JPS6044301B2 - Method for producing 4-sulfonaphthalic acid imides - Google Patents
Method for producing 4-sulfonaphthalic acid imidesInfo
- Publication number
- JPS6044301B2 JPS6044301B2 JP14206375A JP14206375A JPS6044301B2 JP S6044301 B2 JPS6044301 B2 JP S6044301B2 JP 14206375 A JP14206375 A JP 14206375A JP 14206375 A JP14206375 A JP 14206375A JP S6044301 B2 JPS6044301 B2 JP S6044301B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- formulas
- represented
- acid
- 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.)
- Expired
Links
- -1 4-sulfonaphthalic acid imides Chemical class 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
- 239000002253 acid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 235000010265 sodium sulphite Nutrition 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- YHJLQHCBUHWBNY-UHFFFAOYSA-N 4-chloro-n-methylnaphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(O)=NC)=CC=C(Cl)C2=C1 YHJLQHCBUHWBNY-UHFFFAOYSA-N 0.000 description 1
- OESMXMMJMGTCAJ-UHFFFAOYSA-N 4-chloronaphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1Cl OESMXMMJMGTCAJ-UHFFFAOYSA-N 0.000 description 1
- HBBNWQNDMASDAC-UHFFFAOYSA-N 4-sulfonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(S(O)(=O)=O)C2=C1 HBBNWQNDMASDAC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は４−スルホナフタル酸イミド類の製造法に関す
るものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 4-sulfonaphthalic acid imides.
更に詳しくは、本発明は染料、顔料等の中間体として有
用な一般式〔Ｉ〕／Ｎ＼、
ｄ中
７（式中、Ｒは水素原子、置換または非置換のアルキル
基、シクロアルキル基、アラルキル基またはアリール基
等を示し、Ｍはアルカリ金属を示す。More specifically, the present invention provides general formula [I]/N\, 7 in d (wherein R is a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, It represents an aralkyl group or an aryl group, and M represents an alkali metal.
）で表わされる４−スルホナフタル酸イミド類を工業的
有利に製造することを目的とするものてある。しかして
、この目的は本発明の方法に従つて一般式〔旧（式中、
Ｒは前示一般式〔１〕におけると同一の意義を有し、Ｘ
はハロゲン原子を示す。) The object of this invention is to produce 4-sulfonaphthalic acid imides represented by the following in an industrially advantageous manner. This objective can thus be achieved according to the method of the invention by using the general formula [formula
R has the same meaning as in the general formula [1] shown above, and
indicates a halogen atom.
）で表わされる４−ハロゲノナフタル酸イミド類を一般
式〔■〕（式中、Ｍはアルカリ金属を示す。) 4-halogenonaphthalic acid imides represented by the general formula [■] (where M represents an alkali metal).
）で表わされる亜硫酸塩と反応させることによつて達成
される。本発明を更に詳細に説明するに本発明方法の一
方の原料てある前示一般式〔■〕て表わされる４−ハロ
ゲノナフタル酸イミド類の置換基Ｒとしては、水素原子
、メチル基、エチル基、直鎖状ないしは分枝状のプロピ
ル基、ブチル基、ペンチル基、ヘキシル基のようなアル
キル基；置換アルキル基例えばヒドロキシエチル基のよ
うなヒドロキシアルキル基、３−メトキシプロピル基の
ようなアルコキシアルキル基、シアノエチル基のような
シアノアルキル基、エトキシカルボニルメチル基のよう
なアルコキシカルボニルアルキル基、ベンゾイルオキシ
エチル基のようなアシルオキシアルキル基、２−アミノ
エチル基のようなアミノアルキル基、Ｎ−Ｎ−ジメチル
アミノエチル基のよう．なジアルキルアミノアルキル基
、Ｎ−エチルアミノエチル基のようなアルキルアミノア
ルキル基、カルボキシエチル基のようなりルボキシアル
キル基、メトキシメトキシプロピル基のようなアルコキ
シアルコキシアルキル基、２−クロロエチル基一のよう
なハロゲノアルキル基、モルホリノメチル基のようなヘ
テロ環系置換アルキル基など；シクロヘキシル基のよう
なシクロアルキル基；ベンジル基、フェネチル基等のよ
うなアラルキル基；フェニル基、クロロフェニル基、ト
リル基、メトキシフェニル基、ニトロフェニル基、メチ
ルアミノフェニル基等のようなアリール基等があげられ
る。また、Ｘで表わされるハロゲン原子としては塩素原
子、臭素原子等が挙げられる。また、他方の原料である
前示一般式〔■〕で表わされる亜硫酸塩としては亜硫酸
ナトリウム、亜硫酸カリウム等が挙げられる。) is achieved by reacting with a sulfite represented by: To explain the present invention in more detail, the substituent R of the 4-halogenonaphthalic acid imide represented by the general formula [■], which is one of the raw materials for the method of the present invention, is a hydrogen atom, a methyl group, an ethyl linear or branched alkyl groups such as propyl, butyl, pentyl, hexyl; substituted alkyl groups such as hydroxyalkyl such as hydroxyethyl, alkoxy such as 3-methoxypropyl; Alkyl group, cyanoalkyl group such as cyanoethyl group, alkoxycarbonylalkyl group such as ethoxycarbonylmethyl group, acyloxyalkyl group such as benzoyloxyethyl group, aminoalkyl group such as 2-aminoethyl group, N-N -Like dimethylaminoethyl group. dialkylaminoalkyl group such as N-ethylaminoethyl group, ruboxyalkyl group such as carboxyethyl group, alkoxyalkoxyalkyl group such as methoxymethoxypropyl group, 2-chloroethyl group, etc. heterocyclic substituted alkyl groups such as halogenoalkyl groups and morpholinomethyl groups; cycloalkyl groups such as cyclohexyl groups; aralkyl groups such as benzyl groups and phenethyl groups; phenyl groups, chlorophenyl groups, tolyl groups, and methoxy Examples include aryl groups such as phenyl, nitrophenyl, methylaminophenyl, and the like. Further, examples of the halogen atom represented by X include a chlorine atom and a bromine atom. The other raw material, the sulfite represented by the general formula [■], includes sodium sulfite, potassium sulfite, and the like.
本発明方法において、スルホン化反応は一般に゛行なわ
れている方法が適用される。In the method of the present invention, a commonly used method for the sulfonation reaction is applied.
すなわち、前示一般式〔■〕で表わされる４−ハロゲノ
ナフタル酸イミド類を前示一般式〔■〕で表わされる亜
硫酸塩と水中で常圧ないしは加圧下で８０〜２５０℃に
加熱すればよい。亜硫酸塩の使用量は理論量以上ならば
特に限定されないが、通常理論量の２〜５倍で充分であ
る。反応時間は反応温度、亜硫酸塩の使用量に依存する
が３〜２Ｃ＠間である。反応後、反応生成物を取り出す
には、析出結晶をそのまま淵取するか、あるいは溶解し
ている場合には食塩、または塩酸のような鉱酸で塩析ま
たは酸析後、析出物を沖取すればよい。前示一般式〔１
〕で表わされる化合物が極めて収率よく高純度で得られ
るが、所望によつては再結晶その他精製処理によつて更
に純度を高めることができる。本発明方法によつて得ら
れた４−スルホナフタル酸イミド類は種々の螢光増白剤
、染料、顔料、医薬品等の中間体として極めて価値ある
化合物である。例えば、カセイアルカリ水溶液と反応し
て下記構造式〔■〕（式中、Ｒは前示一般式〔１〕にお
ける同一の意義を有する。That is, if 4-halogenonaphthalic acid imide represented by the above general formula [■] is heated to 80 to 250°C under normal pressure or pressurization in water with a sulfite represented by the above general formula [■], good. The amount of sulfite used is not particularly limited as long as it is at least the theoretical amount, but 2 to 5 times the theoretical amount is usually sufficient. The reaction time depends on the reaction temperature and the amount of sulfite used, but is between 3 and 2C@. After the reaction, to remove the reaction product, the precipitated crystals can be distilled off as is, or if they are dissolved, salting out or acid precipitation with common salt or a mineral acid such as hydrochloric acid can be used to remove the precipitated product. do it. General formula [1]
The compound represented by the following formula can be obtained in extremely good yield and with high purity, but if desired, the purity can be further increased by recrystallization or other purification treatment. The 4-sulfonaphthalic acid imides obtained by the method of the present invention are extremely valuable compounds as intermediates for various fluorescent brighteners, dyes, pigments, pharmaceuticals, and the like. For example, by reacting with a caustic aqueous solution, the following structural formula [■] (wherein R has the same meaning as in the above general formula [1]) is obtained.
）で表わされる４−ヒドロキシナフタル酸イミド類を製
造することができ、更に本化合物〔■〕をカップリング
成分として用いた下記構造式〔■〕（式中、Ｒは前示一
般式〔１〕におけると同一の意義を有し、Ｄはジアゾ成
分の残基を示す。) 4-hydroxynaphthalic acid imides represented by the following structural formula [■] (wherein R is the general formula [1]) using the present compound [■] as a coupling component. ], and D represents a residue of a diazo component.
）で表わされる化合物は、優れた堅牢性を有する鮮明な
赤色系の色素である。次に本発明を実施例によつて更に
具体的に説明する。) is a bright red pigment with excellent fastness. Next, the present invention will be explained in more detail with reference to Examples.
実施例１
４−クロロナフタル酸メチルイミド２４．６ダと亜硫酸
ナトリウム２５．２ｙを水２００ｍ１中で１０時間加熱
還流した。Example 1 24.6 da of 4-chloronaphthalic acid methylimide and 25.2 y of sodium sulfite were heated under reflux for 10 hours in 200 ml of water.
室温に冷却し、析出結晶を沖取し、飽和食塩水て洗浄後
乾燥して下記構造式で表わされる４−スルホナフタル酸
メチルイミドのナトリウム塩２９．８ｇを得た。After cooling to room temperature, the precipitated crystals were collected, washed with saturated brine, and dried to obtain 29.8 g of sodium salt of 4-sulfonaphthalic acid methylimide represented by the following structural formula.
本品の融点は３５０℃以上であり、また元素分析の結果
は次のとおりで計算値とよく合致した。（計算値はＣｌ
３Ｈ８ＮＯ５ＳＮａの値を示す。The melting point of this product was 350°C or higher, and the results of elemental analysis were as follows, which agreed well with the calculated values. (The calculated value is Cl
The value of 3H8NO5SNa is shown.
）実施例２４−クロロフタル酸メチルイミドの代りに４
ープロモナフタル酸メチルイミド２９．０Ｖを用いた以
外は実施例１と同様の操作を行ない４−スルホナ，フタ
ル酸メチルイミドのナトリウム塩２９．６ｙを得た。) Example 24 instead of 4-chlorophthalic acid methylimide
-Promonaphthalic acid methylimide The same operation as in Example 1 was carried out except that 29.0V of 4-sulfonaphthalic acid methylimide was used to obtain 29.6y of the sodium salt of 4-sulfonaphthalic acid methylimide.
実施例３
４−クロロナフタル酸−３″−メトキシプロピルイミド
３０．４ｇと亜硫酸ナトリウム２５．２ｙを水１５０ｍ
１中で１時間加熱還流した。Example 3 30.4 g of 4-chloronaphthalic acid-3″-methoxypropylimide and 25.2 y of sodium sulfite were added to 150 m of water.
The mixture was heated under reflux for 1 hour in 1 hour.
室温に冷却し、析出結晶を淵取し、飽和食塩水で洗浄後
乾燥して下記構造式で表わされる４−スルホナフタル酸
−３″−メトキシプロピルイミドのナトリウム塩３５．
３１を得た。Cool to room temperature, filter out the precipitated crystals, wash with saturated saline and dry to obtain sodium salt of 4-sulfonaphthalic acid-3''-methoxypropylimide represented by the following structural formula 35.
I got 31.
本品の融点は３５０℃以上であり、また元素分析の結果
は次のとおり計算値とよく倉整５グ，（計算値はＣｌ６
Ｈｌ４ＮＯ６ＳＮａの値を示す。The melting point of this product is 350℃ or higher, and the results of elemental analysis are as follows:
The value of Hl4NO6SNa is shown.
）実施例４４−クロロナフタル酸フェニルイミド３０．
８ｇ、亜硫酸ナトリウム１８．９ｙと水１５０ｍ１をオ
ートクレーブ中にて１５０℃で８時間攪拌した。) Example 4-Chloronaphthalic acid phenyl imide 30.
8 g of sodium sulfite, 18.9 y of sodium sulfite, and 150 ml of water were stirred at 150° C. for 8 hours in an autoclave.
室温に冷却し、析出結晶を泊取し、飽和食塩水で洗浄後
乾燥して下記構造式で表わされる４−スルホナフタル酸
フェニルイミドのナトリウム塩３５．１ｑを得た。After cooling to room temperature, the precipitated crystals were collected, washed with saturated brine, and dried to obtain 35.1q of sodium salt of 4-sulfonaphthalic acid phenyl imide represented by the following structural formula.
Claims (1)
・・・〔II〕（式中、Ｒは水素原子、置換または非置換
のアルキル基、シクロアルキル基、アラルキル基または
アリール基等を示し、Ｘはハロゲン原子を示す。 ）で表わされる４−ハロゲノナフタル酸イミド類を一般
式〔III〕Ｍ＿２ＳＯ＿３・・・・・・〔III〕 （式中、Ｍはアルカリ金属を示す。 ）で表わされる亜硫酸塩と水中で反応させることを特徴
とする一般式〔 I 〕▲数式、化学式、表等があります
▼・・・・・・・・・〔 I 〕（式中、ＲおよびＭは前
示一般式〔II〕および〔III〕におけると同一の意義を
有する。 ）で表わされる４−スルホナフタル酸イミド類の製造法
。[Claims] 1. General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
... [II] (wherein R represents a hydrogen atom, a substituted or unsubstituted alkyl group, cycloalkyl group, aralkyl group, or aryl group, etc., and X represents a halogen atom) 4-halogeno A general formula characterized by reacting naphthalic acid imides with a sulfite represented by the general formula [III] M_2SO_3...[III] (in the formula, M represents an alkali metal) in water. [I]▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・[I] (In the formulas, R and M have the same meanings as in the general formulas [II] and [III] above. A method for producing a 4-sulfonaphthalic acid imide represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14206375A JPS6044301B2 (en) | 1975-11-28 | 1975-11-28 | Method for producing 4-sulfonaphthalic acid imides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14206375A JPS6044301B2 (en) | 1975-11-28 | 1975-11-28 | Method for producing 4-sulfonaphthalic acid imides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5268185A JPS5268185A (en) | 1977-06-06 |
| JPS6044301B2 true JPS6044301B2 (en) | 1985-10-02 |
Family
ID=15306556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14206375A Expired JPS6044301B2 (en) | 1975-11-28 | 1975-11-28 | Method for producing 4-sulfonaphthalic acid imides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6044301B2 (en) |
-
1975
- 1975-11-28 JP JP14206375A patent/JPS6044301B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5268185A (en) | 1977-06-06 |
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