JP2008050276A - 抗菌剤 - Google Patents
抗菌剤 Download PDFInfo
- Publication number
- JP2008050276A JP2008050276A JP2006225816A JP2006225816A JP2008050276A JP 2008050276 A JP2008050276 A JP 2008050276A JP 2006225816 A JP2006225816 A JP 2006225816A JP 2006225816 A JP2006225816 A JP 2006225816A JP 2008050276 A JP2008050276 A JP 2008050276A
- Authority
- JP
- Japan
- Prior art keywords
- benzotriazole
- silver
- water
- antibacterial
- compound
- 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.)
- Granted
Links
- 239000004599 antimicrobial Substances 0.000 title abstract 4
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 53
- 229940100890 silver compound Drugs 0.000 claims abstract description 33
- IBWXIFXUDGADCV-UHFFFAOYSA-N 2h-benzotriazole;silver Chemical compound [Ag].C1=CC=C2NN=NC2=C1 IBWXIFXUDGADCV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000010949 copper Substances 0.000 claims abstract description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052802 copper Inorganic materials 0.000 claims abstract description 11
- 239000011701 zinc Substances 0.000 claims abstract description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 66
- 230000000844 anti-bacterial effect Effects 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 239000012964 benzotriazole Substances 0.000 claims description 42
- 239000003960 organic solvent Substances 0.000 claims description 28
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 25
- 239000003973 paint Substances 0.000 claims description 23
- 239000005749 Copper compound Substances 0.000 claims description 21
- 239000012046 mixed solvent Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000002245 particle Substances 0.000 claims description 17
- 150000003379 silver compounds Chemical class 0.000 claims description 17
- 150000001880 copper compounds Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- HEUUBWQOIYCBCI-UHFFFAOYSA-N 2h-benzotriazole;copper Chemical compound [Cu].C1=CC=CC2=NNN=C21 HEUUBWQOIYCBCI-UHFFFAOYSA-N 0.000 claims description 10
- 239000011342 resin composition Substances 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 5
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- 229920005989 resin Polymers 0.000 abstract description 41
- 239000011347 resin Substances 0.000 abstract description 41
- 229910052709 silver Inorganic materials 0.000 abstract description 30
- 239000004332 silver Substances 0.000 abstract description 30
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- 238000002845 discoloration Methods 0.000 abstract description 20
- 229910021536 Zeolite Inorganic materials 0.000 abstract description 9
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract description 9
- 239000010457 zeolite Substances 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 6
- 125000005843 halogen group Chemical group 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 238000013329 compounding Methods 0.000 abstract description 2
- 239000008187 granular material Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 35
- 239000007788 liquid Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 238000012360 testing method Methods 0.000 description 23
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 22
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- 238000013268 sustained release Methods 0.000 description 11
- 239000012730 sustained-release form Substances 0.000 description 11
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 9
- 238000002441 X-ray diffraction Methods 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 238000005342 ion exchange Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 8
- 239000011630 iodine Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- FMBAYMGUEFDJRH-UHFFFAOYSA-N silver;2h-benzotriazole Chemical compound [Ag+].C1=CC=C2NN=NC2=C1 FMBAYMGUEFDJRH-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 4
- 238000007922 dissolution test Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 4
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
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- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
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- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
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- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
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- 230000001771 impaired effect Effects 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
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Landscapes
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Abstract
【解決手段】本発明の抗菌剤は下記一般式(1)で表されるベンゾトリアゾール銀化合物を含有することを特徴とする。粒子径が0.05〜50μmの粉粒体であり、水分が5重量%以下に調整されていることが好ましい。更に、銅含有化合物又は/及び亜鉛含有化合物を含有することも好ましい。
【化1】
【選択図】なし
Description
以下、前記一般式(3)で表わされるベンゾトリアゾール銅化合物の製造方法について説明する。前記一般式(4)で表されるベンゾトリアゾール化合物の式中のR3、R4は前記一般式(3)の式中のR3及びR4に相当する基であり、また、式中のp2及びq2は0〜2の整数を示す。一方の水溶性銅化合物としては、例えば、硫酸銅、過塩素酸銅、塩化銅、テトラフルオロホウ酸銅、ギ酸銅、塩素酸銅、硝酸銅等を使用することができる。なお、これら水溶性銅化合物としては含水塩であっても無水塩であってもよい。使用できる有機溶媒としては、メタノール、エタノール、プロパノール、ブタノール、ペンタノール等の炭素数1〜5のアルコール、アセトン等が挙げられ、この中、アルコールが結晶性が良いものが得られる点で特に好ましい。
合成または天然脂肪酸及びそれらのアルカリ金属塩またはアルカリ土類金属塩、亜鉛塩、アルミニウム塩など。例えばステアリン酸、オレイン酸等及びそれらのナトリウム塩やアンモニウム塩等が挙げられる。
例えば、エルカ酸アミド、オレイルパルミトアマイド、ステアリルエルカミド、2−ステアロミドエチルステアレート、エチレンビス脂肪酸アマイド、N,N’−オレオイルステアリルエチレンジアミン、N,N’−ビス(2ヒドロキシエチル)アルキル(C12〜C18)アマイド、N,N’−ビス(ヒドロキシエチル)ラウロアマイド、脂肪酸ジエタノールアミン等が挙げられる。
例えば、ステアリン酸n−ブチル、水添ロジンメチルエステル、セバチン酸ジブチル(n−ブチル)、セバチン酸ジオクチル(2−エチルヘキシル、n−オクチル共)、グリセリン脂肪酸エステル、ペンタエリスリトールテトラステアレート、ポリエチレングリコール脂肪酸エステル、ポリエチレングリコール脂肪酸ジエステル、ジエチレングリコール脂肪酸ジエステル、プロピレングリコール脂肪酸ジエステル等が挙げられる。
例えば、スパームアセチワックス、モンタンワックス、カルナバワックス、蜜蝋、木蝋、ラノリン、ポリエチレンワックス、ポリプロピレンワックス、エポキシ変性ポリエチレンワックス、石油系ワックス等が挙げられる。
融点或いは軟化点が40〜200℃、特に70〜160℃である各種樹脂、例えば、エポキシ樹脂、キシレン−ホルムアルデヒド樹脂、スチレン系樹脂、クロマン−インデン樹脂、その他の石油樹脂、アルキッド樹脂、エチレン−酢酸ビニル共重合体、エチレン−アクリル酸エステル共重合体、低融点アクリル樹脂、ポリビニルブチラール、低融点コポリアミド、低融点コポリエステル等を挙げることができる。
(1)シラン系カップリング剤:
γ−アミノプロピルトリエトキシシラン、N−β(アミノエチル)γ−アミノプロピルトリメトキシシラン、N−フェニル−γ−アミノプロピルトリメトキシシラン、N−β(アミノエチル)γ−アミノプロピルメチルジメトキシシラン、などのアミノ系シラン。γ−メタクリロキシプロピルトリメトキシシラン、などのメタクリロキシ系シラン。
ビニルトリス(βメトキシエトキシ)シラン、ビニルトリエトキシシラン、ビニルトリメトキシシラン、ビニルトリクロルシラン、などのビニル系シラン。
β−(3,4エポキシシクロヘキシル)エチルトリメトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルメチルジエトキシシラン、などのエポキシ系シラン。γ−メルカプトプロピルトリメトキシシラン、などのメルカプト系シラン。γ−クロロプロピルトリメトキシシラン、などのクロロプロピル系シラン。
イソプロピルトリイソステアロイルチタネート、イソプロピルトリドデシルベンゼンスルホニルチタネート、イソプロピルトリス(ジオクチルバイロホスフェート)チタネート、テトラオクチルビス(ジトリデシルホスファイト)チタネート、テトラ(2,2−ジアリルオキシメチル−1−ブチル)ビス(ジ−トリデシル)ホスファイトチタネート、ビス(ジオクチルバイロホスフェート)オキシアセテートチタネート、ビス(ジオクチルバイロホスフェート)エチレンチタネート、イソプロピルトリオクタノイルチタネート、イソプロピルジメタクリルイソステアロイルチタネート、イソプロピルイソステアロイルジアクリルチタネート、イソプロピルトリ(ジオクチルホスフェート)チタネート、イソプロピルトリクミルフェニルチタネート、イソプロピルトリ(N−アミノエチル−アミノエチル)チタネート、ジクミルフェニルオキシアセテートチタネート、ジイソステアロイルエチレンチタネート、ポリジイソプロピルチタネート、テトラノルマルブチルチタネート、ポリジノルマルブチルチタネート。
(a)組成分析:
抗菌性金属はICP(Varian製LIBERTYII型)によって定量した。ベンゾトリアゾールは、全有機炭素計(島津製作所製、TOC−5000A)により炭素量を測定し、分子量に換算して定量した。
(b)粒子の形状:
SEM(日立製作所製S−4500型)により観察した。
(c)X線回折パターン(XRD):
X線回折装置(理学製RINT2400型)を用いた。
硝酸銀20.0gを水−エタノール(重量比10:1)混合溶媒220gに溶解し、A1液とした。硝酸銀のモル数に対して1倍当量のベンゾトリアゾール(C6H5N3;純正化学製 試薬)14.0gを水−エタノール(重量比10:1)混合溶媒220gに溶解し、B1液とした。A1液にB1液を徐々に添加し25℃で3時間反応を行った。発生した沈殿物をろ過および水洗し、50℃で10時間乾燥することによりベンゾトリアゾール銀(I)を得た。得られたベンゾトリアゾール銀(I)について元素分析を行った結果、組成はAg(C6H5N3)1.10であった。また、110℃乾燥減量による水分は0.85%であった。XRDの測定結果を図1および表1に記載した。また、これのSEM写真を図4に示した。SEM写真では、粒子の形状は板状結晶であり、その粒子径は厚さが0.1〜0.2μmであり、平面が0.5〜5μmであり平均して2μmくらいである。
硝酸銀20.0gを水−エタノール(重量比5:1)混合溶媒240gに溶解し、A1液とした。硝酸銀のモル数に対して2倍当量のベンゾトリアゾール(C6H5N3;純正化学製 試薬)28.1gを水−エタノール(重量比5:1)混合溶媒240gに溶解し、B1液とした。A1液にB1液を徐々に添加し20℃で6時間反応を行った。発生した沈殿物をろ過および水洗し、50℃で24時間乾燥することによりベンゾトリアゾール銀(I)を得た。得られたベンゾトリアゾール銀(I)について元素分析を行った結果、組成はAg(C6H5N3)1.21であった。また、110℃乾燥減量による水分は2%であった。XRDの測定結果を図2および表2に記載した。また、これのSEM写真を図5に示した。SEM写真では、粒子の形状は丸みのある立方体乃至長方体に近い形の定まらない結晶であり、その粒子径は0.1〜1.0μmであり、平均して0.3μmくらいである。
硫酸銅(II)五水和物20.0gを水−エタノール(重量比4:1)混合溶媒125gに溶解し、A2液とした。硫酸銅のモル数に対して2倍当量のベンゾトリアゾール(C6H5N3;純正化学製 試薬)19.1gを水−エタノール(重量比4:1)混合溶媒125gに溶解し、B2液とした。A2液にB2液を徐々に添加し25℃で3時間反応を行った。発生た沈殿物をろ過および水洗し、50℃で24時間乾燥することによりジベンゾトリアゾール銅を得た。得られたジベンゾトリアゾール銅(II)について元素分析を行った結果、組成はCu(C6H5N3)2.00であった。XRDの測定結果を図3および表3に記載した。また、これのSEM写真を図6に示した。SEM写真では、粒子の形状は球に近いが凝集しており、棒状につながったものもある。一次粒子の粒子径は0.03〜0.3μmであり、平均して0.1μmくらいである。
本実施例では、抗菌成分の徐放性の確認を行った。実施例1で得られたベンゾトリアゾール銀粉末5gを、純水45gに投入し24時間攪拌を続けた。その後、ろ過分離して粉末を取り除き、水を回収した。水を化学分析したところ水中の銀の濃度は5ppmであった。さらに、溶出試験を35回繰り返し、35回目の溶出試験液についても水中の銀の濃度を測定した。35回目の水中銀濃度は0.16ppmであった。
ガラスビーカーを用いて、エタノール40重量部に23.8重量部のベンゾトリアゾール(C6H5N3;純正化学製 試薬)を加え、10分間攪拌を行って溶解した。次に17重量部の硝酸銀と160重量部の純水を加えた。硝酸銀の溶解と白色沈殿の生成が同時に進行し、硝酸銀は3時間で溶解し、その後も16時間攪拌を続けた、白色沈殿をろ過、水洗して50℃で24時間乾燥した。こうして白色の結晶を得た。この結晶はXRDではベンゾトリアゾールおよびAgNO3の存在は認められず、組成分析及びTG/DTA測定によりビス(ベンゾトリアゾール)銀硝酸([Ag(C6H5N3)2 +NO3 -]の結晶であることを確認した。
実施例1で得られた抗菌剤(A)、実施例2で得られた抗菌剤(B)、および実施例3で得られた抗菌剤と実施例1の抗菌剤を同量混合した抗菌剤(C)について、抗菌性試験を行った。試験結果を以下の表4に示す。試験方法は以下の通りである。
(1)Escherichia coli NBRC 3301 (大腸菌)
(2)Pseudomonas aeruginosa NBRC 13275 (緑膿菌)
(3)Aspergillus niger IFO 6341 (クロコウジカビ)
(4)Penicillium citrinum IFO 6352 (アオカビ)
NA培地:普通寒天培地[栄研化学株式会社]
NB培地:肉エキスを0.2%添加した普通ブイヨン培地[栄研化学株式会社]
PDA培地:ポテトデキストロース寒天培地[栄研化学株式会社]
SDA培地:サブロー寒天培地[栄研化学株式会社]
a)試験菌(1)及び(2)
NA培地で37℃±1℃、24〜48時間培養した試験菌をNB培地に接種し、37℃±1℃、22〜26時間培養した。この培養液をNB培地を用いて1ml当たりの菌数が106〜107となるように調整し、菌液とした。
b)試験菌(3)及び(4)
PDA培地で25℃±1℃、7日間培養後、形成された胞子を0.05%ポリソルベート80添加生理食塩水に懸濁させ、1ml当たりの胞子数が106〜107となるように調整し、菌液とした。
試験菌(1)及び(2)はNA培地、試験菌(3)及び(4)はSDA培地150mlに菌液10mlをそれぞれ添加、混合し、これらをシャーレに15ml分注して固化させた。さらに、シャーレを室温で30分間放置して培地表面を乾燥させた後、乾熱滅菌(180℃、30分間)した円筒ガラス(直径:12mm)で穴を開け、これを試験用平板培地とした。
検体を試料とした。試験用平板培地中央の穴全体に試料を充填し、試験菌(1)及び(2)は37℃±1℃、24時間、試験菌(3)及び(4)は25℃±1℃、7日間培養後、試料の周囲のハローの有無を肉眼観察により判定した。なお、菌液の生菌数を試験菌(1)及び(2)はNA培地を用いた混釈平板培養法(37℃±1℃、2日間培養)、試験菌(3)及び(4)はSDA培地を用いた混釈平板培養法(25℃±1℃、7日間培養)により測定し、試験用平板培地1mlあたりの菌濃度に換算した。
本実施例及び比較例では塩化ビニル製シートを製造した。実施例6では、抗菌剤として、実施例1で作成したベンゾトリアゾール銀(I)を2重量部配合した。参考例2では、参考例1で得られたビス(ベンゾトリアゾール)銀硝酸を2重量部配合した。比較例1では、抗菌剤は配合しなかった。比較例2では、市販の抗菌剤である銀イオン交換ゼオライトを2重量部配合した。
塩化ビニルシートの試験片を蛍光灯(60W×2本)の直下1mの位置に置き、30日間暴露後の変色度を下記の評点で評価した。
○:変色しない。
△:やや変色した。
×:激しく変色した。
抗菌製品の抗菌力評価試験法(抗菌製品技術協議会)で制定された方法に準拠して評価した。
試験方法:フィルム密着法
評価菌種:大腸菌、黄色ブドウ球菌
菌液接種時間:24時間
評価:抗菌剤添加樹脂成形品に菌液を接種して、フィルムでカバーして24時間後の菌数を測定し、以下の基準で評価する。
○:接種菌液からの減少率が1/100以上。
△:接種菌液からの減少率が1/10以上、1/100未満。
×:接種菌液からの減少率が1/10未満。
Claims (14)
- 下記一般式(1)で表されるベンゾトリアゾール銀化合物を含有することを特徴とする抗菌剤。
- ベンゾトリアゾール銀化合物が水と有機溶媒との混合溶媒中で下記一般式(2)で表わされるベンゾトリアゾール化合物と水溶性銀化合物との反応を行って生成されたものであることを特徴とする請求項1記載の抗菌剤。
- ベンゾトリアゾール銀化合物がベンゾトリアゾール銀であることを特徴とする請求項1記載の抗菌剤。
- 粒子径が0.05〜50μmの粉粒体であり、水分が5重量%以下に調整されていることを特徴とする請求項1記載の抗菌剤。
- 更に、銅含有化合物又は/及び亜鉛含有化合物を含有することを特徴とする請求項1記載の抗菌剤。
- 銅含有化合物が下記一般式(3)で表わされることを特徴とする請求項5記載の抗菌剤。
- 水と有機溶媒との混合溶媒中で下記一般式(2)で表わされるベンゾトリアゾール化合物と水溶性銀化合物との反応を行うことを特徴とする下記一般式(1)で表わされる抗菌性ベンゾトリアゾール銀化合物の製造方法。
- 有機溶媒がアルコールである請求項7記載の抗菌性ベンゾトリアゾール銀化合物の製造方法。
- 下記一般式(3)で表わされることを特徴とする抗菌性ベンゾトリアゾール銅化合物。
- 水と有機溶媒との混合溶媒中で下記一般式(4)で表わされるベンゾトリアゾール化合物と水溶性銅化合物との反応を行うことを特徴とする下記一般式(3)で表わされる抗菌性ベンゾトリアゾール銅化合物の製造方法。
- 請求項1ないし6の何れかに記載の抗菌剤を含有する化粧料組成物。
- 請求項1ないし6の何れかに記載の抗菌剤を含有する樹脂組成物。
- 請求項1ないし6の何れかに記載の抗菌剤を含有する塗料。
- 請求項1ないし6の何れかに記載の抗菌剤を含有する植物用殺菌剤。
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WO2009041548A1 (ja) * | 2007-09-28 | 2009-04-02 | Nippon Chemical Industrial Co., Ltd | 抗菌剤 |
JP2011190220A (ja) * | 2010-03-16 | 2011-09-29 | Nitto Boseki Co Ltd | 抗菌防かび剤 |
JP2017137275A (ja) * | 2016-02-05 | 2017-08-10 | 大成建設株式会社 | 抗微生物部材 |
CN112048084A (zh) * | 2020-08-21 | 2020-12-08 | 浙江隆泰医疗科技股份有限公司 | 一种低温交联的聚乙烯醇复合抗菌肽材料的制备方法 |
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