JP2022046642A - Bactericidal/antibacterial composition - Google Patents
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- JP2022046642A JP2022046642A JP2021210632A JP2021210632A JP2022046642A JP 2022046642 A JP2022046642 A JP 2022046642A JP 2021210632 A JP2021210632 A JP 2021210632A JP 2021210632 A JP2021210632 A JP 2021210632A JP 2022046642 A JP2022046642 A JP 2022046642A
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- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 54
- 239000010949 copper Substances 0.000 claims abstract description 34
- 229910052802 copper Inorganic materials 0.000 claims abstract description 27
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910001431 copper ion Inorganic materials 0.000 claims abstract description 17
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims abstract description 15
- -1 copper chelate complex Chemical class 0.000 claims abstract description 15
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000001954 sterilising effect Effects 0.000 claims description 17
- 238000004659 sterilization and disinfection Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 239000002738 chelating agent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 22
- 239000007864 aqueous solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 241000894006 Bacteria Species 0.000 description 9
- 239000013522 chelant Substances 0.000 description 9
- 241000588724 Escherichia coli Species 0.000 description 8
- 238000007865 diluting Methods 0.000 description 7
- 239000012085 test solution Substances 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 4
- 102000004856 Lectins Human genes 0.000 description 4
- 108090001090 Lectins Proteins 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000005018 casein Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 239000002523 lectin Substances 0.000 description 4
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- 229940068968 polysorbate 80 Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000700605 Viruses Species 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 208000028169 periodontal disease Diseases 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- PYUCXAUCMGTTBY-UHFFFAOYSA-N O.O.CC(O)=O.CC(O)=O.CC(O)=O Chemical compound O.O.CC(O)=O.CC(O)=O.CC(O)=O PYUCXAUCMGTTBY-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
本発明は、殺菌・抗菌用組成物に関する。 The present invention relates to a bactericidal / antibacterial composition.
銅の殺菌・抗菌作用は昔から知られている。この銅の殺菌・抗菌作用を利用して様々な商品が考案されている。銅金属をそのまま使用できる場合であれば良いが、液体として使用する場合には、銅イオンとして作用させなければならず、銅イオンを単独で溶液中に長時間、留めておくことは困難で、時間経過と共に水酸化銅の形で沈殿してしまう。銅イオンは、１９８５年に文部省「環境科学」特別研究人体影響班によるサルでの長期実験で安全性が確認されている。 The bactericidal and antibacterial effects of copper have long been known. Various products have been devised by utilizing the bactericidal and antibacterial action of copper. It is acceptable if the copper metal can be used as it is, but when it is used as a liquid, it must act as a copper ion, and it is difficult to keep the copper ion alone in the solution for a long time. It precipitates in the form of copper hydroxide over time. The safety of copper ion was confirmed in 1985 by a long-term experiment in monkeys by the Ministry of Education's "Environmental Science" Special Research Human Body Impact Group.
しかしながら、従来の方法では、銅イオン単独では、銅イオンの存在が不安定なため、殺菌・抗菌効果が不十分な場合があり、より効果で、安全で新たな殺菌・抗菌用組成物が求められている。特許文献１に記載の技術は、金属塩として用いるため、殺菌力が低く、安定性に問題がある。また、特許文献２も金属化合物とキレート剤を別に使用しているため、殺菌力と安定性に問題がある。また更に、特許文献３においては、銅化合物と過酸化水素を含有することとなっているため、人体に直接的に使用するにあたって、安全性に欠ける。 However, in the conventional method, the presence of copper ions is unstable with copper ions alone, so that the bactericidal / antibacterial effect may be insufficient, and a more effective, safe and new bactericidal / antibacterial composition is required. Has been done. Since the technique described in Patent Document 1 is used as a metal salt, it has low bactericidal activity and has a problem in stability. Further, since Patent Document 2 also uses a metal compound and a chelating agent separately, there is a problem in bactericidal activity and stability. Furthermore, in Patent Document 3, since it contains a copper compound and hydrogen peroxide, it lacks safety when used directly on the human body.
本発明は、上記事情に鑑みてなされたものであり、銅イオンとしての高い殺菌・抗菌効果を発揮し、かつ、安定性に優れ、人体に安全な殺菌・抗菌用組成物を提供することを課題とする。 The present invention has been made in view of the above circumstances, and is to provide a bactericidal / antibacterial composition which exhibits a high bactericidal / antibacterial effect as a copper ion, has excellent stability, and is safe for the human body. Make it an issue.
本発明の殺菌・抗菌用組成物は、銅イオンとのキレート剤が、下記、一般式（Ｉ）または（ＩＩ）の少なくともいずれか一つで、銅キレート錯体として含有することを特徴とする。 The bactericidal / antibacterial composition of the present invention is characterized in that the chelating agent with copper ions is contained as a copper chelate complex in at least one of the following general formulas (I) or (II).
（式中、Ｘ１～Ｘ４は同一でも異なっていてもよく、それぞれ水素原子、アルカリ金属、アルカリ土類金属、カチオン性アンモニウム基からなる群より選ばれる１種を表している。）
（式中、Ｙはアルキル基、カルボキシル基、スルホ基、アミノ基、水酸基、または水素原子を表し、Ｘ５～Ｘ７は同一でも異なっていてもよく、それぞれ水素原子、アルカリ金属、アルカリ土類金属、カチオン性アンモニウム基からなる群より選ばれる１種を表し、ｎは０から５の整数を表す。） (In the formula, Y represents an alkyl group, a carboxyl group, a sulfo group, an amino group, a hydroxyl group, or a hydrogen atom, and X5 to X7 may be the same or different, and hydrogen atom, alkali metal, and alkaline earth metal, respectively. Represents one selected from the group consisting of cationic ammonium groups, where n represents an integer from 0 to 5).
本発明によれば、銅イオンとしての高い殺菌・抗菌効果を発揮し、かつ、安定性に優れ、人体に安全な殺菌・抗菌用組成物を提供することができる。 According to the present invention, it is possible to provide a bactericidal / antibacterial composition which exhibits a high bactericidal / antibacterial effect as a copper ion, has excellent stability, and is safe for the human body.
生体中におけるウイルス及び細菌感染による炎症部位では、白血球が作用し、感染部位においてウイルス及び細菌と白血球との接近部位では強酸性を呈し、全体としてその炎症部位は酸性を呈する。 Leukocytes act at the site of inflammation caused by virus and bacterial infection in the living body, and at the site of infection, the site of close contact between the virus and bacteria and leukocytes exhibits strong acidity, and the site of inflammation exhibits acidity as a whole.
また、一般式（Ｉ）または（ＩＩ）の水溶液中で陰イオンとなる－ＣＯＯ－の部分が酸性下においてはキレート能が低下する。 In addition, the chelating ability of the -COO- moiety , which becomes an anion in the aqueous solution of the general formula (I) or (II), is lowered under acidic conditions.
そのため、炎症部位においては、該銅キレート錯体のキレート能が低下して、銅イオンがキレート剤から解放される。 Therefore, at the site of inflammation, the chelating ability of the copper chelate complex is reduced, and copper ions are released from the chelating agent.
炎症が起こっている酸性部位でキレートが解かれ、銅イオンが炎症部位でウイルス及び細菌に対して殺菌や抗菌の作用をする。よって、該銅レート錯体による殺菌・抗菌用組成物を提供することができる。 The chelate is released at the acidic site where inflammation is occurring, and copper ions act as a bactericidal and antibacterial action against viruses and bacteria at the inflamed site. Therefore, it is possible to provide a bactericidal / antibacterial composition using the copper rate complex.
以下、本発明を詳細に説明する。
本発明の殺菌・抗菌用組成物は、銅イオンのキレート剤として、下記一般式（Ｉ）または（ＩＩ）のいずれかの構造の化合物（以下、化合物（Ａ）、（Ｂ）という。）であることを特徴とする。
Hereinafter, the present invention will be described in detail.
The bactericidal / antibacterial composition of the present invention is a compound having any of the following general formulas (I) or (II) as a chelating agent for copper ions (hereinafter referred to as compounds (A) and (B)). It is characterized by being.
化合物（Ａ）は、下記一般式（Ｉ）で示される。 Compound (A) is represented by the following general formula (I).
化合物（Ａ）において、Ｘ１～Ｘ４は同一でも異なっていてもよく、それぞれ水素原子、アルカリ金属、アルカリ土類金属、カチオン性アンモニウム基からなる群より選ばれる１種を表す。
Ｘ１～Ｘ４が上記のものであると、本発明の殺菌・除菌用組成物を水に溶解すると、この化合物（Ａ）は、－ＣＯＯＸ１、－ＣＯＯＸ２、－ＣＯＯＸ３、－ＣＯＯＸ４が電離して、それぞれ－ＣＯＯ－となり、陰イオンを生成する。そして、この陰イオンの－ＣＯＯ－の部分が銅元素と錯形成可能となる。
好ましくは、Ｘ１～Ｘ４はいずれもナトリウムまたはカリウムである。なお、Ｘ１～Ｘ４のうちの１種以上がアルカリ土類金属Ｍである場合には、その部分は－ＣＯＯＭと示されることとなる。
In compound (A), X1 to X4 may be the same or different, and represent one selected from the group consisting of a hydrogen atom, an alkali metal, an alkaline earth metal, and a cationic ammonium group, respectively.
When X1 to X4 are the above, when the sterilizing / sterilizing composition of the present invention is dissolved in water, -COOX1, -COOX2, -COOX3, and -COOX4 are ionized in this compound (A). Each becomes -COO - and produces anions. Then , the -COO- portion of this anion can form a complex with the copper element.
Preferably, X1 to X4 are all sodium or potassium. When one or more of X1 to X4 is an alkaline earth metal M, that portion is indicated as −COOM.
化合物（Ａ）の具体例としては、エチレンジアミン四酢酸二水素二ナトリウムなどが挙げられる。 Specific examples of the compound (A) include ethylenediaminetetraacetic acid dihydrogen disodium and the like.
化合物（Ｂ）は、下記一般式（ＩＩ）で示される。 Compound (B) is represented by the following general formula (II).
化合物（Ｂ）において、Ｙはアルキル基、カルボキシル基、スルホ基、アミノ基、水酸基、または水素原子を表し、Ｘ５～Ｘ７は同一でも異なっていてもよく、それぞれ水素原子、アルカリ金属、アルカリ土類金属、カチオン性アンモニウム基からなる群より選ばれる１種を表す。
Ｘ５～Ｘ７が上記のものである場合、本発明の殺菌・除菌用組成物を洗濯時に水に溶解すると、この化合物（Ｂ）は、－ＣＯＯＸ５、－ＣＯＯＸ６、－ＣＯＯＸ７が電離して、それぞれ－ＣＯＯ－となり、陰イオンを生成する。そして、この陰イオンの－ＣＯＯ－の部分が銅元素と錯形成可能となる。
好ましくは、Ｘ５～Ｘ７はいずれもナトリウムまたはカリウムである。なお、Ｘ５～Ｘ７のうちの１種以上がアルカリ土類金属Ｍである場合には、その部分は－ＣＯＯＭと示されることとなる。また、ｎは０から５の整数を表し、好ましくは０から２である。
In compound (B), Y represents an alkyl group, a carboxyl group, a sulfo group, an amino group, a hydroxyl group, or a hydrogen atom, and X5 to X7 may be the same or different, and hydrogen atom, alkali metal, and alkaline earth, respectively. Represents one selected from the group consisting of a metal and a cationic ammonium group.
When X5 to X7 are the above, when the sterilizing / sterilizing composition of the present invention is dissolved in water at the time of washing, -COOX5, -COOX6, and -COOX7 are ionized in this compound (B), respectively. It becomes -COO- and produces anions. Then , the -COO- portion of this anion can form a complex with the copper element.
Preferably, X5 to X7 are all sodium or potassium. When one or more of X5 to X7 is an alkaline earth metal M, that portion is indicated as −COOM. Further, n represents an integer from 0 to 5, preferably 0 to 2.
化合物（Ｂ）の具体例としては、Ｎ－（２－ヒドロキシエチル）エチレンジアミン－Ｎ，Ｎ’，Ｎ’－三酢酸三ナトリウムなどが挙げられる。 Specific examples of the compound (B) include N- (2-hydroxyethyl) ethylenediamine-N, N', N'-trisodium triacetate and the like.
なお、殺菌効果とは、表面に存在する菌数を減少させる効果を示し、抗菌効果とは、表面に付着した菌の増殖を抑制する効果を示す。 The bactericidal effect indicates an effect of reducing the number of bacteria existing on the surface, and the antibacterial effect indicates an effect of suppressing the growth of bacteria adhering to the surface.
銅イオンをエチレンジアミン四酢酸（ＥＤＴＡ）又は、Ｎ－（２－ヒドロキシエチル）エチレンジアミン－Ｎ，Ｎ’，Ｎ’－三酢酸（ＨＥＤＴＡ）の少なくともいずれか一つで、銅キレート錯体とした塩は、銅が抗菌組成物中に６２５ｐｐｍ以上となるように配合すると好ましく、１０００ｐｐｍ以上であると更に好ましく、１２５０ｐｐｍ以上であると特に好ましい。 A salt in which the copper ion is at least one of ethylenediaminetetraacetic acid (EDTA) or N- (2-hydroxyethyl) ethylenediamine-N, N', N'-triacetic acid (HEDTA) to form a copper chelate complex is a salt. It is preferable to add copper to the antibacterial composition so as to be 625 ppm or more, more preferably 1000 ppm or more, and particularly preferably 1250 ppm or more.
該銅キレート錯体の作用場のｐＨ値は、０～６．０が好ましく、０～４．０であると更に好ましい。 The pH value of the action field of the copper chelate complex is preferably 0 to 6.0, more preferably 0 to 4.0.
下記に錯体化の具体的方法の例について説明するが、特に制限されるものではない。 An example of a specific method of complexing will be described below, but the present invention is not particularly limited.
実施例１
＜エチレンジアミン四酢酸（ＥＤＴＡ）銅キレート錯体水溶液作成＞
既に銅イオンとエチレンジアミン四酢酸（ＥＤＴＡ）でキレートされているキレストＣｕ（キレスト株式会社製）を用いて調整し作成した溶液を作成する。
水はイオン交換水を用いた。
銅濃度として、
（Ａ－１）２００ｐｐｍは、
キレストＣｕを０．１６ｇ取り、を注入して１００ｍｌとする溶液。
（Ｂ－１）５００ｐｐｍは、
キレストＣｕを０．４ｇ取り、水を注入して１００ｍｌとする溶液。
（Ｃ－１）６２５ｐｐｍは、
キレストＣｕを０．５ｇ取り、水を注入して１００ｍｌとする溶液。
（Ｄ－１）１０００ｐｐｍは、
キレストＣｕを０．８ｇ取り、水を注入して１００ｍｌとする溶液。
（Ｅ－１）１２５０ｐｐｍは、
キレストＣｕを１．０ｇ取り、水を注入して１００ｍｌとする溶液。
（Ｆ－１）１５００ｐｐｍは、
キレストＣｕを１．２ｇ取り、水を注入して１００ｍｌとする溶液。
をそれぞれ作成した。
Example 1
<Preparation of ethylenediamine tetraacetic acid (EDTA) copper chelate complex aqueous solution>
A solution prepared by adjusting with Kirest Cu (manufactured by Kirest Co., Ltd.) already chelated with copper ion and ethylenediaminetetraacetic acid (EDTA) is prepared.
Ion-exchanged water was used as the water.
As a copper concentration
(A-1) 200 ppm is
A solution in which 0.16 g of Kirest Cu is taken and injected to make 100 ml.
(B-1) 500 ppm is
A solution in which 0.4 g of Kirest Cu is taken and water is injected to make 100 ml.
(C-1) 625 ppm is
A solution in which 0.5 g of Kirest Cu is taken and water is injected to make 100 ml.
(D-1) 1000 ppm is
A solution in which 0.8 g of Kirest Cu is taken and water is injected to make 100 ml.
(E-1) 1250 ppm is
A solution in which 1.0 g of Kirest Cu is taken and water is injected to make 100 ml.
(F-1) 1500 ppm is
A solution in which 1.2 g of Kirest Cu is taken and water is injected to make 100 ml.
Was created respectively.
＜ｐＨ３．０の希塩酸作成＞
ｐＨメーターで測定しながら、１００ｍＬのイオン交換水に１Ｎの塩酸をパスツールピペットで１滴ずつ入れていきｐＨ３．０の塩酸を作成する。
<Making dilute hydrochloric acid with pH 3.0>
While measuring with a pH meter, add 1N hydrochloric acid to 100 mL of ion-exchanged water drop by drop with a Pasteur pipette to make hydrochloric acid with a pH of 3.0.
大腸菌は、酸に対して非常に耐性が高い、そのため酸性下の殺菌力評価に大腸菌を用いた。 Escherichia coli is extremely resistant to acid, so Escherichia coli was used to evaluate the bactericidal activity under acidic conditions.
「殺菌力評価」
殺菌・抗菌用組成物が、銅濃度といて、比較例は０質量％、上記で調整した（Ａ－１）、（Ｂ－１）、（Ｃ－１）、（Ｄ－１）、（Ｅ－１）、（Ｆ－１）の溶液から試験液として８．９ｍＬをそれぞれ取り、ｐＨ３．０の希塩酸１ｍＬを各試験液に加え、さらに各試験液へ菌数が１００個／ｍＬとなるように調整された大腸菌母液（ＩＦＯ３９７２）０．１ｍＬを添加し、均一に攪拌した。１０分後に１ｍＬ採取し、９ｍＬのＳＣＤＬＰ培地（Ｓｏｙｂｅａｎ－Ｃａｓｅｉｎ Ｄｉｇｅｓｔ Ｂｒｏｔｈ ｗｉｔｈ Ｌｅｃｔｉｎ ＆ Ｐｏｌｙｓｏｒｂａｔｅ ８０：和光純薬工業株式会社製）に加え、１０倍希釈液とした。得られた希釈液をさらに１０倍に希釈する操作を４回繰り返し、１０倍から１０００００倍の希釈を得た。これら各希釈液から１．０ｍＬをシャーレに採取し、ＳＣＤＬＰ寒天培地（Ｓｏｙｂｅａｎ－Ｃａｓｅｉｎ Ｄｉｇｅｓｔ Ａｇｅｒ ｗｉｔｈ Ｌｅｃｔｉｎ ＆ Ｐｏｌｙｓｏｒｂａｔｅ ８０：和光純薬工業株式会社製）１５ｍＬを加えて均一化し、３７℃で２日間培養した後、コロニー数７０～３００の範囲にあるものを選んでコロニーをカウントして生存菌数を求め、初菌数の対数値と試験後の生存菌数の対数値との差を殺菌数とした。
"Sterilization power evaluation"
The bactericidal / antibacterial composition has a copper concentration of 0% by mass in Comparative Example, which was adjusted above (A-1), (B-1), (C-1), (D-1), (E). -1) Take 8.9 mL of the solution of (F-1) as a test solution, add 1 mL of dilute hydrochloric acid with pH 3.0 to each test solution, and add 100 cells / mL to each test solution. 0.1 mL of the E. coli mother liquor (IFO3972) adjusted to the above was added, and the mixture was uniformly stirred. After 10 minutes, 1 mL was collected and added to 9 mL of SCDLP medium (Soybean-Casein Disease Brost with Lectin & Polysorbate 80: manufactured by Wako Pure Chemical Industries, Ltd.) to prepare a 10-fold diluted solution. The operation of further diluting the obtained diluted solution 10-fold was repeated 4 times to obtain a dilution of 10-fold to 100,000-fold. 1.0 mL of each of these diluted solutions is collected in a petri dish, homogenized by adding 15 mL of SCDLP agar medium (Soybean-Casein Disease Age Lectin & Polysorbate 80: manufactured by Wako Pure Chemical Industries, Ltd.), and cultured at 37 ° C. for 2 days. After that, select those in the range of 70 to 300 colonies, count the colonies to obtain the number of surviving bacteria, and determine the difference between the logarithmic value of the initial bacterial count and the logarithmic value of the viable cell count after the test as the sterilization number. did.
（殺菌力評価基準）
比較例の場合と比較して、以下の４段階で殺菌力を評価した。
・大腸菌に対する抗菌効果基準
×：殺菌数１桁未満。
△：殺菌数２桁未満。
○：殺菌数２桁以上だが、全滅には至らない。
◎：残存菌数０（全滅）。
結果を表１に示す。
(Criteria for evaluating bactericidal activity)
The bactericidal activity was evaluated in the following four stages as compared with the case of the comparative example.
・ Antibacterial effect standard against E. coli ×: Number of sterilization is less than one digit.
Δ: The number of sterilization is less than 2 digits.
◯: The number of sterilization is 2 digits or more, but it does not lead to annihilation.
⊚: Number of residual bacteria is 0 (annihilation).
The results are shown in Table 1.
実施例１－２
歯周病患者１０人に対して１２５０ｐｐｍのエチレンジアミン四酢酸（ＥＤＴＡ）銅キレート錯体水溶液にて、朝夕２回、洗口して２週間後の経過を診た。
Example 1-2
Ten patients with periodontal disease were washed with 1250 ppm ethylenediaminetetraacetic acid (EDTA) copper chelate complex aqueous solution twice in the morning and evening, and the progress was examined 2 weeks later.
結果、すべての患者で改善がみられた。
効果（改善） 判定
◎：大いにある → ８名
○：あり → １名
△：有無判定困難 → １名
×：なし → ０名
また副反応は０名でした。
As a result, improvement was seen in all patients.
Effect (improvement) Judgment ◎: Greatly present → 8 people ○: Yes → 1 person △: Presence / absence judgment difficult → 1 person ×: None → 0 people And no side reaction.
実施例２
＜Ｎ－（２－ヒドロキシエチル）エチレンジアミン－Ｎ，Ｎ’，Ｎ’－三酢酸（ＨＥＤＴＡ）銅キレート錯体水溶液作成＞
Ｎ－（２－ヒドロキシエチル）エチレンジアミン－Ｎ，Ｎ’，Ｎ’－三酢酸三ナトリウム二水和物（東京化成工業株式会社製）８．１６ｇをイオン交換水にて１Ｌに溶解する。該溶液を有限会社エルアンドアール製の銅イオン水生成器「銅しましょ」にて７時間通電して、２４時間放置後、ろ過し、１５００ｐｐｍの銅－ＨＥＤＴＡキレート水溶液を１Ｌ作成。
Example 2
<Preparation of N- (2-hydroxyethyl) ethylenediamine-N, N', N'-triacetic acid (HEDTA) copper chelate complex aqueous solution>
8.16 g of N- (2-hydroxyethyl) ethylenediamine-N, N', N'-trisodium triacetate dihydrate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) is dissolved in 1 L with ion-exchanged water. The solution was energized with a copper ion water generator "Copper Shimasho" manufactured by L & R Co., Ltd. for 7 hours, left for 24 hours, and then filtered to prepare 1 L of a 1500 ppm copper-HEDTA chelate aqueous solution.
上記１５００ｐｐｍの銅－ＨＥＤＴＡキレート水溶液を用いて下記の濃度に調整し作成する。
銅濃度として、
（Ａ－２）３００ｐｐｍは、
該銅－ＨＥＤＴＡキレート水溶液を５倍に希釈し１００ｍｌとする溶液。
（Ｂ－２）５００ｐｐｍは、
該銅－ＨＥＤＴＡキレート水溶液を３倍に希釈し１００ｍｌとする溶液。
（Ｃ－２）７５０ｐｐｍは、
該銅－ＨＥＤＴＡキレート水溶液を２倍に希釈し１００ｍｌとする溶液。
（Ｄ－２）１０００ｐｐｍは、
該銅－ＨＥＤＴＡキレート水溶液を１．５倍に希釈し１００ｍｌとする溶液。
（Ｅ－２）１２５０ｐｐｍは、
該銅－ＨＥＤＴＡキレート水溶液を１．２倍に希釈し１００ｍｌとする溶液。
（Ｆ－２）１５００ｐｐｍは、
該銅－ＨＥＤＴＡキレート水溶液を１００ｍｌとする溶液。
をそれぞれ作成した。
It is prepared by adjusting the concentration to the following using the above 1500 ppm copper-HEDTA chelate aqueous solution.
As a copper concentration
(A-2) 300 ppm is
A solution obtained by diluting the copper-HEDTA chelate aqueous solution 5-fold to make 100 ml.
(B-2) 500 ppm is
A solution obtained by diluting the copper-HEDTA chelate aqueous solution 3-fold to 100 ml.
(C-2) 750 ppm is
A solution obtained by diluting the copper-HEDTA chelate aqueous solution twice to make 100 ml.
(D-2) 1000ppm is
A solution obtained by diluting the copper-HEDTA chelate aqueous solution 1.5 times to make 100 ml.
(E-2) 1250 ppm is
A solution obtained by diluting the copper-HEDTA chelate aqueous solution 1.2 times to make 100 ml.
(F-2) 1500 ppm is
A solution containing 100 ml of the copper-HEDTA chelate aqueous solution.
Was created respectively.
＜ｐＨ３．０の希塩酸作成＞
ｐＨメーターで測定しながら、１００ｍＬのイオン交換水に１Ｎの塩酸をパスツールピペットで１滴ずつ入れていきｐＨ３．０の塩酸を作成する。
<Making dilute hydrochloric acid with pH 3.0>
While measuring with a pH meter, add 1N hydrochloric acid to 100 mL of ion-exchanged water drop by drop with a Pasteur pipette to make hydrochloric acid with a pH of 3.0.
大腸菌は、酸に対して非常に耐性が高い、そのため酸性下の殺菌力評価に大腸菌を用いた。 Escherichia coli is extremely resistant to acid, so Escherichia coli was used to evaluate the bactericidal activity under acidic conditions.
「殺菌力評価」
殺菌・抗菌用組成物が、銅濃度といて、比較例は０質量％、上記で調整した（Ａ－２）
、（Ｂ－２）、（Ｃ－２）、（Ｄ－２）、（Ｅ－２）、（Ｆ－２）の溶液から試験液として８．９ｍＬをそれぞれ取り、ｐＨ３．０の希塩酸１ｍＬを各試験液に加え、さらに各試験液へ菌数が１００個／ｍＬとなるように調整された大腸菌母液（ＩＦＯ３９７２）０．１ｍＬを添加し、均一に攪拌した。１０分後に１ｍＬ採取し、９ｍＬのＳＣＤＬＰ培地（Ｓｏｙｂｅａｎ－Ｃａｓｅｉｎ Ｄｉｇｅｓｔ Ｂｒｏｔｈ ｗｉｔｈ Ｌｅｃｔｉｎ ＆ Ｐｏｌｙｓｏｒｂａｔｅ ８０：和光純薬工業株式会社製）に加え、１０倍希釈液とした。得られた希釈液をさらに１０倍に希釈する操作を４回繰り返し、１０倍から１０００００倍の希釈を得た。これら各希釈液から１．０ｍＬをシャーレに採取し、ＳＣＤＬＰ寒天培地（Ｓｏｙｂｅａｎ－Ｃａｓｅｉｎ Ｄｉｇｅｓｔ Ａｇｅｒ ｗｉｔｈ Ｌｅｃｔｉｎ ＆ Ｐｏｌｙｓｏｒｂａｔｅ ８０：和光純薬工業株式会社製）１５ｍＬを加えて均一化し、３７℃で２日間培養した後、コロニー数７０～３００の範囲にあるものを選んでコロニーをカウントして生存菌数を求め、初菌数の対数値と試験後の生存菌数の対数値との差を殺菌数とした。
"Evaluation of bactericidal activity"
The bactericidal / antibacterial composition had a copper concentration of 0% by mass in Comparative Example, which was adjusted above (A-2).
, (B-2), (C-2), (D-2), (E-2), (F-2), take 8.9 mL as a test solution, and add 1 mL of dilute hydrochloric acid with pH 3.0. In addition to each test solution, 0.1 mL of Escherichia coli mother liquor (IFO3972) adjusted to have a bacterial count of 100 cells / mL was further added to each test solution, and the mixture was uniformly stirred. After 10 minutes, 1 mL was collected and added to 9 mL of SCDLP medium (Soybean-Casein Disease Brost with Lectin & Polysorbate 80: manufactured by Wako Pure Chemical Industries, Ltd.) to prepare a 10-fold diluted solution. The operation of further diluting the obtained diluted solution 10-fold was repeated 4 times to obtain a dilution of 10-fold to 100,000-fold. 1.0 mL of each of these diluted solutions is collected in a petri dish, homogenized by adding 15 mL of SCDLP agar medium (Soybean-Casein Disease Age Lectin & Polysorbate 80: manufactured by Wako Pure Chemical Industries, Ltd.), and cultured at 37 ° C. for 2 days. After that, select those in the range of 70 to 300 colonies, count the colonies to obtain the number of surviving bacteria, and determine the difference between the logarithmic value of the initial bacterial count and the logarithmic value of the viable cell count after the test as the sterilization number. did.
（殺菌力評価基準）
比較例の場合と比較して、以下の４段階で殺菌力を評価した。
・大腸菌に対する抗菌効果基準
×：殺菌数１桁未満。
△：殺菌数２桁未満。
○：殺菌数２桁以上だが、全滅には至らない。
◎：残存菌数０（全滅）。
結果を表２に示す。
(Criteria for evaluating bactericidal activity)
The bactericidal activity was evaluated in the following four stages as compared with the case of the comparative example.
・ Antibacterial effect standard against E. coli ×: Number of sterilization is less than one digit.
Δ: The number of sterilization is less than 2 digits.
◯: The number of sterilization is 2 digits or more, but it does not lead to annihilation.
⊚: Number of residual bacteria is 0 (annihilation).
The results are shown in Table 2.
実施例２－２
歯周病患者１０人に対して１２５０ｐｐｍのＮ－（２－ヒドロキシエチル）エチレンジアミン－Ｎ，Ｎ’，Ｎ’－三酢酸（ＨＥＤＴＡ）銅キレート錯体水溶液にて、朝夕２回、洗口して２週間後の経過を診た。
Example 2-2
For 10 patients with periodontal disease, wash the mouth twice in the morning and evening with 1250 ppm N- (2-hydroxyethyl) ethylenediamine-N, N', N'-triacetic acid (HEDTA) copper chelate complex aqueous solution 2 I examined the progress after a week.
結果、すべての患者で改善がみられた。
効果（改善） 判定
◎：大いにある → ６名
○：あり → ２名
△：有無判定困難 → ２名
×：なし → ０名
また副反応は０名でした。
As a result, improvement was seen in all patients.
Effect (improvement) Judgment ◎: Greatly present → 6 people ○: Yes → 2 people △: Difficult to judge presence / absence → 2 people ×: None → 0 people And 0 side reactions.
本発明によれば、エチレンジアミン四酢酸（ＥＤＴＡ）銅キレート錯体、Ｎ－（２－ヒドロキシエチル）エチレンジアミン－Ｎ，Ｎ’，Ｎ’－三酢酸（ＨＥＤＴＡ）銅キレート錯体が、人体に対して抗生物質を用いることなく殺菌・抗菌することができ、そのため耐性菌を増やすことがなく、副作用が少なくない殺菌・抗菌組成物を提供することができる。 According to the present invention, ethylenediaminetetraacetic acid (EDTA) copper chelate complex and N- (2-hydroxyethyl) ethylenediamine-N, N', N'-triacetic acid (HEDTA) copper chelate complex are antibiotics for the human body. It is possible to provide a bactericidal / antibacterial composition without increasing the number of resistant bacteria and having many side effects.
Claims (2)
（式中、Ｘ１～Ｘ４は同一でも異なっていてもよく、それぞれ水素原子、アルカリ金属、アルカリ土類金属、カチオン性アンモニウム基からなる群より選ばれる１種を表している。）
（式中、Ｙはアルキル基、カルボキシル基、スルホ基、アミノ基、水酸基、または水素原子を表し、Ｘ５～Ｘ７は同一でも異なっていてもよく、それぞれ水素原子、アルカリ金属、アルカリ土類金属、カチオン性アンモニウム基からなる群より選ばれる１種を表し、ｎは０から５の整数を表す。） A composition for sterilization and sterilization, wherein the chelating agent with copper ions is contained as a copper chelate complex in at least one of the following general formulas (I) or (II).
(In the formula, X1 to X4 may be the same or different, and represent one selected from the group consisting of a hydrogen atom, an alkali metal, an alkaline earth metal, and a cationic ammonium group, respectively.)
(In the formula, Y represents an alkyl group, a carboxyl group, a sulfo group, an amino group, a hydroxyl group, or a hydrogen atom, and X5 to X7 may be the same or different, and hydrogen atom, alkali metal, and alkaline earth metal, respectively. Represents one selected from the group consisting of cationic ammonium groups, where n represents an integer from 0 to 5).
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| JP2004051635A (en) * | 2002-07-18 | 2004-02-19 | Rohm & Haas Co | Stabilized haloalkynyl microbicide composition |
| AU2004205086A1 (en) * | 2004-08-17 | 2006-03-09 | Unisearch Limited | Metal ion chelate complexes and use thereof |
| JP2006526664A (en) * | 2003-06-04 | 2006-11-24 | タイコ・ヘルスケアー・グループ・エルピー | Bactericidal composition, method and system |
| JP2013170160A (en) * | 2012-02-22 | 2013-09-02 | Adeka Corp | Peptide-containing antimicrobial composition |
| WO2017079589A1 (en) * | 2015-11-05 | 2017-05-11 | Board Of Regents, The University Of Texas System | Antimicrobial solutions with enhanced stability |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2004051635A (en) * | 2002-07-18 | 2004-02-19 | Rohm & Haas Co | Stabilized haloalkynyl microbicide composition |
| JP2006526664A (en) * | 2003-06-04 | 2006-11-24 | タイコ・ヘルスケアー・グループ・エルピー | Bactericidal composition, method and system |
| AU2004205086A1 (en) * | 2004-08-17 | 2006-03-09 | Unisearch Limited | Metal ion chelate complexes and use thereof |
| JP2013170160A (en) * | 2012-02-22 | 2013-09-02 | Adeka Corp | Peptide-containing antimicrobial composition |
| WO2017079589A1 (en) * | 2015-11-05 | 2017-05-11 | Board Of Regents, The University Of Texas System | Antimicrobial solutions with enhanced stability |
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