JPS63250354A - Production of terephthalic acid dianilides - Google Patents
Production of terephthalic acid dianilidesInfo
- Publication number
- JPS63250354A JPS63250354A JP8499887A JP8499887A JPS63250354A JP S63250354 A JPS63250354 A JP S63250354A JP 8499887 A JP8499887 A JP 8499887A JP 8499887 A JP8499887 A JP 8499887A JP S63250354 A JPS63250354 A JP S63250354A
- Authority
- JP
- Japan
- Prior art keywords
- anilines
- terephthalic acid
- terephthalate
- dialkyl
- reaction
- 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 13
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 26
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 150000001448 anilines Chemical class 0.000 abstract description 13
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract description 10
- 239000011541 reaction mixture Substances 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 5
- -1 terephthalic acid diesters Chemical class 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture 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
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 1
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-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
- 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
- 241000861914 Plecoglossus altivelis Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229960003564 cyclizine Drugs 0.000 description 1
- GXJPKIGCMGAHTL-UHFFFAOYSA-N dipropyl benzene-1,4-dicarboxylate Chemical compound CCCOC(=O)C1=CC=C(C(=O)OCCC)C=C1 GXJPKIGCMGAHTL-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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１７ド類の製造法に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing terephthalic acid diani-17.
本発明の方法によれば、収率よく高純度で目的とするテ
レフタル酸ジアニリド類が製造できる。According to the method of the present invention, the desired terephthalic acid dianilides can be produced with high yield and high purity.
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（例えば特開
昭６０−４４５４７号公報参照）など有用な物質でめる
っ
〔従来の技術〕
カルボン酸エステルを原料としてアミンと反応させて、
相当するカルボン酸アミドを製造する方法においては、
触媒としてナトリウムメチラートを用いる方法（ジャー
ナルオプオルガニツクケミストリイ（Ｊ、 Ｏｒｇ、
Ｃｈｅｍ、 ） ２８．２９１５（１９６３））、ｎ−
ブチルリチウムを用いる方法（テトラヘドロンレターズ
（Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔ、 ）、 １７９
１（１９７０））、水素化ナトリウムを用いる方法（テ
トラヘドロンレターＸ （Ｔｅｔｒａｈｅｄｒｏｎ Ｌ
ｅｔｔ、 ） ３２１（１９７１） ）等が提案されて
いるが、いずれの場合も触媒がアミンと等モル以上必要
でろム工業的には満足のいく方法ではなかった。Terephthalic acid dianilides are useful substances such as fluidity improvers for thermoplastic resins such as polyphenylene ether resins (for example, see Japanese Patent Application Laid-Open No. 60-44547). React with amine as
In the method for producing the corresponding carboxylic acid amide,
Method using sodium methylate as a catalyst (Journal of Oporganic Chemistry (J, Org,
Chem, ) 28.2915 (1963)), n-
Method using butyllithium (Tetrahedron Lett, ), 179
1 (1970)), a method using sodium hydride (Tetrahedron L
ett, ) 321 (1971)), but in any case, the catalyst was required in an amount equal to or more than the amine, and was not a satisfactory method in the filtration industry.
一方、カルボン酸エステルとアをンの混合物を加熱して
生成するアルコールを留去する方法（オルガニツクシン
セシス（Ｏｒｇ、 ５ｙｎｔｈ、 ） Ｐｉ、 ｇ。On the other hand, there is a method of distilling off the alcohol produced by heating a mixture of a carboxylic acid ester and an atom (organic synthesis (Org, 5ynth, ) Pi, g.
（１９６３））も提案されている。(1963)) have also been proposed.
前記の、カルボン酸エステルとアミンの混合物を加熱し
て生成するアルコールを留去する方法を、テレフタル酸
ジメチルエステルとアニリン類との反応に適用した場合
、アニＩＪンの沸点近傍まで反６混合物を加熱しても、
反応の進行が極めて遅い。When the above-described method of heating a mixture of a carboxylic acid ester and an amine to distill off the alcohol produced is applied to the reaction between dimethyl terephthalate and anilines, the mixture is heated to around the boiling point of aniline. Even if heated,
The reaction progresses extremely slowly.
（比較例参照）従って原料であるテレフタル酸ジメチル
エステルを反応で消失させるには、多大の時間を要し、
実質的に効率よく純度の高いテレフタル酸・２アニリド
を得ることはできない。(See Comparative Example) Therefore, it takes a lot of time to eliminate the raw material dimethyl terephthalate through the reaction.
It is not possible to substantially efficiently obtain highly pure terephthalic acid 2-anilide.
本発明は、テレフタル酸ジアルキルエステルと、アニリ
ン類とを加圧下、２００〜３５０℃で反応させることを
特徴とする上記問題点を解消した、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 is a method for producing terephthalic acid dianilides with high yield and high purity, which solves the above problems and is characterized by reacting a terephthalic acid dialkyl ester and an aniline at 200 to 350°C under pressure. This is what we are trying to provide.
本発明の方法において用いられるテレフタル酸（式中Ｒ
１け、Ｃ１〜４のアルキル基）で表わされる化合物でろ
って、例えば、テレフタル酸ジメチル、テレフタル酸ジ
ノルマルプロピル、テレフタル酸ジインプロピル、テレ
フタル酸ジノルマルブデル等が例示される。Terephthalic acid (in the formula R
Examples of the compounds represented by C1-4 alkyl groups include dimethyl terephthalate, di-n-propyl terephthalate, di-impropyl terephthalate, and di-n-n-budel terephthalate.
本発明の方法において用いられるアニリン類は、一般式
、Ｒζ（シ→伍２ （式中Ｒ２は水素、 Ｃ１〜１５の
アルキル基、アルケニル基、アリール基を示“ｆ、 ）
で表わされる化合物でろって、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
−キクリジン、３，４−キシリジン、４−ｎ−フｆルア
ニリン、４−ｎ−へキシルアニリン、４−ｎ−オフデル
アニリン、４−ｎ−デクルアニリン、４−ｎ−ドデシル
アニリン、２，５−ジーを一ブチルアニリン、２，４．
６− トリーｔ−フ゛チルアニリン等が例示される。The anilines used in the method of the present invention have the general formula:
For example, aniline, 0-
Toluidine, m-toluidine, p-toluidine, 2.4
- cyclizine, 3,4-xylidine, 4-n-fluoraniline, 4-n-hexylaniline, 4-n-ofderaniline, 4-n-decluaniline, 4-n-dodecylaniline, 2,5- G is monobutylaniline, 2,4.
Examples include 6-tri-t-phthylaniline.
原料のテレフタル酸ジアルキルエステルに対するアニリ
ン類の使用モル比はＶ１〜２ｏ／１の範囲が好ましく、
特にＶ１〜１５／１の範囲が好ましい。The molar ratio of the aniline to the raw material dialkyl terephthalate is preferably in the range of V1 to 2o/1,
Particularly preferred is a range of V1 to 15/1.
該モル比が”／１よ抄少なく、アニリン類の鼠が少なく
なると、原料テレフタル酸ジアルキルエステルを消失さ
せることが困難になるばかりでなく、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。また、該モル比が２０／１
を超えてアニリン類の敵が多い場合には、反応混合物量
が多くなり、釜収率低下によし、経済性が悪化するので
工業的実施において不利である。When the molar ratio is less than 1/1 and the amount of anilines is reduced, not only is it difficult to eliminate the raw material dialkyl terephthalate, but as the reaction progresses, the fluidity of the reaction mixture decreases. In addition, when the molar ratio is 20/1, it becomes disadvantageous in industrial implementation.
If the number of anilines exceeds 1, the amount of reaction mixture increases, the pot yield decreases, and economic efficiency deteriorates, which is disadvantageous in industrial implementation.
反応温度は、２００〜３５０℃の範囲であるが、２３０
〜３２０℃の範囲が好ましい。該温度が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ジ
アルキルエステルを消失すせることが困難であ妙、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い。The reaction temperature is in the range of 200 to 350°C, but 230°C
A range of 320°C to 320°C is preferred. If the temperature is below 200° C., the reaction rate is slow and it is difficult to substantially eliminate the raw material dialkyl terephthalate, making it impossible to obtain highly pure terephthalic acid dianilides.
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
しくない。Furthermore, if the temperature is 350° C. or higher, the anilines will undergo significant thermal deterioration, which may cause discoloration of the product, which is not preferable.
反応圧力は、アルコールが副生するので加圧条件下で実
施する。用いるアニリン類の沸点が、所定反応温度以下
の場合は、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、自然発生圧
力下で反応を実施する。The reaction is carried out under pressurized conditions since alcohol is produced as a by-product. If the boiling point of the aniline used is below the predetermined reaction temperature, the reaction mixture may be pressurized using an inert gas or the like to reach the predetermined reaction temperature. If this is the case, the reaction is carried out under autogenous pressure.
反応時間は、反応温度、原料仕込みモル比によ９異なっ
てくるので一律に規定できないが、通常１時間以上実施
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 carry out the reaction for more than 1 hour, but unnecessarily extending the reaction time may cause the thermal This is not desirable because it causes deterioration.
本発明を、具体的に実施する方法としては、テレフタル
酸ジアルキルエステルと、アニリン類とを、所定の温度
、圧力の条件下で反応させる。得られるテレフタル酸ジ
アニリド類は、用いられる ゛アニリン類に対
応した一般式
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、炉別すると、徂テ
レフタル酸ジアニリド類が得られる。As a specific method for implementing the present invention, a terephthalic acid dialkyl ester and an aniline are reacted under conditions of predetermined temperature and pressure. The obtained terephthalic acid dianilides are compounds having the general formula corresponding to the anilines used. After the reaction is completed, the reaction mixture is cooled and the terephthalic dianilides are crystallized and separated from the furnace to obtain the terephthalic dianilides.
このものを、メタノール、エタノール等の脂肪族低級ア
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ｎ
製テレフタル酸ジアニリド類が得られる。By washing this material with aliphatic lower alcohols such as methanol and ethanol, or aromatic hydrocarbons such as toluene, xylene, and ethylbenzene, white
terephthalic acid dianilides are obtained.
反応混合物から目的物を晶出させた後のＦ液には、アニ
リン類、テレフタル酸ジアルキルエステル類、テレフタ
ル酸モノアルキルエステルモノアニリド類を含有してい
るので、これを反応工程に循環し、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 F solution after crystallizing the target product from the reaction mixture contains anilines, terephthalic acid dialkyl esters, and terephthalic acid monoalkyl ester monoanilides, so it is recycled to the reaction process and terephthalate It can be reused as a raw material for acid dianilides.
以下、実施例によし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
テレフタル酸ジメチル１９．４ ｆ （０，１モル）、
アニリン９３．Ｏｆ （１，０モル）を内容Ｎ２５０１
１１のステンレス製オートクレーブに仕込み、Ｎｚガス
にて置換した後、自然発生圧力下、反応混合物の温度が
２８０℃で６時間加熱攪拌した。反応終了後、反応混合
物を４０℃以下に冷却し、結晶を析出させた。この結晶
を濾過し、次いで１００Ｆのトルエンを用いて５０℃で
洗浄した後、戸別し、減圧下にて乾燥させたところ、テ
レフタル醒ジアニリドが２６．６ ｔ （仕込みテレフ
タル酸基準で８４．２％収率）得られた。Example 1 Dimethyl terephthalate 19.4 f (0.1 mol),
Aniline 93. Of (1,0 mol) content N2501
The reaction mixture was placed in a stainless steel autoclave No. 11, and after purging with Nz gas, the reaction mixture was heated and stirred at a temperature of 280° C. for 6 hours under naturally generated pressure. After the reaction was completed, the reaction mixture was cooled to 40° C. or lower to precipitate crystals. The crystals were filtered, washed at 50°C with 100F toluene, and then separated and dried under reduced pressure, resulting in 26.6 tons of terephthalic dianilide (84.2% based on the charged terephthalic acid). yield) was obtained.
実施例２〜１１
表１に示すテレフタル酸ジアルキルエステル及びアニリ
ン類を用いた他は、実施例１と同様の操作を行ない、相
当するテレフタル酸ジア二すド類を得た。結果を表１に
示した。ここで、テレフタル酸ジアニリド収率け、仕込
みテレフタル酸ジアルキルエステルｌ（ｍｏｌ）に対す
る生成テレフタル酸ジアニＩＪド類量（ｍｏｌ）の割合
を％で示したものである。Examples 2 to 11 The same operations as in Example 1 were carried out except that the terephthalic acid dialkyl esters and anilines shown in Table 1 were used to obtain corresponding terephthalic acid dianides. The results are shown in Table 1. Here, based on the yield of terephthalic acid dianilide, the ratio of the amount of produced terephthalic acid dianilide (mol) to the charged terephthalic acid dialkyl ester (mol) is shown in %.
比較例
テレフタル酸ジメチルａ ｓ、ｓ ｙ （０，２モル）
、アニリン１８６．Ｏｆ （２，０モル）を内容１ｔ３
００ｄの三つロフラスコに仕込み、生成するメタノール
を反応系外に留出式せる方法で加熱したところ、内温１
８６℃近傍で、アユ１フンが沸騰し、６時間加熱を続け
ても、メタノールは留出せず、実質的に反応は進行しな
かった。Comparative example dimethyl terephthalate a s, sy (0.2 mol)
, aniline 186. Of (2,0 mol) content 1t3
00d was charged into a three-bottle flask and heated by distilling the generated methanol out of the reaction system, the internal temperature was 1.
The sweetfish boiled at around 86°C, and even after continued heating for 6 hours, methanol could not be distilled out and the reaction did not substantially proceed.
（以下余白）(Margin below)
Claims (1)
圧下、２００〜３５０℃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。A method for producing terephthalic acid dianilides, which comprises reacting a terephthalic acid dialkyl ester and an aniline under pressure at 200 to 350°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8499887A JPH0759542B2 (en) | 1987-04-07 | 1987-04-07 | Method for producing dianilide terephthalic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8499887A JPH0759542B2 (en) | 1987-04-07 | 1987-04-07 | Method for producing dianilide terephthalic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63250354A true JPS63250354A (en) | 1988-10-18 |
| JPH0759542B2 JPH0759542B2 (en) | 1995-06-28 |
Family
ID=13846297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8499887A Expired - Lifetime JPH0759542B2 (en) | 1987-04-07 | 1987-04-07 | Method for producing dianilide terephthalic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0759542B2 (en) |
-
1987
- 1987-04-07 JP JP8499887A patent/JPH0759542B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0759542B2 (en) | 1995-06-28 |
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