JP4277239B2 - Antibacterial composition - Google Patents
Antibacterial composition Download PDFInfo
- Publication number
- JP4277239B2 JP4277239B2 JP12943298A JP12943298A JP4277239B2 JP 4277239 B2 JP4277239 B2 JP 4277239B2 JP 12943298 A JP12943298 A JP 12943298A JP 12943298 A JP12943298 A JP 12943298A JP 4277239 B2 JP4277239 B2 JP 4277239B2
- Authority
- JP
- Japan
- Prior art keywords
- undecylenate
- magnesium
- antibacterial
- liquids
- antibacterial composition
- 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
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 10
- FGTKEJFEOAIYAX-UHFFFAOYSA-L magnesium;undec-10-enoate Chemical compound [Mg+2].[O-]C(=O)CCCCCCCCC=C.[O-]C(=O)CCCCCCCCC=C FGTKEJFEOAIYAX-UHFFFAOYSA-L 0.000 claims description 12
- 239000007788 liquid Substances 0.000 description 11
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 7
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 6
- 229960002703 undecylenic acid Drugs 0.000 description 6
- 229940118257 zinc undecylenate Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 description 3
- 229940118258 calcium undecylenate Drugs 0.000 description 3
- BKACVSPFRDCXGK-JGMJEEPBSA-L copper;(e)-undec-2-enoate Chemical compound [Cu+2].CCCCCCCC\C=C\C([O-])=O.CCCCCCCC\C=C\C([O-])=O BKACVSPFRDCXGK-JGMJEEPBSA-L 0.000 description 3
- 239000002781 deodorant agent Substances 0.000 description 3
- 208000017520 skin disease Diseases 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008278 cosmetic cream Substances 0.000 description 2
- 230000000249 desinfective effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229960002337 magnesium chloride Drugs 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- MMJHZNSTBWIZNS-UHFFFAOYSA-L magnesium;undecanoate Chemical compound [Mg+2].CCCCCCCCCCC([O-])=O.CCCCCCCCCCC([O-])=O MMJHZNSTBWIZNS-UHFFFAOYSA-L 0.000 description 2
- DKYPZNSPQXLRRQ-UHFFFAOYSA-M sodium;undec-10-enoate Chemical compound [Na+].[O-]C(=O)CCCCCCCCC=C DKYPZNSPQXLRRQ-UHFFFAOYSA-M 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 239000000606 toothpaste Substances 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229960003390 magnesium sulfate Drugs 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940098458 powder spray Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011076 safety test Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
【0001】
【発明の属する技術分野】
本発明は抗菌用組成物に関する。具体的には、身近な生活環境におけるカビ・細菌の繁殖抑制・死滅により衛生的環境を保つための抗菌剤、防臭剤、ベビーパウダー、入浴剤、毛髪剤、歯磨きペースト、歯磨き粉、化粧品、洗剤、石鹸などの家庭用品、皮膚病などの治療薬、等に係わるものである。
【0002】
【従来の技術】
抗菌剤・殺菌剤としては、石炭酸、クレゾールや逆性石鹸(4級アンモニウム塩)などが身近である。しかし、石炭酸やクレゾールは皮膚刺激性や特有の悪臭があり更にその有毒性から、直ちに清水でこれらを洗い落とす必要があり、一般に好まれない。また逆性石鹸も皮膚をヌルヌルとさせ不快感がある。近年汗に含まれる成分としてウンデシレン酸が安全性の点で注目され、ウンデシレン酸およびウンデシレン酸亜鉛が化粧品や医薬への使用が国内において既に認められている。更に最近ウンデシレン酸カルシウムのボディパウダーとしての使用(US696,260:CA113 11957v)やウンデシレン酸銅の抗菌軟膏(CA 54 13547i)や水虫薬(特許開81−87521)への使用が報告され、既に米国ではウンデシレン酸カルシウムとウンデシレン酸銅を含む人用抗菌剤としての販売が許可されている(CA119 210348w)。しかしウンデシレン酸マグネシウムについてはこれまで検討された報告はない。
【0003】
【発明が解決しようとする課題】
従来のウンデシレン酸系抗菌成分のうち、ウンデシレン酸は独特の臭気があり用途が制限されている。ウンデシレン酸亜鉛は溶解性に乏しくて配合上の制約があり高価である。ウンデシレン酸銅は鮮やかな緑色のため用途が制限される。またウンデシレン酸カルシウムは溶解性に乏しく配合上の制約がある。
【0004】
【課題を解決するための手段】
本発明者は、ウンデシレン酸化合物の幅広い探索を行い、ウンデシレン酸マグネシウムが、人および環境に安全であり、しかもウンデシレン酸亜鉛より優れる抗菌性と溶解性をもち、また無色であるので幅広い抗菌用組成物の配合成分に利用できることを見いだした。すなわち、本発明は、ウンデシレン酸マグネシウムを必須成分として含有することを特徴とする抗菌用組成物に関する。
【0005】
ウンデシレン酸マグネシウムは、ウンデシレン酸ナトリウムと塩化マグネシウム、硫酸マグネシウム、硝酸マグネシウム、酢酸マグネシウムなどの可溶性マグネシウム塩との反応やウンデシレン酸と水酸化マグネシウムとの反応などにより製造できる。経済性と安全性の観点から、海水の苦り成分である塩化マグネシウムの使用が好ましい。
【0006】
ウンデシレン酸マグネシウムは、エタノール、1,3−ブタンジオールや脂肪酸アミドなどへの溶解性に優れるのでこのような希釈剤により液体、クリーム状の抗菌用組成物に配合できる。また脂肪酸ジエタノールアミドなどに溶解する場合には多量の水での希釈も可能である。このようにした希釈溶液は各種の抗菌液、殺菌液、消毒液、皮膚病治療薬、更には防臭液、化粧液や化粧クリーム等に利用できる。
【0007】
ウンデシレン酸マグネシウムは、通常微細なパウダー状で得ることができるが目的により粒径のより大きな粒にすることも可能である。このような固体状のウンデシレン酸マグネシウムは、ベビーパウダー、パウダースプレーなどにタルク、亜鉛華などと共に配合できる。
【0008】
本発明の組成物の好ましい範囲は、ウンデシレン酸マグネシウムが0.0001〜100重量%であり、更に好ましくは、0.001〜50重量%である。またその他の公知の抗菌成分や溶剤、界面活性剤、色素、香料、増粘剤、安定化剤、保湿剤、皮膚浸透向上剤などの物質も必要に応じて添加できる。
【0009】
【発明の実施の形態】
本発明の実施の形態の例として、各種の抗菌液、殺菌液、消毒液、皮膚病治療薬、防臭液、化粧液や化粧クリーム、ベビーパウダー、パウダースプレーなどが上げられる。
【0010】
【実施例】
参考例1
2Lのセパラブルフラスコにイオン交換水500ml、水酸化ナトリウム40g(1モル)、ウンデシレン酸184g(1モル)を加えウンデシレン酸ナトリウム水溶液とする。攪拌しながらイオン交換水500mlに塩化マグネシウム六水和物102g(0.5モル)を溶解させた水溶液をやく1時間かけて加える。次に濾過、水洗してケーキ状のウンデシレン酸マグネシウムを得る。120°Cの熱風乾燥機で恒量になるまで乾燥しウンデシレン酸マグネシウム214gを得た。 純度98.1%(キレート法)
揮発分1.0%(1g,105°C,1時間)であった。
【0011】
実施例1
ウンデシレン酸マグネシウムの溶解性を調べた結果を表1に示した。
【0012】
比較例1
ウンデシレン酸亜鉛の溶解性を、実施例と同様に試験し表1に示した。
【0013】
【表1】
実施例2
ウンデシレン酸マグネシウムの抗菌性能を試験し表2に示した。
【0014】
比較例2
ウンデシレン酸亜鉛の抗菌性能を試験し表2に示した。
【0015】
【表2】
【0016】
実施例3
ウンデシレン酸マグネシウムの安全性試験を実施した。その結果を表3に示した。
【0017】
【表3】
【0018】
本発明の抗菌用組成物は、上述の通りウンデシレン酸亜鉛よりエタノール、1,3−ブタンジオールへの溶解性に優れる上、白せん菌に対する最小発育阻止濃度(MIC)が低く抗菌性に優れ、さらにカビ・細菌を繁殖抑制し、人体や環境に安全であるので幅広い抗菌剤の商品化が可能となる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an antibacterial composition . Specifically, antibacterial agents, deodorants, baby powders, bathing agents, hair preparations, toothpastes, toothpastes, cosmetics, detergents, to maintain a hygienic environment by inhibiting and killing mold and bacteria in a familiar living environment It relates to household items such as soap, remedies for skin diseases, etc.
[0002]
[Prior art]
As antibacterial agents and bactericides, carboxylic acids, cresols and reverse soaps (quaternary ammonium salts) are familiar. However, carboxylic acid and cresol have skin irritation and peculiar odor, and since they are toxic, it is necessary to immediately wash them off with clean water, which is generally not preferred. Inverse soap also makes the skin slimy and uncomfortable. In recent years, undecylenic acid has attracted attention as a component contained in sweat in terms of safety, and undecylenic acid and zinc undecylenate have already been approved for use in cosmetics and medicine in Japan. Recently, the use of calcium undecylenate as a body powder (US696,260: CA113 11957v) and the use of copper undecylenate in antibacterial ointments (CA54 13547i) and athlete's foot drugs (Patent Opening 81-87521) have already been reported. Is permitted to be sold as a human antibacterial agent containing calcium undecylenate and copper undecylenate (CA119 210348w). However, there has been no report on magnesium undecylate.
[0003]
[Problems to be solved by the invention]
Among conventional undecylenic acid antibacterial components, undecylenic acid has a unique odor and its use is limited. Zinc undecylenate is poor in solubility, is limited in formulation, and is expensive. Copper undecylenate is limited in use because of its bright green color. In addition, calcium undecylenate is poorly soluble and has restrictions in formulation.
[0004]
[Means for Solving the Problems]
The present inventor has conducted a wide search for undecylenic acid compounds, and magnesium undecylenate is safe for humans and the environment, has antibacterial properties and solubility superior to zinc undecylenate, and is colorless, so it has a wide range of antibacterial compositions. It was found that it can be used as a compounding component of products . That is, the present invention relates to an antibacterial composition characterized by containing magnesium undecylenate as an essential component.
[0005]
Magnesium undecylenate can be produced by reacting sodium undecylenate with a soluble magnesium salt such as magnesium chloride, magnesium sulfate, magnesium nitrate, and magnesium acetate, or reacting undecylenic acid with magnesium hydroxide. From the viewpoint of economy and safety, it is preferable to use magnesium chloride which is a bitter component of seawater.
[0006]
Magnesium undecylenate is excellent in solubility in ethanol, 1,3-butanediol, fatty acid amides, and the like, and therefore can be blended into a liquid or cream antibacterial composition using such a diluent. When dissolved in fatty acid diethanolamide or the like, dilution with a large amount of water is also possible. The diluted solution thus prepared can be used for various antibacterial liquids, bactericidal liquids, disinfecting liquids, skin disease therapeutic agents, deodorant liquids, cosmetic liquids, cosmetic creams and the like.
[0007]
Magnesium undecylenate can usually be obtained in the form of a fine powder, but it can also be made larger in size depending on the purpose. Such a solid magnesium undecylate can be blended with baby powder, powder spray, and the like together with talc and zinc white.
[0008]
The preferable range of the composition of the present invention is 0.0001 to 100% by weight of magnesium undecylenate, and more preferably 0.001 to 50% by weight. Other known substances such as antibacterial components, solvents, surfactants, dyes, fragrances, thickeners, stabilizers, moisturizers, skin penetration enhancers, and the like can be added as necessary.
[0009]
DETAILED DESCRIPTION OF THE INVENTION
Examples of embodiments of the present invention include various antibacterial liquids, bactericidal liquids, disinfecting liquids, skin disease therapeutic agents, deodorant liquids, cosmetic liquids and cosmetic creams, baby powders, powder sprays, and the like.
[0010]
【Example】
Reference example 1
To a 2 L separable flask, 500 ml of ion exchange water, 40 g (1 mol) of sodium hydroxide and 184 g (1 mol) of undecylenic acid are added to obtain a sodium undecylenate aqueous solution. While stirring, an aqueous solution in which 102 g (0.5 mol) of magnesium chloride hexahydrate is dissolved in 500 ml of ion-exchanged water is added over 1 hour. Next, it is filtered and washed with water to obtain a cake-like magnesium undecylenate. It dried until it became constant weight with a 120 degreeC hot air dryer, and 214g of magnesium undecylenates were obtained. Purity 98.1% (chelate method)
The volatile content was 1.0% (1 g, 105 ° C., 1 hour).
[0011]
Example 1
The results of examining the solubility of magnesium undecylenate are shown in Table 1.
[0012]
Comparative Example 1
The solubility of zinc undecylenate was tested in the same manner as in the Examples and is shown in Table 1.
[0013]
[Table 1]
Example 2
The antibacterial performance of magnesium undecylenate was tested and is shown in Table 2.
[0014]
Comparative Example 2
The antibacterial performance of zinc undecylenate was tested and is shown in Table 2.
[0015]
[Table 2]
[0016]
Example 3
A safety test of magnesium undecylenate was conducted. The results are shown in Table 3.
[0017]
[Table 3]
[0018]
The antibacterial composition of the present invention is excellent in solubility in ethanol and 1,3-butanediol from zinc undecylenate as described above, and has a low minimum inhibitory concentration (MIC) against fungus and excellent in antibacterial properties. In addition, it suppresses the growth of mold and bacteria, and is safe for the human body and the environment, making it possible to commercialize a wide range of antimicrobial agents.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12943298A JP4277239B2 (en) | 1998-04-03 | 1998-04-03 | Antibacterial composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12943298A JP4277239B2 (en) | 1998-04-03 | 1998-04-03 | Antibacterial composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11292760A JPH11292760A (en) | 1999-10-26 |
| JP4277239B2 true JP4277239B2 (en) | 2009-06-10 |
Family
ID=15009352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12943298A Expired - Fee Related JP4277239B2 (en) | 1998-04-03 | 1998-04-03 | Antibacterial composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4277239B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100362885B1 (en) * | 2000-08-18 | 2003-01-24 | 엔프라니 주식회사 | Antimicrobial makeup compositions containing calcium undecylenate |
-
1998
- 1998-04-03 JP JP12943298A patent/JP4277239B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11292760A (en) | 1999-10-26 |
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