JPS6355498B2 - - Google Patents
Info
- Publication number
- JPS6355498B2 JPS6355498B2 JP57173966A JP17396682A JPS6355498B2 JP S6355498 B2 JPS6355498 B2 JP S6355498B2 JP 57173966 A JP57173966 A JP 57173966A JP 17396682 A JP17396682 A JP 17396682A JP S6355498 B2 JPS6355498 B2 JP S6355498B2
- Authority
- JP
- Japan
- Prior art keywords
- cis
- butylcyclohexanol
- formula
- isomer
- represented
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 229910017052 cobalt Inorganic materials 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 230000003197 catalytic effect Effects 0.000 claims description 8
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RCHLXMOXBJRGNX-UHFFFAOYSA-N 1-butylcyclohexan-1-ol Chemical compound CCCCC1(O)CCCCC1 RCHLXMOXBJRGNX-UHFFFAOYSA-N 0.000 description 1
- FDZSOJOJVCBNNI-UHFFFAOYSA-N 1-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1(O)CCCCC1 FDZSOJOJVCBNNI-UHFFFAOYSA-N 0.000 description 1
- DLTWBMHADAJAAZ-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCCCC1O DLTWBMHADAJAAZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- RPNNPZHFJPXFQS-UHFFFAOYSA-N methane;rhodium Chemical compound C.[Rh] RPNNPZHFJPXFQS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SBUXRMKDJWEXRL-ZWKOTPCHSA-N trans-body Chemical compound O=C([C@@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ZWKOTPCHSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、香料物質として重要な公知化合物２
―シス―ｔ―ブチルシクロヘキサノールの製法に
関し、従来法に比して顕著に改善された収率をも
つて、トランス―体に比して香気的に遥かに優れ
たシス―体を選択的に生成せしめることのでき
る、オルト―ｔ―ブチルフエノールの接触水素還
元による２―シス―ｔ―ブチルシクロヘキサノー
ルの選択的製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention describes the use of known compounds 2 which are important as fragrance substances.
- Regarding the production method of cis-t-butylcyclohexanol, it has a significantly improved yield compared to the conventional method, and selectively produces the cis-form, which has a much superior aroma compared to the trans-form. The present invention relates to a method for selectively producing 2-cis-t-butylcyclohexanol by catalytic hydrogen reduction of ortho-t-butylphenol.
更に詳しくは、本発明は下記式(2)
で表わされるオルト―ｔ―ブチルフエノールを、
ラネーコバルト触媒の存在下に、接触水素還元す
ることを特徴とする下記式(1)
で表わされる２―シス―ｔ―ブチルシクロヘキサ
ノールの製法に関する。 More specifically, the present invention is based on the following formula (2) Ortho-t-butylphenol represented by
The following formula (1) is characterized by catalytic hydrogen reduction in the presence of a Raney cobalt catalyst. This invention relates to a method for producing 2-cis-t-butylcyclohexanol represented by
上記式(1)で表わされる２―シス―ｔ―ブチルシ
クロヘキサノールは、その異性体である２―トラ
ンス―ｔ―ブチルシクロヘキサノールに較べて香
気的に遥かに優れた香料物質である。又、該式(1)
化合物は例えば２―シス―ｔ―ブチルシクロヘキ
シルアセテートの如き他の香料物質の製造原料と
しても重要な化合物である。 2-cis-t-butylcyclohexanol represented by the above formula (1) is a fragrance substance that has a far superior aroma compared to its isomer, 2-trans-t-butylcyclohexanol. Also, the formula (1)
The compound is also an important compound as a raw material for the production of other fragrance substances such as 2-cis-t-butylcyclohexyl acetate.
従つて、式(2)オルト―ｔ―ブチルフエノールを
接触水素還元して式(1)化合物を製造するに際し、
トランス―体の生成を抑制し、シス―体の生成を
選択的に進行させることができれば、すなわち、
工業的に分離困難なトランス―体の生成を回避
し、香気的に優れたシス―体を選択的に生成させ
ることが可能な方法が開発できれば、工業的に極
めて有利である。 Therefore, when producing the compound of formula (1) by catalytic hydrogen reduction of ortho-t-butylphenol of formula (2),
If it is possible to suppress the production of the trans-isomer and selectively promote the production of the cis-isomer, that is,
It would be extremely advantageous industrially if a method could be developed that could selectively produce the aromatic cis-isomer while avoiding the production of the trans-isomer, which is difficult to separate industrially.
従来、式(2)オルト―ｔ―ブチルフエノールを接
触水素還元して２―ｔ―ブチルシクロヘキサノー
ルを製造することは行われている。そして該接触
水素還元反応に用いる触媒としてラネーニツケル
が専ら利用され、他に、より高価につくがパラジ
ウムカーボン、ロジウムカーボン、白金カーボン
などの貴金属カーボン触媒の使用も知られてい
る。 Conventionally, 2-t-butylcyclohexanol has been produced by subjecting ortho-t-butylphenol of formula (2) to catalytic hydrogen reduction. Raney nickel is exclusively used as a catalyst for the catalytic hydrogen reduction reaction, and it is also known to use noble metal carbon catalysts such as palladium carbon, rhodium carbon, and platinum carbon, although they are more expensive.
しかしながら、上記従来法に於てはシス―体と
トランス―体との生成割合は、シス：トランス＝
50〜80：50〜20程度が普通であつて、最もよくて
もシス―体の選択率は高さ80％前後である。斯く
て、得られる生成物は、実質的に香気に悪影響を
与える量のトランス―体を含有する混合物の形で
しか得られず、このトランス―体は工業的に実施
可能な精製方法では分離できないため、香気的に
満足し得る目的物を製造することは極めて困難で
ある。 However, in the above conventional method, the production ratio of cis-isomer and trans-isomer is cis:trans=
50-80: Usually about 50-20, and at best the selectivity for the cis-isomer is around 80%. The resulting product is thus obtained only in the form of a mixture containing an amount of the trans-isomer that is substantially detrimental to the aroma, and this trans-isomer cannot be separated by industrially viable purification methods. Therefore, it is extremely difficult to produce a target product that is aroma-satisfactory.
本発明者等は、式(2)化合物から式(1)シス―体を
選択的に製造できる方法を開発すべく研究を行つ
てきた。 The present inventors have conducted research to develop a method for selectively producing the cis-isomer of formula (1) from the compound of formula (2).
その結果、従来全く使用されたことがないし、
その使用が示唆されたこともないラネーコバルト
触媒を用いて上記の接触水素還元反応を行うこと
によつて、約98％以上の格段に優れた選択率をも
つて高収率で、実質的に不都合なトランス―体を
含有しない香気的に遥かに優れた２―シス―ｔ―
ブチルシクロヘキサノールが製造できることを発
見した。 As a result, it has never been used before,
By carrying out the above catalytic hydrogen reduction reaction using a Raney cobalt catalyst, the use of which has never been suggested, it is possible to achieve substantial 2-cis-t-, which has a far superior aroma and does not contain the inconvenient trans-body
It was discovered that butylcyclohexanol can be produced.
従つて、本発明の目的は式(1)２―シス―ｔ―ブ
チルシクロヘキサノールを製造する改善方法を提
供するにある。 Therefore, it is an object of the present invention to provide an improved method for producing 2-cis-t-butylcyclohexanol of formula (1).
本発明の上記目的及び更に多くの他の目的なら
びに利点は、以下の記載から一層明らかとなるで
あろう。 The above objects and many other objects and advantages of the present invention will become more apparent from the following description.
本発明方法によれば、上記式(2)で表わされるオ
ルト―ｔ―ブチルフエノールをラネーコバルト触
媒の存在下に、接触水素還元して、98％以上の高
選択率をもつて上記式(1)で表わされる２―シス―
ｔ―ブチルシクロヘキサノールを高収率で容易に
製造することが出来る。 According to the method of the present invention, ortho-t-butylphenol represented by the above formula (2) is subjected to catalytic hydrogen reduction in the presence of a Raney cobalt catalyst to reduce the ortho-t-butylphenol represented by the above formula (2) with a high selectivity of 98% or more. ) represented by 2-cis-
T-butylcyclohexanol can be easily produced in high yield.
本発明方法実施の一態様によれば、例えばオー
トクレーブ中、上記式(2)で表わされるオルト―ｔ
―ブチルフエノールを好ましくは不活性有機溶媒
中、ラネーコバルト触媒の存在下に水素と接触せ
しめて上記式(1)で表わされる２―シス―ｔ―ブチ
ルシクロヘキサノールに容易に変換できる。 According to one embodiment of the method of the present invention, for example, in an autoclave, ortho-t represented by the above formula (2)
-Butylphenol can be easily converted to 2-cis-t-butylcyclohexanol represented by the above formula (1) by contacting it with hydrogen, preferably in an inert organic solvent, in the presence of a Raney cobalt catalyst.
上記反応に於ける水素圧としては、例えば約１
Kg／cm2〜約100Kg／cm2程度の範囲好ましくは約５
Kg／cm2〜約50Kg／cm2程度の範囲が例示でき、又、
反応温度としては、例えば約100℃〜約200℃程度
の範囲好ましくは約120℃〜約180℃程度の範囲の
温度を例示することができる。 The hydrogen pressure in the above reaction is, for example, about 1
Kg/ cm2 to about 100Kg/ cm2 , preferably about 5
Examples include a range of Kg/cm 2 to about 50 Kg/cm 2 , and
The reaction temperature may be, for example, in the range of about 100°C to about 200°C, preferably in the range of about 120°C to about 180°C.
又、不活性有機溶媒を用いて反応を行う場合の
溶媒としては、例えばヘキサン、ベンゼン、トル
エン、メタノール、エタノール、などの如き炭化
水素類、アルコール類などを例示できる。これら
の有機溶媒の使用量には特別な制約はないが、例
えば上記式(2)化合物に対し、約１〜約200重量％
程度の範囲が例示できる。 Further, examples of the solvent when carrying out the reaction using an inert organic solvent include hydrocarbons such as hexane, benzene, toluene, methanol, and ethanol, and alcohols. There are no particular restrictions on the amount of these organic solvents used, but for example, about 1 to about 200% by weight based on the compound of formula (2) above.
Examples include a range of degrees.
又、ラネーコバルト触媒の使用量としては、式
(2)化合物に対し、例えば、約0.01〜約10重量％程
度、好ましくは、約0.5〜約５重量％程度の範囲
が例示できる。又、炭酸水素ナトリウム、炭酸ナ
トリウム等の弱アルカリ性物質を原料に対して、
たとえば約0.1％〜約５重量％程度の量で反応素
に添加して接触還元することもできる。 In addition, the amount of Raney cobalt catalyst used is calculated using the formula
For example, the amount may be about 0.01 to about 10% by weight, preferably about 0.5 to about 5% by weight, based on the compound (2). Also, if weakly alkaline substances such as sodium hydrogen carbonate and sodium carbonate are used as raw materials,
For example, it can be added to the reactant in an amount of about 0.1% to about 5% by weight for catalytic reduction.
反応時間は、理論量の水素を吸収した時点で終
了すれば、水素圧、温度などによつても適宜に選
択されるが、例えば、約１〜約８時間程度の範囲
を好ましく例示することができる。 The reaction time is appropriately selected depending on the hydrogen pressure, temperature, etc., as long as it ends when the theoretical amount of hydrogen is absorbed, but for example, a range of about 1 to about 8 hours is preferably exemplified. can.
反応終了後は、触媒を除去して、例えば減圧蒸
留の如き精製手段により高純度、高収率で上記式
(1)化合物を容易に得ることができる。 After the reaction is complete, the catalyst is removed and the above formula is purified with high purity and high yield using a purification method such as vacuum distillation.
(1) The compound can be easily obtained.
以下実施例により、本発明方法実施の数例につ
いて更に詳細に説明する。 EXAMPLES Below, several examples of implementing the method of the present invention will be explained in more detail with reference to Examples.
実施例 １
0.3オートクレーブに、ｏ―ｔ―ブチルフエ
ノール：50ｇ及びラネーコバルト触媒：1.0ｇを
仕込む。水素圧；50Kg／cm2、温度；150℃の条件
で接触水添反応を行つた。約２時間で理論量の水
素を吸収した。反応容器内より生成物を取り出し
ガスクロマトグラフイーで分析すると98.5％の２
―シス―ｔ―ブチルシクロヘキサノールと1.5％
の２―トランス―ｔ―ブチルシクロヘキサノール
を含有している事が判明した。上記反応物をトル
エンに溶解し、触媒を別した後溶媒を回収し、
２―シス―ｔ―ブチルシクロヘキサノール49ｇ
（収率：94％）を得た。Example 1 A 0.3 autoclave was charged with 50 g of ot-butylphenol and 1.0 g of Raney cobalt catalyst. Catalytic hydrogenation reaction was carried out under the conditions of hydrogen pressure: 50 Kg/cm 2 and temperature: 150°C. The theoretical amount of hydrogen was absorbed in about 2 hours. When the product was taken out from the reaction vessel and analyzed by gas chromatography, it was found to be 98.5% 2.
-cis-t-butylcyclohexanol and 1.5%
It was found that it contained 2-trans-t-butylcyclohexanol. Dissolve the above reactant in toluene, separate the catalyst and recover the solvent,
2-cis-t-butylcyclohexanol 49g
(yield: 94%).
実施例 ２
実施例１のオートクレーブに、ｏ―ｔ―ブチル
フエノール：25ｇ、ｎ―ヘキサン：25ｇ及びラネ
ーコバルト触媒：0.5ｇを仕込む。実施例１と同
様の条件で接触水添を行つた。1.5時間で理論量
の水素を吸収した。触媒を別した後溶媒を回収
し、２―シス―ｔ―ブチルシクロヘキサノール：
24ｇを得た。この方法による２―シス―ｔ―ブチ
ルシクロヘキサノールの純度はガスクロマトグラ
フイー分析により98.7％であつた。Example 2 The autoclave of Example 1 was charged with 25 g of ot-butylphenol, 25 g of n-hexane, and 0.5 g of Raney cobalt catalyst. Catalytic hydrogenation was carried out under the same conditions as in Example 1. The theoretical amount of hydrogen was absorbed in 1.5 hours. After removing the catalyst, the solvent was recovered and 2-cis-t-butylcyclohexanol was added:
Obtained 24g. The purity of 2-cis-t-butylcyclohexanol obtained by this method was 98.7% as determined by gas chromatography analysis.
比較例 １
実施例１に於いて、ラネーコバルト触媒の代り
にラネーニツケル触媒を用いた他は、実施例１と
全く同一方法により実施した。その結果、２―シ
ス―ｔ―ブチルシクロヘキサノールを50ｇ得た。
このものの純度は、ガスクロマトグラフイー分析
により79％であつた。Comparative Example 1 The same method as in Example 1 was carried out except that a Raney nickel catalyst was used instead of the Raney cobalt catalyst. As a result, 50 g of 2-cis-t-butylcyclohexanol was obtained.
The purity of this product was found to be 79% by gas chromatography analysis.
Claims (1)
ラネーコバルト触媒の存在下に、接触水素還元す
ることを特徴とする下記式(1) で表わされる２―シス―ｔ―ブチルシクロヘキサ
ノールの製法。[Claims] 1. The following formula (2) Ortho-t-butylphenol represented by
The following formula (1) is characterized by catalytic hydrogen reduction in the presence of a Raney cobalt catalyst. A method for producing 2-cis-t-butylcyclohexanol represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57173966A JPS5965031A (en) | 1982-10-05 | 1982-10-05 | Preparation of 2-cis-tert-butylcyclohexanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57173966A JPS5965031A (en) | 1982-10-05 | 1982-10-05 | Preparation of 2-cis-tert-butylcyclohexanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5965031A JPS5965031A (en) | 1984-04-13 |
| JPS6355498B2 true JPS6355498B2 (en) | 1988-11-02 |
Family
ID=15970332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57173966A Granted JPS5965031A (en) | 1982-10-05 | 1982-10-05 | Preparation of 2-cis-tert-butylcyclohexanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5965031A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10061540C2 (en) | 2000-12-11 | 2002-11-28 | Haarmann & Reimer Gmbh | Process for the preparation of cis-2-tertiary-butylcyclohexanol by catalytic hydrogenation of 2-tertiary-butylphenol |
| JP4870275B2 (en) * | 2001-04-17 | 2012-02-08 | 花王株式会社 | Fragrance composition |
| JP4707281B2 (en) * | 2001-08-10 | 2011-06-22 | 花王株式会社 | Optically active ester |
-
1982
- 1982-10-05 JP JP57173966A patent/JPS5965031A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5965031A (en) | 1984-04-13 |
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