JP2893471B2 - Bath additive - Google Patents
Bath additiveInfo
- Publication number
- JP2893471B2 JP2893471B2 JP21529390A JP21529390A JP2893471B2 JP 2893471 B2 JP2893471 B2 JP 2893471B2 JP 21529390 A JP21529390 A JP 21529390A JP 21529390 A JP21529390 A JP 21529390A JP 2893471 B2 JP2893471 B2 JP 2893471B2
- Authority
- JP
- Japan
- Prior art keywords
- bath
- group
- effect
- methoxy
- reference example
- 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 - Fee Related
Links
Landscapes
- Cosmetics (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、特定のフタリド誘導体を含有し、血行を促
進して温浴効果を高める入浴剤に関する。Description: TECHNICAL FIELD The present invention relates to a bathing agent containing a specific phthalide derivative, which promotes blood circulation and enhances a warm bath effect.
従来より数多くの入浴剤が製造されており、これらの
入浴剤には無機塩類、生薬、油類、酵素、香料、色素等
多くの物質が配合されて使用されている。これらのう
ち、生薬とりわけ薬用植物は、浴湯に加えた場合に優れ
た温まり効果等の浴用効果を有することが古くから知ら
れており、現在も薬用植物を細かく刻んだものを袋詰め
して入浴剤としたものや、抽出物を配合した入浴剤が上
市されている。Conventionally, a large number of bathing agents have been manufactured, and these bathing agents are used by blending many substances such as inorganic salts, crude drugs, oils, enzymes, fragrances, and pigments. Of these, crude drugs, especially medicinal plants, have long been known to have a bathing effect such as an excellent warming effect when added to bath water. Bath salts and extracts containing an extract are commercially available.
また、薬用植物の中でも、セリ科植物の根茎又は根
は、古くより 当帰などの生薬として使用されており、更にこれらの持
つ浴用効果も知られている。In addition, among medicinal plants, rhizomes or roots of Umbelliferae plants are It is used as a crude drug such as Toki, and its bathing effect is also known.
しかしながら、 当帰などのセリ科植物の生薬をそのまま使用して充分な
浴用効果を得ようとする場合には、大量に使用する必要
があるために浴湯の濁りを生じたり、１回の使用量が多
くなって嵩ばって使用に不便であるなどの問題があっ
た。However, When trying to obtain a sufficient bathing effect by using a crude drug of the Umbelliferae plant such as Toki, it is necessary to use a large amount, so that the bath water becomes cloudy and There was a problem that it became bulky and inconvenient to use.
そこで、熱水、水−アルコール等によって抽出した抽
出物を使用する方法も提案されているが、依然として浴
湯の濁りは解消されず、かえって抽出操作によってその
浴用効果が低下したり、経済的に不利であるという欠点
が生じてくる。Therefore, a method of using an extract extracted with hot water, water-alcohol, or the like has been proposed. However, the turbidity of the bath water has not yet been eliminated, and the effect of the bath has been reduced by the extraction operation, or it has been economically required. A disadvantage arises that is disadvantageous.
また、斯かる生薬を含む入浴剤はその強い独特のにお
いのため、万人に好かれるというものではなく、商品学
的に嗜好性にも問題があった。Further, the bath preparation containing such a crude drug has a strong and unique smell, so that it is not liked by everyone, and there is also a problem in commercial taste.
斯かる実情に鑑み、本発明者らは生薬と同等以上の浴
用効果を有し、浴湯の濁り等の問題点のない入浴剤を開
発すべく鋭意研究を行った結果、後記式（Ｉ）で表わさ
れるフタリド誘導体を含有する入浴剤が上記欠点がな
く、優れた血行促進効果を有し、温浴効果が高いことを
見出し本発明を完成した。In view of such circumstances, the present inventors have conducted intensive research to develop a bathing agent having a bathing effect equal to or higher than that of crude drugs and having no problems such as turbidity of bath water. It has been found that a bath preparation containing a phthalide derivative represented by the formula (1) does not have the above-mentioned disadvantages, has an excellent blood circulation promoting effect, and has a high warm bath effect, and has completed the present invention.
すなわち、本発明は次の一般式（Ｉ） 〔式中、R1は水酸基又はメトキシ基を、R2、R3及びR4は
水素原子を、R5はアルキル基を示す〕 で表わされるフタリド誘導体を含有する入浴剤を提供す
るものである。That is, the present invention provides the following general formula (I) [Wherein, R 1 represents a hydroxyl group or a methoxy group, R 2 , R 3 and R 4 represent a hydrogen atom, and R 5 represents an alkyl group.] .
本発明で用いるフタリド誘導体（Ｉ）は前記一般式
（Ｉ）で表わされるものであるが、この式中、R5で表わ
されるアルキル基としては、例えばプロピル基、ブチル
基、ペンチル基、ヘキシル基、ヘプチル基、オクチル
基、イソプロピル基、イソブチル基、イソアミル基等が
挙げられ、アルコキシ基としては例えばイソプロポキシ
基、プロポキシ基、ブトキシ基等が挙げられる。The phthalide derivative (I) used in the present invention is represented by the general formula (I). In the formula, the alkyl group represented by R 5 includes, for example, a propyl group, a butyl group, a pentyl group, a hexyl group , A heptyl group, an octyl group, an isopropyl group, an isobutyl group, an isoamyl group, and the like. Examples of the alkoxy group include an isopropoxy group, a propoxy group, and a butoxy group.
これらのフタリド誘導体（Ｉ）は、天然又は合成され
たものの何れでも良く、例えばセリ科植物からエタノー
ル等の有機溶媒又は熱水により抽出してもよいが、例え
ば次の方法により合成したものを用いることがより好ま
しい。These phthalide derivatives (I) may be either natural or synthetic, and may be extracted from a Umbelliferae plant with an organic solvent such as ethanol or hot water. For example, those synthesized by the following method are used. Is more preferable.
（１） 無水フタル酸誘導体と酸無水物との反応（特開
昭63−83080号） （式中、R1、R2、R3及びR4は前記と同じ意味を有し、R6
はアルキル基を示す） すなわち、無水フタル酸誘導体と種々の酸無水物とを
加熱反応せしめてアルキリデンフタリド誘導体とし、次
いでこれを水素添加することにより、フタリド誘導体
（II）が得られる。(1) Reaction of phthalic anhydride derivative with acid anhydride (JP-A-63-83080) (Wherein, R 1, R 2, R 3 and R 4 are as defined above, R 6
Represents an alkyl group. That is, the phthalic anhydride derivative is reacted with various acid anhydrides to form an alkylidene phthalide derivative, which is then hydrogenated to obtain the phthalide derivative (II).
（２） 安息香酸誘導体のｏ−位アルキル化（J.Org.Ch
em.,49,737（1984），特開昭63−83080号、同63−83081
号） （式中、R2、R3及びR4は前記と同じ意味を有し、R7、R8
はアルキル基を示す） すなわち、安息香酸アミド誘導体に、ブチルリチウム
などの塩基を作用させ、これとアルデヒドを反応させた
後、加水分解することによりフタリド誘導体（III）が
得られる。(2) O-Alkylation of benzoic acid derivatives (J. Org. Ch.
em., 49 , 737 (1984), JP-A-63-83080 and JP-A-63-83081.
issue) (Wherein, R 2 , R 3 and R 4 have the same meaning as described above, and R 7 , R 8
Represents an alkyl group. That is, a phthalamide derivative (III) is obtained by reacting a benzoic acid amide derivative with a base such as butyllithium and reacting it with an aldehyde, followed by hydrolysis.
（式中、R2、R3、R4及びR8は前記と同じ意味を有する） すなわち、４−メトキシフタリド誘導体（III）に、
三臭化ホウ素、三フッ化ホウ素などのルイス酸を作用さ
せることによりフタリド誘導体（IV）が得られる。 (Wherein R 2 , R 3 , R 4 and R 8 have the same meaning as described above). That is, the 4-methoxyphthalide derivative (III)
The phthalide derivative (IV) can be obtained by the action of a Lewis acid such as boron tribromide or boron trifluoride.
（４） フタルアルデヒド酸とアルコールとの反応 （式中、R9はアルキル基を示す） すなわち、フタルアルデヒド酸とアルコールとを加熱
反応させることにより、フタリド誘導体（Ｖ）が得られ
る。(4) Reaction of phthalaldehyde acid with alcohol (Wherein, R 9 represents an alkyl group) That is, a phthalide derivative (V) can be obtained by causing a phthalaldehyde acid and an alcohol to react with heat.
これらのフタリド誘導体（Ｉ）は単独で、又は二種以
上を組み合わせて用いることができ、その浴湯への添加
量は、浴湯中で0.03〜60ppm、特に0.3〜20ppmになるよ
うにするのが好ましい。These phthalide derivatives (I) can be used alone or in combination of two or more kinds. The amount of the phthalide derivative (I) added to the bath water is adjusted to 0.03 to 60 ppm, particularly 0.3 to 20 ppm in the bath water. Is preferred.
0.03ppm未満であると本発明の効果が充分に発揮され
ず、60ppmを超えてもその増加分に見合った効果の向上
は望めない。If the amount is less than 0.03 ppm, the effect of the present invention cannot be sufficiently exhibited, and if the amount exceeds 60 ppm, the effect corresponding to the increase cannot be expected.
尚、本発明の入浴剤の剤型は、液体、粉末、顆粒、結
晶、錠剤等適宜選択することができ、浴用剤として用い
られる各種の成分、例えば塩化ナトリウム、塩化カリウ
ム、塩化アンモニウム、硫酸ナトリウム、硫酸アルミニ
ウム、硫酸鉄、炭酸ナトリウム、炭酸水素ナトリウム、
炭酸カルシウム、炭酸マグネシウム、セスキ炭酸ナトリ
ウム、イオウ、硫化ナトリウム、硫化カリウム、リン酸
ナトリウム、ポリリン酸ナトリウム、チオ硫酸ナトリウ
ム等の無機塩、酵素、エモリエント剤、保湿剤、香料、
色素等も配合することが可能である。The dosage form of the bath preparation of the present invention can be appropriately selected from liquids, powders, granules, crystals, tablets and the like, and various components used as bath preparations, for example, sodium chloride, potassium chloride, ammonium chloride, sodium sulfate , Aluminum sulfate, iron sulfate, sodium carbonate, sodium bicarbonate,
Inorganic salts such as calcium carbonate, magnesium carbonate, sodium sesquicarbonate, sulfur, sodium sulfide, potassium sulfide, sodium phosphate, sodium polyphosphate, sodium thiosulfate, enzymes, emollients, moisturizers, fragrances,
Dyes and the like can also be blended.
本発明の入浴剤は剤型により、常法に従って製造する
ことができる。The bath agent of the present invention can be produced according to a conventional method according to the dosage form.
以下、参考例及び実施例を挙げて本発明を更に詳細に
説明するが、本発明はこれらに限定されるものではな
い。Hereinafter, the present invention will be described in more detail with reference to Reference Examples and Examples, but the present invention is not limited thereto.
参考例１ ４−メトキシ−３−ブチルフタリドの合成： 乾燥テトラヒドロフラン（THF）40ml、ｎ−ブチルリ
チウム/n−ヘキサン14ml（22.0mmol）、テトラメチルエ
チレンジアミン（2.56g,22.0mmol）を混和し、−68℃に
冷却し、N,N−ジエチル−３−メトキシ安息香酸アミド
（4.15g,20.0mmol）/THFを徐々に加え、30分後に、白色
結晶を得た。臭化マグネシウム・エーテル（11.0g,42.6
mmol）を加え反応させた後、１−ペンタナール（3.5g,4
0.0mmol）を−78℃で反応させた。酸加水分解、クロロ
ホルム抽出後、減圧蒸留により、４−メトキシ−３−ブ
チルフタリドを得た。収率22％。Reference Example 1 Synthesis of 4-methoxy-3-butylphthalide: 40 ml of dry tetrahydrofuran (THF), 14 ml (22.0 mmol) of n-butyllithium / n-hexane, and tetramethylethylenediamine (2.56 g, 22.0 mmol) were mixed, and -68 was added. After cooling to ° C., N, N-diethyl-3-methoxybenzoic acid amide (4.15 g, 20.0 mmol) / THF was gradually added, and after 30 minutes, white crystals were obtained. Magnesium bromide ether (11.0 g, 42.6
mmol) and reacted for 1-pentanal (3.5 g, 4 g).
0.0 mmol) was reacted at -78 ° C. After acid hydrolysis and chloroform extraction, 4-methoxy-3-butylphthalide was obtained by distillation under reduced pressure. Yield 22%.
m.p. 44.3−45.3℃1 H−NMR（270MHz,CDCl3,TMS）δ： 0.89（3H,t,J＝6.96Hz）,1.5−1.2（4H,m）,1.8−1.6
（1H,m）,2.35−2.20（1H,m）,5.5（1H,dd,J＝7.69Hz,J
＝2.93Hz）,7.09（1H,t,J＝4.4Hz）,7.5−7.4（2H,m） IR（KBr,cm-1） 3000（ｍ）,2960（ｍ）,2900（ｗ）,1780（ｓ）， 1630（ｍ）,1520（ｍ）,1300（ｓ）,1060（ｓ） 参考例２ ４−メトキシ−３−ヘプチルフタリドの合
成： 窒素ガス雰囲気下、乾燥THF中、ｍ−アニス酸（15.2
g,100mmol）と塩化チオニル（36.3g,305mmol）から、ｍ
−アニシルクロリドを得た。２−アミノ−２−メチル−
１−プロパノール（17.8g,200mmol）と、このｍ−アニ
シルクロリノを反応させ、更に塩化チオニルを作用さ
せ、２−（３−メトキシフェニル）−4,4−ジメチルア
キサゾリン塩酸塩を得た。次にｎ−ブチルリチウム/n−
ヘキサン（1.6N,20.6ml）と反応させ、更に、オクタナ
ール（7.7g,60mmol）を加え、反応後、反応物を6N HCl
中、120℃で処理し、４−メトキシ−３−ヘプチルフタ
リドを得た。収率48％。mp 44.3-45.3 ° C 1 H-NMR (270 MHz, CDCl 3 , TMS) δ: 0.89 (3H, t, J = 6.96 Hz), 1.5-1.2 (4H, m), 1.8-1.6
(1H, m), 2.35-2.20 (1H, m), 5.5 (1H, dd, J = 7.69Hz, J
= 2.93Hz), 7.09 (1H, t, J = 4.4Hz), 7.5-7.4 (2H, m) IR (KBr, cm- 1 ) 3000 (m), 2960 (m), 2900 (w), 1780 ( s), 1630 (m), 1520 (m), 1300 (s), 1060 (s) Reference Example 2 Synthesis of 4-methoxy-3-heptylphthalide: m-anisic acid in dry THF under nitrogen gas atmosphere (15.2
g, 100 mmol) and thionyl chloride (36.3 g, 305 mmol), m
-Anisyl chloride was obtained. 2-amino-2-methyl-
1-Propanol (17.8 g, 200 mmol) was reacted with this m-anisylchlorino, and further reacted with thionyl chloride to obtain 2- (3-methoxyphenyl) -4,4-dimethylaxazoline hydrochloride. Next, n-butyllithium / n-
Reaction with hexane (1.6N, 20.6ml), further addition of octanal (7.7g, 60mmol), and after the reaction, the reaction product was treated with 6N HCl
Treatment at 120 ° C. in the middle gave 4-methoxy-3-heptylphthalide. 48% yield.
m.p. 63.9−64.5℃1 H−NMR（60MHz,CDCl3,TMS）δ： 1.0−0.6（3H,m）,2.3−1.0（12H,m）,3.9（3H,m）,
5.6−5.3（1H,m）,7.1（1H,t,J＝4Hz）,7.5（2H,J＝4H
z） IR（KBr,cm-1） 2950（ｍ）,2900（ｗ）,1780（ｓ）,1640（ｗ）， 1520（ｍ）,1300（ｓ）,1060（ｍ） 参考例３ ４−メトキシ−３−デシルフタリドの合成： 参考例２と同様にして４−メトキシ−３−デシルフタ
リドを得た。収率99.3％。mp 63.9-64.5 ° C 1 H-NMR (60 MHz, CDCl 3 , TMS) δ: 1.0-0.6 (3H, m), 2.3-1.0 (12H, m), 3.9 (3H, m),
5.6−5.3 (1H, m), 7.1 (1H, t, J = 4Hz), 7.5 (2H, J = 4H
z) IR (KBr, cm -1 ) 2950 (m), 2900 (w), 1780 (s), 1640 (w), 1520 (m), 1300 (s), 1060 (m) Reference Example 3 4-methoxy Synthesis of -3-decylphthalide: In the same manner as in Reference Example 2, 4-methoxy-3-decylphthalide was obtained. 99.3% yield.
m.p. 57.8−60.7℃1 H−NMR（27MHz,CDCl3,TMS）δ： 0.88（3H,t,J＝6.2Hz）,1.5−1.1（18H,m）,5.55（1
H,dd,J＝3.1Hz,J＝7.8Hz）,7.00（1H,d,J＝7.7Hz）,7.3
7（1H,t,J＝7.6Hz）,7.47（1H,d,J＝7.1Hz） IR（KBr,cm-1） 2950（ｍ）,2900（ｗ）,1790（ｓ）,1640（ｗ）， 1520（ｍ）,1500（ｓ）,1295（ｓ）,1060（ｍ）， 参考例４ ４−ヒドロキシ−３−ブチルフタリドの合
成： 窒素ガス雰囲気下、参考例１で合成した４−メトキシ
−３−ブチルフタリドと三臭化ホウ素／塩化メチレン
（9ml,1N）を作用させ、４−ヒドロキシ−３−ブチルフ
タリドを得た。収率63％。mp 57.8-60.7 ° C. 1 H-NMR (27 MHz, CDCl 3 , TMS) δ: 0.88 (3H, t, J = 6.2 Hz), 1.5-1.1 (18H, m), 5.55 (1
H, dd, J = 3.1Hz, J = 7.8Hz), 7.00 (1H, d, J = 7.7Hz), 7.3
7 (1H, t, J = 7.6Hz), 7.47 (1H, d, J = 7.1Hz) IR (KBr, cm -1 ) 2950 (m), 2900 (w), 1790 (s), 1640 (w) , 1520 (m), 1500 (s), 1295 (s), 1060 (m), Reference Example 4 Synthesis of 4-hydroxy-3-butylphthalide: 4-methoxy-3 synthesized in Reference Example 1 under a nitrogen gas atmosphere. -Butylphthalide and boron tribromide / methylene chloride (9 ml, 1N) were reacted to obtain 4-hydroxy-3-butylphthalide. 63% yield.
m.p. 162.5−164℃1 H−NMR（60MHz,CDCl3,TMS）δ： 0.9（3H,t,J＝5Hz）,2.3−1.2（6H,m）,2.9（1H,b
s）,5.6（1H,dd,J＝8.4Hz）,7.5−7.1（3H,m） IR（KBr,cm-1） 3240（br）,2980（ｗ）,2880（ｗ）,1730（ｓ）， 1620（ｍ）,1510（ｍ）,1480（ｍ）,1300（ｍ）， 1100（ｗ） 参考例５ ４−ヒドロキシ−３−ヘプチルフタリドの合
成： 参考例２で合成した４−メトキシ−３−ヘプチルフタ
リドと三臭化ホウ素を用い、参考例４と同様にして４−
ヒドロキシ−３−ヘプチルフタリドを得た。収率74％。1 H−NMR（60MHz,CDCl3,TMS）δ： 0.9（3H,t,J＝5Hz）,2.3−1.2（6H,m）,2.8（1H,b
s）,5.6−5.3（1H,m）,7.5−7.0（3H,m） IR（KBr,cm-1） 3250（br）,2980（ｗ）,2850（ｗ）,2900（ｍ）， 1740（ｓ）,1630（ｍ）,1480（ｍ）,1300（ｓ）， 1100（ｍ） 参考例６ ４−ヒドロキシ−３−デシルフタリドの合
成： 参考例３で合成した４−メトキシ−３−デシルフタリ
ドと三臭化ホウ素を用い、参考例４と同様にして４−ヒ
ドロキシ−３−デシルフタリドを得た。収率62％。mp 162.5-164 ° C. 1 H-NMR (60 MHz, CDCl 3 , TMS) δ: 0.9 (3H, t, J = 5 Hz), 2.3-1.2 (6H, m), 2.9 (1H, b
s), 5.6 (1H, dd, J = 8.4Hz), 7.5-7.1 (3H, m) IR (KBr, cm- 1 ) 3240 (br), 2980 (w), 2880 (w), 1730 (s) , 1620 (m), 1510 (m), 1480 (m), 1300 (m), 1100 (w) Reference Example 5 Synthesis of 4-hydroxy-3-heptylphthalide: 4-methoxy-synthesized in Reference Example 2 Using 3-heptylphthalide and boron tribromide, 4-
Hydroxy-3-heptylphthalide was obtained. 74% yield. 1 H-NMR (60 MHz, CDCl 3 , TMS) δ: 0.9 (3H, t, J = 5 Hz), 2.3-1.2 (6H, m), 2.8 (1H, b
s), 5.6-5.3 (1H, m), 7.5-7.0 (3H, m) IR (KBr, cm- 1 ) 3250 (br), 2980 (w), 2850 (w), 2900 (m), 1740 ( s), 1630 (m), 1480 (m), 1300 (s), 1100 (m) Reference Example 6 Synthesis of 4-hydroxy-3-decylphthalide: 4-methoxy-3-decylphthalide synthesized in Reference Example 3 Using boron bromide, 4-hydroxy-3-decylphthalide was obtained in the same manner as in Reference Example 4. Yield 62%.
m.p. 155.6−157.1℃ IR（KBr,cm-1） 3250（br）,2950（ｍ）,2900（ｗ）,1740（ｓ）， 1640（ｍ）,1500（ｍ）,1310（ｍ）,1120（ｍ） 実施例１ 温浴効果の検討： 参考例１で得た４−メトキシ−３−ブチルフタリドを
用い表１に示す組成の入浴剤を調製した。mp 155.6-157.1 ° C IR (KBr, cm -1 ) 3250 (br), 2950 (m), 2900 (w), 1740 (s), 1640 (m), 1500 (m), 1310 (m), 1120 ( m) Example 1 Examination of warm bath effect: The 4-methoxy-3-butylphthalide obtained in Reference Example 1 was used to prepare a bath additive having the composition shown in Table 1.
健康な男子10名を被験者（年齢20〜25才）とし、それ
ぞれの右前腕部を38℃、15のウォーターバス中に浸漬
し、血流が安定した後、本発明品１又は比較品１を溶解
し、20分後の血流量を測定した。測定は同一被験者に対
して連続した２日間、同じ時刻に実施した。血流量はレ
ーザードップラー血流計（PERIMED社製,PERIFULX RF
1）を用いて測定し、血流変化は試料溶解前値を100とし
た場合の相対値の平均で示した。結果を表１に示す。Ten healthy males were set as subjects (age 20 to 25), and their right forearms were immersed in a water bath at 38 ° C and 15 to stabilize blood flow. After lysis, the blood flow after 20 minutes was measured. The measurement was performed on the same subject for two consecutive days at the same time. The blood flow was measured using a laser Doppler blood flow meter (PERIMED, PERIFULX RF
The blood flow change was indicated by the average of relative values when the value before sample dissolution was set to 100. Table 1 shows the results.
表１の結果から明らかな如く、本発明の入浴剤は血流
を増加させる効果が高いことがわかる。 As is clear from the results in Table 1, the bathing agent of the present invention has a high effect of increasing blood flow.
実施例２ 温浴効果の官能評価： 下記表２に示す組成の本発明品２、３及び比較品２を
用い、各々約150の浴湯に溶かした。この浴湯をパネ
ラー30名に10日間ずつ常法に従って使用してもらい、温
まり感、湯冷めの有無及び肌のしっとり感を調べた。こ
の結果を表３に示す。Example 2 Sensory evaluation of warm bath effect: Using products 2 and 3 of the present invention and comparative product 2 having the compositions shown in Table 2 below, each was dissolved in about 150 baths. The bath water was used by 30 panelists for 10 days in accordance with a conventional method, and the feeling of warmth, the presence or absence of hot water cooling, and the moist feeling of the skin were examined. Table 3 shows the results.
この結果、すべての評価項目において、比較品に比べ
て本発明品の方が優れていることがわかる。 As a result, it can be seen that the product of the present invention is superior to the comparative product in all the evaluation items.
また、本発明品２及び３のいずれも浴湯の濁りは生じ
なかった。Neither of the present invention products 2 nor 3 produced turbidity of the bath water.
本発明入浴剤は、浴湯に濁りを生じさせることなく、
温浴効果に優れたものである。The bath agent of the present invention does not cause turbidity in the bath water,
It has excellent warm bath effect.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭63−83080（ＪＰ，Ａ) 特開 平２−167216（ＪＰ，Ａ) (58)調査した分野(Int.Cl.6，ＤＢ名) A61K 7/50 ────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-63-83080 (JP, A) JP-A-2-167216 (JP, A) (58) Fields investigated (Int. Cl. 6 , DB name) A61K 7/50
Claims (1)
水素原子を、R5はアルキル基を示す） で表わされるフタリド誘導体を含有する入浴剤。1. The following general formula (I) (Wherein, R 1 represents a hydroxyl group or a methoxy group, R 2 , R 3 and R 4 represent a hydrogen atom, and R 5 represents an alkyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21529390A JP2893471B2 (en) | 1990-08-15 | 1990-08-15 | Bath additive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21529390A JP2893471B2 (en) | 1990-08-15 | 1990-08-15 | Bath additive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0499714A JPH0499714A (en) | 1992-03-31 |
| JP2893471B2 true JP2893471B2 (en) | 1999-05-24 |
Family
ID=16669924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21529390A Expired - Fee Related JP2893471B2 (en) | 1990-08-15 | 1990-08-15 | Bath additive |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2893471B2 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0798815B2 (en) * | 1986-09-29 | 1995-10-25 | 株式会社ツムラ | Phthalide derivative |
| JPH02167216A (en) * | 1988-09-02 | 1990-06-27 | Kao Corp | Bath additive |
-
1990
- 1990-08-15 JP JP21529390A patent/JP2893471B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0499714A (en) | 1992-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Flynn et al. | Inhibition of human neutrophil 5-lipoxygenase activity by gingerdione, shogaol, capsaicin and related pungent compounds | |
| Khan et al. | Synthesis and antihepatotoxic activity of some new chalcones containing 1, 4-dioxane ring system | |
| WO1997019044A1 (en) | Hydrochalcone derivatives, comestic compositions containing the same, and processes for the preparation of both | |
| CN101511350A (en) | Dioxo-alkanes and dioxo-alkenes | |
| US7705188B2 (en) | Structural modification of resveratrol: sodium resverastatin phosphate | |
| US6777578B2 (en) | Hydroxyphenstatin and the prodrugs thereof | |
| WO2008004788A1 (en) | Novel derivatives of cyclic compound and the use thereof | |
| JPS6027646B2 (en) | cosmetics | |
| EP0163270A2 (en) | A lipoxygenase inhibitor | |
| JP2893471B2 (en) | Bath additive | |
| JPS5951240A (en) | Novel glyceride ester, manufacture and pharmaceutical composition for preventing and treating normal acne | |
| JP2610524B2 (en) | Hair restorer | |
| EP0136195B1 (en) | Microbicidal benzamidine derivatives, their preparation and their use in pharmaceutical compositions as disinfection or preservation agents | |
| JPH0840970A (en) | Method for producing gingerol and shogaol | |
| JPH11209322A (en) | Isovanillyl alcohol derivative | |
| KR101195288B1 (en) | Derivatives of novel bicyclic compound and the use thereof | |
| JPH0469314A (en) | Skin cosmetic | |
| JP2006124358A (en) | 4-alkylresorcinol derivative and bleaching agent containing the same as active ingredient | |
| US20070281991A1 (en) | Preparation Of Phenol-Amide Compounds With Anti-Oxidizing Properties | |
| JP2006124357A (en) | 4-alkylresorcinol derivative and bleaching agent containing the same as active ingredient | |
| JPH09104630A (en) | Agent inhibiting cholesterol acyl transferase activity and composition containing the agent | |
| JP2609145B2 (en) | Aliphatic ketones and aliphatic alcohols | |
| JPH09227400A (en) | Corticosteroid secretion inhibitor | |
| JP3084413B2 (en) | Pyridine derivative and fragrance composition containing the derivative | |
| JPH08188528A (en) | Skin temperature raising agent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Year of fee payment: 9 Free format text: PAYMENT UNTIL: 20080305 |
|
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Year of fee payment: 10 Free format text: PAYMENT UNTIL: 20090305 |
|
| LAPS | Cancellation because of no payment of annual fees |