JPH0580225B2 - - Google Patents
Info
- Publication number
- JPH0580225B2 JPH0580225B2 JP58104571A JP10457183A JPH0580225B2 JP H0580225 B2 JPH0580225 B2 JP H0580225B2 JP 58104571 A JP58104571 A JP 58104571A JP 10457183 A JP10457183 A JP 10457183A JP H0580225 B2 JPH0580225 B2 JP H0580225B2
- Authority
- JP
- Japan
- Prior art keywords
- latex
- antibacterial
- acid
- parts
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000126 latex Polymers 0.000 claims description 46
- 239000004816 latex Substances 0.000 claims description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 23
- 230000000844 anti-bacterial effect Effects 0.000 claims description 22
- -1 biguanide compound Chemical class 0.000 claims description 13
- 229940123208 Biguanide Drugs 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 229920006173 natural rubber latex Polymers 0.000 claims description 8
- 229920001059 synthetic polymer Polymers 0.000 claims description 6
- HTYFFCPFVMJTKM-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=C(Cl)C=C1 HTYFFCPFVMJTKM-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003242 anti bacterial agent Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 238000005054 agglomeration Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 150000004283 biguanides Chemical class 0.000 description 5
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229960003260 chlorhexidine Drugs 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000002459 sustained effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 230000002485 urinary effect Effects 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229940050410 gluconate Drugs 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- JGIZWNFPEUFBOA-UHFFFAOYSA-N 2-(6,6-diaminohexyl)-1-(diaminomethylidene)guanidine Chemical compound NC(N)CCCCCNC(=N)NC(N)=N JGIZWNFPEUFBOA-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241001156739 Actinobacteria <phylum> Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000286663 Ficus elastica Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 241001467460 Myxogastria Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 1
- 229960003333 chlorhexidine gluconate Drugs 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- GEAWFZNTIFJMHR-UHFFFAOYSA-N hepta-1,6-diene Chemical compound C=CCCCC=C GEAWFZNTIFJMHR-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- HJLHTTJLVALHOP-UHFFFAOYSA-N hexane;hydron;chloride Chemical compound Cl.CCCCCC HJLHTTJLVALHOP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical group NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 201000004537 pyelitis Diseases 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Materials For Medical Uses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
Description
本発明は、抗菌性ラテツクス組成物に関するも
のであり、その目的とするところは持続的な抗菌
活性を有する医療器具、衛生用品、食品製造用機
器又は備品等のラテツクス成型品を製造するに好
適な抗菌性ラテツクス組成物を提供するところに
ある。
従来から医療、検査あるいは食品分野において
は、種々雑多な細菌、放射菌、真菌、粘菌あるい
はウイルス等からの汚染や感染を防止するため
に、種々の殺菌消毒剤が用いられている。なかで
も１，６−ジ−（４−クロロフエニルビグアニド）
ヘキサン（別名クロルヘキシジンともいう。）に
代表されるビグアニド化合物は、広い範囲の微生
物に強力な殺菌力を有し、かつ人体に対する毒性
も低いところから、今日、数あるいは抗菌剤の中
でも最も広く使用されている殺菌消毒剤の一つで
ある。現在、これらは通常、水溶液（例えばクロ
ルヘキシジンのグリコン酸塩水溶液）として提供
されるため、医療器具等は使用に先立ちこの水溶
液に浸漬するか又はこの水溶液を噴霧することに
より一応、所期の目的は達せられている。
しかし、医療器具等を長期間にわたり使用する
場合には初期の消毒のみでは抗菌剤としての効力
が次第に低下ないし消失することは、我々が日常
しばしば経験するところでありその改善が強く望
まれている。
その最も有効な対策としてその使用過程におい
て、上記器具中より最小（発育）阻止濃度以上の
抗菌剤が一定量ずつ徐放されるシステムが考えら
れる。このようなシステムの実現のためには、抗
菌剤が均一かつ安定に分散したラテツクスを得、
このものを、例えば医療器具等に成型することが
必要であるが、ビグアニド化合物が均一かつ安定
に分散したラテツクスは、以下に述べるように、
これまでに得られていない。
まず、疎水性の天然ゴム又は合成高分子化合物
を水媒体中に分散させた高分子ラテツクスは、今
日、種々の有用な用途に用いられているが、通
常、これらラテツクス中にはラテツクス粒子の安
定な浮遊分散を助けるために各種界面活性剤や保
護コロイド等が含まれている。例えば天然ゴムラ
テツクスにおいては、その成分中に含まれる両性
電解質であるタンパク質がゴム粒子の表面に吸着
することにより一種の保護コロイド的な役割を果
たし、ラテツクス粒子の安定な分散を助けてい
る。また、天然ゴムラテツクスは、その中に含ま
れている酵素や細菌の作用で酸を生じて凝固しや
すいので、通常、これを防ぐため、0.5〜1.0％の
アンモニアが添加され、液はアルカリ性を保つて
いる。従つてゴム粒子は基本的には負に帯電する
ことにより、粒子間相互の静電気的な反撥力によ
り凝集することなく安定に浮遊分散していること
になる。また、合成高分子系ラテツクスにおいて
も重合前又は重合後にアニオン系あるいは／及び
ノニオン系界面活性剤が添加されており、実用的
には特別な事情がない限りカチオン系界面活性剤
が用いられている例は極めて少ない。一方、抗菌
剤としてのビグアニド化合物は、その化学構造か
らもわかるように、一分子内に正電荷と疎水性基
をもつカチオン型殺菌剤に属し、そのビグアニド
基は有機塩基の中でも最も強い塩基の一つであ
り、PKa値は約12と高く生理PH領域ではほとん
ど100％プロトン化しているものである。従つて、
例えば市販品であるクロルヘキシジンの易水溶性
の塩であるグルコン酸塩の水溶液にアニオン系界
面活性剤である石鹸等を加えることは、グルコン
酸の脱離又は置換をもたらし難水溶性の塩を形成
し、その結果、殺菌力の低下をもたらすため従来
より配合禁忌とされている。このことは第十改正
日本薬局法解説書（日本公定書協会、廣川書店、
1981）Ｃ−677にも記載されているとおりである。
以上のような技術的背景の下においては、例え
ばクロルヘキシジンのグルコン酸塩水溶液を天然
ゴムラテツクスに加えると、ラテツクス粒子の負
荷電が中和され、かつ不安定化される結果、ラテ
ツクスは直ちに不可逆的なゲル化を起こすため、
これらクロルヘキシジン系抗菌剤をラテツクスに
添加することは、従来、非常識とされ、それ以上
真剣に検討が加えられることはなかつた。
本発明者らは、持続的な抗菌活性を有するラテ
ツクスから成る医療器具、衛生用品、食品製造用
備品等を製造するに好適な抗菌性ラテツクス組成
物について鋭意検討を進めた結果、驚くべきこと
に難水溶性のビグアニド化合物又はその塩を上記
ラテツクス中に加えてもゲル化を起こすことなく
安定した抗菌性ラテツクス組成物が得られること
を見い出し、本発明に到達したものである。
すなわち本発明は、天然ゴムラテツクス又は合
成高分子系ラテツクスと、難水溶性のビグアニド
化合物又はその塩とを配合してなる抗菌性ラテツ
クス組成物である。
本発明におけるビグアニド化合物とは、下記の
一般式（Ｉ）又は（）で示されるものである。
The present invention relates to an antibacterial latex composition, and its purpose is to provide a latex composition suitable for producing latex molded products such as medical instruments, sanitary products, food manufacturing equipment, and fixtures having sustained antibacterial activity. An antibacterial latex composition is provided. Conventionally, various sterilizing disinfectants have been used in the medical, testing, and food fields to prevent contamination and infection from various types of bacteria, actinobacteria, fungi, slime molds, viruses, and the like. Among them, 1,6-di-(4-chlorophenyl biguanide)
Biguanide compounds, represented by hexane (also known as chlorhexidine), are the most widely used antibacterial agents today because they have strong bactericidal activity against a wide range of microorganisms and have low toxicity to the human body. It is one of the most popular disinfectants. Currently, these are usually provided as an aqueous solution (for example, an aqueous solution of chlorhexidine glyconate), and medical devices can be immersed in this aqueous solution or sprayed with this aqueous solution before use to achieve the intended purpose. has been achieved. However, when medical instruments are used for a long period of time, we often experience in our daily lives that the effectiveness of antibacterial agents gradually decreases or disappears if only the initial disinfection is performed, and there is a strong desire to improve this situation. The most effective countermeasure would be a system in which a constant amount of antibacterial agent at a minimum (growth) inhibitory concentration or higher is slowly released from the device during the use process. In order to realize such a system, it is necessary to obtain latex in which antibacterial agents are uniformly and stably dispersed.
It is necessary to mold this material into, for example, a medical device, etc., but the latex in which the biguanide compound is uniformly and stably dispersed can be
Haven't gotten it so far. First, polymer latexes in which hydrophobic natural rubber or synthetic polymer compounds are dispersed in an aqueous medium are used for a variety of useful purposes today, but these latexes usually contain a substance that stabilizes the latex particles. Contains various surfactants and protective colloids to aid in floating and dispersion. For example, in natural rubber latex, protein, which is an ampholyte contained in its components, is adsorbed onto the surface of rubber particles, thereby acting as a kind of protective colloid and helping to stabilize the dispersion of latex particles. In addition, natural rubber latex tends to generate acid and coagulate due to the action of enzymes and bacteria contained in it, so to prevent this, 0.5 to 1.0% ammonia is usually added to keep the liquid alkaline. ing. Therefore, since the rubber particles are basically negatively charged, they are stably suspended and dispersed without agglomeration due to the mutual electrostatic repulsion between the particles. Also, anionic and/or nonionic surfactants are added to synthetic polymer latexes before or after polymerization, and cationic surfactants are used in practice unless there are special circumstances. There are very few examples. On the other hand, as can be seen from its chemical structure, biguanide compounds as antibacterial agents belong to cationic fungicides that have a positive charge and a hydrophobic group in one molecule, and the biguanide group is one of the strongest organic bases. It has a high PKa value of about 12, and is almost 100% protonated in the physiological PH range. Therefore,
For example, adding soap, which is an anionic surfactant, to an aqueous solution of gluconate, which is a readily water-soluble salt of chlorhexidine, which is a commercially available product, causes the elimination or substitution of gluconic acid, forming a poorly water-soluble salt. However, as a result, it has been considered contraindicated in combination because it results in a decrease in bactericidal activity. This is explained in the 10th revised Japanese Pharmacy Law Explanation (Japan Official Publications Association, Hirokawa Shoten,
1981) C-677. Under the above technical background, for example, when an aqueous solution of chlorhexidine gluconate is added to natural rubber latex, the negative charge of latex particles is neutralized and destabilized, and as a result, the latex immediately becomes irreversible. To cause gelation,
Adding these chlorhexidine-based antibacterial agents to latex was conventionally considered to be nonsense, and no further serious consideration was given. The present inventors have conducted intensive studies on antibacterial latex compositions suitable for manufacturing medical devices, sanitary products, food manufacturing equipment, etc. made of latex with sustained antibacterial activity, and have surprisingly found that The present invention was achieved based on the discovery that a stable antibacterial latex composition can be obtained without causing gelation even when a poorly water-soluble biguanide compound or its salt is added to the latex. That is, the present invention is an antibacterial latex composition comprising a natural rubber latex or a synthetic polymer latex and a poorly water-soluble biguanide compound or its salt. The biguanide compound in the present invention is represented by the following general formula (I) or ().
【化】[ka]
【化】
ここでＲはアルキル基、アミノアルキル基、フ
エニル基、アルキルフエニル基、ハロゲン化フエ
ニル基、ハイドロキシフエニル基、メトキシフエ
ニル基、カルボキシルフエニル基、ナフチル基又
はニトリル基であり、R′は水素又はアルキル基
である。ｎは正の整数であるが、２〜10の範囲が
好適である。かかるビグアニド化合物の好適な具
体的な例をあげれば１，６−ジ−（４−クロロフ
エニルビグアニド）ヘキサン、ジアミノヘキシル
ビグアニド、１，６−ジ−（アミノヘキシルビグ
アニド）ヘキサン等である。
本発明におけるビグアニド化合物の塩とは、ビ
グアニド化合物と、無機酸もしくは有機酸とから
形成される塩をいう。ビグアニド化合物と難水溶
性の塩を形成する無機酸又は有機酸としては、例
えば塩酸、臭化水素酸、硝酸、硫酸、炭酸、重炭
酸、クエン酸、リン酸、ホウ酸、ギ酸、酢酸、安
息香酸、酒石酸等があげられる。
本発明にいう難水溶性とは20℃における100g
の蒸留水に対する溶解度が0.001〜3.0g、好まし
くは0.005〜2.0gの範囲のものを指す。水に対す
る溶解度が0.001g未満では殺菌剤としての効力が
減退し、一方3.0gをこえるとラテツクス中に加え
た時ラテツクスの不可逆的なゲル化を起こし好ま
しくない。
本発明における抗菌性ラテツクス組成物におけ
る難水溶性のビグアニド化合物又はその塩の含有
量は、その目的とするところにより異なるが、通
常、ラテツクスの固形分に対して好ましくは0.01
〜30wt％、より好ましくは0.1〜10wt％である。
含有量が30wt％をこえる場合はこのラテツクス
組成物より得られた成型品の皮膜の物理的強度が
劣る傾向があり、一方、0.01wt％未満では抗菌剤
としての効力を発揮しにくくなるので好ましくな
い。
本発明に用いられる天然ゴムラテツクスとは、
ゴム植物の樹皮に切付を行つた時に流れ出る種々
の有機物及び無機物を含有した水溶液を分散媒体
とし、ゴム分を分散質とし、必要に応じてPH調整
剤、加硫剤、加硫促進剤、軟化剤、充填剤、老化
防止剤、着色剤等を配合したものをいう。また合
成高分子系ラテツクスとしては、例えばエチレ
ン、スチレン、酢酸ビニル、塩化ビニル、塩化ビ
ニリデン、アクリロニトリル、（メタ）アクリル
酸エステル、ビニルピリジン、メチルビニルエー
テル等のビニル系モノマーの単一重合体又はその
共重合体、ブタジエン、イソプレン、１，３−ペ
ンタジエン、１，５−ヘキサジエン、１，６−ヘ
プタジエン、クロロプレン等のジエン系モノマー
の単一重合体あるいはその共重合体、上記ビニル
系モノマーとジエン系モノマーの共重合体、その
他官能基としてエポキシド基、アミノ基、カルボ
キシル基、酸無水物基、水酸基、アミド基、Ｎ−
メチロ−ルアミド基、イソシアネート基等を有す
るビニル系モノマーと上記各種モノマーとの共重
合体等を主成分とし、必要に応じて界面活性剤、
架橋剤、充填剤、軟化剤等を配合したものがあげ
られる。
本発明の抗菌性ラテツクス組成物を調製する方
法は、各成分が均一に混合される方法であれば特
に限定されず、公知の種々の方法を利用すること
ができるが、例えば抗菌剤をボールミル内で摩砕
しながら均一なペースト状水分散物とし、これに
天然ゴムラテツクス又は合成高分子系ラテツクス
を加えて攪拌混合するなどの方法が好ましく採用
される。
本発明の抗菌性ラテツクス組成物は、長期の使
用過程においても持続的な抗菌性を有する医療器
具、衛生器具、食品製造用機器又は備品等の成型
加工に好適に用いられる。具体的な成型品の例と
しては、導尿カテーテルをはじめとする各種カテ
ーテル類、給排液チユーブ、スポンジ、ゴム引
布、紙のサイジング剤、不織布のバインダー、塗
料、接着剤等があげられる。これらは従来公知の
浸漬法、キヤステイング法又は電着法等により成
型される。さらに具体的な応用例をあげるならば
長期間における体内留置においてカテーテルを通
じて侵入する細菌により尿道炎、膀胱炎、腎う炎
等が頻発する導尿カテーテルについて、本発明の
抗菌性ラテツクス組成物を用いて成型された導尿
カテーテルは抗菌剤を徐放する性能を有し、その
使用過程において尿又は体液により抗菌剤が持続
的に徐放されるので、種々の細菌からの***
を防止する上で極めて効果的である。
以下に具体的な実施例を記し本発明を詳述す
る。
なお、例中の「部」は「重量部」を意味する。
実施例 １
固形分濃度が約50wt％の天然ゴムラテツクス
溶液（PH10.7）100部に、ジメチルジチオカルバ
ミン酸亜鉛0.3部、硫黄1.5部、亜鉛華３部及びス
テアリン酸1.2部を加え、均一に分散させて天然
ゴムを主成分とする配合ラテツクスを得た。この
配合ラテツクスに、抗菌剤として、１，６−ジ−
（４−クロロフエニルビグアニド）ヘキサンの塩
酸塩（20℃における水に対する溶解度は約0.06wt
％）10部をあらかじめ蒸留水12部にペースト状に
均一に分散させたものを攪拌しながら加えたとこ
ろ、ラテツクスは凝集することなく、抗菌剤が均
一に分散したラテツクス組成物を得ることができ
た。
得られた組成物からはフイルムを成型すること
ができ、このフイルムについてBacillus Subtilis
ATCC 6633（培地 NUTRIENT AGAR）を検
定菌として円筒平板法（デイスク法）により抗菌
活性テストを行つたところ阻止円を生じ、この組
成物が抗菌性を有することが認められた。
比較例 １
実施例１で用いたと同じ配合ラテツクス100部
に、１，６−ジ−（４−クロロフエニルビグアニ
ド）ヘキサンのグルコン酸塩の20wt％水溶液を
攪拌しながら少しずつ加えたところ、ラテツクス
は徐々に粘性を増し、およそ３ml加えたところで
完全にゲル化した。
実施例 ２
実施例１で用いたと同じ配合ラテツクス100部
に、１，６−ジ−（４−クロロフエニルビグアニ
ド）ヘキサン（水に対する溶解度は約0.08wt％）
10部をあらかじめ蒸留水12部にペースト状に分散
させたものを攪拌しながら加えたところ、ラテツ
クスは凝集することなく均一に分散した。
得られた組成物について実施例１と同様の試験
を行つたところフイルムは抗菌性を示した。
実施例 ３
実施例１で用いたと同じ配合ラテツクス100部
に、１，６−ジ−（４−クロロフエニルビグアニ
ド）ヘキサンの酢酸塩（20℃における水に対する
溶解度は約1.8wt％）10部をあらかじめ蒸留水12
部にペースト状に均一に分散させたものを攪拌し
ながら加えたところ、ラテツクスは凝集すること
なく均一に分散した。
得られた組成物について実施例１と同様の試験
を行つたところフイルムは抗菌性を示した。
実施例 ４
固形分濃度約50wt％のアニオン性スチレン−
ブタジエン共重合体ラテツクス（PH＝9.5）100部
に、１，６−ジ−（４−クロロフエニルビグアニ
ド）ヘキサンの硫酸塩（20℃における水に対する
溶解度は約0.01wt％）10部をあらかじめ蒸留水12
部に均一に分散させたものを攪拌しながら加えた
ところ、ラテツクスは凝集することなく均一に分
散した。
得られた組成物について実施例１と同様の試験
を行つたところフイルムは抗菌性を示した。
実施例 ５
固形分濃度約45wt％のアニオン性塩化ビニル
−塩化ビニリデン共重合体ラテツクス（PH＝9.0）
100部に、１，６−ジ（アミノヘキシルビグアニ
ド）ヘキサンのリン酸塩（水に対する溶解度は約
0.05wt％）10部をあらかじめ蒸留水12部に均一に
分散したものを加えたところ、上記ラテツクス浴
液は凝集することなく均一に分散した。
得られた組成物について実施例１と同様の試験
を行つたところフイルムは抗菌性を示した。[Chemical formula] Here, R is an alkyl group, an aminoalkyl group, a phenyl group, an alkylphenyl group, a halogenated phenyl group, a hydroxyphenyl group, a methoxyphenyl group, a carboxyl phenyl group, a naphthyl group, or a nitrile group, R' is hydrogen or an alkyl group. n is a positive integer, preferably in the range of 2 to 10. Preferred specific examples of such biguanide compounds include 1,6-di-(4-chlorophenylbiguanide)hexane, diaminohexylbiguanide, and 1,6-di(aminohexylbiguanide)hexane. The salt of a biguanide compound in the present invention refers to a salt formed from a biguanide compound and an inorganic acid or an organic acid. Examples of inorganic or organic acids that form poorly water-soluble salts with biguanide compounds include hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, carbonic acid, bicarbonate, citric acid, phosphoric acid, boric acid, formic acid, acetic acid, and benzoic acid. Examples include acid, tartaric acid, etc. In the present invention, poorly water-soluble means 100g at 20°C.
The solubility in distilled water is in the range of 0.001 to 3.0 g, preferably 0.005 to 2.0 g. If the solubility in water is less than 0.001 g, the efficacy as a bactericidal agent will be reduced, while if it exceeds 3.0 g, the latex will irreversibly gel when added to the latex, which is undesirable. The content of the poorly water-soluble biguanide compound or its salt in the antibacterial latex composition of the present invention varies depending on the purpose, but is usually preferably 0.01% of the solid content of the latex.
~30wt%, more preferably 0.1-10wt%.
If the content exceeds 30 wt%, the physical strength of the film of a molded product obtained from this latex composition tends to be poor, while if it is less than 0.01 wt%, it becomes difficult to exert its effectiveness as an antibacterial agent, so it is preferable. do not have. The natural rubber latex used in the present invention is
The dispersion medium is an aqueous solution containing various organic and inorganic substances that flows out when the bark of a rubber plant is cut, and the rubber component is used as the dispersoid. This refers to products that contain softeners, fillers, anti-aging agents, colorants, etc. Synthetic polymer latexes include, for example, homopolymers or copolymers of vinyl monomers such as ethylene, styrene, vinyl acetate, vinyl chloride, vinylidene chloride, acrylonitrile, (meth)acrylic acid esters, vinyl pyridine, and methyl vinyl ether. homopolymers of diene monomers such as butadiene, isoprene, 1,3-pentadiene, 1,5-hexadiene, 1,6-heptadiene, chloroprene, etc., or copolymers thereof; copolymers of the above vinyl monomers and diene monomers; Polymers and other functional groups such as epoxide groups, amino groups, carboxyl groups, acid anhydride groups, hydroxyl groups, amide groups, N-
The main component is a copolymer of a vinyl monomer having a methylolamide group, an isocyanate group, etc. and the various monomers mentioned above, and if necessary, a surfactant,
Examples include those containing crosslinking agents, fillers, softeners, etc. The method for preparing the antibacterial latex composition of the present invention is not particularly limited as long as each component is mixed uniformly, and various known methods can be used. For example, the antibacterial agent may be mixed in a ball mill. Preferably, a method is employed in which a homogeneous paste-like aqueous dispersion is obtained by grinding with a grinder, and natural rubber latex or synthetic polymer latex is added thereto and mixed with stirring. The antibacterial latex composition of the present invention can be suitably used for molding medical instruments, sanitary instruments, food manufacturing equipment or fixtures, etc., which have sustained antibacterial properties even during long-term use. Specific examples of molded products include various catheters including urinary catheters, fluid supply and drainage tubes, sponges, rubberized cloth, paper sizing agents, nonwoven fabric binders, paints, adhesives, and the like. These are molded by a conventionally known dipping method, casting method, electrodeposition method, or the like. To give a more specific application example, the antibacterial latex composition of the present invention can be used for urinary catheters, which frequently cause urethritis, cystitis, pyelitis, etc. due to bacteria that invade through the catheter when left in the body for a long period of time. The molded urinary catheter has the ability to release antibacterial agents in a sustained manner, and during its use, the antibacterial agents are continuously released through urine or body fluids, thereby preventing urinary tract infections from various bacteria. It is extremely effective. The present invention will be described in detail with reference to specific examples below. Note that "parts" in the examples mean "parts by weight." Example 1 0.3 parts of zinc dimethyldithiocarbamate, 1.5 parts of sulfur, 3 parts of zinc white, and 1.2 parts of stearic acid were added to 100 parts of a natural rubber latex solution (PH 10.7) with a solid content concentration of approximately 50 wt%, and the mixture was dispersed uniformly. A compounded latex containing natural rubber as the main component was obtained. This compounded latex contains 1,6-di-
(4-chlorophenyl biguanide) hexane hydrochloride (solubility in water at 20℃ is approximately 0.06wt
%) was uniformly dispersed in 12 parts of distilled water in the form of a paste, and added to the mixture while stirring, the latex did not aggregate and a latex composition in which the antibacterial agent was uniformly dispersed could be obtained. Ta. A film can be formed from the obtained composition, and about this film, Bacillus subtilis
When an antibacterial activity test was conducted using ATCC 6633 (medium NUTRIENT AGAR) as a test bacterium by the cylindrical plate method (disk method), an inhibition zone was produced, indicating that this composition had antibacterial properties. Comparative Example 1 When a 20 wt % aqueous solution of gluconate of 1,6-di-(4-chlorophenylbiguanide)hexane was added little by little to 100 parts of the same compounded latex used in Example 1 while stirring, the latex The viscosity gradually increased, and it completely gelled when approximately 3 ml was added. Example 2 1,6-di-(4-chlorophenylbiguanide)hexane (solubility in water is about 0.08 wt%) was added to 100 parts of the same compounded latex used in Example 1.
When 10 parts of the latex was preliminarily dispersed in 12 parts of distilled water to form a paste and added with stirring, the latex was uniformly dispersed without agglomeration. When the obtained composition was subjected to the same test as in Example 1, the film showed antibacterial properties. Example 3 To 100 parts of the same compounded latex used in Example 1, 10 parts of acetate of 1,6-di-(4-chlorophenylbiguanide)hexane (solubility in water at 20°C is approximately 1.8 wt%) was added in advance. distilled water 12
When the latex was uniformly dispersed into a paste and added to the mixture while stirring, the latex was uniformly dispersed without agglomeration. When the obtained composition was subjected to the same test as in Example 1, the film showed antibacterial properties. Example 4 Anionic styrene with a solid content concentration of approximately 50 wt%
To 100 parts of butadiene copolymer latex (PH=9.5), 10 parts of 1,6-di-(4-chlorophenylbiguanide)hexane sulfate (solubility in water at 20°C is approximately 0.01 wt%) was added in advance to distilled water. 12
When the latex was added while stirring, the latex was uniformly dispersed without agglomeration. When the obtained composition was subjected to the same test as in Example 1, the film showed antibacterial properties. Example 5 Anionic vinyl chloride-vinylidene chloride copolymer latex with a solid content concentration of approximately 45 wt% (PH = 9.0)
100 parts of 1,6-di(aminohexyl biguanide)hexane phosphate (solubility in water is approx.
When 10 parts of 0.05wt%) were uniformly dispersed in 12 parts of distilled water in advance, the latex bath liquid was uniformly dispersed without agglomeration. When the obtained composition was subjected to the same test as in Example 1, the film showed antibacterial properties.
Claims (1)
スと、難水溶性のビグアニド化合物又はその塩と
を配合してなる抗菌性ラテツクス組成物。 ２ 難水溶性のビグアニド化合物が１，６−ジ−
（４−クロロフエニルビグアニド）ヘキサンであ
る特許請求の範囲第１項記載の抗菌性ラテツクス
組成物。[Scope of Claims] 1. An antibacterial latex composition comprising natural rubber latex or synthetic polymer latex and a poorly water-soluble biguanide compound or its salt. 2 The poorly water-soluble biguanide compound is 1,6-di-
The antibacterial latex composition according to claim 1, which is (4-chlorophenylbiguanide)hexane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58104571A JPS59227824A (en) | 1983-06-10 | 1983-06-10 | Antibacterial latex composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58104571A JPS59227824A (en) | 1983-06-10 | 1983-06-10 | Antibacterial latex composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59227824A JPS59227824A (en) | 1984-12-21 |
| JPH0580225B2 true JPH0580225B2 (en) | 1993-11-08 |
Family
ID=14384124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58104571A Granted JPS59227824A (en) | 1983-06-10 | 1983-06-10 | Antibacterial latex composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59227824A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0781566A2 (en) | 1995-12-26 | 1997-07-02 | Toyo Boseki Kabushiki Kaisha | Organic solvent-soluble mucopolysaccharide, antibacterial antithrombogenic composition and medical material |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2636838B2 (en) * | 1986-01-13 | 1997-07-30 | ユニチカ株式会社 | Antimicrobial sustained release urinary catheter |
| US5019378A (en) * | 1987-12-29 | 1991-05-28 | Cuno, Incorporated | Elastomeric composition containing therapeutic agents and articles manufactured therefrom |
| US5019601A (en) * | 1987-12-29 | 1991-05-28 | Cuno, Incorporated | Elastomeric composition containing therapeutic agents and articles manufactured therefrom |
| US5013306A (en) * | 1989-01-18 | 1991-05-07 | Becton, Dickinson And Company | Anti-infective and antithrombogenic medical articles and method for their preparation |
| US5165952A (en) * | 1989-01-18 | 1992-11-24 | Becton, Dickinson And Company | Anti-infective and antithrombogenic medical articles and method for their preparation |
| US6261271B1 (en) | 1989-01-18 | 2001-07-17 | Becton Dickinson And Company | Anti-infective and antithrombogenic medical articles and method for their preparation |
| GB2263114A (en) * | 1991-12-19 | 1993-07-14 | Yad Hygiene Products Limited | Biocidal rubber latex products and methods of making same |
| GB201308926D0 (en) * | 2013-05-17 | 2013-07-03 | Univ Bristol | Antibacterial micro-and nanoparticles comprising a chlorhexidine salt, method of production and uses thereof |
-
1983
- 1983-06-10 JP JP58104571A patent/JPS59227824A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0781566A2 (en) | 1995-12-26 | 1997-07-02 | Toyo Boseki Kabushiki Kaisha | Organic solvent-soluble mucopolysaccharide, antibacterial antithrombogenic composition and medical material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59227824A (en) | 1984-12-21 |
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