WO2016114310A1 - ジアミン前駆体化合物の製造方法 - Google Patents
ジアミン前駆体化合物の製造方法 Download PDFInfo
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- WO2016114310A1 WO2016114310A1 PCT/JP2016/050851 JP2016050851W WO2016114310A1 WO 2016114310 A1 WO2016114310 A1 WO 2016114310A1 JP 2016050851 W JP2016050851 W JP 2016050851W WO 2016114310 A1 WO2016114310 A1 WO 2016114310A1
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- compound represented
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- 0 *C(OCCc(c([N+]([O-])=O)c1)ccc1[N+]([O-])=O)=O Chemical compound *C(OCCc(c([N+]([O-])=O)c1)ccc1[N+]([O-])=O)=O 0.000 description 1
- AONMTYOVKUOHQP-UHFFFAOYSA-N [O-][N+](c1ccc(CCO)c([N+]([O-])=O)c1)=O Chemical compound [O-][N+](c1ccc(CCO)c([N+]([O-])=O)c1)=O AONMTYOVKUOHQP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/14—Preparation of nitro compounds by formation of nitro groups together with reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
Definitions
- the present invention relates to a novel method for producing a dinitro compound, which is a precursor of a specific diamine compound, which is a raw material for producing a polyimide used for a liquid crystal aligning agent or the like, with high purity and efficiency.
- the diamine compound is widely used as a kind of monomer that is a raw material for polymer compounds such as polyamide, polyamic acid, polyimide, polyamic acid ester, polyamideimide, and polyetherimide. Many of these polymer compounds have excellent mechanical strength and heat resistance, and are used in various applications such as automobile parts and home appliances.
- polyimide and polyamic acid and polyamic acid ester which are polyimide precursors are generally used as a liquid crystal alignment film which is one of constituent members of a liquid crystal display element.
- the liquid crystal alignment film is formed by a so-called rubbing process in which a polymer film formed on an electrode substrate is rubbed with a cloth made of rayon or the like under pressure.
- the polymer film formed on the substrate is rubbed in a plurality of directions, and liquid crystal molecules are tilted along the rubbing direction to generate domains in a plurality of directions, thereby realizing alignment division necessary for wide viewing angle.
- a method is known (Patent Document 1).
- Patent Document 2 a method for controlling the pretilt angle by using a polyimide using a specific diamine compound for a liquid crystal alignment film is known.
- Patent Document 3 a method for forming a liquid crystal alignment film.
- Patent Document 4 a method of easily forming a desired pretilt angle by using a polyimide using a specific diamine compound for a liquid crystal alignment film.
- the manufacturing process includes a step of irradiating ultraviolet rays while applying a voltage to the liquid crystal molecules.
- a photopolymerizable compound is generally added to the liquid crystal composition in advance.
- Patent Document 5 a method of introducing a photoreactive group into a polymer of a liquid crystal alignment film is also known (Non-Patent Document 1), as in the above-described photo-alignment. A method in which no photopolymerizable compound is added is also known.
- Patent Document 6 a method of easily forming a desired pretilt angle by using a polyimide using a specific diamine compound for a liquid crystal alignment film.
- Patent Document 2 a diamine compound having a 2- (2,4-diaminophenyl) ethyl ester structure is included in common. It is. This diamine compound is synthesized by reducing a compound having a 2- (2,4-dinitrophenyl) ethyl ester structure.
- the problem to be solved by the present invention is to provide a novel method for producing a 2- (2,4-dinitrophenyl) ethyl ester derivative with high purity and efficiency.
- the present invention is as follows. 1. According to the following reaction formula (1), the dinitro compound represented by formula 1 and the compound represented by formula 2 are reacted in the absence of a base while discharging the generated hydrogen chloride out of the reaction system as a gas. A method for producing a diamine precursor compound represented by Formula 3. (In the formula, R 1 is a monovalent organic group.)
- diamine which is a raw material for polyamic acid and / or polyimide used for liquid crystal aligning agent or the like from 2- (2,4-dinitrophenyl) ethanol and carboxylic acid chloride with high purity and efficiency.
- a dinitro compound which is a precursor compound of the compound can be produced.
- the production method of the present invention follows the following reaction formula (1). That is, while discharging the dinitro compound represented by Formula 1 and the compound represented by Formula 2 (wherein R 1 is a monovalent organic group) as a gas out of the reaction system, This is a method for producing a diamine precursor compound represented by Formula 3.
- the amount of the acid chloride represented by the formula 2 relative to the dinitro compound represented by the formula 1 is preferably 0.5 to 3.0 mol times, and more preferably 0.9 to 1.5 mol times.
- reaction solvent any organic solvent can be used as long as it does not react with the acid chloride represented by Formula 2 and can be mixed uniformly with the raw material.
- aromatic hydrocarbon solvents such as benzene, toluene and xylene are preferable, and toluene is particularly preferable.
- the amount of the reaction solvent used is preferably 1 to 50 times by mass, more preferably 3 to 15 times by mass with respect to the dinitro compound represented by Formula 1.
- the reaction temperature ranges from room temperature to the boiling point of the solvent, but is preferably 50 to 120 ° C. in order to efficiently remove by-produced hydrogen chloride and to allow the reaction to proceed smoothly without a base. ⁇ 120 ° C. is particularly preferred.
- the reaction solution is treated as follows to obtain the target product.
- the reaction solution is concentrated under reduced pressure to obtain a crude reaction product.
- the reaction crude is dissolved in ethyl acetate, preferably 30 to 77 ° C., more preferably 40 to 70 ° C., and then cooled to room temperature. Then, this solution is washed with water, concentrated under reduced pressure, and further dried under reduced pressure (gauge pressure, preferably 0.1 to 200 mmHg, temperature is preferably 10 to 80 ° C., more preferably 25 to 50 ° C.) to obtain the target compound. can get.
- This reaction can be performed under normal pressure, reduced pressure, or increased pressure, and may be batch-wise or continuous.
- the reaction can be carried out under normal pressure or reduced pressure.
- the reaction is carried out under absolute pressure, preferably 100 to 700 mmHg, more preferably 200 to 600 mmHg. It is preferable.
- the dinitro compound represented by the formula 1, which is one of the raw materials, is a known compound and can be obtained by reducing 2,4-dinitrophenylacetic acid using a borane dimethyl sulfide complex. It is published in the 005266 pamphlet. In addition, as for 2,4-dinitrophenylacetic acid, commercially available products can be used (for example, manufactured by Tokyo Chemical Industry Co., Ltd.).
- the acid chloride represented by Formula 2 which is the other raw material, can be obtained by halide-forming a known carboxylic acid with various halogenating agents.
- a halogenating agent for example, by using thionyl chloride or oxalyl chloride as a halogenating agent, an acid chloride can be obtained from a known carboxylic acid in a high yield.
- the amount of the halogenating agent used is preferably 0.5 to 2.0 mol times, particularly preferably 1.0 to 1.5 mol times relative to the carboxylic acid.
- the reaction temperature is preferably 0 to 80 ° C.
- the dinitro compound thus obtained is derived into a diamine compound by performing a reduction reaction by a known method.
- the obtained diamine compound is obtained by various methods such as a TN liquid crystal display element, an STN liquid crystal display element, a TFT liquid crystal display element, an OCB liquid crystal display element, a lateral electric field type (IPS) liquid crystal display element, and a VA liquid crystal display element. It is useful as a raw material for polyimide (precursor) suitably used for display elements.
- Example 1 2- (2,4-dinitrophenyl) ethanol (128 g, 601 mmol) was added to toluene (422 g) and heated at 90 ° C. while (E) -4- (6- (methacryloyloxy) hexyloxy) cinnamic acid chloride. A solution of (211 g, 601 mmol) dissolved in toluene (422 g) was added dropwise over 25 minutes. Then, after stirring at 90 ° C. for 2 hours, HPLC was measured.
- the area ratio of 1,4-dinitrostyrene was 100: 0.
- the reaction solution was cooled, water (422 g) and ethyl acetate (1477 g) were added, stirred for 10 minutes and allowed to stand, and then the aqueous layer was removed.
- 5% by weight aqueous sodium hydrogen carbonate solution (422 g) was added to the organic layer, stirred for 5 minutes, allowed to stand, and then the aqueous layer was removed.
- the production method of the present invention is a process capable of producing a diamine compound useful as a raw material for a liquid crystal aligning agent from an inexpensive raw material with high purity, simply and efficiently, and capable of large-scale industrial production.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
また、基板上に形成したポリマー被膜を、複数方向にラビングし、該ラビング方向に沿って液晶分子を傾けることで複数方向のドメインを発生させ、広視野角化に必要な配向分割化を実現する方法が知られている(特許文献1)。
液晶配向膜を形成する別の方法として、ポリマー被膜に偏光又は非偏光の紫外線を照射する光配向と呼ばれる方法がある(特許文献3)。
また、液晶を配向させる他の方法として、その製造工程において、液晶分子に電圧を印加しながら紫外線を照射する工程を含むものがある。この方法では、あらかじめ液晶組成物中に光重合性化合物を添加するのが一般的である。(特許文献5)。
また、上記の光配向と同様に、液晶配向膜のポリマーに光反応性基を導入する方法も知られている(非特許文献1)。また、光重合性化合物を添加しない方法も知られている。(特許文献6)
1.下記の反応式(1)に従って、式1で表わされるジニトロ化合物と式2で表される化合物とを、発生する塩化水素を反応系外へガスとして排出しながら塩基の非存在下で反応させて、式3で表わされるジアミン前駆体化合物を製造する方法。
3.芳香族炭化水素を反応溶媒として用いる上記1に記載の製造方法。
4.トルエンを反応溶媒として用いる上記1に記載の方法。
5.反応溶媒の使用量が、式1で表されるジニトロ化合物に対し1~50質量倍である上記1乃至4のいずれかに記載の方法。
6.温度50~120℃にて反応せしめる上記1乃至5のいずれかに記載の方法。
7.絶対圧で100~700mmHgの減圧下で反応せしめる上記1~6のいずれか一項に記載の方法。
8.式1で表されるジニトロ化合物に対する式2で表される化合物の使用量が、0.5~3.0モル倍である上記1乃至7のいずれかに記載の方法。
9.式2で表される化合物が式4で表される化合物である上記1乃至8のいずれかに記載の方法。
得られたジアミン化合物は、TN液晶表示素子、STN液晶表示素子、TFT液晶表示素子、OCB液晶表示素子、更には、横電界型(IPS)液晶表示素子、VA液晶表示素子など、種々の方式による表示素子に好適に用いられるポリイミド(前駆体)の原料として有用である。
HPLC分析
装置:LC-20Aシステム(島津製作所社製)
カラム:Inertsil ODS-3(4.6mmΦ×250mm、ジーエルサイエンス社製)
検出器:UV検出(波長254nm)
溶離液:アセトニトリル/0.1wt%酢酸水溶液(70/30、v/v)
2-(2,4-ジニトロフェニル)エタノール(128g、601mmol)をトルエン(422g)に加え、90℃で加熱しながら、(E)-4-(6―(メタクリロイルオキシ)ヘキシルオキシ)桂皮酸クロリド(211g、601mmol)をトルエン(422g)に溶解させた溶液を25分間かけて滴下した。その後、90℃で2時間撹拌後、HPLCを測定したところ、(E)-4-(6―(メタクリロイルオキシ)ヘキシルオキシ)桂皮酸(2-(2,4-ジニトロフェニル)エチル)エステルと2,4-ジニトロスチレンの面積の比は100:0であった。
その後、反応液を冷却し、水(422g)、及び、酢酸エチル(1477g)を加えて、10分間撹拌し、静置した後、水層を除去した。次いで、有機層に5重量%炭酸水素ナトリウム水溶液(422g)を加えて、5分間撹拌し、静置した後、水層を除去した。さらに、有機層に水(422g)を加えて、5分間撹拌し、静置した後、水層を除去した。その後、有機層を減圧留去し、残渣に酢酸エチル(352g)を加えて溶解した。次いで、メタノール(1059g)を25℃で30分間かけて滴下し、結晶を析出させた。その後、5℃に冷却後、析出している結晶をろ過し、乾燥して、(E)-4-(6―(メタクリロイルオキシ)ヘキシルオキシ)桂皮酸(2-(2,4-ジニトロフェニル)エチル)エステルを得た(外観:黄色固体、収量:281g、収率:89%、HPLC相対面積%:99.1%)。
2-(2,4-ジニトロフェニル)エタノール(0.32g、1.5mmol)、及び、(E)-4-(6―(メタクリロイルオキシ)ヘキシルオキシ)桂皮酸(0.50g、1.5mmol)をジクロロメタン(4.0g)に加え、EDC-HCl(1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride)(0.72g、3.8mmol)、及び、DMAP(N,N-dimethyl-4-aminopyridine)(0.037g、0.30mmol)を加え、室温で撹拌した。20時間後、HPLCを測定した結果、(E)-4-(6―(メタクリロイルオキシ)ヘキシルオキシ)桂皮酸(2-(2,4-ジニトロフェニル)エチル)エステルと2,4-ジニトロスチレンの面積の比は62:37であった。
なお、2015年1月13日に出願された日本特許出願2015-004366号の明細書、特許請求の範囲、及び要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。
Claims (9)
- さらに、反応溶媒を用いる請求項1に記載の製造方法。
- 芳香族炭化水素を反応溶媒として用いる請求項1に記載の製造方法。
- トルエンを反応溶媒として用いる請求項1に記載の製造方法。
- 反応溶媒の使用量が、式1で表されるジニトロ化合物に対し1~50質量倍である、請求項1乃至4のいずれか一項に記載の製造方法。
- 温度50~120℃にて反応せしめる請求項1乃至5のいずれか一項に記載の方法。
- 絶対圧で100~700mmHgの減圧下で反応せしめる請求項1乃至6のいずれか一項に記載の方法。
- 式1で表されるジニトロ化合物に対する式2で表される化合物の使用量が、0.5~3.0モル倍である請求項1乃至7のいずれか一項に記載の方法。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP16737381.0A EP3246307B1 (en) | 2015-01-13 | 2016-01-13 | Method for producing diamine precursor compound |
CN201680005747.3A CN107108460B (zh) | 2015-01-13 | 2016-01-13 | 二胺前体化合物的制造方法 |
KR1020177018787A KR102575113B1 (ko) | 2015-01-13 | 2016-01-13 | 디아민 전구체 화합물의 제조 방법 |
JP2016569484A JP6733552B2 (ja) | 2015-01-13 | 2016-01-13 | ジアミン前駆体化合物の製造方法 |
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JP2015-004366 | 2015-01-13 | ||
JP2015004366 | 2015-01-13 |
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WO2016114310A1 true WO2016114310A1 (ja) | 2016-07-21 |
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EP (1) | EP3246307B1 (ja) |
JP (1) | JP6733552B2 (ja) |
KR (1) | KR102575113B1 (ja) |
CN (1) | CN107108460B (ja) |
TW (1) | TWI682918B (ja) |
WO (1) | WO2016114310A1 (ja) |
Citations (6)
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JPS6025955A (ja) * | 1983-07-22 | 1985-02-08 | Nippon Synthetic Chem Ind Co Ltd:The | γ−クロルアセト酢酸エステルの製造方法 |
JP2005112764A (ja) * | 2003-10-07 | 2005-04-28 | Toagosei Co Ltd | 芳香族エステルの製造方法 |
JP2007204438A (ja) * | 2006-02-02 | 2007-08-16 | Kawasaki Kasei Chem Ltd | 新規なアントラセン化合物及び光重合用増感剤 |
JP2008133262A (ja) * | 2006-10-24 | 2008-06-12 | Central Glass Co Ltd | アルコキシカルボニルフルオロアルカンスルホン酸塩類の製造方法 |
JP2014006442A (ja) * | 2012-05-29 | 2014-01-16 | Jsr Corp | 液晶配向剤 |
WO2014208609A1 (ja) * | 2013-06-25 | 2014-12-31 | 日産化学工業株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子 |
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JP3985261B2 (ja) | 2001-10-03 | 2007-10-03 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
JP4175826B2 (ja) | 2002-04-16 | 2008-11-05 | シャープ株式会社 | 液晶表示装置 |
JP3925813B2 (ja) | 2003-11-17 | 2007-06-06 | シャープ株式会社 | 液晶表示装置およびその製造方法、ハードマスク |
US7414148B2 (en) * | 2006-10-24 | 2008-08-19 | Central Glass Company Limited | Process for producing alkoxycarbonylfluoroalkanesulfonates |
EP1975687A1 (en) * | 2007-03-29 | 2008-10-01 | Rolic AG | Method of uniform and defect free liquid crystal aligning layers |
TWI591096B (zh) | 2010-02-12 | 2017-07-11 | 羅利克股份公司 | 具橫向取代之光配向材料 |
KR101998907B1 (ko) | 2011-12-28 | 2019-07-10 | 닛산 가가쿠 가부시키가이샤 | 액정 배향제, 액정 배향막, 액정 표시 소자 및 디아민 화합물 |
JP6153512B2 (ja) | 2012-03-16 | 2017-06-28 | 株式会社壮驥 | 液晶配向膜形成用組成物及び液晶表示素子 |
-
2016
- 2016-01-13 KR KR1020177018787A patent/KR102575113B1/ko active IP Right Grant
- 2016-01-13 JP JP2016569484A patent/JP6733552B2/ja active Active
- 2016-01-13 CN CN201680005747.3A patent/CN107108460B/zh active Active
- 2016-01-13 EP EP16737381.0A patent/EP3246307B1/en active Active
- 2016-01-13 TW TW105100960A patent/TWI682918B/zh active
- 2016-01-13 WO PCT/JP2016/050851 patent/WO2016114310A1/ja active Application Filing
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JPS6025955A (ja) * | 1983-07-22 | 1985-02-08 | Nippon Synthetic Chem Ind Co Ltd:The | γ−クロルアセト酢酸エステルの製造方法 |
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Publication number | Publication date |
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JP6733552B2 (ja) | 2020-08-05 |
EP3246307A1 (en) | 2017-11-22 |
CN107108460B (zh) | 2019-10-22 |
TW201630865A (zh) | 2016-09-01 |
EP3246307B1 (en) | 2019-11-27 |
JPWO2016114310A1 (ja) | 2017-10-19 |
KR102575113B1 (ko) | 2023-09-05 |
CN107108460A (zh) | 2017-08-29 |
KR20170102482A (ko) | 2017-09-11 |
TWI682918B (zh) | 2020-01-21 |
EP3246307A4 (en) | 2018-07-25 |
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