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1. 发明授权

US4629290A Liquid crystal compounds and method of preparation 失效
标题翻译：液晶化合物及其制备方法
公开(公告)号：US4629290A
公开(公告)日：1986-12-16
申请号：US592497
申请日：1984-03-22
申请人： Yoshio Shionozaki , Hiroshi Mukai
发明人： Yoshio Shionozaki , Hiroshi Mukai
IPC分类号： C09K19/26 , G02F1/13 , C07C105/00 , C09K3/34
CPC分类号： C09K19/26
摘要： Asymmetric trans-4,4'-dialkyl-ONN-azoxybenzenes having the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are straight-chain alkyl groups having from 1 to 10 carbon atoms and R.sub.1 .noteq.R.sub.2 are provided. The azoxybenzene compounds are prepared by condensing corresponding P-alkylaniline ##STR2## and P-alkylnitrobenzene ##STR3## placing the reaction mixture into ammonium chloride and hydrolyzing to yield the asymmetrical azoxybenzene compound, corresponding asymmetrical azobenzene compound and asymmetric azobenzene compound. The asymmetric azoxy compound is then separated from the mixture by column chromotography and recrystallization. The asymmetric azoxybenzene compounds have a wide range of nematic liquid crystal temperature and are particularly well suited for liquid crystal compositions for use in matrix-addressing driving systems.
摘要翻译：提供了具有以下通式的不对称的反式-4,4'-二烷基-ONN-偶氮苯：其中R1和R2是具有1-10个碳原子的直链烷基和R1等于R2。通过将相应的对烷基苯胺和P-烷基硝基苯（IMA）将反应混合物放入氯化铵中并水解，得到不对称的偶氮苯化合物，相应的不对称偶氮苯化合物和不对称偶氮苯化合物，制备偶氮氧苯化合物。然后通过柱层析和重结晶从混合物中分离出不对称的氧化偶氮化合物。不对称的苯氧基苯化合物具有宽范围的向列液晶温度，特别适用于用于矩阵寻址驱动系统的液晶组合物。

2. 发明授权

US4684220A 2-phenylpyridine derivatives and liquid crystal compositions including same 失效
标题翻译： 2-苯基吡啶衍生物和包含它们的液晶组合物
公开(公告)号：US4684220A
公开(公告)日：1987-08-04
申请号：US754056
申请日：1985-07-11
申请人： Yoshio Shionozaki , Hiroshi Mukai , Tsuyoshi Obikawa , Shuhei Yamada
发明人： Yoshio Shionozaki , Hiroshi Mukai , Tsuyoshi Obikawa , Shuhei Yamada
IPC分类号： C07D213/16 , C07C45/46 , C07C49/807 , C07D213/06 , C07D213/50 , C07D213/57 , C07D213/65 , C07D213/73 , C07D213/85 , C09K19/34 , C09K19/42 , C07D239/02 , C07D239/72 , C07D241/36 , C07D241/46 , G02F1/13
CPC分类号： C07D213/73 , C07C45/46 , C07C49/807 , C07D213/06 , C07D213/50 , C07D213/57 , C07D213/65 , C07D213/85 , C09K19/3444 , C09K19/42
摘要： 2-phenylpyridine derivatives represented by the general formula: ##STR1## wherein when Y is R--, Z is one of R--, RO--, ##STR2## when Y is RO--, Z is one of straight chain pentyl, ##STR3## and --CN; and when Y is one of ##STR4## Z is one of R--, RO-- and --CN; when Y is --CN, Z is one of RO--, ##STR5## and R is a straight chain alkyl group from 1 to 12 carbon atoms, are disclosed. The 2-phenylpyridine derivatives in accordance with the invention are particularly well-suited for use in nematic liquid crystal compositions for reducing the steepness and response time of the liquid crystal compositions in a liquid crystal display device.
摘要翻译：由以下通式表示的2-苯基吡啶衍生物：其中当Y为R-时，当Y为RO-时，Z为R-，RO-， + TR 之一，Z为直链戊基，和-CN; 当Y是 + TR 之一时，Z是R-，RO-和-CN之一; 当Y为-CN时，Z为RO-， + TR 之一，R为1至12个碳原子的直链烷基。根据本发明的2-苯基吡啶衍生物特别适用于向列型液晶组合物，用于降低液晶组合物在液晶显示装置中的陡度和响应时间。

3. 发明授权

US4879060A 2-phenylpyridine derivatives and liquid crystal compositions including same 失效
标题翻译： 2-苯基吡啶衍生物和包含它们的液晶组合物
公开(公告)号：US4879060A
公开(公告)日：1989-11-07
申请号：US68996
申请日：1987-05-22
申请人： Yoshio Shionozaki , Hiroshi Mukai , Tsuyoshi Obikawa , Shuhei Yamada
发明人： Yoshio Shionozaki , Hiroshi Mukai , Tsuyoshi Obikawa , Shuhei Yamada
IPC分类号： C07D213/16 , C07C45/46 , C07C49/807 , C07D213/06 , C07D213/50 , C07D213/57 , C07D213/65 , C07D213/73 , C07D213/85 , C09K19/34 , C09K19/42
CPC分类号： C07D213/73 , C07C45/46 , C07C49/807 , C07D213/06 , C07D213/50 , C07D213/57 , C07D213/65 , C07D213/85 , C09K19/3444 , C09K19/42
摘要： 2-phenylpyridine derivatives represented by the general formula: ##STR1## wherein when Y is R--, Z is one of R--, RO--, ##STR2## when Y is RO--, Z is one of straight chain pentyl, ##STR3## and when Y is one of Z is one of R--, RO-- and --CN; when Y is --CN, Z is one of RO--, ##STR4## and R is a straight chain alkyl group from 1 to 12 carbon atoms, are disclosed. The 2-phenylpyridine derivatives in accordance with the invention are particularly well-suited for use in nematic liquid crystal compositions for reducing the steepness and response time of the liquid crystal compositions in a liquid crystal display device.
摘要翻译：由以下通式表示的2-苯基吡啶衍生物：其中当Y为R-时，当Y为RO-时，Z为R-，RO-， + TR 之一，Z为直链当Y是 + TR 之一时，Z是R-，RO和-CN之一; 当Y为-CN时，Z为RO-， + TR 之一，R为1至12个碳原子的直链烷基。根据本发明的2-苯基吡啶衍生物特别适用于向列型液晶组合物，用于降低液晶组合物在液晶显示装置中的陡度和响应时间。

4. 发明授权

US4723018A 2-phenylpyridine derivatives 失效
标题翻译： 2-苯基吡啶衍生物
公开(公告)号：US4723018A
公开(公告)日：1988-02-02
申请号：US5798
申请日：1987-01-21
申请人： Yoshio Shionozaki , Hiroshi Mukai , Tsuyoshi Obikawa , Shuhei Yamada , Rei Miyazaki
发明人： Yoshio Shionozaki , Hiroshi Mukai , Tsuyoshi Obikawa , Shuhei Yamada , Rei Miyazaki
IPC分类号： C07D213/30 , C07D213/55 , C09K19/34
CPC分类号： C07D213/30 , C07D213/55 , C09K19/3444
摘要： 2-phenylpyridine derivatives having the general formula: ##STR1## wherein Y is ##STR2## and Z is a straight chain alkyl group having from 1 to 16 carbon atoms, ##STR3## R' is a straight chain alkyl group having from 2 to 12 carbon atoms, R.sup.2 is a straight chain alkyl group having from 1 to 12 carbon atoms, n is an integer from 1 to 10 and * is an asymmetric carbon are provided. The derivatives are stable, have low viscosity, excellent electro-optical response properties and broaden the ferroelectric temperature range when added to ferroelectric liquid crystal compositions.
摘要翻译：具有以下通式的2-苯基吡啶衍生物：其中Y是，并且Z是具有1至16个碳原子的直链烷基，其中R 1是具有2至12个碳原子的直链烷基，R 2是具有1至12个碳原子的直链烷基，n是1至10的整数，和*是不对称碳。衍生物稳定，粘度低，电光响应性能优异，加入铁电液晶组合物时，铁电温度范围扩大。

5. 发明授权

US4279771A (2'-Cyano-4'-n-alkyl)phenyl-3-chloro-4-n-alkoxy benzoates and liquid crystal compositions thereof 失效
标题翻译：（2'-氰基-4'-正烷基）苯基-3-氯-4-正烷基苯甲酸酯及其液晶组合物
公开(公告)号：US4279771A
公开(公告)日：1981-07-21
申请号：US114775
申请日：1980-01-23
申请人： Yoshio Shionozaki , Sakao Kanbe , Katsumori Takei
发明人： Yoshio Shionozaki , Sakao Kanbe , Katsumori Takei
IPC分类号： C07C255/51 , C07C255/53 , C09K19/00 , C09K19/20 , C07C121/75 , C09K3/34 , G02F1/13
CPC分类号： C07C255/00 , C09K19/2007
摘要： A new ester compound suitable for use in a liquid crystal composition is provided. The compound is a (2'-cyano-4'-alkyl)phenyl-3-chloro-4 alkoxybenzoate represented by the following formula: ##STR1## wherein R and R' are selected from straight-chain alkyl groups having from one to eight carbon atoms. The ester is not a liquid crystal compound, but upon addition to a liquid crystal composition increases the absolute value of the dielectric anisotropy in the high frequency range. Such compositions are particularly well suited for the two frequency matrix-addressing drive in a liquid crystal display for complex character and graphic displays. The esters are prepared by condensing an acid chloride having the general formula ##STR2## and a phenol having the general formula ##STR3## wherein R and R' are as defined above.
摘要翻译：提供适用于液晶组合物的新型酯化合物。该化合物是由下式表示的（2'-氰基-4'-烷基）苯基-3-氯-4-烷氧基苯甲酸酯：其中R和R'选自具有1至8个碳原子的直链烷基碳原子。该酯不是液晶化合物，但是当添加到液晶组合物时，在高频范围内增加介电各向异性的绝对值。这种组合物特别适用于用于复杂字符和图形显示的液晶显示器中的两个频率矩阵寻址驱动。酯通过将具有通式的酰氯与具有通式的苯酚缩合而制备，其中R和R'如上定义。

6. 发明授权

US4740630A Chiral phenylether compound 失效
标题翻译：手性苯醚化合物
公开(公告)号：US4740630A
公开(公告)日：1988-04-26
申请号：US944636
申请日：1986-12-19
申请人： Yoshio Shionozaki , Toshihiro Shibata
发明人： Yoshio Shionozaki , Toshihiro Shibata
IPC分类号： C07C43/225 , C09K19/34
CPC分类号： C07C43/225 , C09K19/3444
摘要： A chiral phenylether compound having the formula ##STR1## wherein X is a halogen atom; m is an integer from 3 to 5, n is an integer from 3 to 12 and * designates an asymmetric carbon is disclosed. The chiral phenylether compounds are useful to prepare chiral smectic phase pyrimidine phenylether liquid crystal compounds of the formula. ##STR2## The reaction is carried by reacting (I) with butylithium, dissolving in ether and reacting with a 1-bromoalkane to yield (IV). Compounds (IV) are particularly well suited to broaden the useful temperature range of ferroelectric liquid crystal materials.
摘要翻译：具有式（I）的手性苯基醚化合物，其中X是卤素原子; m为3〜5的整数，n为3〜12的整数，*表示不对称碳。手性苯基醚化合物可用于制备下式的手性近晶相嘧啶苯醚液晶化合物。（IV）反应是通过（I）与丁基锂反应，溶于乙醚中，与1-溴烷烃反应得到（Ⅳ）。化合物（IV）特别适合于扩大铁电液晶材料的有用温度范围。

7. 发明授权

US4518226A Ester-azoxy compounds 失效
标题翻译：酯 - 偶氮化合物
公开(公告)号：US4518226A
公开(公告)日：1985-05-21
申请号：US540985
申请日：1983-10-11
申请人： Yoshio Shionozaki
发明人： Yoshio Shionozaki
IPC分类号： C09K19/30 , C07C67/00 , C07C241/00 , C07C291/08 , C09K19/46 , C09K3/34 , C07C105/00 , G02F1/13
CPC分类号： C07C291/08 , C09K19/3086 , C07C2101/14
摘要： Ester-azoxy compounds represented by the general formula: ##STR1## wherein R and R' are straight-chain alkyl groups having one to eight carbon atoms are provided. When added to a twisted nematic-type liquid crystal composition, the liquid crystal temperature range is increased.
摘要翻译：提供由以下通式表示的酯 - 偶氮化合物：其中R和R'是具有1-8个碳原子的直链烷基。当添加到扭曲向列型液晶组合物时，液晶温度范围增加。

8. 发明授权

US4287085A (2'-Cyano-4'-alkylphenyl)-3-cyano-4-alkoxybenzoates and liquid crystal composition including same 失效
标题翻译：（2'-氰基-4'-烷基苯基）-3-氰基-4-烷氧基苯甲酸酯及其液晶组合物
公开(公告)号：US4287085A
公开(公告)日：1981-09-01
申请号：US144809
申请日：1980-04-29
申请人： Katsumori Takei , Sadao Kanbe , Yoshio Shionozaki
发明人： Katsumori Takei , Sadao Kanbe , Yoshio Shionozaki
IPC分类号： C07C51/363 , C07C65/21 , C09K19/54 , C07C121/75 , C09K3/34
CPC分类号： C09K19/54 , C07C51/363 , C07C65/21
摘要： Ester compounds suitable for use in liquid crystal compositions are provided. The ester compounds are (2'-cyano-4'-alkylphenyl)-3-cyano-4-n-alkoxybenzoates represented by the general formula: ##STR1## wherein R and R' each is a straight-chain alkyl group having one to eight carbon atoms. The ester compounds alone do not exhibit a liquid crystal phase, but have a relatively low melting point. Addition of at least one such ester compound to a liquid crystal composition lowers the value of the dielectric anisotropy of the composition at frequencies higher than the critical frequency, and lowers it at frequencies lower than the critical frequency. Such compositions are particularly well suited for the two-frequency matrix-addressing drive in a display of complex characters or graphic displays.The ester compounds in accordance with the invention are prepared by condensing a 3-bromo-4-n-alkoxybenzoyl chloride having the general formula: ##STR2## and a 2-cyano-4-n-alkylphenol having the general formula: ##STR3## to prepare a (2'-cyano-4'-n-alkylphenol)-3-bromo-4-n-alkoxybenzoate having the general formula: ##STR4## wherein R and R' each is a straight-chain alkyl group having from one to eight carbon atoms, and reacting the benzoate (IV) with cuprous cyanide to yield the desired ester (I).
摘要翻译：提供适用于液晶组合物的酯化合物。酯化合物是由以下通式表示的（2'-氰基-4'-烷基苯基）-3-氰基-4-正烷基苯甲酸酯：其中R和R'各自为直链烷基具有1-8个碳原子。单独的酯化合物不表现出液晶相，但熔点相对较低。将至少一种这样的酯化合物加入到液晶组合物中，在高于临界频率的频率下降低组合物的介电各向异性的值，并且在低于临界频率的频率下降低组成物的介电各向异性的值。这样的组合物特别适用于复杂字符或图形显示器的显示器中的双频矩阵寻址驱动器。根据本发明的酯化合物通过将具有以下通式的3-溴-4-正烷氧基苯甲酰氯与具有以下通式的2-氰基-4-正烷基苯酚缩合制备：（III）制备具有以下通式的（2'-氰基-4'-正烷基苯酚）-3-溴-4-正烷基苯甲酸酯：其中R和R'各自为具有1至8个碳原子的直链烷基，并使苯甲酸酯（IV）与氰化亚铜反应以产生所需的酯（I）。

9. 发明授权

US4341652A Ester compounds, liquid crystal composition including same and method of production 失效
标题翻译：酯化合物，包括其的液晶组合物和生产方法
公开(公告)号：US4341652A
公开(公告)日：1982-07-27
申请号：US171938
申请日：1980-07-18
申请人： Katsumori Takei , Sadao Kanbe , Yoshio Shionozaki
发明人： Katsumori Takei , Sadao Kanbe , Yoshio Shionozaki
IPC分类号： C09K19/20 , C09K19/30 , C09K3/34 , C07C121/60 , C07C121/75 , G02F1/13
CPC分类号： C09K19/3068 , C09K19/2007
摘要： Ester compounds suitable for use in liquid crystal compositions are provided. The ester compounds are (2'-chloro-4'-n-alkylphenyl)-3-cyano-4-n-alkoxybenzoates represented by the general formula: ##STR1## wherein R and R' are straight-chain alkyl groups having from one to eight carbon atoms. The ester compounds alone do not exhibit a liquid crystal phase, but have a relatively high value of dielectric anisotropy. Addition of minor amounts of at least one such ester compound to a liquid crystal composition lowers the value of the dielectric anisotropy of the composition in the high frequencies range. Such compositions are particularly well suited for the two-frequency matrix-addressing drive in a display of complex characters or graphic displays by reducing the driving voltage.The ester compounds in accordance with the invention are prepared by condensing a 3-bromo-4-n-alkoxybenzoyl chloride having the general formula: ##STR2## and a 2-chloro-4-n-alkylphenol having the general formula: ##STR3## to prepare a (2'-chloro-4'-n-alkylphenyl)-3-bromo-4-n-alkoxybenzoate having the general formula: ##STR4## wherein R and R' are straight-chain alkyl groups having from one to eight carbon atoms, and reacting the benzoate (IV) with cuprous cyanide to yield the desired ester (I).
摘要翻译：提供适用于液晶组合物的酯化合物。酯化合物是由以下通式表示的（2'-氯-4'-正烷基苯基）-3-氰基-4-正烷基苯甲酸酯：其中R和R'是直链烷基具有1-8个碳原子。单独的酯化合物不表现出液晶相，但具有相对高的介电各向异性值。向液晶组合物中加入少量至少一种这样的酯化合物降低了组合物在高频范围内的介电各向异性的值。通过降低驱动电压，这种组合物特别适用于复杂字符或图形显示器的双频矩阵寻址驱动器。根据本发明的酯化合物通过将具有以下通式的3-溴-4-正烷基苯甲酰氯与具有以下通式的2-氯-4-正烷基苯酚缩合制备：（III）制备具有以下通式的（2'-氯-4'-正烷基苯基）-3-溴-4-正烷基苯甲酸酯：其中R和R'是直链的具有1至8个碳原子的链烷基，并使苯甲酸酯（IV）与氰化亚铜反应以产生所需的酯（I）。

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