JPH06329749A - Liquid crystal polyurethane - Google Patents
Liquid crystal polyurethaneInfo
- Publication number
- JPH06329749A JPH06329749A JP5116735A JP11673593A JPH06329749A JP H06329749 A JPH06329749 A JP H06329749A JP 5116735 A JP5116735 A JP 5116735A JP 11673593 A JP11673593 A JP 11673593A JP H06329749 A JPH06329749 A JP H06329749A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- polyurethane
- represented
- molecular weight
- 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
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 18
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 18
- 239000004973 liquid crystal related substance Substances 0.000 title description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 6
- 235000010290 biphenyl Nutrition 0.000 abstract description 3
- 239000004305 biphenyl Substances 0.000 abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 abstract description 3
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- -1 polytetramethylene Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- 239000005264 High molar mass liquid crystal Substances 0.000 description 1
- IXQBIOPGDNZYNA-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C IXQBIOPGDNZYNA-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- SFHGONLFTNHXDX-UHFFFAOYSA-N [4-[4-(hydroxymethyl)phenyl]phenyl]methanol Chemical group C1=CC(CO)=CC=C1C1=CC=C(CO)C=C1 SFHGONLFTNHXDX-UHFFFAOYSA-N 0.000 description 1
- SSFGHKDDKYEERH-UHFFFAOYSA-N [6-(hydroxymethyl)naphthalen-2-yl]methanol Chemical compound C1=C(CO)C=CC2=CC(CO)=CC=C21 SSFGHKDDKYEERH-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002887 superconductor Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、液晶性ポリウレタン類
に関する。FIELD OF THE INVENTION The present invention relates to liquid crystalline polyurethanes.
【０００２】[0002]
【従来技術とその課題】ポリウレタンは、電気・電子工
業における透明導電フィルム、有機半導体、有機超伝導
体、感光感熱材料として、また塗料、繊維、合成皮革等
の分野で広く使用されている。一般的に、ポリウレタン
には機能性を有するもの、特に液晶性を示すものも見つ
けられているが、液晶転移温度が高温であるか又は液晶
温度巾が小さいために、溶融加工時に熱分解を起こした
り、使用に耐える機能を備えていないものであった。BACKGROUND OF THE INVENTION Polyurethane is widely used as a transparent conductive film, an organic semiconductor, an organic superconductor, a light and heat sensitive material in the electric and electronic industries, and in the fields of paints, fibers, synthetic leather and the like. In general, polyurethanes having functionality, especially those exhibiting liquid crystallinity, have been found, but due to high liquid crystal transition temperature or small liquid crystal temperature range, thermal decomposition occurs during melt processing. Or, it was not equipped with a function that can be used.
【０００３】ある有機結晶を融解するとき、結晶から直
ちに液体にならず、一旦濁った液体になり、更に加熱し
て始めて液体になるものを液晶と呼ぶ。電気・電子材料
で使用されている液晶は、光学的性質（散乱、屈折干渉
等）を有しており、その性質には電場や磁場の影響を受
け易く、液晶温度範囲が広く、また化学的な安定性を有
していることが要求される。When a certain organic crystal is melted, it is called a liquid crystal that does not immediately become a liquid from the crystal but becomes a turbid liquid and then becomes a liquid only when heated. Liquid crystals used in electrical and electronic materials have optical properties (scattering, refraction interference, etc.), which are easily affected by electric and magnetic fields, have a wide liquid crystal temperature range, and have chemical properties. It is required to have stable stability.
【０００４】ところが、今日まで工業的に使用されてい
る液晶化合物は、単分子化合物が多く、化学的に安定で
剛直な高分子液晶ポリウレタンは未だ知られていない。However, most of the liquid crystal compounds industrially used to date are monomolecular compounds, and a chemically stable and rigid polymer liquid crystal polyurethane has not been known yet.
【０００５】[0005]
【課題を解決するための手段】本発明の目的は、分解温
度以下で液晶を示し、剛直で化学的に安定なビフェニル
骨格又はナフタリン骨格を有する新規なポリウレタンを
提供することにある。SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel polyurethane having a rigid and chemically stable biphenyl skeleton or naphthalene skeleton which exhibits a liquid crystal at a decomposition temperature or lower.
【０００６】本発明のポリウレタン類は、一般式The polyurethanes of the present invention have the general formula
【０００７】[0007]
【化３】 [Chemical 3]
【０００８】で表わされる繰返し単位を有し、分子量が
５０００〜２０００００の範囲にあるポリウレタン類及
び一般式Polyurethanes having a repeating unit represented by the formula and having a molecular weight in the range of 5,000 to 200,000, and general formulas
【０００９】[0009]
【化４】 [Chemical 4]
【００１０】で表わされる繰返し単位を有し、分子量が
５０００〜２０００００の範囲にあるポリウレタン類で
ある。Polyurethanes having a repeating unit represented by and having a molecular weight in the range of 5,000 to 200,000.
【００１１】上記一般式（１）で表わされるポリウレタ
ン類は、例えば式Polyurethanes represented by the above general formula (1) are represented by the formula
【００１２】[0012]
【化５】 [Chemical 5]
【００１３】で表わされる４，４´−ビス（ヒドロキシ
メチル）ビフェニル（以下「ＢＨＢ」という）、一般式 ＯＣＮ−Ｒ1 −ＮＣＯ （４） （式中Ｒ1 は前記に同じ。）で表わされるジイソシアナ
ート類及び一般式 ＨＯ（Ｒ2 Ｏ）ｎＨ （５） （式中Ｒ2 及びｎは前記に同じ。）で表わされるα，ω
−ジヒドロキシ化合物を反応させることにより製造され
る。また、上記一般式（１）で表わされるポリウレタン
類は、例えば式4,4'-bis (hydroxymethyl) biphenyl (hereinafter referred to as "BHB") represented by the general formula OCN-R 1 -NCO (4) (wherein R 1 is the same as above). Diisocyanates and α, ω represented by the general formula HO (R 2 O) nH (5) (wherein R 2 and n are the same as above).
-Produced by reacting a dihydroxy compound. Further, the polyurethanes represented by the above general formula (1) are represented by the formula
【００１４】[0014]
【化６】 [Chemical 6]
【００１５】で表わされる２，６−ビス（ヒドロキシメ
チル）ナフタリン（以下「ＢＨＮ」という）、上記一般
式（４）で表わされるジイソシアナート類及び上記一般
式（５）で表わされるα，ω−ジヒドロキシ化合物を反
応させることにより製造される。2,6-bis (hydroxymethyl) naphthalene represented by (BHN), diisocyanates represented by the general formula (4) and α, ω represented by the general formula (5). -Produced by reacting a dihydroxy compound.
【００１６】一般式（４）のジイソシアナート類として
は、例えばエチレンジイソシアナート、トリメチレンジ
イソシアナート、テトラメチレンジイソシアナート、ペ
ンタメチレンジイソシアナート、ヘキサメチレンジイソ
シアナート（以下「ＨＤＩ」という）、ペプタメチレン
ジイソシアナート、オクタメチレンジイソシアナート、
２，４′−トルイレンジイソシアナート、３，３′−ジ
メチル−４，４′−ビフェニルジイソシアナート（以下
「ＤＤＩ」という）、１，５−ナフタリンジイソシアナ
ート（以下「ＮＤＩ」という）等を挙げることができ
る。Examples of the diisocyanates of the general formula (4) include ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate and hexamethylene diisocyanate (hereinafter referred to as "HDI"). ,), Peptamethylene diisocyanate, octamethylene diisocyanate,
2,4'-toluylene diisocyanate, 3,3'-dimethyl-4,4'-biphenyl diisocyanate (hereinafter "DDI"), 1,5-naphthalene diisocyanate (hereinafter "NDI"), etc. Can be mentioned.
【００１７】一般式（５）のα，ω−ジヒドロキシ化合
物としては、従来公知のものを広く使用でき、例えばポ
リエチレングリコール、ポリプロピレングリコール、ポ
リテトラメチレングリコール等の重合体等の両末端が水
酸基である化合物を挙げることができる。As the α, ω-dihydroxy compound of the general formula (5), conventionally known compounds can be widely used. For example, polymers such as polyethylene glycol, polypropylene glycol and polytetramethylene glycol have hydroxyl groups at both ends. A compound can be mentioned.
【００１８】ＢＨＢ又はＢＨＮ、ジイソシアナート類及
びα，ω−ジヒドロキシ化合物の使用割合としては、特
に限定されるものではないが、通常ＢＨＢ又はＢＨＮ１
モルに対してジイソシアナート類を２モル程度、α，ω
−ジヒドロキシ化合物を１モル程度用いるのがよい。該
反応は、通常適当な溶媒中で行なわれる。ここで溶媒と
しては、例えばトルエン、ベンゼン、ｏ−ジクロロベン
ゼン、ジメチルホルムアミド等を用いてもよいが、上記
α，ω−ジヒドロキシ化合物を溶媒として兼用すること
もできる。該反応は、通常８０〜３００℃程度の温度条
件下、２〜４８時間程度で完結する。The proportions of BHB or BHN, diisocyanates and α, ω-dihydroxy compound used are not particularly limited, but are usually BHB or BHN1.
About 2 moles of diisocyanates relative to moles, α, ω
-It is preferable to use about 1 mol of the dihydroxy compound. The reaction is usually performed in a suitable solvent. Here, as the solvent, for example, toluene, benzene, o-dichlorobenzene, dimethylformamide, or the like may be used, but the above α, ω-dihydroxy compound may also be used as the solvent. The reaction is usually completed in about 2 to 48 hours under a temperature condition of about 80 to 300 ° C.
【００１９】斯くして生成する本発明の一般式（１）及
び（２）で表わされるポリウレタン類は、反応終了後、
再沈殿法等の慣用の手段により単離、精製される。The polyurethanes represented by the general formulas (1) and (2) of the present invention thus produced are
It is isolated and purified by a conventional means such as a reprecipitation method.
【００２０】[0020]
【発明の効果】本発明によれば、液晶を示す、剛直で化
学的に安定なビフェニル骨格又はナフタリン骨格を有す
るポリウレタンが提供される。According to the present invention, there is provided a polyurethane having a rigid and chemically stable biphenyl skeleton or naphthalene skeleton, which exhibits liquid crystal.
【００２１】[0021]
【実施例】以下に実施例を掲げて本発明をより一層明ら
かにする。EXAMPLES The present invention will be further clarified with reference to the following examples.
【００２２】実施例１ ポリテトラメチレングリコール−１００（保土谷化学
（株）製、ＰＴＧ−１００、平均分子量Ｍｎ＝８７６）
１ミリモル及びＢＨＢ１ミリモルを２０ｍｌ三口フラス
コに入れ、窒素置換した後、攪拌しながら２００℃に加
熱均一にした。次に室温まで冷却し、１．０２５ミリモ
ルのＤＤＩを加えた後、溶媒のｏ−ジクロロベンゼン５
ｍｌを加え、窒素置換し、１８０℃で攪拌した。反応器
内の溶液が均一になった後、更に１．０２５ミリモルの
ＤＤＩを加え、窒素置換した後、１８０℃で２４時間攪
拌した。反応終了後、多量のメタノールを用いて生成物
を沈降精製した。収率は８５％であった。Example 1 Polytetramethylene glycol-100 (Hodogaya Chemical Co., Ltd., PTG-100, average molecular weight Mn = 876)
1 mmol and 1 mmol of BHB were placed in a 20 ml three-necked flask, the atmosphere was replaced with nitrogen, and the mixture was heated to 200 ° C. with stirring to make the mixture uniform. Next, after cooling to room temperature and adding 1.025 mmol of DDI, the solvent o-dichlorobenzene 5 was added.
ml was added, and the atmosphere was replaced with nitrogen, followed by stirring at 180 ° C. After the solution in the reactor became uniform, 1.025 mmol of DDI was further added, the atmosphere was replaced with nitrogen, and the mixture was stirred at 180 ° C. for 24 hours. After the reaction was completed, the product was precipitated and purified using a large amount of methanol. The yield was 85%.
【００２３】斯くして得られるポリウレタン（ＤＤＩ−
ＢＨＢ−ＰＴＧ−１００）の物性は以下の通りである。The polyurethane thus obtained (DDI-
The physical properties of BHB-PTG-100) are as follows.
【００２４】Ｔｍ（液晶転移温度）：２３０℃ Ｔｉ（等方性液体化温度）：２９２℃ 粘度〔η〕（ｄｌ／ｇ、３０℃、ジメチルホルムアミド
中）：０．２７ ＩＲ（フィルム、ｃｍ-1）：３３００（−ＮＨ−），２
９５０，１４５０，７７０（−ＣＨ2 −），１７３０
（Ｃ＝Ｏ），１５９０，８００，４４０（−Ｃ6 Ｈ
4 −），１５２０，１３７０，１２４０（−ＣＯＮＨ
−），１１００（−ＣＨ2−Ｏ−ＣＨ2 −） 実施例２〜１３ 対応する適当な原料を用い、実施例１と同様に処理し
て、下記表１に示すポリマーを得た。該ポリマーの収
率、Ｔｍ（℃）、Ｔｉ（℃）及び粘度も表１に併せて示
す。Tm (liquid crystal transition temperature): 230 ° C. Ti (isotropic liquefying temperature): 292 ° C. Viscosity [η] (dl / g, 30 ° C. in dimethylformamide): 0.27 IR (film, cm − 1 ): 3300 (-NH-), 2
950,1450,770 (-CH 2 -), 1730
(C = O), 1590,800,440 ( -C 6 H
4 -), 1520,1370,1240 (-CONH
-), 1100 (-CH 2 -O -CH 2 - with) Example 2-13 corresponding appropriate starting materials, and treated in the same manner as in Example 1 to obtain a polymer shown in Table 1. The yield, Tm (° C.), Ti (° C.) and viscosity of the polymer are also shown in Table 1.
【００２５】[0025]
【表１】 [Table 1]
Claims (2)
０００００の範囲にあるポリウレタン類。1. A general formula: And has a molecular weight of 5,000 to 2
Polyurethanes in the range of 00000.
０００００の範囲にあるポリウレタン類。2. A general formula: And has a molecular weight of 5,000 to 2
Polyurethanes in the range of 00000.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5116735A JP2588830B2 (en) | 1993-05-19 | 1993-05-19 | Liquid crystalline polyurethanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5116735A JP2588830B2 (en) | 1993-05-19 | 1993-05-19 | Liquid crystalline polyurethanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06329749A true JPH06329749A (en) | 1994-11-29 |
| JP2588830B2 JP2588830B2 (en) | 1997-03-12 |
Family
ID=14694496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5116735A Expired - Lifetime JP2588830B2 (en) | 1993-05-19 | 1993-05-19 | Liquid crystalline polyurethanes |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2588830B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3318588A4 (en) * | 2015-07-01 | 2019-01-23 | Toyo Tire & Rubber Co., Ltd. | LIQUID CRYSTAL URETHANE COMPOUND, THERMOSENSITIVE LIQUID CRYSTAL POLYURETHANE ELASTOMER, AND CORRESPONDING PREPARATION METHOD |
| KR20200061970A (en) * | 2018-11-26 | 2020-06-03 | 한국생산기술연구원 | Composition for forming polyurethane-based film, Polyurethane-based film formed from the composition, Articles comprising the polyurethane-based film |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6351413A (en) * | 1986-08-19 | 1988-03-04 | バイエル・アクチエンゲゼルシヤフト | Linear polyurethane elastomer and manufacture |
| JPH0641263A (en) * | 1992-07-22 | 1994-02-15 | Osaka Gas Co Ltd | Liquid crystal polyurethane |
-
1993
- 1993-05-19 JP JP5116735A patent/JP2588830B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6351413A (en) * | 1986-08-19 | 1988-03-04 | バイエル・アクチエンゲゼルシヤフト | Linear polyurethane elastomer and manufacture |
| JPH0641263A (en) * | 1992-07-22 | 1994-02-15 | Osaka Gas Co Ltd | Liquid crystal polyurethane |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3318588A4 (en) * | 2015-07-01 | 2019-01-23 | Toyo Tire & Rubber Co., Ltd. | LIQUID CRYSTAL URETHANE COMPOUND, THERMOSENSITIVE LIQUID CRYSTAL POLYURETHANE ELASTOMER, AND CORRESPONDING PREPARATION METHOD |
| KR20200061970A (en) * | 2018-11-26 | 2020-06-03 | 한국생산기술연구원 | Composition for forming polyurethane-based film, Polyurethane-based film formed from the composition, Articles comprising the polyurethane-based film |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2588830B2 (en) | 1997-03-12 |
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