JPH029872A - Diol oligomer for high polymer liquid crystal - Google Patents
Diol oligomer for high polymer liquid crystalInfo
- Publication number
- JPH029872A JPH029872A JP63159637A JP15963788A JPH029872A JP H029872 A JPH029872 A JP H029872A JP 63159637 A JP63159637 A JP 63159637A JP 15963788 A JP15963788 A JP 15963788A JP H029872 A JPH029872 A JP H029872A
- Authority
- JP
- Japan
- Prior art keywords
- high polymer
- diol oligomer
- polymer liquid
- raw material
- liquid crystal
- 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.)
- Pending
Links
- 150000002009 diols Chemical class 0.000 title claims abstract description 8
- 239000005264 High molar mass liquid crystal Substances 0.000 title abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 4
- 239000004973 liquid crystal related substance Substances 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 5
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 4
- 229920002635 polyurethane Polymers 0.000 abstract description 4
- 239000004814 polyurethane Substances 0.000 abstract description 4
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 239000004417 polycarbonate Substances 0.000 abstract description 3
- 229920000728 polyester Polymers 0.000 abstract description 3
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003436 Schotten-Baumann reaction Methods 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 229920000515 polycarbonate Polymers 0.000 abstract description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 230000001588 bifunctional effect Effects 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- -1 -NO8 Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- GWJXPQLRAJGAOI-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dione Chemical compound OC1=NNC(=O)S1 GWJXPQLRAJGAOI-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920001692 polycarbonate urethane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Liquid Crystal Substances (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、高機能構造材として使用される高分子液晶用
の原料として用いられる１、３．４−チアジアゾール系
化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to 1,3,4-thiadiazole compounds used as raw materials for polymeric liquid crystals used as highly functional structural materials.
［従来の技術］
近年、優れた分子配向による高強度や自己強化による高
モジュラスなどの特徴を有する高機能性液晶ポリマーが
注目されている。例えば液晶ポリエステルやポリアラミ
ドの構造と液晶性に関しては可成りの知見が得られてお
り、実用化されているものもあるが、ポリカーボネート
、ポリウレタンなどのポリマーについては報告が少ない
。今までに得られた知見によると、高分子液晶について
も低分子液晶と類似の挙動が見られ、メソゲン構造を持
つポリマーにおいて液晶相を形成する場合が多いが、分
子量のようなポリマーに特有の因子が液晶性に影響を与
える点が低分子液晶に見られぬ特徴で、液晶特有の高配
向性に基いて高弾性、耐熱性、長寸法安定性が出現する
ものと思われる。[Prior Art] In recent years, highly functional liquid crystal polymers, which have characteristics such as high strength due to excellent molecular orientation and high modulus due to self-strengthening, have attracted attention. For example, considerable knowledge has been obtained regarding the structure and liquid crystallinity of liquid crystalline polyesters and polyaramids, and some of them have been put to practical use, but there are few reports on polymers such as polycarbonate and polyurethane. According to the knowledge obtained so far, behavior similar to that of low-molecular liquid crystals has been observed in polymer liquid crystals, and a liquid crystal phase is often formed in polymers with mesogenic structures, but there are The fact that factors influence liquid crystallinity is a feature not seen in low-molecular liquid crystals, and it is thought that high elasticity, heat resistance, and long-dimensional stability appear based on the high orientation characteristic of liquid crystals.
一般に、次に示すような構造を持つ化合物が液晶相を形
成することが知られており、メソゲンといわれる。Generally, compounds having the structure shown below are known to form a liquid crystal phase and are called mesogens.
Ｒ−■−Ｘ−■−Ｒ′
ここでＸは、ｎｉｌ、−ＣＩｌ＝ＣＩ＋−１−ＣＷＣ−
１−Ｎ＝卜、−Ｎ〒Ｎ−し、またＲ、Ｒ’はアルキル、
アルコキシ、−ＮＯ８，−ＣＮ、−Ｃ−ＯＲ、ハロゲン
などを示す。これらのメソゲンは、分子の直線性を維持
するための剛直で板状の部位と、ある程度の柔らかさを
付与するためのフレキシブルな部位を分子内に持ち、か
つ分子の平行配列を維持するために必要とする適当な大
きさの分子間力を有することが特徴である。また上に挙
げたメソゲン基の外に、複素環化合物の中にも液晶性を
示す化合物、例えばチオフェンやピリミジンなどがしら
れており、これらは類似構造のベンゼン系の誘導体に比
べて低い液晶転移温度を示す傾向がある。今後も更に種
々の液晶性を示す複素環化合物が見出される可能性があ
る。R-■-X-■-R' where X is nil, -CIl=CI+-1-CWC-
1-N=卜, -N〒N-, and R and R' are alkyl,
Indicates alkoxy, -NO8, -CN, -C-OR, halogen, etc. These mesogens have a rigid, plate-like part in the molecule to maintain molecular linearity, and a flexible part to give a certain degree of softness, and they also have a flexible part to maintain the parallel alignment of the molecules. It is characterized by having an appropriate amount of intermolecular force. In addition to the mesogenic groups mentioned above, some heterocyclic compounds are also known to exhibit liquid crystallinity, such as thiophene and pyrimidine, which have a lower liquid crystal transition than benzene-based derivatives with similar structures. It tends to indicate temperature. It is possible that more heterocyclic compounds exhibiting various liquid crystal properties will be discovered in the future.
［発明が解決しようとする課Ｍｉ１
ところで複素環を含むポリマーについては以前から研究
されでおり実用に供されているものもあるが、液晶性を
示すポリマーについては殆ど報告されていない。しかし
ながら、あらかじめ綿密な分子設計を行うことにより、
液晶性を有する複素環ポリマーの開発は可能と考えられ
る。[Issue to be solved by the invention Mi1 By the way, polymers containing heterocycles have been studied for some time and some have been put to practical use, but there have been almost no reports on polymers exhibiting liquid crystallinity. However, by performing careful molecular design in advance,
It is considered possible to develop a heterocyclic polymer with liquid crystallinity.
我々は複素環化合物として、安価で容易に人手可能な１
，３．４−チアジアゾールを取り上げ、これを出発物質
とする高分子液晶用のジオールオリゴマーを得た。As a heterocyclic compound, we have developed 1, which is inexpensive and easily manmade.
, 3.4-thiadiazole was taken up, and a diol oligomer for polymeric liquid crystals was obtained using this as a starting material.
［課題を解決するための手段］
１．３．４−チアジアゾールの類似物である１、３．４
−オキサジアゾールを含む複素環ポリマーは数多く報告
されているが、液晶性ポリマーは見られないばかりでな
く、低分子化合物においても液晶性は報告されていない
。しかし１，３．４−チアジアゾールは硫黄を含んでお
り、他の硫黄系化合物、例えばチオフェンなどでは液晶
性が見られることから、中間体だけでなく高分子物も液
晶性を有する可能性は十分あると考えられた。[Means for solving the problem] 1,3.4 which is an analogue of 1.3.4-thiadiazole
Although many heterocyclic polymers containing -oxadiazole have been reported, not only have liquid crystalline polymers not been found, but also liquid crystallinity has not been reported in low molecular weight compounds. However, 1,3,4-thiadiazole contains sulfur, and other sulfur-based compounds, such as thiophene, exhibit liquid crystallinity, so it is highly possible that not only the intermediate but also the polymer has liquid crystallinity. It was thought that there was.
［作用］
高分子液晶を得るための新規ジオールオリゴマーの合成
に関する化学反応式は次のとおりである。[Operation] The chemical reaction formula for the synthesis of a new diol oligomer for obtaining a polymeric liquid crystal is as follows.
すなわぢ
＋ ２ｎｌｌＸ
＋ （ｍ＋ｌ］ＩＯＲ，０１１
一−−→
ここでＸは反応性基、例えば塩素などのハロゲン原子を
表わし、Ｒｘはアルキレン基または２価のアルキレン誘
導体を表わし、またｍ、ｎは反応分子のモル数を示す。That is, + 2nll1 indicates the number of moles of reacting molecules.
［実施例］
２．５−ジメチルカプト−１，３，４−チアジアゾ・−
ルを出発物質として、上記化学反応式（１）よって官能
基を有する中間体を合成し、次いでショツテンバウマン
反応を利用した化学反応式（２）によってジオールオリ
ゴマーを合成した。[Example] 2,5-dimethylcapto-1,3,4-thiadiazole-
Using the compound as a starting material, an intermediate having a functional group was synthesized according to the chemical reaction formula (1) above, and then a diol oligomer was synthesized according to the chemical reaction formula (2) using the Schotten-Baumann reaction.
すなわち、２，５−ジメルカプト−１，３，４−チアゾ
ール４．５８をとリジン４．７４ｇ、 Ｎ−メチル−ピ
ロリドン２０ｍ ｌに溶解させた後、氷冷下でテレフタ
ル酸クロライド１２．２ｇを加えて攪拌した。この反応
はピリジン塩酸塩を含む混合不均一系で更に攪拌効果を
良くするため半日撹拌の後ピリジン４．７４ｇ、 Ｎ−
メチル−２−ピロリドン２０ｍ１を加え約３時間攪拌を
続けた、そして反応生成物を系から取り出すことなくブ
タンジオール６．２７ｇを一度に加え、史に半日室温で
攪拌してから反応混合物を水に投入し、生じた沈澱物を
減圧下６０°Ｃで乾燥した。収率は８０％であフた。That is, 4.58 g of 2,5-dimercapto-1,3,4-thiazole was dissolved in 4.74 g of lysine and 20 ml of N-methyl-pyrrolidone, and then 12.2 g of terephthalic acid chloride was added under ice cooling. and stirred. This reaction was carried out in a heterogeneous mixed system containing pyridine hydrochloride, and in order to further improve the stirring effect, 4.74 g of pyridine and N- were stirred for half a day.
20 ml of methyl-2-pyrrolidone was added and stirring was continued for about 3 hours, and 6.27 g of butanediol was added at once without removing the reaction product from the system. After stirring at room temperature for half a day, the reaction mixture was poured into water. The resulting precipitate was dried at 60°C under reduced pressure. The yield was 80%.
これらの反応に用いたテレフタル酸クロライドとブタン
ジオールは夫々化学量論的に大過剰加えたため生じた化
学反応は次の様に進行したと考えられる。すなわち、化
学反応式（ｌＸ２）中でｍ＝ｎ＝１となり、
＋
ｌｏ−（Ｃ１１２）４−Ｏｌｌ
生成物は
液晶性を示し、
その
赤外吸収
スベ
♀
６−Ｃ−０−１−Ｃ１１２−０１１、−Ｃ１１，−０１
１、−（ＣＩｌ□）ｎ−測定の結果、実測値は５９０で
あり、上記化学反応式より導かれた化合物Ｃ２゜１１□
６Ｎ２０８Ｓ３の理論値５９０と一致した。更に元素分
析の理論［Ｃ＝５２．９、＋１＝４．４、Ｎ＝４．７．
５＝１６．３．０＝２１．７（％）に対し実測値Ｃ＝５
１．６．１１＝４．２、Ｎ＝５．０．５＝１５．９．０
＝２３．３（％）もよく一致していることが確認された
。It is thought that the chemical reactions that occurred because terephthalic acid chloride and butanediol used in these reactions were each added in large stoichiometric excesses proceeded as follows. That is, m=n=1 in the chemical reaction formula (l 011, -C11, -01
1, -(CIl□)n- As a result of measurement, the actual value was 590, and the compound C2゜11□ was derived from the above chemical reaction formula.
It matched the theoretical value of 590 for 6N208S3. Furthermore, the theory of elemental analysis [C=52.9, +1=4.4, N=4.7.
Actual value C=5 for 5=16.3.0=21.7(%)
1.6.11=4.2, N=5.0.5=15.9.0
= 23.3 (%) was also confirmed to be in good agreement.
（参考例）
実施例によって得られた１、３．４−チアジアゾール系
ジオールオリゴマー０．２３６ｇ（０，４ミリモル）と
フェノールでマスクされたヘキサメチレンジイソシアネ
ート、すなわち、ヘキサメチレンジイソシアネート１モ
ルとフェノール２モルより得られるウレタン化合物０．
１４２ｇ（０，０４ミリモル）を１８０〜２１０°Ｃで
１５分間加熱後、生成したフェノールを留去するために
減圧下（１７〜２０トール）で１０分間さらに加熱・し
た、放冷後掲色の固化物なＮ−メチル−２−ピロリドン
（ＮＭＰ）に加熱溶解してから水に投入して再沈澱し、
収率８０％でポリウレタン液晶を得た。(Reference Example) 0.236 g (0.4 mmol) of the 1,3,4-thiadiazole diol oligomer obtained in Example and phenol-masked hexamethylene diisocyanate, that is, 1 mol of hexamethylene diisocyanate and 2 mol of phenol. Urethane compound obtained from 0.
After heating 142 g (0.04 mmol) at 180-210 °C for 15 minutes, further heating under reduced pressure (17-20 torr) for 10 minutes to distill off the formed phenol. After heating and dissolving in solidified N-methyl-2-pyrrolidone (NMP), it is poured into water and reprecipitated.
A polyurethane liquid crystal was obtained with a yield of 80%.
［発明の効果］
本発明による化合物は、液晶性を示すポリエステル、ポ
リカーボネート、ポリウレタン等の原料を提供するもの
であり、本発明は有用な効果を有する。[Effects of the Invention] The compound according to the present invention provides raw materials for polyester, polycarbonate, polyurethane, etc. that exhibit liquid crystallinity, and the present invention has useful effects.
図は、本発明の実施例により得られた化合物（ジオール
オリゴマー）の赤外線吸収スペクトルである。The figure shows an infrared absorption spectrum of a compound (diol oligomer) obtained in an example of the present invention.
Claims (1)
誘導体を、またｍ、ｎは夫々反応分子のモル数を示す。 ］ で示される高分子液晶用ジオールオリゴマー。[Claims] 1. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [Here, R_x represents an alkylene group or a divalent alkylene derivative, and m and n each represent the number of moles of the reactant molecules. ] A diol oligomer for polymeric liquid crystals represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63159637A JPH029872A (en) | 1988-06-28 | 1988-06-28 | Diol oligomer for high polymer liquid crystal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63159637A JPH029872A (en) | 1988-06-28 | 1988-06-28 | Diol oligomer for high polymer liquid crystal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH029872A true JPH029872A (en) | 1990-01-12 |
Family
ID=15698067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63159637A Pending JPH029872A (en) | 1988-06-28 | 1988-06-28 | Diol oligomer for high polymer liquid crystal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH029872A (en) |
-
1988
- 1988-06-28 JP JP63159637A patent/JPH029872A/en active Pending
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