JP6813544B2 - Antibacterial complex and its manufacturing method - Google Patents
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- 230000000844 anti-bacterial effect Effects 0.000 title claims description 200
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- 239000000126 substance Substances 0.000 claims description 103
- 239000000412 dendrimer Substances 0.000 claims description 81
- 229920000736 dendritic polymer Polymers 0.000 claims description 81
- 239000004094 surface-active agent Substances 0.000 claims description 58
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 39
- 239000004530 micro-emulsion Substances 0.000 claims description 34
- 239000005639 Lauric acid Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 238000000593 microemulsion method Methods 0.000 claims description 15
- -1 3-dimethylaminopropyl Chemical group 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 13
- 238000000576 coating method Methods 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 5
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
- 238000001223 reverse osmosis Methods 0.000 claims description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 2
- 238000012412 chemical coupling Methods 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000004033 plastic Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002131 composite material Substances 0.000 description 12
- 230000002209 hydrophobic effect Effects 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
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- 229930182470 glycoside Natural products 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000004064 cosurfactant Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000002059 diagnostic imaging Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
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- 230000002708 enhancing effect Effects 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
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- 230000000877 morphologic effect Effects 0.000 description 1
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- 125000003729 nucleotide group Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000006320 pegylation Effects 0.000 description 1
- 210000002706 plastid Anatomy 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000012384 transportation and delivery Methods 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
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Description
本発明は、抗菌性複合体及びその製造方法に関し、特に、本発明の抗菌性複合体は、抗菌性物質をマイクロエマルション（ｍｉｃｒｏｅｍｕｌｓｉｏｎ）方式で被覆してデンドリマー（ｄｅｎｄｒｉｍｅｒｓ）に配置してなるものであり、この抗菌性複合体を一般に使用されているプラスチック基材に適用することで、プラスチック基材の抗菌効果を増大させることができる。 The present invention relates to an antibacterial complex and a method for producing the same. In particular, the antibacterial complex of the present invention is formed by coating an antibacterial substance with a microemulsion method and arranging the antibacterial substance in dendrimers. Yes, by applying this antibacterial composite to a commonly used plastic substrate, the antibacterial effect of the plastic substrate can be increased.
デンドリマー（ｄｅｎｄｒｉｍｅｒｓ）は、高度に分岐したポリマーであり、内部にキャビティを有するほか、表面上に改質のための多数の官能基を有する。ＰＥＧ化、アセチル化、グリコシル化及びアミノ酸等の官能基化による表面改質により、表面上のカチオン電荷を中和し、そのデンドリマーの生体適合性及び生体分解性を改善する。構造上には、キャビティ内は、疎水性又は非極性を有し、キャビティ外は、親水性を有し、界面活性剤の特性と同じように水及び油物質に対して乳化作用を有する。また、その最大の特徴は、同時に表面の特別な官能基と内部細孔を同時に利用することにより、抗菌性物質、色素体ＤＮＡ、ヌクレオチドや抗体等の異なる種類の物質を配置して安定した複合体を形成することである。したがって、デンドリマーは、物質送達、遺伝子治療、診断イメージングや難溶性薬物の溶解度の増加等、様々な用途に適用可能である。 Dendrimers are highly branched polymers that have cavities inside and a number of functional groups on the surface for modification. Surface modification by PEGylation, acetylation, glycosylation and functionalization of amino acids and the like neutralizes cation charges on the surface and improves the biocompatibility and biodegradability of the dendrimer. Structurally, the inside of the cavity is hydrophobic or non-polar, and the outside of the cavity is hydrophilic and has an emulsifying action on water and oil substances as well as the characteristics of surfactants. In addition, its greatest feature is that by simultaneously utilizing special functional groups on the surface and internal pores, different types of substances such as antibacterial substances, plastid DNA, nucleotides and antibodies are arranged and stably complexed. It is to form the body. Therefore, dendrimers can be applied in various applications such as substance delivery, gene therapy, diagnostic imaging and increased solubility of poorly soluble drugs.
マイクロエマルション（ｍｉｃｒｏｅｍｕｌｓｉｏｎ）は、油相、水相、補助界面活性剤及び界面活性剤の混合物からなる３元系耐温性等方性液体である。通常、外観は半透明〜透明であり、一般的なエマルジョンに使用される高剪断を必要とすることなく、容易に攪拌し調製可能である。水相は、１つ以上の塩及び／又は他の可溶性水成分を含有してもよく、油相は、実際に単一の油やオレフィン等の水不溶性物質、又は複雑な水不溶性混合物であってもよい。ここで、２つの不混和性相（水及び油）が界面活性剤と共に存在し、界面活性剤分子は、油と水との間の界面で単層を形成することができる。界面活性剤分子の疎水性尾部が油相に、親水性頭部基が水相に溶解する。最大の特徴は、水不溶性抗菌性物質を可溶化して安定化させ、抗菌力を高めることである。安価で、高エネルギー消費機器を必要とせず、化粧品や医薬品等の産業で適用される。 A microemulsion is a ternary temperature-resistant isotropic liquid composed of a mixture of an oil phase, an aqueous phase, an auxiliary surfactant and a surfactant. Generally, the appearance is translucent to transparent and can be easily stirred and prepared without the high shear required for common emulsions. The aqueous phase may contain one or more salts and / or other soluble water components, and the oil phase is actually a single water-insoluble substance such as an oil or olefin, or a complex water-insoluble mixture. You may. Here, two immiscible phases (water and oil) are present with the surfactant, and the surfactant molecule can form a monolayer at the interface between the oil and water. The hydrophobic tail of the surfactant molecule dissolves in the oil phase and the hydrophilic head group dissolves in the aqueous phase. The greatest feature is that it solubilizes and stabilizes water-insoluble antibacterial substances and enhances antibacterial activity. It is inexpensive, does not require high energy consumption equipment, and is applied in industries such as cosmetics and pharmaceuticals.
抗菌性物質は、その機能を発揮するために細菌体と接触する必要があるが、抗菌性複合体をプラスチック基材と混合すると、抗菌性複合体中の抗菌性物質の放出が遮蔽される恐れがある。そのため、抗菌作用の有効性を効果的に高めるために、この抗菌性複合体の濃度を増加させなければならない。 Antibacterial substances need to come into contact with bacteria in order to perform their function, but mixing the antibacterial complex with a plastic substrate may block the release of antibacterial substances in the antibacterial complex. There is. Therefore, the concentration of this antibacterial complex must be increased in order to effectively enhance the effectiveness of the antibacterial action.
本発明は、上記課題に鑑みてなされたものであり、一つの目的は、有害な細菌を抑制するのに用いられ、抗菌性物質を徐々に放出することができ、わずかな濃度で細菌の増殖抑制効果の優れた抗菌性複合体を提供することである。 The present invention has been made in view of the above problems, and one object of the present invention is to suppress harmful bacteria, to gradually release antibacterial substances, and to grow bacteria at a small concentration. The purpose is to provide an antibacterial complex having an excellent inhibitory effect.
本発明の他の目的は、有害な細菌を抑制するのに用いられ、抗菌性物質を徐々に放出することができ、わずかな濃度で細菌の増殖抑制効果の優れた抗菌性複合体の製造方法を提供することである。 Another object of the present invention is a method for producing an antibacterial complex which is used for suppressing harmful bacteria, can gradually release an antibacterial substance, and has an excellent effect of suppressing bacterial growth at a small concentration. Is to provide.
本発明の別の目的は、抗菌性複合体とプラスチック基材との間の親水性及び疎水性の相違により、抗菌性複合体がプラスチック基材の表面に滞在することで、プラスチック基材の表面の抗菌性複合体の濃度が増加して抗菌効果を高めることが可能な他の抗菌性複合体の製造方法を提供することである。 Another object of the present invention is that the difference in hydrophilicity and hydrophobicity between the antibacterial composite and the plastic base material causes the antibacterial composite to stay on the surface of the plastic base material, thereby causing the surface of the plastic base material to stay. It is an object of the present invention to provide a method for producing another antibacterial complex capable of increasing the concentration of the antibacterial complex in the above and enhancing the antibacterial effect.
本発明者は、上記課題を解決するために鋭意検討した結果、抗菌及び防カビ製品として抗菌性物質をマイクロエマルション方式で被覆してデンドリマーに配置してなるものを見出し、産業発展の促進と生活の質の向上のために、この抗菌性複合体をプラスチック基材に添加する可能性を研究し、本発明を完成するに至った。 As a result of diligent studies to solve the above problems, the present inventor has found an antibacterial and antifungal product coated with an antibacterial substance by a microemulsion method and placed on a dendrimer to promote industrial development and livelihood. We have studied the possibility of adding this antibacterial composite to a plastic substrate in order to improve the quality of the product, and have completed the present invention.
上記目的を達成するために、本発明に係る抗菌性複合体は、抗菌性物質をマイクロエマルション方式で被覆してなる抗菌性物質含有マイクロエマルションが配置技術によりデンドリマーに配置されてなり、デンドリマーと抗菌性物質含有マイクロエマルションの重量比は、１：１〜１０：１であり、配置技術は、抗菌性物質含有マイクロエマルションをデンドリマーに化学結合させるための化学結合技術、又は抗菌性物質含有マイクロエマルションをデンドリマーに包埋させるための包埋技術である。 In order to achieve the above object, in the antibacterial composite according to the present invention, an antibacterial substance-containing microemulsion formed by coating an antibacterial substance by a microemulsion method is arranged on a dendrimer by an arrangement technique, and the dendrimer and antibacterial are obtained. the weight ratio of the sex substance-containing microemulsion, 1: 1 to 10: 1, arrangement technique, because of the chemical coupling techniques are chemically bound antimicrobial agent containing microemulsion dendrimer, or antibacterial substance-containing microemulsion It is an embedding technique for embedding a dendrimer.
上記他の目的を達成するために、本発明に係る抗菌性複合体の製造方法は、界面活性剤と抗菌性物質とを１：１〜１０：１の重量比で溶解させて抗菌性物質含有界面活性剤を調製する工程と、補助界面活性剤と、水と、抗菌性物質含有界面活性剤とを１：１０：０．１〜２：１０：０．５の重量比で混合し、１〜２時間攪拌して抗菌性物質含有マイクロエマルションを調製する工程と、抗菌性物質含有マイクロエマルションを配置技術によりデンドリマーに配置して抗菌性複合体を調製する工程とを含む。 In order to achieve the above other object, the method for producing an antibacterial complex according to the present invention contains an antibacterial substance by dissolving a surfactant and an antibacterial substance in a weight ratio of 1: 1 to 10: 1. The step of preparing the surfactant, the auxiliary surfactant, water, and the antibacterial substance-containing surfactant are mixed at a weight ratio of 1:10: 0.1 to 2: 10: 0.5 and 1 It includes a step of preparing an antibacterial substance-containing microemulsion by stirring for about 2 hours and a step of arranging the antibacterial substance-containing microemulsion on a dendrimer by an arrangement technique to prepare an antibacterial complex.
上記別の目的を達成するために、本発明に係る抗菌性複合体の製造方法は、ラウリン酸とデンドリマーとを１０：１〜１：１０の重量比で、逆浸透水中に温度５０〜７０℃で加熱して均一に攪拌し、架橋剤を添加して室温で５時間反応させて、ラウリン酸をデンドリマーの表面に充分に化学結合させる工程と、シクロヘキサンで３〜５回繰り返し洗浄し、減圧下に濃縮してラウリン酸に化学結合されたデンドリマーを得る工程と、ラウリン酸に化学結合されたデンドリマーと抗菌性物質と界面活性剤と補助界面活性剤とを１：０．１：２：１〜１：０．５：３：２の重量比で混合して抗菌性複合体を得る工程とを含む。 In order to achieve the above-mentioned other object, the method for producing an antibacterial complex according to the present invention is to mix lauric acid and a dendrimer in a weight ratio of 10: 1 to 1:10 in back-permeated water at a temperature of 50 to 70 ° C. in heated uniformly stirring and reacted for 5 hours at room temperature with the addition of cross-linking agent, a step of Ru laurate is sufficiently chemically bonded to the surface of the dendrimer, repeatedly washed 3-5 times with cyclohexane, vacuum obtaining a dendrimer which is chemically bonded to the lauric acid was concentrated under a chemically bonded to the lauric acid and dendrimer with antibacterial substance and surfactant and cosurfactant 1: 0.1: 2: 1 Includes a step of mixing at a weight ratio of ~ 1: 0.5: 3: 2 to obtain an antibacterial complex.
本発明の利点は次の通りである。
１．本発明は、抗菌性物質をマイクロエマルション方式で被覆してデンドリマーに配置してなる最終的な抗菌性複合体と、プラスチック基材との間の親水性及び疎水性の相違により、抗菌性複合体がプラスチック基材の表面に滞在することで、プラスチック基材の表面の抗菌性複合体の濃度が増加して抗菌効果を高めることができる。
２．本発明は、抗菌性物質をマイクロエマルション方式で被覆してデンドリマーに配置してなる抗菌性複合体をプラスチック基材と混合することにより、抗菌性複合体中の抗菌性物質の放出を遮蔽せずに、抗菌性物質を徐々に放出することができ、わずかな濃度で細菌の増殖抑制効果を達成することができる。
３．本発明は、抗菌性物質をマイクロエマルション方式で被覆することにより、水不溶性抗菌性物質を可溶化して安定化させ、抗菌力を高めることができる。
４．本発明は、抗菌性物質をマイクロエマルション方式で被覆する技術が簡単で製造が容易かつ安価であるため、高エネルギー消費機器が必要なく、化粧品や医薬品等の産業に適用可能である。
The advantages of the present invention are as follows.
1. 1. The present invention is based on the difference in hydrophilicity and hydrophobicity between the final antibacterial composite obtained by coating an antibacterial substance with a microemulsion method and arranging it on a dendrimer, and the plastic substrate. By staying on the surface of the plastic base material, the concentration of the antibacterial complex on the surface of the plastic base material can be increased to enhance the antibacterial effect.
2. 2. The present invention does not block the release of the antibacterial substance in the antibacterial complex by mixing the antibacterial complex formed by coating the antibacterial substance with a microemulsion method and arranging it on the dendrimer with the plastic substrate. In addition, antibacterial substances can be released gradually, and the effect of suppressing bacterial growth can be achieved at a small concentration.
3. 3. According to the present invention, by coating an antibacterial substance by a microemulsion method, the water-insoluble antibacterial substance can be solubilized and stabilized, and the antibacterial activity can be enhanced.
4. Since the technique of coating an antibacterial substance by a microemulsion method is simple, easy to manufacture, and inexpensive, the present invention does not require high energy consuming equipment and can be applied to industries such as cosmetics and pharmaceuticals.
本発明の詳細な説明及び技術内容について、図面を参照して以下に説明するが、図面は、ただ参考及び説明に用いるのみであり、本発明の特許請求の範囲に制限を加えるものではない。 The detailed description and technical contents of the present invention will be described below with reference to the drawings, but the drawings are merely used for reference and description, and do not limit the scope of claims of the present invention.
本発明の一実施例に係る抗菌性複合体は、抗菌性物質をマイクロエマルション（ｍｉｃｒｏｅｍｕｌｓｉｏｎ）方式で被覆してデンドリマー（ｄｅｎｄｒｉｍｅｒｓ）に配置してなるものである。ここで、デンドリマーと抗菌性物質含有マイクロエマルションの重量比が１：１〜１０：１である。これにより、抗菌性複合体は、有害な細菌を抑制するのに用いられ、抗菌性物質を徐々に放出することができ、わずかな濃度で細菌に対する優れた増殖抑制効果を有している。具体的に、上述した抗菌性物質含有マイクロエマルションをデンドリマーに配置することは、抗菌性物質含有マイクロエマルションをデンドリマーに化学結合するか、又は抗菌性物質含有マイクロエマルションをデンドリマーに包埋させるという改質（ｍｏｄｉｆｉｅｄ）技術を指す。 The antibacterial composite according to an embodiment of the present invention is formed by coating an antibacterial substance with a microemulsion method and arranging it on dendrimers. Here, the weight ratio of the dendrimer and the microemulsion containing an antibacterial substance is 1: 1 to 10: 1. As a result, the antibacterial complex is used to suppress harmful bacteria, can gradually release the antibacterial substance, and has an excellent growth inhibitory effect on bacteria at a small concentration. Specifically, placing the above-mentioned antibacterial substance-containing microemulsion in the dendrimer is a modification in which the antibacterial substance-containing microemulsion is chemically bonded to the dendrimer or the antibacterial substance-containing microemulsion is embedded in the dendrimer. (Modified) Refers to technology.
本発明の他の実施例に係る抗菌性複合体は、抗菌性物質をマイクロエマルション（ｍｉｃｒｏｅｍｕｌｓｉｏｎ）方式で被覆することで、有害な細菌を抑制するのに用いられ、この抗菌性物質含有マイクロエマルションをデンドリマー（ｄｅｎｄｒｉｍｅｒｓ）に配置してなるものである。最終的な抗菌性複合体とプラスチック基材との間の親水性及び疎水性の相違により、抗菌性複合体がプラスチック基材の表面に滞在することで、プラスチック基材の表面の抗菌性複合体の濃度が増加して抗菌効果を高めることができる。別の実施例において、マイクロエマルションの油相は、水不溶性の抗菌性物質であってもよいし、他の高疎水性物質であってもよい。水相は、逆浸透水である。界面活性剤及び補助界面活性剤は、主鎖が長炭素鎖であり、末端がアニオン性又は非荷電性である。デンドリマーは、複数のアミン基（−ＮＨ２）を有する物質であってもよい。本実施例では、適用する油相が、例えばフェニルアクロレイン、ベンズアルデヒド及びシンナムアルデヒドの単一物質又は混合物等の疎水性抗菌性物質である。界面活性剤としては、例えばドデカン酸（ラウリン酸）やアルキルグリコシドが挙げられる。補助界面活性剤としては、例えばドデシルベンゼンスルホン酸又はその塩化合物が挙げられる。デンドリマーは、ポリアミドアミンデンドリマー（ｐｏｌｙａｍｉｄｏａｍｉｎｅ ｄｅｎｄｒｉｍｅｒｓ，ＰＡＭＡＭ ｄｅｎｄｒｉｍｅｒｓ）である。 The antibacterial composite according to another embodiment of the present invention is used to suppress harmful bacteria by coating an antibacterial substance with a microemulsion method, and this antibacterial substance-containing microemulsion is used. It is placed in dendrimers. Due to the difference in hydrophilicity and hydrophobicity between the final antibacterial composite and the plastic substrate, the antibacterial composite stays on the surface of the plastic substrate, thereby causing the antibacterial composite on the surface of the plastic substrate. The concentration of plastic can be increased to enhance the antibacterial effect. In another embodiment, the oil phase of the microemulsion may be a water-insoluble antibacterial substance or another highly hydrophobic substance. The aqueous phase is reverse osmosis water. Surfactants and auxiliary surfactants have a long carbon chain as the main chain and anionic or uncharged terminals at the ends. The dendrimer may be a substance having a plurality of amine groups (-NH 2 ). In this example, the oil phase to be applied is a hydrophobic antibacterial substance such as, for example, a single substance or a mixture of phenylacrolein, benzaldehyde and cinnamaldehyde. Examples of the surfactant include dodecanoic acid (lauric acid) and alkyl glycosides. Examples of the auxiliary surfactant include dodecylbenzenesulfonic acid or a salt compound thereof. The dendrimer is a polyamide amine dendrimer (PAMAM dendrimers).
以下、本発明の抗菌性複合体の製造方法について詳細に説明する。図１に示すように、抗菌性複合体の製造方法は、以下の工程を含む。工程Ｓ１５０では、界面活性剤と抗菌性物質とを１：１〜１０：１の重量比で溶解させた。一実施例において、界面活性剤はラウリン酸であり、抗菌性物質はフェニルアクロレインの疎水性抗菌性物質である。この場合、工程Ｓ１５０では、ラウリン酸とフェニルアクロレイン等の疎水性抗菌性物質とを１０：１の重量比で混合し、５０℃〜７０℃で加熱溶解して抗菌性物質含有界面活性剤を調製した。ここで、加熱温度が６０℃に近いほど、より良好な溶解効果は得られ、加熱温度が６０℃である場合、溶解効果は最も高い。 Hereinafter, the method for producing the antibacterial complex of the present invention will be described in detail. As shown in FIG. 1, the method for producing an antibacterial complex includes the following steps. In step S150, the surfactant and the antibacterial substance were dissolved in a weight ratio of 1: 1 to 10: 1. In one example, the surfactant is lauric acid and the antibacterial substance is the hydrophobic antibacterial substance of phenylacrolein. In this case, in step S150, lauric acid and a hydrophobic antibacterial substance such as phenylacrolein are mixed at a weight ratio of 10: 1 and dissolved by heating at 50 ° C. to 70 ° C. to prepare an antibacterial substance-containing surfactant. did. Here, the closer the heating temperature is to 60 ° C., the better the melting effect is obtained, and when the heating temperature is 60 ° C., the melting effect is the highest.
第２実施例において、界面活性剤はラウリン酸及びアルキルグリコシドであり、抗菌性物質はフェニルアクロレイン等のような疎水性抗菌性物質である。工程Ｓ１５０では、ラウリン酸とアルキルグリコシドとフェニルプロペニルの疎水性抗菌性物質とを３：２：１の重量比で、疎水性抗菌性物質を溶解可能な有機溶媒、例えばプロピレングリコールモノメチルエーテルアセテート、ジメチルスルホキシド（ｄｉｍｅｔｈｙｌ ｓｕｌｆｏｘｉｄｅ，ＤＭＳＯ）、ジメチルホルムアミド（ｄｉｍｅｔｈｙｌ ｆｏｒｍｍｉｄｅ，ＤＭＦ）等の中に予め添加して、抗菌性物質含有界面活性剤を調製した。 In the second embodiment, the surfactant is lauric acid and an alkyl glycoside, and the antibacterial substance is a hydrophobic antibacterial substance such as phenylacrolein. In step S150, an organic solvent capable of dissolving the hydrophobic antibacterial substance in a weight ratio of 3: 2: 1 of lauric acid, alkyl glycoside and phenylpropenyl, for example, propylene glycol monomethyl ether acetate, dimethyl An antibacterial substance-containing surfactant was prepared by adding it in advance into sulfoxide (dimethyl sulfoxide, DMSO), dimethylformamide (DMF), or the like.
第３の実施例において、界面活性剤はアルキルグリコシドであり、抗菌性物質はシンナムアルデヒドとベンズアルデヒドの混合物である。工程Ｓ１５０では、アルキルグリコシドと、シンナムアルデヒドとベンズアルデヒドの混合物とを１：１の重量比で、疎水性抗菌性物質を溶解可能な有機溶媒、例えばジメチルスルホキシド（ｄｉｍｅｔｈｙｌ ｓｕｌｆｏｘｉｄｅ，ＤＭＳＯ）、ジメチルホルムアミド（ｄｉｍｅｔｈｙｌ ｆｏｒｍｍｉｄｅ，ＤＭＦ）、又はプロピレングリコールメチルエーテルとコハク酸の混合物の中に予め添加して、抗菌性物質含有界面活性剤を調製した。 In the third embodiment, the surfactant is an alkyl glycoside and the antibacterial substance is a mixture of cinnamaldehyde and benzaldehyde. In step S150, an organic solvent capable of dissolving a hydrophobic antibacterial substance in a weight ratio of 1: 1 of an alkyl glycoside and a mixture of cinnamaldehyde and benzaldehyde, for example, dimethyl sulfoxide (DMSO), dimethylformamide (dimethyl). Formmide, DMF), or a mixture of propylene glycol methyl ether and succinic acid was added in advance to prepare an antibacterial substance-containing surfactant.
次に、工程Ｓ１６０では、補助界面活性剤と、水と、抗菌性物質含有界面活性剤とを１：１０：０．１〜２：１０：０．５の重量比で混合し、マイクロエマルションが確実に完了するように１〜２時間攪拌して、マイクロエマルション方式で被覆された抗菌性物質を調製した。一実施例において、補助界面活性剤は、ドデシルベンゼンスルホン酸又はその塩化合物である。ここで、攪拌時間が２時間に近いほど、より良好な混合効果は得られ、攪拌時間が２時間である場合、混合効果は最も高い。 Next, in step S160, the auxiliary surfactant, water, and the antibacterial substance-containing surfactant are mixed at a weight ratio of 1:10: 0.1 to 2: 10: 0.5 to form a microemulsion. Stirring for 1-2 hours to ensure completion prepared an antibacterial material coated by a microemulsion method. In one example, the co-surfactant is dodecylbenzenesulfonic acid or a salt compound thereof. Here, the closer the stirring time is to 2 hours, the better the mixing effect can be obtained, and when the stirring time is 2 hours, the mixing effect is the highest.
一実施例において、最後に、工程Ｓ１７０をさらに実行する。工程Ｓ１７０では、工程Ｓ１６０で得られた抗菌性物質含有マイクロエマルションにデンドリマーを添加し、デンドリマーと抗菌性物質含有マイクロエマルションとの重量比が１：１〜１０：１であり、６時間攪拌を続けて、抗菌性物質含有マイクロエマルションをデンドリマーに包埋して、デンドリマーに包埋された抗菌性複合体を得た。一実施例において、デンドリマーはポリアミンデンドリマーである。ここで、デンドリマーと抗菌性物質含有マイクロエマルションとの重量比が１：１に近いほど、より良好な抗菌効果は得られ、デンドリマーと抗菌性物質含有マイクロエマルションとの重量比が１：１である場合、抗菌効果は最も高い。 Finally, in one embodiment, step S170 is further performed. In step S170, a dendrimer was added to the antibacterial substance-containing microemulsion obtained in step S160, the weight ratio of the dendrimer to the antibacterial substance-containing microemulsion was 1: 1 to 10: 1, and stirring was continued for 6 hours. Then, the microemulsion containing an antibacterial substance was embedded in a dendrimer to obtain an antibacterial complex embedded in the dendrimer. In one embodiment, the dendrimer is a polyamine dendrimer. Here, the closer the weight ratio of the dendrimer to the antibacterial substance-containing microemulsion is to 1: 1, the better the antibacterial effect can be obtained, and the weight ratio of the dendrimer to the antibacterial substance-containing microemulsion is 1: 1. If so, the antibacterial effect is the highest.
他の実施例において、最後に、工程Ｓ１７０’をさらに実行する。工程Ｓ１７０’では、工程Ｓ１６０で得られた抗菌性物質含有マイクロエマルションにデンドリマー及び架橋剤を添加し、室温で５時間反応させて、抗菌性物質含有マイクロエマルションをデンドリマーに化学結合して、化学結合形態の抗菌性複合体を得た。一実施例において、架橋剤は１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミドとＮ−ヒドロキシスクシンイミドとの混合物であり、デンドリマーはポリアミンデンドリマーである。 In another embodiment, finally, step S170'is further performed. In step S170', a dendrimer and a cross-linking agent are added to the antibacterial substance-containing microemulsion obtained in step S160, and the mixture is reacted at room temperature for 5 hours to chemically bond the antibacterial substance-containing microemulsion to the dendrimer to form a chemical bond. A morphological antibacterial complex was obtained. In one example, the cross-linking agent is a mixture of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide and N-hydroxysuccinimide, and the dendrimer is a polyamine dendrimer.
図２は、抗菌性複合体の他の製造方法を示す図である。図２に示す製造方法は、デンドリマーの表面が界面活性剤に化学結合される点で、図１に示す製造方法と異なっている。まず、デンドリマーの表面に界面活性剤を化学結合する製造方法は、以下の工程Ｓ２１０〜Ｓ２３０を含む。以下、この製造方法について説明する。一実施例において、工程Ｓ２１０では、界面活性剤とデンドリマーとを１０：１〜１：１０の重量比で、逆浸透水中に温度５０℃〜７０℃で加熱して均一に攪拌し、架橋剤を添加して室温で５時間反応させて、界面活性剤をデンドリマーの表面に充分に化学結合させた。ここで、界面活性剤とデンドリマーとの重量比が１０：１に近く、かつ加熱温度が６０℃に近ければ近いほど、界面活性剤のデンドリマーの表面への化学結合効果はより良好になる。界面活性剤とデンドリマーとの重量比が１０：１であり、かつ加熱温度が６０℃である場合、界面活性剤のデンドリマーの表面への化学結合効果は最も高い。 FIG. 2 is a diagram showing another method for producing an antibacterial complex. The production method shown in FIG. 2 differs from the production method shown in FIG. 1 in that the surface of the dendrimer is chemically bonded to the surfactant. First, a production method for chemically bonding a surfactant to the surface of a dendrimer includes the following steps S210 to S230. Hereinafter, this manufacturing method will be described. In one embodiment, in step S210, the surfactant and the dendrimer are heated at a weight ratio of 10: 1 to 1:10 in reverse osmosis water at a temperature of 50 ° C. to 70 ° C. and uniformly stirred to obtain a cross-linking agent. The detergent was added and reacted at room temperature for 5 hours to allow the surfactant to be sufficiently chemically bonded to the surface of the dendrimer. Here, the closer the weight ratio of the surfactant to the dendrimer is to 10: 1 and the closer the heating temperature is to 60 ° C., the better the chemical bonding effect of the surfactant on the surface of the dendrimer. When the weight ratio of the surfactant to the dendrimer is 10: 1 and the heating temperature is 60 ° C., the chemical bonding effect of the surfactant on the surface of the dendrimer is the highest.
一実施例において、架橋剤は、１−エチル−３−（３−ジメチルアミノプロピル）カボジイミドとＮ−ヒドロキシスクシミドとの混合物であり、界面活性剤の長炭素鎖分子は、ラウリン酸であり、デンドリマーは、ポリアミンデンドリマーである。次に、工程Ｓ２２０を実行する。工程Ｓ２２０では、工程Ｓ２１０で界面活性剤と、デンドリマーと、架橋剤とを完全に作用させた後、シクロヘキサンで３〜５回繰り返し洗浄した。そして、工程Ｓ２３０では、減圧下に濃縮して表面がラウリン酸に化学結合されたデンドリマーを得た。 In one example, the cross-linking agent is a mixture of 1-ethyl-3- (3-dimethylaminopropyl) cabodiimide and N-hydroxysuccimid, and the long carbon chain molecule of the surfactant is lauric acid. , Dendrimer is a polyamine dendrimer. Next, step S220 is executed. In step S220, the surfactant, dendrimer, and cross-linking agent were completely allowed to act in step S210, and then washed repeatedly with cyclohexane 3 to 5 times. Then, in step S230, the dendrimer was concentrated under reduced pressure to obtain a dendrimer whose surface was chemically bonded to lauric acid.
次に、工程Ｓ２４０では、表面がラウリン酸に化学結合されたデンドリマーと、抗菌性物質と、界面活性剤と、補助界面活性剤とを１：０．１：２：１〜１：０．５：３：２の重量比で混合して抗菌性複合体を得た。具体的に、一実施例では、疎水性抗菌性物質に界面活性剤及び補助界面活性剤を添加し、逆浸透水を添加して５時間攪拌した後、最後に表面がラウリン酸に化学結合されたデンドリマーを添加して１８時間攪拌を続けると、抗菌性複合体を得た。ここで、疎水性抗菌性物質は、フェニルアクロレイン又はベンズアルデヒドと、シンナムアルデヒドとの混合物であり、界面活性剤はアルキルグリコシドであり、補助界面活性剤は、ドデシルベンゼンスルホン酸又はその塩化合物である。ここで、表面がラウリン酸に化学結合されたデンドリマーと、抗菌性物質と、界面活性剤と、補助界面活性剤との重量比が１：０．５：３：２に近い割合で混合されるほど、より良好な抗菌効果は得られ、表面がラウリン酸に化学結合されたデンドリマーと、抗菌性物質と、界面活性剤と、補助界面活性剤との重量比が１：０．５：３：２の割合で混合されると、最適な抗菌効果は得られる。 Next, in step S240, the dendrimer whose surface is chemically bonded to lauric acid, the antibacterial substance, the surfactant, and the auxiliary surfactant are mixed in a ratio of 1: 0.1: 2: 1 to 1: 0.5. The mixture was mixed at a weight ratio of 3: 2 to obtain an antibacterial complex. Specifically, in one example, a surfactant and an auxiliary surfactant were added to the hydrophobic antibacterial substance, reverse osmosis water was added, and the mixture was stirred for 5 hours, and finally the surface was chemically bonded to lauric acid. The dendrimer was added and stirring was continued for 18 hours to obtain an antibacterial complex. Here, the hydrophobic antibacterial substance is a mixture of phenylacrolein or benzaldehyde and cinnamaldehyde, the surfactant is an alkylglycoside, and the auxiliary surfactant is dodecylbenzenesulfonic acid or a salt compound thereof. Here, the weight ratio of the dendrimer whose surface is chemically bonded to lauric acid, the antibacterial substance, the surfactant, and the auxiliary surfactant is mixed at a ratio close to 1: 0.5: 3: 2. The better the antibacterial effect was obtained, and the weight ratio of the dendrimer whose surface was chemically bonded to lauric acid, the antibacterial substance, the surfactant, and the auxiliary surfactant was 1: 0.5: 3: 3: When mixed in a ratio of 2, the optimum antibacterial effect can be obtained.
本発明は、抗菌性複合体の実験データを以下の表に示す。表１は、デンドリマーに包埋された抗菌性複合体の試験結果を示す。表２は、デンドリマーの表面が界面活性剤に化学結合された抗菌性複合体の試験結果を示す。 The present invention shows the experimental data of the antibacterial complex in the table below. Table 1 shows the test results of the antibacterial complex embedded in the dendrimer. Table 2 shows the test results of the antibacterial complex in which the surface of the dendrimer is chemically bonded to the surfactant.
上記の表１に示すように、デンドリマーとマイクロエマルションとの重量比が、それぞれ１０：１、５：１、３：１及び１：１である条件の下で、大腸菌、黄色ブドウ球菌及び肺炎桿菌に対する抗菌性複合体の抗菌効果を試験した。以上の試験結果より、抗菌効果の仕様に照らして、重量比の混合比が１０：１である場合、抗菌活性が低下することが分かる（抗菌領域の直径が１０ｍｍ未満であるものは、顕著な抗菌活性を有しないことを示す）。重量比の混合比が５：１である場合、抗菌性複合体は、少なくとも軽度〜中等度の抗菌活性を有する（抗菌領域の直径が１０〜１１ｍｍであるものは、軽度の抗菌活性を有することを示す）。重量比の混合比が３：１である場合、抗菌性複合体は、少なくとも中等度〜高度の抗菌活性を有する（抗菌領域の直径が１１〜１５ｍｍであるものは、中等度の抗菌活性を有することを示す）。重量比の混合比が１：１である場合、抗菌性複合体は、少なくとも高度の抗菌活性を有する（抗菌領域の直径が１５ｍｍより大きいものは、高度の抗菌活性を有することを示す）。このことから、デンドリマーと抗菌性物質含有マイクロエマルションとの重量比が１：１に近いほど、抗菌効果がより良好であることが分かる。 As shown in Table 1 above, Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae under the conditions that the weight ratios of the dendrimer and the microemulsion are 10: 1, 5: 1, 3: 1 and 1: 1, respectively. The antibacterial effect of the antibacterial complex against S. coli was tested. From the above test results, it can be seen that the antibacterial activity decreases when the mixing ratio of the weight ratio is 10: 1 in light of the specifications of the antibacterial effect (the diameter of the antibacterial region is less than 10 mm, which is remarkable. Shows no antibacterial activity). When the mixing ratio by weight is 5: 1, the antibacterial complex has at least mild to moderate antibacterial activity (those having an antibacterial region diameter of 10 to 11 mm have mild antibacterial activity. Shows). When the mixing ratio of the weight ratio is 3: 1, the antibacterial complex has at least moderate to high antibacterial activity (those having an antibacterial region diameter of 11 to 15 mm have moderate antibacterial activity. Indicates that). When the mixed weight ratio is 1: 1, the antibacterial complex has at least a high degree of antibacterial activity (those with a diameter of the antibacterial region larger than 15 mm indicate a high degree of antibacterial activity). From this, it can be seen that the closer the weight ratio of the dendrimer to the microemulsion containing an antibacterial substance is to 1: 1, the better the antibacterial effect.
上記の表２に示すように、化学結合デンドリマーと抗菌性物質と界面活性剤と補助界面活性剤との重量比が、それぞれ１：０．１：２：１、１：０．４：２：２及び１：０．５：３：２である条件の下で、大腸菌、黄色ブドウ球菌及び肺炎桿菌に対する抗菌性複合体の抗菌効果を試験した。以上の試験結果より、抗菌効果の仕様に照らして、重量比の混合比が１：０．１：２：１である場合、抗菌性複合体は、少なくとも軽度〜中等度の抗菌活性を有する（抗菌領域の直径が１０〜１１ｍｍであるものは、軽度の抗菌活性を有することを示す）。重量比の混合比が１：０．４：２：２である場合、抗菌性複合体は、少なくとも中等度〜高度の抗菌活性を有する（抗菌領域の直径が１１〜１５ｍｍであるものは、中等度の抗菌活性を有することを示す）。重量比の混合比が１：０．５：３：２である場合、抗菌性複合体は、少なくとも高度の抗菌活性を有する（抗菌領域の直径が１５ｍｍより大きいものは、高度の抗菌活性を有することを示す）。このことから、表面がラウリン酸に化学結合されたデンドリマーと抗菌性物質と界面活性剤と補助界面活性剤との重量比が１：０．５：３：２に近いほど、抗菌効果がより良好であることが分かる。 As shown in Table 2 above, the weight ratios of the chemically bonded dendrimer, the antibacterial substance, the surfactant and the auxiliary surfactant are 1: 0.1: 2: 1 and 1: 0.4: 2: respectively. The antibacterial effect of the antibacterial complex against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae was tested under the conditions of 2 and 1: 0.5: 3: 2. From the above test results, the antibacterial complex has at least mild to moderate antibacterial activity when the mixing ratio of the weight ratio is 1: 0.1: 2: 1 in light of the specifications of the antibacterial effect ( An antibacterial region having a diameter of 10 to 11 mm indicates that it has mild antibacterial activity). When the mixing ratio of the weight ratio is 1: 0.4: 2: 2, the antibacterial complex has at least moderate to high antibacterial activity (those having an antibacterial region diameter of 11 to 15 mm are moderate). Shows that it has a degree of antibacterial activity). When the mixing ratio of the weight ratio is 1: 0.5: 3: 2, the antibacterial complex has at least a high degree of antibacterial activity (those having an antibacterial region diameter larger than 15 mm have a high degree of antibacterial activity. Indicates that). From this, the closer the weight ratio of the dendrimer whose surface is chemically bonded to lauric acid, the antibacterial substance, the surfactant, and the auxiliary surfactant is to 1: 0.5: 3: 2, the better the antibacterial effect. It turns out that.
以上により、本発明の一つ又は複数の実施例は、以下の利点の少なくとも一つを有している。
１．本発明は、抗菌性物質をマイクロエマルション方式で被覆してデンドリマーに配置してなる最終的な抗菌性複合体と、プラスチック基材との間の親水性及び疎水性の相違により、抗菌性複合体がプラスチック基材の表面に滞在することで、プラスチック基材の表面の抗菌性複合体の濃度が増加して抗菌効果を高めることができる。
２．本発明は、抗菌性物質をマイクロエマルション方式で被覆してデンドリマーに配置してなる抗菌性複合体をプラスチック基材と混合することにより、抗菌性複合体中の抗菌性物質の放出を遮蔽せずに、抗菌性物質を徐々に放出することができ、わずかな濃度で細菌の増殖抑制効果を達成することができる。
３．本発明は、抗菌性物質をマイクロエマルション方式で被覆することにより、水不溶性抗菌性物質を可溶化して安定化させ、抗菌力を高めることができる。
４．本発明は、抗菌性物質をマイクロエマルション方式で被覆する技術が簡単で製造が容易かつ安価であるため、高エネルギー消費機器が必要なく、化粧品や医薬品産業に適用可能である。
As described above, one or more embodiments of the present invention have at least one of the following advantages.
1. 1. The present invention is based on the difference in hydrophilicity and hydrophobicity between the final antibacterial composite obtained by coating an antibacterial substance with a microemulsion method and arranging it on a dendrimer, and the plastic substrate. By staying on the surface of the plastic base material, the concentration of the antibacterial complex on the surface of the plastic base material can be increased to enhance the antibacterial effect.
2. 2. The present invention does not block the release of the antibacterial substance in the antibacterial complex by mixing the antibacterial complex formed by coating the antibacterial substance with a microemulsion method and arranging it on the dendrimer with the plastic substrate. In addition, antibacterial substances can be released gradually, and the effect of suppressing bacterial growth can be achieved at a small concentration.
3. 3. According to the present invention, by coating an antibacterial substance by a microemulsion method, the water-insoluble antibacterial substance can be solubilized and stabilized, and the antibacterial activity can be enhanced.
4. Since the technique for coating an antibacterial substance by a microemulsion method is simple, easy to manufacture, and inexpensive, the present invention does not require high energy consuming equipment and can be applied to the cosmetics and pharmaceutical industries.
以上、本発明の好適な実施例を挙げて説明したが、これは本発明の実施例の一例に過ぎない。説明した実施例は、本発明の範囲を限定するものではないことが理解されたい。当業者であれば本発明の概念又は技術的思想を含む各種の変動や交換は、本発明の保護を求める範囲内に属するものである。また、特許請求の範囲及び明細書の範囲に記載された特徴は、単独又は任意の組み合わせで実施されることが可能である。
Although preferable examples of the present invention have been described above, this is only an example of the examples of the present invention. It should be understood that the examples described do not limit the scope of the invention. As a person skilled in the art, various variations and exchanges including the concept or technical idea of the present invention belong to the scope of seeking protection of the present invention. In addition, the features described in the claims and the scope of the specification can be implemented alone or in any combination.
Claims (10)
前記デンドリマーと前記抗菌性物質含有マイクロエマルションの重量比は、１：１〜１０：１であり、
前記配置技術は、前記抗菌性物質含有マイクロエマルションを前記デンドリマーに化学結合させるための化学結合技術、又は前記抗菌性物質含有マイクロエマルションを前記デンドリマーに包埋させるための包埋技術である、抗菌性複合体。 An antibacterial complex in which an antibacterial substance-containing microemulsion formed by coating an antibacterial substance by a microemulsion method is arranged on a dendrimer by an arrangement technique.
The weight ratio of the dendrimer to the antibacterial substance-containing microemulsion is 1: 1 to 10: 1.
The placement technique is embedded technology for causing embedding the antibacterial substance-containing microemulsion the order of chemical coupling techniques is chemically bonded to the dendrimer, or the antibacterial substance-containing microemulsion to said dendrimer, antibacterial Sex complex.
（ｂ）補助界面活性剤と、水と、前記抗菌性物質含有界面活性剤とを１：１０：０．１〜２：１０：０．５の重量比で混合し、１〜２時間攪拌して抗菌性物質含有マイクロエマルションを調製する工程と、
（ｃ）前記抗菌性物質含有マイクロエマルションを配置技術によりデンドリマーに配置して抗菌性複合体を調製する工程と、を含む、抗菌性複合体の製造方法。 (A) A step of preparing an antibacterial substance-containing surfactant by dissolving a surfactant and an antibacterial substance in a weight ratio of 1: 1 to 10: 1.
(B) The auxiliary surfactant, water, and the antibacterial substance-containing surfactant are mixed at a weight ratio of 1:10: 0.1 to 2: 10: 0.5 and stirred for 1 to 2 hours. And the process of preparing a microemulsion containing an antibacterial substance
(C) A method for producing an antibacterial complex, which comprises a step of arranging the antibacterial substance-containing microemulsion on a dendrimer by an arrangement technique to prepare an antibacterial complex.
（ｂ）前記工程（ａ）で得られた産物をシクロヘキサンで３〜５回繰り返し洗浄し、減圧下に濃縮して前記ラウリン酸に化学結合されたデンドリマーを得る工程と、
（ｃ）前記ラウリン酸に化学結合されたデンドリマーと抗菌性物質と界面活性剤と補助界面活性剤とを１：０．１：２：１〜１：０．５：３：２の重量比で混合して抗菌性複合体を得る工程とを含む、抗菌性複合体の製造方法。 (A) Lauric acid and dendrimer are heated at a weight ratio of 10: 1 to 1:10 in reverse osmosis water at a temperature of 50 to 70 ° C., stirred uniformly, a cross-linking agent is added, and the reaction is carried out at room temperature for 5 hours. by the steps of Ru sufficiently by chemically bonding the lauric acid to the surface of the dendrimer,
And (b) repeatedly washed 3-5 times the product obtained in step (a) with cyclohexane and concentrated to give under reduced pressure chemically bonded to said lauric acid dendrimer step,
(C) A dendrimer chemically bonded to the lauric acid, an antibacterial substance, a surfactant and an auxiliary surfactant in a weight ratio of 1: 0.1: 2: 1 to 1: 0.5: 3: 2. A method for producing an antibacterial complex, which comprises a step of mixing to obtain an antibacterial complex.
（ｃ１）前記抗菌性物質に前記界面活性剤及び前記補助界面活性剤を添加し、逆浸透水を添加して５時間攪拌した後、前記ラウリン酸に化学結合されたデンドリマーをさらに添加し、１８時間攪拌を続けて前記抗菌性複合体を得る工程、を含む、請求項８に記載の抗菌性複合体の製造方法。 The step (c) is
(C1) The surfactant and the auxiliary surfactant were added to the antibacterial substance, reverse osmosis water was added, and the mixture was stirred for 5 hours, and then a dendrimer chemically bonded to the lauric acid was further added. The method for producing an antibacterial complex according to claim 8, which comprises a step of continuously stirring for a time to obtain the antibacterial complex.
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