JP3834655B2 - 抗菌性材料、及びその製造方法 - Google Patents
抗菌性材料、及びその製造方法 Download PDFInfo
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- JP3834655B2 JP3834655B2 JP2003417951A JP2003417951A JP3834655B2 JP 3834655 B2 JP3834655 B2 JP 3834655B2 JP 2003417951 A JP2003417951 A JP 2003417951A JP 2003417951 A JP2003417951 A JP 2003417951A JP 3834655 B2 JP3834655 B2 JP 3834655B2
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- Prior art keywords
- antibacterial
- silane compound
- ammonium chloride
- octadecyldimethyl
- trimethoxysilylpropyl
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- 230000000844 anti-bacterial effect Effects 0.000 title claims description 78
- 239000000463 material Substances 0.000 title claims description 48
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 38
- -1 silane compound Chemical class 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 28
- WSFMFXQNYPNYGG-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC WSFMFXQNYPNYGG-UHFFFAOYSA-M 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000919 ceramic Substances 0.000 claims description 10
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 101710196985 Antibacterial substance A Proteins 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 29
- 239000010936 titanium Substances 0.000 description 18
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 15
- 229910052719 titanium Inorganic materials 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 14
- 244000005700 microbiome Species 0.000 description 9
- 108090000765 processed proteins & peptides Proteins 0.000 description 9
- 125000003172 aldehyde group Chemical group 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- 230000003100 immobilizing effect Effects 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
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- 108090000623 proteins and genes Proteins 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 4
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 4
- 239000000645 desinfectant Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 208000031729 Bacteremia Diseases 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 101800004361 Lactoferricin-B Proteins 0.000 description 2
- 108010063045 Lactoferrin Proteins 0.000 description 2
- 102000010445 Lactoferrin Human genes 0.000 description 2
- 102000016943 Muramidase Human genes 0.000 description 2
- 108010014251 Muramidase Proteins 0.000 description 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 108010053775 Nisin Proteins 0.000 description 2
- NVNLLIYOARQCIX-MSHCCFNRSA-N Nisin Chemical compound N1C(=O)[C@@H](CC(C)C)NC(=O)C(=C)NC(=O)[C@@H]([C@H](C)CC)NC(=O)[C@@H](NC(=O)C(=C/C)/NC(=O)[C@H](N)[C@H](C)CC)CSC[C@@H]1C(=O)N[C@@H]1C(=O)N2CCC[C@@H]2C(=O)NCC(=O)N[C@@H](C(=O)N[C@H](CCCCN)C(=O)N[C@@H]2C(NCC(=O)N[C@H](C)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@H](CS[C@@H]2C)C(=O)N[C@H](CC(N)=O)C(=O)N[C@H](CCSC)C(=O)N[C@H](CCCCN)C(=O)N[C@@H]2C(N[C@H](C)C(=O)N[C@@H]3C(=O)N[C@@H](C(N[C@H](CC=4NC=NC=4)C(=O)N[C@H](CS[C@@H]3C)C(=O)N[C@H](CO)C(=O)N[C@H]([C@H](C)CC)C(=O)N[C@H](CC=3NC=NC=3)C(=O)N[C@H](C(C)C)C(=O)NC(=C)C(=O)N[C@H](CCCCN)C(O)=O)=O)CS[C@@H]2C)=O)=O)CS[C@@H]1C NVNLLIYOARQCIX-MSHCCFNRSA-N 0.000 description 2
- 206010029803 Nosocomial infection Diseases 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
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- 239000008280 blood Substances 0.000 description 2
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- 150000001718 carbodiimides Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
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- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 206010014665 endocarditis Diseases 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- CSSYQJWUGATIHM-IKGCZBKSSA-N l-phenylalanyl-l-lysyl-l-cysteinyl-l-arginyl-l-arginyl-l-tryptophyl-l-glutaminyl-l-tryptophyl-l-arginyl-l-methionyl-l-lysyl-l-lysyl-l-leucylglycyl-l-alanyl-l-prolyl-l-seryl-l-isoleucyl-l-threonyl-l-cysteinyl-l-valyl-l-arginyl-l-arginyl-l-alanyl-l-phenylal Chemical compound C([C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 CSSYQJWUGATIHM-IKGCZBKSSA-N 0.000 description 2
- CFFMZOZGXDAXHP-HOKBLYKWSA-N lactoferricin Chemical compound C([C@H](NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CSSC[C@@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](C)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CO)C(=O)N[C@H](C(N[C@H](C(=O)N1)[C@@H](C)O)=O)[C@@H](C)CC)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 CFFMZOZGXDAXHP-HOKBLYKWSA-N 0.000 description 2
- 235000021242 lactoferrin Nutrition 0.000 description 2
- 229940078795 lactoferrin Drugs 0.000 description 2
- 235000010335 lysozyme Nutrition 0.000 description 2
- 239000004325 lysozyme Substances 0.000 description 2
- 229960000274 lysozyme Drugs 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000004309 nisin Substances 0.000 description 2
- 235000010297 nisin Nutrition 0.000 description 2
- 208000028169 periodontal disease Diseases 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical group OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
- YYSCJLLOWOUSHH-UHFFFAOYSA-N 4,4'-disulfanyldibutanoic acid Chemical compound OC(=O)CCCSSCCCC(O)=O YYSCJLLOWOUSHH-UHFFFAOYSA-N 0.000 description 1
- 208000032484 Accidental exposure to product Diseases 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010017076 Fracture Diseases 0.000 description 1
- 206010067268 Post procedural infection Diseases 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 241000194019 Streptococcus mutans Species 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229960001040 ammonium chloride Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000010065 bacterial adhesion Effects 0.000 description 1
- 239000000560 biocompatible material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000011350 dental composite resin Substances 0.000 description 1
- 239000004053 dental implant Substances 0.000 description 1
- 239000005548 dental material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229960000587 glutaral Drugs 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- Materials For Medical Uses (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
アセトン、エーテルからなる群から選択される少なくとも1種であることを特徴とする。
(但し、R1、R2はアルキル基を示し、Rnは、(CH2)n(nは整数)で表したときのアルキル基を示す。)で表される。nは、整数で特に限定されない。したがって、nの数に関して、極度に疎水性が高くなった場合でも本発明に適用可能可能であり、かかる場合であっても、本発明の技術的範囲に属する。
Ti−NH2 + CHOR1 → Ti−N=C−R1 + H2O
である。アルデヒド基とカルボキシル基とを有する薬剤が、グリオキシル酸の場合R1がカルボキシル基(−COOH)となる。
Ti−NH2 + R2R3C=O → Ti−NH=C−R2R3
である。例えば、ケトンがアセトンジカルボン酸(CO(CH2COOH)2)の場合、R2R3が両方ともカルボキシル基である。
具体的な材料としては、例えば、修復材料、インプラント材料などで用いられる金属、ガラス(歯科用コンポジットレジン内のガラスフィラーも含む)、セラミックス等のほか、クラウン、ブリッジ、義歯、矯正用ブラケット、ワイヤーなどを挙げることができる。
本実施例においては、抗菌物質として、アンモニウムクロライドを用いて、抗菌性材料の効果について検討した。抗菌物質を有するシラン化合物として、具体的に、オクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライドを用いた。
抗菌物質を有するシラン化合物を含有するメタノール溶液を適宜、蒸留水、アセトン、エーテルなどで希釈し、最終濃度で約2〜20%とすることで、調整することができる。
次に、オクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライドを使用した場合の処理濃度と処理時間との関係を検討した。図3は、オクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライドを使用した場合の処理濃度と処理時間の関係を示す。この結果、抗菌処理としては、1%水溶液20分の処理で十分であることが判明した。
次に種々のシラン化合物を使用して、抗菌作用、具体的には、細菌類の付着阻害作用及び付着菌に対する抗菌作用について調べた。
Claims (5)
- 抗菌物質を有するシラン化合物としてオクタデシルトリメトキシシラン、又はオクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライドから選択された化合物を、表面に固定化したことを特徴とする抗菌性材料。
- 固定化が共有結合である請求項1記載の抗菌性材料。
- 抗菌性材料が、金属、セラミックス、シリカ又はガラスである請求項1又は2に記載の抗菌性材料。
- 抗菌物質を有するシラン化合物として、オクタデシルトリメトキシシラン、又はオクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロライドから選択された化合物を含有する溶媒を、金属、セラミックス、シリカ又はガラスの表面に処理することを特徴とする抗菌性材料の製造方法。
- 溶媒が、メタノール、アセトン、エーテルからなる群から選択される少なくとも1種である請求項4に記載の方法。
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Cited By (3)
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WO2011089840A1 (ja) | 2010-01-19 | 2011-07-28 | 株式会社テラモト | 表面多機能処理剤組成物 |
US10980236B2 (en) | 2014-11-04 | 2021-04-20 | Allied Bioscience, Inc. | Broad spectrum antimicrobial coatings comprising combinations of organosilanes |
US10993441B2 (en) | 2014-11-04 | 2021-05-04 | Allied Bioscience, Inc. | Antimicrobial coatings comprising organosilane homopolymers |
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JP4810150B2 (ja) * | 2005-07-22 | 2011-11-09 | 国立大学法人広島大学 | 抗菌剤水溶液及びその保存方法 |
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2003
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