例1相同的方法，得到淡黄色粉末状的上述化合物0.66g(融点：205℃、分解点：258℃)。
该物质的红外吸收图谱(KBr法)如图3所示。
实施例31
除用1，4-二溴丁烷-2，3-酮1.1g代替实施例1中的1，2-二溴乙烷外，按照与实施例1相同的方法，得到淡黄色粉末状的上述化合物1.8g(融点：136℃、分解点：218℃)。
实施例32
将2-羟基-3，6-二甲氧基羰基萘3.1g悬浊在N，N-二甲基甲酰胺30g中，向其中加入1-溴-3-氯丙烷1.6g、碳酸钾1.5g和聚乙二醇(平均分子量3000)0.1g，50℃下反应15小时。然后将反应悬浊液注入到水400g和甲醇100g组成的混合液中，约1小时后，过滤回收析出物。用甲醇和水充分洗涤该物质，干燥，得到2-(3’-氯丙基氧)-3，6-二甲氧基羰基萘的淡黄色粉末2.6g(融点：115℃)。
将其中的2.4g悬浊在N，N-二甲基甲酰胺30g中，向其中加入2-羟基-3-(2’-甲基苯基)氨基羰基-6-正十二烷基氨基羰基萘3.5g、碳酸钾1.0g和聚乙二醇(平均分子量3000)0.1g，再在100℃下反应15小时。然后，将反应悬浊液注入到水400g和四氢呋喃100g组成的混合液中，约1小时后，过滤回收析出物。用水充分洗涤该物质后，干燥，得到黄褐色粉末状的上述化合物4.8g(融点：158℃、分解点：350℃)。
实施例33
除用2，6-吡啶二酰氯0.9g代替实施例1中的1，2-二溴乙烷，以及用四氢噻吩砜(スルホラソ)50g代替N，N-二甲基甲酰胺，不加入碳酸钾，并且反应温度为140℃以外，按照与实施例1相同的方法，得到褐色粉末状的含有杂环的本发明化合物2.5g。
产业上利用的领域
本发明化合物作为聚酯或聚酰胺等的结构成分是有用的，当Y1、Y2、Y3和/或Y4为羧基时，特别是用作液晶聚合物的结构成分时，能够期待大大改善熔接强度和各向异性。

Claims (1)

1.通式〔1〕表示的化合物，
Figure C008013440002C1
式中，Y1、Y2、Y3、Y4可以相同，也可以不同，表示羧基、具有1-6个碳原子的烷氧羰基、取代或未取代的苯氧羰基、苯甲酰甲基羰基或式-(CONH)n-X表示的基团，式中X表示可以具有支链、可以具有取代基、可以具有不饱和键的碳原子数1～20的烷基，或可以具有取代基的选自苯基、萘基和蒽醌基的芳香基，或具有共轭双键的选自苯并咪唑啉酮基、咔唑基、吡啶基、噻唑基、苯并噻唑基、咪唑基、吲哚基、噻吩基、吩噻嗪基、吖啶基和喹啉基的杂环基团，
n表示1或2的整数，
A为取代或未取代的选自直链的碳原子数1～12的亚烷基、直链的碳原子数1～12的亚烯基、羰基、草酰基、亚甲基羰基和2，6-二氧代八亚甲基的烃基，或者A为选自下述的基团：
和
Figure C008013440003C2
其中上述基团的取代基选自卤素、硝基、具有1-6个碳原子的烷基、具有1-6个碳原子的烷氧基、氰基、苯氧基、苯氨基甲酰基、甲氧羰基、苯氧羰基和二烷基氨基磺酰基；当取代基含有一芳环时，该芳基可以进一步具有一个以上选自卤素、具有1-6个碳原子的烷基、具有1-6个碳原子的烷氧基、苯基和腈基的取代基。
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