JP6008382B2 - Industrial antibacterial composition - Google Patents
Industrial antibacterial composition Download PDFInfo
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- JP6008382B2 JP6008382B2 JP2012057492A JP2012057492A JP6008382B2 JP 6008382 B2 JP6008382 B2 JP 6008382B2 JP 2012057492 A JP2012057492 A JP 2012057492A JP 2012057492 A JP2012057492 A JP 2012057492A JP 6008382 B2 JP6008382 B2 JP 6008382B2
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- JP
- Japan
- Prior art keywords
- isothiazolone
- antibacterial composition
- formula
- antibacterial
- industrial antibacterial
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 34
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 27
- -1 isothiazolone compound Chemical class 0.000 claims description 16
- 239000003638 chemical reducing agent Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229940043810 zinc pyrithione Drugs 0.000 claims description 5
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 2
- 239000011787 zinc oxide Substances 0.000 claims 1
- 241000894006 Bacteria Species 0.000 description 17
- 241000233866 Fungi Species 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 7
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000845 anti-microbial effect Effects 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FMNZAHDAULEOSO-UHFFFAOYSA-N 2,2-dibromo-2-nitroethanol Chemical compound OCC(Br)(Br)[N+]([O-])=O FMNZAHDAULEOSO-UHFFFAOYSA-N 0.000 description 2
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical class N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- YLZGKZDEFJIHIJ-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl) carbamate Chemical compound C1=CC=C2N(C)C(OC(N)=O)=NC2=C1 YLZGKZDEFJIHIJ-UHFFFAOYSA-N 0.000 description 1
- KANAPVJGZDNSCZ-UHFFFAOYSA-N 1,2-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)N=CC2=C1 KANAPVJGZDNSCZ-UHFFFAOYSA-N 0.000 description 1
- SQRDRPSVGROPHX-UHFFFAOYSA-N 2,3,3-triiodoprop-2-en-1-ol Chemical compound OCC(I)=C(I)I SQRDRPSVGROPHX-UHFFFAOYSA-N 0.000 description 1
- CRTPTZMJMAGFEQ-UHFFFAOYSA-N 2-butyl-1,2-thiazol-3-one Chemical compound CCCCN1SC=CC1=O CRTPTZMJMAGFEQ-UHFFFAOYSA-N 0.000 description 1
- ASKFWACWQQZSSS-UHFFFAOYSA-N 2-ethyl-1,2-thiazol-3-one Chemical compound CCN1SC=CC1=O ASKFWACWQQZSSS-UHFFFAOYSA-N 0.000 description 1
- HFOCAQPWSXBFFN-UHFFFAOYSA-N 2-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=CC=C1C=O HFOCAQPWSXBFFN-UHFFFAOYSA-N 0.000 description 1
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 description 1
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 1
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 description 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
- GKMYABWKGJTJHN-UHFFFAOYSA-N 4-octyl-1,2-thiazol-3-one Chemical compound CCCCCCCCC1=CSNC1=O GKMYABWKGJTJHN-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000009989 Posterior Leukoencephalopathy Syndrome Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229960003237 betaine Drugs 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- QHNCWVQDOPICKC-UHFFFAOYSA-N copper;1-hydroxypyridine-2-thione Chemical compound [Cu].ON1C=CC=CC1=S.ON1C=CC=CC1=S QHNCWVQDOPICKC-UHFFFAOYSA-N 0.000 description 1
- NMCCNOZOBBWFMN-UHFFFAOYSA-N davicil Chemical compound CS(=O)(=O)C1=C(Cl)C(Cl)=NC(Cl)=C1Cl NMCCNOZOBBWFMN-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- ZFAKTZXUUNBLEB-UHFFFAOYSA-N dicyclohexylazanium;nitrite Chemical compound [O-]N=O.C1CCCCC1[NH2+]C1CCCCC1 ZFAKTZXUUNBLEB-UHFFFAOYSA-N 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000008235 industrial water Substances 0.000 description 1
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229940054967 vanquish Drugs 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
一般式(II)
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)
Formula (II)
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)
ポリマーエマルションは重合停止剤として還元剤を用いることが一般的であり、過剰に還元剤が添加されるため組成物中に還元剤が残存する場合が一般的である。このポリマーエマルション以外の水系組成物においても漂白、脱色、酸化防止の目的で還元剤が添加される事例は数多く存在する。 In the polymer emulsion, a reducing agent is generally used as a polymerization terminator, and since the reducing agent is excessively added, the reducing agent generally remains in the composition. Even in aqueous compositions other than this polymer emulsion, there are many cases where a reducing agent is added for the purpose of bleaching, decoloring and oxidation prevention.
ポリマーエマルションをはじめとする水系組成物は細菌や真菌などの微生物による腐敗や汚染を受けやすく、これを回避するために一般的には抗菌剤の添加が必須となっている。工業的に使用される水系組成物の抗菌剤としては、2−ブロモー2−ニトロプロパン−1,3−ジオールや2,2−ジブロモ−2−ニトロエタノールなどのブロモニトロ化合物や、1,2−ベンズ−3−イソチアゾロンや5−クロロ−2−メチル−3(2H)−イソチアゾロン、2−メチル−3(2H)−イソチアゾロン、2−n−オクチル−3(2H)−イソチアゾロンなどのイソチアゾロン化合物や、メチレンビスチオジアネートや2−(4−チオシアノメチルチオ)ベンゾチアゾールなどのチオシアネート化合物などが使用されている。 Aqueous compositions such as polymer emulsions are susceptible to spoilage and contamination by microorganisms such as bacteria and fungi, and in general, the addition of antibacterial agents is essential to avoid this. Antibacterial agents for aqueous compositions used industrially include bromonitro compounds such as 2-bromo-2-nitropropane-1,3-diol and 2,2-dibromo-2-nitroethanol, and 1,2-benz Isothiazolone compounds such as -3-isothiazolone, 5-chloro-2-methyl-3 (2H) -isothiazolone, 2-methyl-3 (2H) -isothiazolone, 2-n-octyl-3 (2H) -isothiazolone, methylene Thiocyanate compounds such as bisthiodianate and 2- (4-thiocyanomethylthio) benzothiazole are used.
しかしながらこれら工業用の水系組成物に使用される抗菌剤は還元剤や還元性物質による影響を受けやすく、比較的短期間で分解することから必要以上に抗菌剤の添加濃度を高める必要があり、より添加濃度が少なくてすみ、かつより長期にわたる抗菌性能を発揮する工業用抗菌組成物が望まれている。 However, antibacterial agents used in these industrial water-based compositions are susceptible to the effects of reducing agents and reducing substances, and it is necessary to increase the concentration of the antibacterial agent more than necessary because it decomposes in a relatively short period of time. There is a demand for an industrial antibacterial composition that requires less additive concentration and exhibits antibacterial performance over a longer period of time.
亜鉛ピリチオン複合化合物についてはWO2009/144929号公報(特許文献1)やWO2009/44523号公報(特許文献2)、特開2006−335757(特許文献3)に開示されているが、これらの亜鉛ピリチオン複合体が還元剤や還元性物質の存在下で抗菌活性を保持することについてはなんら記載がない。 Zinc pyrithione complex compounds are disclosed in WO2009 / 144929 (patent document 1), WO2009 / 44523 (patent document 2), and JP-A 2006-335757 (patent document 3). There is no mention that the body retains antibacterial activity in the presence of reducing agents and reducing substances.
一般式(II)
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)
Formula (II)
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)
本発明が解決しようとする課題は、ポリマーエマルションをはじめとする還元剤や還元性物質を含有する水系組成物を、細菌や真菌等の微生物汚染から少量の添加により長期間にわたって保護することが可能な工業用抗菌組成物を提供することにある。 The problem to be solved by the present invention is that it is possible to protect a water-based composition containing a reducing agent including a polymer emulsion and a reducing substance from microbial contamination such as bacteria and fungi over a long period of time by adding a small amount. It is providing the antibacterial composition for industrial use.
一般式(II)
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)
Formula (II)
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)
上記組成物を用いることにより、還元剤や還元性物質を含有するポリマーエマルションや水系組成物に対して細菌や真菌等の微生物による腐敗から少量の添加により長期間にわたって保護することが可能となる。 By using the above composition, it becomes possible to protect a polymer emulsion or aqueous composition containing a reducing agent or a reducing substance from spoilage by microorganisms such as bacteria and fungi over a long period of time by adding a small amount.
一般式(II)
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)
Formula (II)
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)
本発明の抗菌組成物の対象微生物は、細菌、糸状菌、酵母、藻など広範囲にわたり、本発明の工業用抗菌組成物はかかる広範囲の微生物に対してそれらを防除剤として優れた効果を発揮する。とくに対象物中に重合停止剤として還元剤が含まれるポリマーエマルションや、漂白、脱色、酸化防止の目的で還元剤が添加される水系組成物における有害微生物の防除に有効である他、ポリ塩化ビニルやポリオレフィンなどのプラスチックや、アクリルやウレタンなどのエマルション塗料やエナメルやアルキドなどの油性塗料に添加することによる抗菌効果の付与、得られた抗菌組成物の希釈液に木材を浸漬したり表面処理することによる抗菌効果の付与も可能である。 The target microorganism of the antibacterial composition of the present invention covers a wide range of bacteria, filamentous fungi, yeast, algae and the like, and the industrial antibacterial composition of the present invention exhibits an excellent effect as a control agent against such a wide range of microorganisms. . In particular, it is effective for controlling harmful microorganisms in polymer emulsions containing a reducing agent as a polymerization terminator in the object and aqueous compositions to which a reducing agent is added for the purpose of bleaching, decoloring, and oxidation prevention. Add antibacterial effect by adding it to plastics such as polyolefin, emulsion paints such as acrylic and urethane, and oil paints such as enamel and alkyd, and immerse and surface-treat wood in the diluted solution of the obtained antibacterial composition It is also possible to impart an antibacterial effect.
本発明で使用する一般式(I)で示される亜鉛ピリチオン複合化合物は、WO09/144929に従って調製することが可能である。また「HYBRICIDE(登録商標)−89」としてKOLON LIFE SCIENCE社から市販されているものを使用しても良い。一般式(II)で示されるイソチアゾロン化合物は、1,2−ベンズ−3−イソチアゾロン、N−メチル−1,2−ベンズ−3−イソチアゾロン、N−エチル−1,2−ベンズ−3−イソチアゾロン、N−n−ブチル−1,2−ベンズ−3−イソチアゾロン、2−エチル−3−イソチアゾロン、2−n−ブチル−3−イソチアゾロン、2−n−オクチル−3−イソチアゾロン、5−クロロ−2−n−オクチル−3−イソチアゾロン、4,5−ジクロロ−2−n−オクチル−3−イソチアゾロンなどが挙げられる。これらのうち、1,2−ベンズ−3−イソチアゾロンは例えば、「PROXEL(登録商標) PRESS PASTE」としてARCH CHEMICALS社から市販されているものや、ドイツ特許第3150629号明細書等に記載の方法またはそれに準じる方法によって調製することが可能であり、N−n−ブチル−1,2−ベンズ−3−イソチアゾロンは例えば、「VANQUISH(登録商標)100」としてARCH CHEMICALS社から市販されているものが利用可能であり、2−n−オクチル−3−イソチアゾロンは例えば、「ZONEN(登録商標) O/100」としてケミクレア社から市販されているものが利用可能であり、4,5−ジクロロ−2−n−オクチル−3−イソチアゾロンは例えば、「KATHON(登録商標) 287T」としてROHM AND HAAS社から市販されているものが利用可能である。本発明の抗菌組成物における一般式(I)で示される亜鉛ピリチオン複合化合物と、一般式(II)で示されるイソチアゾロン化合物の含有率はとくに制限を受けないが、好ましくはそれぞれ0.1重量%以上、より好ましくは1重量%以上である。 The zinc pyrithione complex compound represented by the general formula (I) used in the present invention can be prepared according to WO09 / 144929. Moreover, you may use what is marketed from KOLON LIFE SCIENCE as "HYBRICIDE (trademark) -89". The isothiazolone compound represented by the general formula (II) includes 1,2-benz-3-isothiazolone, N-methyl-1,2-benz-3-isothiazolone, N-ethyl-1,2-benz-3-isothiazolone, Nn-butyl-1,2-benz-3-isothiazolone, 2-ethyl-3-isothiazolone, 2-n-butyl-3-isothiazolone, 2-n-octyl-3-isothiazolone, 5-chloro-2- Examples thereof include n-octyl-3-isothiazolone and 4,5-dichloro-2-n-octyl-3-isothiazolone. Among these, for example, 1,2-benz-3-isothiazolone is commercially available from ARCH CHEMICALS as “PROXEL (registered trademark) PRES PASTE”, the method described in German Patent No. 3150629, or the like. The Nn-butyl-1,2-benz-3-isothiazolone is commercially available from ARCH CHEMICALS as “VANQUISH (registered trademark) 100”, for example. 2-n-octyl-3-isothiazolone, for example, commercially available from Chemicrea as “ZONEN® O / 100” can be used, and 4,5-dichloro-2-n -Octyl-3-isothiazolone is exemplified by “KATHON (Registered trademark) 287T "commercially available from ROHM AND HAAS can be used. The contents of the zinc pyrithione complex compound represented by the general formula (I) and the isothiazolone compound represented by the general formula (II) in the antibacterial composition of the present invention are not particularly limited, but preferably 0.1% by weight, respectively. As mentioned above, More preferably, it is 1 weight% or more.
本発明の抗菌組成物に配合可能な溶媒としては、水の他、エタノールやイソプロパノール等の一価アルコール類、エチレングリコール、ジエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール等のグリコール系溶剤およびその誘導体、グリセリン、ジグリセリン等のグリセリン系溶剤およびその誘導体を使用することができる。これら有機溶媒は、単独で使用してもよく、2種類以上を併用することも可能である。亜鉛ピリチオン複合化合物、イソチアゾロン化合物の溶媒に対する溶解性を考慮すると水を主溶媒として、後述する界面活性剤を用いて湿式粉砕した分散懸濁製剤とするのが好ましい。 Solvents that can be blended in the antibacterial composition of the present invention include water, monohydric alcohols such as ethanol and isopropanol, glycol solvents such as ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, and dipropylene glycol, and derivatives thereof. Glycerin solvents such as glycerin and diglycerin and their derivatives can be used. These organic solvents may be used alone or in combination of two or more. In consideration of the solubility of the zinc pyrithione complex compound and the isothiazolone compound in the solvent, it is preferable to prepare a dispersion suspension preparation which is wet-pulverized using water as a main solvent and a surfactant described later.
界面活性剤としては、例えばポリオキシアルキレンアルキルエーテル、ポリオキシアルキレンアリルフェニルエーテル、グリセリン脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシアルキレンソルビタン脂肪酸エステル、ポリオキシアルキレン硬化ヒマシ油等のノニオン界面活性剤や、アルキルサルフェート塩、アルキルエーテルサルフェート塩、アルキルスルホサクシネート塩、アルキルスルホネート塩、アルキルアリルスルホネート塩、脂肪酸アミドスルホネート塩、アルキルホスフェート塩、アルキルエーテルホスフェート塩、ナフタレンスルホン酸ホルムアルデヒド縮合物塩等のアニオン界面活性剤や、アルキルアミン塩、アルキルアンモニウム塩等のカチオン界面活性剤や、グリシン型、ベタイン型、イミダゾリン型等の両性界面活性剤を使用することができる。これら界面活性剤は単独で使用してもよく、2種類以上を組み合わせて使用することも可能である。これらのうちとくにノニオン界面活性剤、アニオン界面活性剤が好ましい。 Examples of the surfactant include nonionic surfactants such as polyoxyalkylene alkyl ether, polyoxyalkylene allyl phenyl ether, glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, polyoxyalkylene hydrogenated castor oil, and alkyl Anionic surfactants such as sulfate salts, alkyl ether sulfate salts, alkyl sulfosuccinate salts, alkyl sulfonate salts, alkyl allyl sulfonate salts, fatty acid amide sulfonate salts, alkyl phosphate salts, alkyl ether phosphate salts, naphthalene sulfonic acid formaldehyde condensate salts And cationic surfactants such as alkylamine salts and alkylammonium salts, glycine type, betaine type, imidazoline type, etc. It can be used sex surfactant. These surfactants may be used alone or in combination of two or more. Of these, nonionic surfactants and anionic surfactants are particularly preferable.
pH調整剤としては、コハク酸やクエン酸、酒石酸等の有機酸やそれらの塩、リン酸やポリリン酸、ホウ酸等の無機酸やそれらの塩等が使用可能であり、消泡剤としては、鉱油系、シリコーン系、ポリエーテル系等が使用可能であり、金属封鎖剤としては、エチレンジアミン四酢酸、1−ヒドロキシエチリデン−1,1−ジホスホン酸、ニトリロ三酢酸やそれらの塩等が使用可能であり、粘度調整剤としてはキサンタンガム、カルボキシメチルセルロース、ヒドロキシエチルセルロース、アラビアガム等が使用可能であり、防錆剤としては、ベンゾトリアゾール、ジシクロヘキシルアンモニウム亜硝酸塩等が使用可能であり、他の抗菌組成物としては、メチレンビスチオシアネート、2−(4−チオシアノメチルチオ)ベンズイミダゾール、2−ブロモーニトロプロパン−1,3−ジオール、2,2−ジブロモ−2−ニトロエタノール、3−ヨード−2−プロピニルブチルカーバメート、2,3,3−トリヨードアリルアルコール、ジヨードメチル−p−トリルスルホン、ベンズイミダゾールカルバミン酸メチル、2−(4−チアゾリル)ベンズイミダゾール、2,3,5,6−テトラクロロ−4−(メチルスルホニル)ピリジン、銅ピリチオン、o−フェニルフェノール、イソプロピルメチルフェノール、パラクロロメタキシレノール、p−オキシ安息香酸アルキルエステル等が使用可能である。 As pH adjusters, organic acids such as succinic acid, citric acid, tartaric acid and their salts, inorganic acids such as phosphoric acid, polyphosphoric acid, boric acid and their salts can be used, and as antifoaming agents , Mineral oils, silicones, polyethers, etc. can be used, and sequestering agents such as ethylenediaminetetraacetic acid, 1-hydroxyethylidene-1,1-diphosphonic acid, nitrilotriacetic acid and their salts can be used As the viscosity modifier, xanthan gum, carboxymethyl cellulose, hydroxyethyl cellulose, gum arabic, etc. can be used, and as the anticorrosive agent, benzotriazole, dicyclohexylammonium nitrite, etc. can be used, and other antibacterial compositions As methylene bis thiocyanate, 2- (4-thiocyanomethylthio) benzimidazole, -Bromo-nitropropane-1,3-diol, 2,2-dibromo-2-nitroethanol, 3-iodo-2-propynylbutylcarbamate, 2,3,3-triiodoallyl alcohol, diiodomethyl-p-tolylsulfone , Methyl benzimidazole carbamate, 2- (4-thiazolyl) benzimidazole, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, copper pyrithione, o-phenylphenol, isopropylmethylphenol, parachloro Metaxylenol, p-oxybenzoic acid alkyl ester, and the like can be used.
以下、実施例および比較例により本発明を具体的に説明するが、本発明はこれらの実施例によって限定されるものではない。
(抗菌組成物実施例)
下記、表1及び表2に従って抗菌組成物を調製した。なお、表1及び表2に示す配合はすべて重量%を表す。ミルベースとして示した配合物をビーズミルにより湿式粉砕・分散した後、レットダウンとして示した配合物と混合することで、組成物中の有効成分濃度が20重量%となる抗菌組成物を得た。
EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention concretely, this invention is not limited by these Examples.
(Antimicrobial composition example)
Antibacterial compositions were prepared according to Table 1 and Table 2 below. In addition, all the formulations shown in Table 1 and Table 2 represent% by weight. The formulation shown as a mill base was wet-ground and dispersed by a bead mill, and then mixed with the formulation shown as a letdown to obtain an antibacterial composition having an active ingredient concentration of 20% by weight in the composition.
(デンプンスラリーに対する抗菌性試験)
溶性デンプン(和光純薬工業社)の10重量%スラリーに亜硫酸ナトリウムを終濃度79mg/L(亜硫酸イオンとして50mg/L)となるように添加したものに、各抗菌組成物を所定濃度添加した後、あらかじめ腐敗させた同品(細菌生菌数;2.0×107CFU/mL、真菌生菌数;1.0×103CFU/mL)を2%接種した。これらを密封静置条件で30℃にて培養し、チオグリコール酸寒天培地もしくはポテトデキストロース寒天培地を用いる平板混釈法によって経時的な生菌数を測定し、抗菌効果を判定した。なお、生菌数測定後、腐敗品を1週間毎に2%接種した。これらの試験結果を表3に示した。また表4には対象物に亜硫酸ナトリウムを添加せずに同じように行った抗菌性試験の結果を示した。これらの結果から本実施例の抗菌組成物は良好な抗菌性能を示すことがわかる。
(Antimicrobial test for starch slurry)
After adding each antibacterial composition to a 10% by weight slurry of soluble starch (Wako Pure Chemical Industries, Ltd.) to which sodium sulfite has been added to a final concentration of 79 mg / L (50 mg / L as sulfite ion) 2% inoculated in advance with the same spoiled product (viable bacterial count; 2.0 × 10 7 CFU / mL, viable fungal count; 1.0 × 10 3 CFU / mL). These were cultured at 30 ° C. under sealed static conditions, and the number of viable bacteria over time was measured by a plate pour method using thioglycolic acid agar medium or potato dextrose agar medium, and the antibacterial effect was judged. After measuring the number of viable bacteria, 2% of the spoiled product was inoculated every week. These test results are shown in Table 3. Table 4 shows the results of an antibacterial test conducted in the same manner without adding sodium sulfite to the object. From these results, it can be seen that the antibacterial composition of this example exhibits good antibacterial performance.
1;細菌および/または真菌の生菌数が102以上104CFU/mL未満
2;細菌および/または真菌の生菌数が104以上106CFU/mL未満
3;細菌および/または真菌の生菌数が106CFU/mL以上
1;細菌および/または真菌の生菌数が102以上104CFU/mL未満
2;細菌および/または真菌の生菌数が104以上106CFU/mL未満
3;細菌および/または真菌の生菌数が106CFU/mL以上
(ポリマーエマルションに対する抗菌性試験)
某社から入手したポリ酢酸ビニルエマルションに亜硫酸ナトリウムを終濃度79mg/L(亜硫酸イオンとして50mg/L)となるように添加したものに、各抗菌組成物を所定濃度添加した後、あらかじめ腐敗させた同品(細菌生菌数;6.0×106CFU/mL)を2%接種した。これらを密封静置条件で30℃にて培養し、チオグリコール酸寒天培地を用いる平板混釈法によって経時的な生菌数を測定し、抗菌効果を判定した。なお、生菌数測定後、腐敗品を1週間毎に2%接種した。これらの試験結果を表5に示した。本実施例の抗菌組成物は良好な抗菌性能を示すことがわかる。
(Antimicrobial test for polymer emulsion)
To the polyvinyl acetate emulsion obtained from a company, sodium sulfite was added to a final concentration of 79 mg / L (50 mg / L as sulfite ion), and after adding each antibacterial composition to a predetermined concentration, 2% of the product (viable bacterial count: 6.0 × 10 6 CFU / mL) was inoculated. These were cultured at 30 ° C. under sealed static conditions, and the number of viable bacteria over time was measured by a plate pour method using a thioglycolic acid agar medium to determine the antibacterial effect. After measuring the number of viable bacteria, 2% of the spoiled product was inoculated every week. The test results are shown in Table 5. It can be seen that the antibacterial composition of this example exhibits good antibacterial performance.
1;細菌の生菌数が102以上104CFU/mL未満
2;細菌の生菌数が104以上106CFU/mL未満
3;細菌の生菌数が106CFU/mL以上
一般式(II)
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)
Formula (II)
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)
Claims (3)
一般式(I)
xZnO・ZnPy2
(式中xは0<x≦1を満足する正数、Pyは2−ピリジルチオ−N−オキシド基を示す。)
一般式(II)
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)
An aqueous composition containing a zinc oxide / zinc pyrithione complex compound represented by general formula (I) and an isothiazolone compound represented by general formula (II) as essential components, and a reducing agent concentration of 50 mg / L or more as sulfite ion Industrial antibacterial composition characterized by being added to
Formula (I)
xZnO · ZnPy 2
(In the formula, x represents a positive number satisfying 0 <x ≦ 1, and Py represents a 2-pyridylthio-N-oxide group.)
Formula (II)
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)
A method of adding the industrial antibacterial composition according to claim 1 to an aqueous composition containing a reducing agent concentration of 50 mg / L or more as sulfite ion.
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