JPS63250353A - Production of terephthalic acid dianilides - Google Patents
Production of terephthalic acid dianilidesInfo
- Publication number
- JPS63250353A JPS63250353A JP8248687A JP8248687A JPS63250353A JP S63250353 A JPS63250353 A JP S63250353A JP 8248687 A JP8248687 A JP 8248687A JP 8248687 A JP8248687 A JP 8248687A JP S63250353 A JPS63250353 A JP S63250353A
- Authority
- JP
- Japan
- Prior art keywords
- terephthalic acid
- anilines
- dianilides
- reaction
- aniline
- 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
- MXHDSBYJGVZESK-UHFFFAOYSA-N 1-n,4-n-diphenylbenzene-1,4-dicarboxamide Chemical class C=1C=C(C(=O)NC=2C=CC=CC=2)C=CC=1C(=O)NC1=CC=CC=C1 MXHDSBYJGVZESK-UHFFFAOYSA-N 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000001448 anilines Chemical class 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 26
- 238000006243 chemical reaction Methods 0.000 abstract description 19
- 239000011541 reaction mixture Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 abstract description 4
- LNCHBBZGCITQPQ-UHFFFAOYSA-N 4-(phenylcarbamoyl)benzoic acid Chemical class C1=CC(C(=O)O)=CC=C1C(=O)NC1=CC=CC=C1 LNCHBBZGCITQPQ-UHFFFAOYSA-N 0.000 abstract description 3
- 229920001955 polyphenylene ether Polymers 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005992 thermoplastic resin Polymers 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 dicarboxylic acid chlorides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical group CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
- REJGDSCBQPJPQT-UHFFFAOYSA-N 2,4,6-tri-tert-butylaniline Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(N)C(C(C)(C)C)=C1 REJGDSCBQPJPQT-UHFFFAOYSA-N 0.000 description 1
- NUZVLYNISQOZOW-UHFFFAOYSA-N 2,5-ditert-butylaniline Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(N)=C1 NUZVLYNISQOZOW-UHFFFAOYSA-N 0.000 description 1
- OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 1
- WGENWPANMZLPIH-UHFFFAOYSA-N 4-decylaniline Chemical compound CCCCCCCCCCC1=CC=C(N)C=C1 WGENWPANMZLPIH-UHFFFAOYSA-N 0.000 description 1
- OVEMTTZEBOCJDV-UHFFFAOYSA-N 4-hexylaniline Chemical compound CCCCCCC1=CC=C(N)C=C1 OVEMTTZEBOCJDV-UHFFFAOYSA-N 0.000 description 1
- 241000219051 Fagopyrum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、テレフタル酸ジアニリド類の創造法に関する
。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for creating terephthalic acid dianilides.
本発明の方法によれば、目的とするテレフタル酸ジアニ
リド類が収率よく製造できる。According to the method of the present invention, the desired terephthalic acid dianilides can be produced in good yield.
テレフタル酸ジアニリド類は、ポリフェニレンエーテル
系樹脂などの熱可塑性樹脂の流動性改良剤と表る（例え
ば特開昭６０−４４５４７号公報参照）など、産業上有
用な物質である。Terephthalic acid dianilides are industrially useful substances, such as fluidity improvers for thermoplastic resins such as polyphenylene ether resins (see, for example, JP-A-60-44547).
一般にジカルボン酸ジアニリド類は、相当するジカルボ
ン酸塩化物とアニリン類とを反応させることにより製造
できることは、既によく知られている。又、ジカルボン
酸塩化物以外のものを出発原料トする、ジカルボン酸ジ
アニリド類の創造法に関しても、ジカルボン酸とジフェ
ニル尿素とを混合加熱する方法（ケミカルアブストラク
ツ（Ｃｈｅｍ、Ａｂｓｔｒ、） ８９９ ｈ （１９５
５））等が提案されて込るが、−ずれの場合本ジカルボ
ン酸塩化物又は、アミド化試剤を合成せねばならず、工
業的には満足のいく方法ではなかった。It is already well known that dicarboxylic acid dianilides can generally be produced by reacting the corresponding dicarboxylic acid chlorides with anilines. In addition, regarding a method for creating dicarboxylic acid dianilides using a starting material other than dicarboxylic acid chloride, a method of mixing and heating dicarboxylic acid and diphenyl urea (Chemical Abstracts (Chem, Abstr.) 899 h ( 195
5)), etc. have been proposed, but in the case of -, the dicarboxylic acid chloride or the amidation reagent must be synthesized, and this method is not industrially satisfactory.
アジピン酸等のジカルボン酸とアニリンとを溶媒の存在
下、１２０〜２００℃で加熱縮合させる方法（特開昭６
１−２５１６４９号公報参照）も提案されている。A method of heating and condensing a dicarboxylic acid such as adipic acid and aniline at 120 to 200°C in the presence of a solvent (Japanese Unexamined Patent Publication No. 6
1-251649) has also been proposed.
前記の、溶媒の存在下にジカルボン酸類とアニリン類を
１２０〜２００℃で反応させ、生成する水を溶媒との共
沸で系外へ留去させる方法を、テレフタル酸ジアニリド
類に適用した場合、反応の進行が極めて遅い（比較例参
照）。さらに、生成するテレフタル酸ジアニリド類及び
原料テレフタル酸共に通常の有機溶媒への溶解度が低く
、残存テレフタル酸の除去精製が困難であり、純度の高
いテレフタル酸ジアニリド類を得ることができない。When the above method of reacting dicarboxylic acids and anilines at 120 to 200°C in the presence of a solvent and distilling the generated water out of the system azeotropically with the solvent is applied to terephthalic acid dianilides, The reaction progresses extremely slowly (see Comparative Example). Furthermore, both the produced terephthalic acid dianilides and the raw material terephthalic acid have low solubility in ordinary organic solvents, and it is difficult to remove and purify the residual terephthalic acid, making it impossible to obtain highly pure terephthalic acid dianilides.
本発明は、上記問題点の解消を図り、高収率で、高純度
のテレフタル酸ジアニリド類の製造法を提供しようとす
るものである。The present invention aims to solve the above-mentioned problems and provides a method for producing terephthalic acid dianilides with high yield and high purity.
Ｃ問題点を解決するための手段〕
本発明は、テレフタル酸ジアニリド類を製造する方法に
おいて、テレフタル酸と一般式Ｒ，＋ｍｚ ｒ式中、Ｒ
は水素、Ｃｓ−１ｇノフル＊ル基、アルケニル基、アリ
ール基を示す）で表わされるアニリン類とを、２００〜
３５０℃の温度範囲で直接反応させることを特徴とする
テレフタル酸アニリド類の製造法である。Means for Solving Problem C] The present invention provides a method for producing terephthalic acid dianilides, in which terephthalic acid and the general formula R, +mz r in the formula R
represents hydrogen, Cs-1g noflu*, alkenyl group, aryl group), and
This is a method for producing terephthalic acid anilides, which is characterized by direct reaction in a temperature range of 350°C.
ル基、アルケニル基、アリール基を示す）で表わされる
化合物であって、例えば、アニリン、０−トルイジン、
ｍ−トルイジン、ｐ−トルイジン、２．４−キシリジン
、３，４−キシリジン、４−ｎ−ブチルアニリン、４−
ｎ−へキシルアニリン、４−ｎ−オｌチルアニリン、４
− ｎ −７シルアニリン、４−ｎ−デシルアニリン、
２，５−ジ−ｔ−ブチルアニリン、２，４．６−トリー
ｔ−ブチルアニリン等が例示される。compounds represented by the following formulas (representing a group such as aniline, alkenyl group, or aryl group), such as aniline, 0-toluidine,
m-toluidine, p-toluidine, 2,4-xylidine, 3,4-xylidine, 4-n-butylaniline, 4-
n-hexylaniline, 4-n-olthylaniline, 4
- n -7 sylaniline, 4-n-decylaniline,
Examples include 2,5-di-t-butylaniline and 2,4.6-tri-t-butylaniline.
原料のテレフタル酸とアニリン類の使用モル比は、１／
−７゜の範囲が好ましく、特に、Ａ−〆１ｓの範囲が好
ましめ。該モル比が曇を超えて、テレフタル酸量が多く
なると、原料テレフタル酸を消失させることが困難にな
るばかりではなく、反応の進行につれて反応混合物の流
動性が低下してくる為に、工業的実施において不利にな
ってくる。The molar ratio of raw materials terephthalic acid and anilines used is 1/
A range of -7° is preferred, and a range of A-〆1s is particularly preferred. When the molar ratio exceeds cloudy and the amount of terephthalic acid increases, it is not only difficult to eliminate the raw material terephthalic acid, but also the fluidity of the reaction mixture decreases as the reaction progresses. This will be a disadvantage in implementation.
また該モル比が、Ｖｚｏを超えてアニリン類の量が多い
場合には、反応混合物量が多くなり、蕎収率低下により
、経済性が悪化するので、工業的実施にお込て不利であ
る。In addition, if the molar ratio exceeds Vzo and the amount of aniline is large, the amount of reaction mixture will increase and the buckwheat yield will decrease, resulting in poor economic efficiency, which is disadvantageous for industrial implementation. .
反応温度は、２００〜３５０℃の範囲である口膣温度が
、２００℃以下の場合は、反応速度が遅く実質的に原料
テレフタル酸を消失させることが困難であり、高純度の
テレフタル酸ジアニリド類を得ることができなｈｏまた
該温度が３５０℃以上の場合は、アニリン類の熱的劣化
が著るしく、製品の着色等の原因となるので好ましくな
り０反応圧力は、常圧、或いは加圧条件のどちらでも良
いが、用いるアニリン類の沸点が所定反応温度以下の場
合には、反応混合物が所定反応温度に到達する様、不活
性ガス等を用いて加圧すればよく、又、アニリン類の沸
点が所定反応温度以上である場合には、常圧、或いは自
然発生圧力下で反応を実施しても何ら問題はない。The reaction temperature is in the range of 200 to 350°C. If the oral temperature is below 200°C, the reaction rate is slow and it is difficult to substantially eliminate the raw material terephthalic acid, resulting in high purity terephthalic acid dianilides. In addition, if the temperature is 350°C or higher, the thermal deterioration of the anilines will be significant and cause coloring of the product, so it is preferable that the reaction pressure is normal pressure or elevated temperature. Either pressure condition may be used, but if the boiling point of the aniline used is below the predetermined reaction temperature, pressure may be applied using an inert gas or the like so that the reaction mixture reaches the predetermined reaction temperature. When the boiling point of the compound is above the predetermined reaction temperature, there is no problem in carrying out the reaction under normal pressure or naturally occurring pressure.
反応時間は、反応温度、原料仕込みモル比により異なっ
てくるので一律に規定できないが、通常１時間以上とす
るのが好ましいが、いたずらに反応時間を延長すること
は、アニリン類の熱的劣化を起こすので好ましくない。The reaction time cannot be uniformly specified because it varies depending on the reaction temperature and the molar ratio of raw materials charged, but it is usually preferable to set it to 1 hour or more, but unnecessarily extending the reaction time may cause thermal deterioration of the anilines. This is not desirable as it can cause
本発明を具体的に実施する方法としては、テレフタル酸
、アニリン類忽部−と−む繻）電を所定の温度、圧力の
条件下で反応させる。In a specific method of carrying out the present invention, terephthalic acid and aniline derivatives are reacted under conditions of predetermined temperature and pressure.
得られるテレフタル酸ジアニリド類は、用いられるアニ
ＩＪン類に対応した一般式
は水素、Ｃｓ〜！Ｓのアルキル基、アルケニル基、了り
−ル基を示す）で表わされる化合物である。反応終了後
、反応混合物を冷却し、テレフタル酸ジアニリド類を晶
出させ、戸別すると、粗テレフタル酸ジアニリド類が得
られる。このものを、メタノール、エタノール等の低級
アルコール類、又はトルエン、キシレン、エチルベンゼ
ン等の芳香族炭化水素等で洗浄することにより、白色の
精製テレフタル酸ジアニリド類が得られる。The resulting terephthalic dianilides have a general formula of hydrogen, Cs~!, corresponding to the aniline used. S represents an alkyl group, alkenyl group, or aryol group). After the reaction is completed, the reaction mixture is cooled and the terephthalic acid dianilides are crystallized, and then the crude terephthalic acid dianilides are obtained. By washing this product with lower alcohols such as methanol and ethanol, or aromatic hydrocarbons such as toluene, xylene, and ethylbenzene, white purified terephthalic acid dianilides are obtained.
反応混合物から目的物を晶出させた後のｐ液には、アニ
リン類、テレフタル酸、テレフタル酸モノアニリド類を
含有しているので、これを反応工種に循環し、テレフタ
ル酸ジアニリド類の原料として再使用が可能である。The p-liquid after crystallizing the target product from the reaction mixture contains anilines, terephthalic acid, and terephthalic acid monoanilides, so it is recycled to the reaction process and recycled as a raw material for terephthalic acid dianilides. Usable.
以下、実施例てより、本発明をさらに具体的に説明する
。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
テレフタル酸１６．６９ （０，１モル）、アニリン９
３ ｆ （１，０モル）を内容量２５０ｍのステンレス
製オートクレーブに仕込み、反応器内を不活性ガス置換
した後、内容物温度が２８０℃で６時間加熱攪拌した。Example 1 Terephthalic acid 16.69 (0.1 mol), aniline 9
3f (1.0 mol) was charged into a stainless steel autoclave with an internal capacity of 250 m, and after purging the inside of the reactor with an inert gas, the contents were heated and stirred at a temperature of 280° C. for 6 hours.
反応終了後、反応混合物を４０℃以下に冷却した結晶を
析出させた後、戸別し粗テレフタル酸ジアニリドを得た
。このものを、トルエン１００ｆを用いて５０℃で洗浄
した後、炉別し、減圧乾燥しテレフタル酸ジアニリド２
７．１ ｆ（収率８５．９ ％ （仕込みテレフタル酸
基準））を得た。After the reaction was completed, the reaction mixture was cooled to 40° C. or below to precipitate crystals, and then separated from each other to obtain crude terephthalic acid dianilide. After washing this product at 50°C using 100f of toluene, it was separated in a furnace and dried under reduced pressure to produce terephthalic acid dianilide 2.
7.1 f (yield 85.9% (based on charged terephthalic acid)) was obtained.
実施例２〜１０
表１に示すアニリン類を使用した他は実施例１と同様の
操作を行ない、それぞれ対応するテレフタル酸ジアニリ
ド類を得た。結果を表１に示す。Examples 2 to 10 The same operations as in Example 1 were performed except that the anilines shown in Table 1 were used to obtain corresponding terephthalic dianilides. The results are shown in Table 1.
ここでテレフタル酸ジアニリド類収率は、仕込みテレフ
タル酸量（モル）に対する生成テレフタル酸ジアニリド
■□ｔ（モル）をチで示したものである。Here, the yield of terephthalic acid dianilides is expressed as the amount of terephthalic acid dianilide (mol) produced relative to the amount (mol) of terephthalic acid charged.
比較例
テレフタル酸３３．２ ｆ （０，２モル）、アニリン
１８６、Ｏｆ （ｚ、ａモル）を内容量３０ＯＮｌの三
つロフラスコに仕込み、生成する水をアニリンとの共沸
混合物として反応系外へ留出させ、アニリン相と水相と
に分離した後アニリン相を反応系へ循環させる方法で反
応を実施したところ、内温１８５℃で６時間加熱しても
生成水が留出せず、実質的に反応は進行しなかった。Comparative Example Terephthalic acid 33.2 f (0.2 mol), aniline 186, Of (z, a mol) were charged into a three-bottle flask with an internal capacity of 30 ONl, and the resulting water was discharged from the reaction system as an azeotrope with aniline. When the reaction was carried out by distilling the water into an aniline phase, separating it into an aniline phase and an aqueous phase, and then circulating the aniline phase to the reaction system, the produced water could not be distilled out even after heating at an internal temperature of 185°C for 6 hours. The reaction did not proceed.
（以下余白）(Margin below)
Claims (1)
す▼（式中、 Ｒは水素、Ｃ＿１＿〜＿１＿５のアルキル基、アルケニ
ル基、アリール基を示す）で表わされるアニリン類とを
、２００〜３５０℃の温度範囲で反応させることを特徴
とするテレフタル酸ジアニリド類の製造法。[Claims] Terephthalic acid and anilines represented by the general formula; ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (wherein R is hydrogen, and represents an alkyl group, alkenyl group, or aryl group of C_1_ to_1_5) A method for producing terephthalic acid dianilides, which comprises reacting the above at a temperature range of 200 to 350°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8248687A JPH0737431B2 (en) | 1987-04-03 | 1987-04-03 | Method for producing dianilide terephthalic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8248687A JPH0737431B2 (en) | 1987-04-03 | 1987-04-03 | Method for producing dianilide terephthalic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63250353A true JPS63250353A (en) | 1988-10-18 |
| JPH0737431B2 JPH0737431B2 (en) | 1995-04-26 |
Family
ID=13775838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8248687A Expired - Lifetime JPH0737431B2 (en) | 1987-04-03 | 1987-04-03 | Method for producing dianilide terephthalic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0737431B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130052447A1 (en) * | 2011-08-29 | 2013-02-28 | Ticona Llc | Liquid Crystalline Polymer Composition Containing a Fibrous Filler |
| CN103764793A (en) * | 2011-08-29 | 2014-04-30 | 提克纳有限责任公司 | High flow liquid crystalline polymer composition |
-
1987
- 1987-04-03 JP JP8248687A patent/JPH0737431B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130052447A1 (en) * | 2011-08-29 | 2013-02-28 | Ticona Llc | Liquid Crystalline Polymer Composition Containing a Fibrous Filler |
| CN103764793A (en) * | 2011-08-29 | 2014-04-30 | 提克纳有限责任公司 | High flow liquid crystalline polymer composition |
| US9051514B2 (en) | 2011-08-29 | 2015-06-09 | Ticona Llc | High flow liquid crystalline polymer composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0737431B2 (en) | 1995-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |