MXPA01002295A - Antibacterial compositions - Google Patents
Antibacterial compositionsInfo
- Publication number
- MXPA01002295A MXPA01002295A MXPA/A/2001/002295A MXPA01002295A MXPA01002295A MX PA01002295 A MXPA01002295 A MX PA01002295A MX PA01002295 A MXPA01002295 A MX PA01002295A MX PA01002295 A MXPA01002295 A MX PA01002295A
- Authority
- MX
- Mexico
- Prior art keywords
- general formula
- represented
- aminocarboxylic acid
- antimicrobial composition
- group
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 127
- 230000000844 anti-bacterial Effects 0.000 title abstract description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamate Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 58
- 230000000845 anti-microbial Effects 0.000 claims description 84
- -1 isothiazolone compound Chemical class 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000004599 antimicrobial Substances 0.000 claims description 39
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 claims description 28
- DHNRXBZYEKSXIM-UHFFFAOYSA-N Methylchloroisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 229940043257 Glycylglycine Drugs 0.000 claims description 14
- 108010008488 Glycylglycine Proteins 0.000 claims description 14
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine zwitterion Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 claims description 14
- 239000011780 sodium chloride Substances 0.000 claims description 14
- 239000004471 Glycine Substances 0.000 claims description 13
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- YIXJRHPUWRPCBB-UHFFFAOYSA-N Magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 claims description 10
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L MgCl2 Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- HJCMDXDYPOUFDY-WHFBIAKZSA-N Ala-Gln Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CCC(N)=O HJCMDXDYPOUFDY-WHFBIAKZSA-N 0.000 claims description 8
- PNMUAGGSDZXTHX-BYPYZUCNSA-N Gly-Gln Chemical compound NCC(=O)N[C@H](C(O)=O)CCC(N)=O PNMUAGGSDZXTHX-BYPYZUCNSA-N 0.000 claims description 8
- 229960002648 alanylglutamine Drugs 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- XKUKSGPZAADMRA-UHFFFAOYSA-N glycyl-glycyl-glycine Chemical compound NCC(=O)NCC(=O)NCC(O)=O XKUKSGPZAADMRA-UHFFFAOYSA-N 0.000 claims description 8
- 108010067216 glycyl-glycyl-glycine Proteins 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 5
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 239000012046 mixed solvent Substances 0.000 claims 1
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 abstract description 25
- 206010040880 Skin irritation Diseases 0.000 abstract description 11
- 231100000475 skin irritation Toxicity 0.000 abstract description 11
- 230000036556 skin irritation Effects 0.000 abstract description 11
- 238000000354 decomposition reaction Methods 0.000 abstract description 10
- 239000002244 precipitate Substances 0.000 description 30
- 239000007788 liquid Substances 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 17
- BEGLCMHJXHIJLR-UHFFFAOYSA-N Methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 15
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 13
- 230000001629 suppression Effects 0.000 description 13
- 229960002449 Glycine Drugs 0.000 description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N Maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 12
- 206010015150 Erythema Diseases 0.000 description 11
- 206010030113 Oedema Diseases 0.000 description 11
- 231100000321 erythema Toxicity 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000012456 homogeneous solution Substances 0.000 description 9
- QMOQBVOBWVNSNO-UHFFFAOYSA-N 2-[[2-[[2-[(2-azaniumylacetyl)amino]acetyl]amino]acetyl]amino]acetate Chemical compound NCC(=O)NCC(=O)NCC(=O)NCC(O)=O QMOQBVOBWVNSNO-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 108010001064 glycyl-glycyl-glycyl-glycine Proteins 0.000 description 7
- 210000003491 Skin Anatomy 0.000 description 6
- UCMIRNVEIXFBKS-UHFFFAOYSA-N β-Alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 240000008371 Bacillus subtilis Species 0.000 description 4
- 229940075615 Bacillus subtilis Drugs 0.000 description 4
- 235000014469 Bacillus subtilis Nutrition 0.000 description 4
- CAHKINHBCWCHCF-JTQLQIEISA-N N-acetyl-L-tyrosine Chemical compound CC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 CAHKINHBCWCHCF-JTQLQIEISA-N 0.000 description 4
- 229960001682 N-acetyltyrosine Drugs 0.000 description 4
- 108010039918 Polylysine Proteins 0.000 description 4
- 229940043230 Sarcosine Drugs 0.000 description 4
- 108010077895 Sarcosine Proteins 0.000 description 4
- 239000003619 algicide Substances 0.000 description 4
- CQOVPNPJLQNMDC-ZETCQYMHSA-N carnosine zwitterion Chemical compound [NH3+]CCC(=O)N[C@H](C([O-])=O)CC1=CNC=N1 CQOVPNPJLQNMDC-ZETCQYMHSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000656 polylysine Polymers 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine zwitterion Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 3
- OKJIRPAQVSHGFK-UHFFFAOYSA-N Aceturic acid Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 3
- 229960003767 Alanine Drugs 0.000 description 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N DL-threonine Chemical compound CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229940000635 beta-Alanine Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000006109 methionine Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002455 scale inhibitor Substances 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N 2-hydroxyethyl 2-methylacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- DQAKJEWZWDQURW-UHFFFAOYSA-N 2-oxopyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1=O DQAKJEWZWDQURW-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N Calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N Copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
- 229960003067 Cystine Drugs 0.000 description 2
- 239000004470 DL Methionine Substances 0.000 description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N DL-asparagine Chemical compound OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
- FFEARJCKVFRZRR-UHFFFAOYSA-N DL-methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N DL-serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 235000017274 Diospyros sandwicensis Nutrition 0.000 description 2
- 206010051814 Eschar Diseases 0.000 description 2
- 229960002743 Glutamine Drugs 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline zwitterion Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 2
- 239000004158 L-cystine Substances 0.000 description 2
- 235000019393 L-cystine Nutrition 0.000 description 2
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine zwitterion Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
- 241000282838 Lama Species 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 229960005190 Phenylalanine Drugs 0.000 description 2
- 229940079889 Pyrrolidonecarboxylic Acid Drugs 0.000 description 2
- 229940073490 Sodium Glutamate Drugs 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229960002173 citrulline Drugs 0.000 description 2
- 235000013477 citrulline Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- XMXOIHIZTOVVFB-JIZZDEOASA-L disodium;(2S)-2-aminobutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CC([O-])=O XMXOIHIZTOVVFB-JIZZDEOASA-L 0.000 description 2
- 231100000333 eschar Toxicity 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000011141 high resolution liquid chromatography Methods 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229910001960 metal nitrate Inorganic materials 0.000 description 2
- LPUQAYUQRXPFSQ-UHFFFAOYSA-M monosodium glutamate Chemical compound [Na+].[O-]C(=O)C(N)CCC(O)=O LPUQAYUQRXPFSQ-UHFFFAOYSA-M 0.000 description 2
- 235000013923 monosodium glutamate Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002035 prolonged Effects 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- VTWKXBJHBHYJBI-VURMDHGXSA-N (NZ)-N-benzylidenehydroxylamine Chemical class O\N=C/C1=CC=CC=C1 VTWKXBJHBHYJBI-VURMDHGXSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N 1,5-Pentanediol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- LAGFUXOTKFAPEC-UHFFFAOYSA-N 1-(2-methylphenyl)-1,2,4-triazole Chemical compound CC1=CC=CC=C1N1N=CN=C1 LAGFUXOTKFAPEC-UHFFFAOYSA-N 0.000 description 1
- UUIVKBHZENILKB-UHFFFAOYSA-N 2,2-Dibromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)(Br)C#N UUIVKBHZENILKB-UHFFFAOYSA-N 0.000 description 1
- FMNZAHDAULEOSO-UHFFFAOYSA-N 2,2-dibromo-2-nitroethanol Chemical compound OCC(Br)(Br)[N+]([O-])=O FMNZAHDAULEOSO-UHFFFAOYSA-N 0.000 description 1
- YKCJZLRVOJGDHI-UHFFFAOYSA-N 2,3-dihydropyrrol-4-one Chemical compound O=C1CCN=C1 YKCJZLRVOJGDHI-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-Methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Acrylamido-2-methylpropane sulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- KBGLIBWPBYLNNK-UHFFFAOYSA-N 2-ethoxypropyl acetate Chemical compound CCOC(C)COC(C)=O KBGLIBWPBYLNNK-UHFFFAOYSA-N 0.000 description 1
- IVXDDXAWVZEZKU-UHFFFAOYSA-N 2-hydroxyethyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(=O)OCCO IVXDDXAWVZEZKU-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- SIHKVAXULDBIIY-UHFFFAOYSA-N 4-(2-bromoacetyl)oxybut-2-enyl 2-bromoacetate Chemical compound BrCC(=O)OCC=CCOC(=O)CBr SIHKVAXULDBIIY-UHFFFAOYSA-N 0.000 description 1
- YVWZBMHCQCVNFR-UHFFFAOYSA-N 4-chloro-2-methyl-1,2-thiazol-3-one Chemical compound CN1SC=C(Cl)C1=O YVWZBMHCQCVNFR-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2H-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 1
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 1
- GBKXRWNDORMHSG-UHFFFAOYSA-N 5-chloro-2,4,6-trifluorobenzene-1,3-dicarbonitrile Chemical compound FC1=C(Cl)C(F)=C(C#N)C(F)=C1C#N GBKXRWNDORMHSG-UHFFFAOYSA-N 0.000 description 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
- CXISPYVYMQWFLE-VKHMYHEASA-N Ala-Gly Chemical compound C[C@H]([NH3+])C(=O)NCC([O-])=O CXISPYVYMQWFLE-VKHMYHEASA-N 0.000 description 1
- OMNVYXHOSHNURL-WPRPVWTQSA-N Ala-Phe Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 OMNVYXHOSHNURL-WPRPVWTQSA-N 0.000 description 1
- ALZVPLKYDKJKQU-XVKPBYJWSA-N Ala-Tyr Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 ALZVPLKYDKJKQU-XVKPBYJWSA-N 0.000 description 1
- DEFJQIDDEAULHB-UHFFFAOYSA-N Alanyl-Alanine Chemical compound CC(N)C(=O)NC(C)C(O)=O DEFJQIDDEAULHB-UHFFFAOYSA-N 0.000 description 1
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Abstract
Antibacterial compositions characterized by containing isothiazolone compounds represented by general formula (1) or (2) and aminocarboxylic acids represented by general formula (3) or derivatives thereof. These compositions, which contain the isothiazolone compounds, can inhibit the decomposition of the isothiazolone compounds and relieve the skin irritation of the isothiazolone compounds.
Description
ANTIMICROBIAL COMPOSITION
Field of the Invention
The present invention relates to an antimicrobial composition. More particularly, the present invention relates to an antimicrobial composition comprising an isothiazolone compound, suppresses the decomposition of the isothiazolone compound and reduces skin irritation caused by the isothiazolone compound.
BACKGROUND OF THE INVENTION
The isothiazolone compounds such as 5-chloro-2-methyl-4-isothiazolin-3-one as a typical example, show an excellent antimicrobial property and are widely used as agents for the control of the lama, bactericides, algaecides and 20 fungicides in various systems such as cooling water systems, paper and pulp industry, coating materials industry, adhesive materials industry, cutting oil treatments and wastewater treatments. However, the isothiazolone compounds are very
Ref: 127567
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^ | ¡J ^ jgg. z ^ AA. ? .1.
unstable and the stability of the agents containing these compounds must be improved in order to use the agents effectively. Therefore, various studies on improvement have been conducted. For example, in the specification of Japanese Patent Application Publication Showa 54 (1979) -23968, complexes of isothiazolone compounds with metal salts such as calcium chloride and zinc chloride are proposed as a complex having the activity to kill organisms, which are useful for controlling various types of organisms, particularly microorganisms, and not readily decomposed in the presence of ordinary additives or contaminating substances or under severe conditions, and exhibit excellent heat stability. In the specification of U.S. Patent No. 3870795, it is reported that isothiazolone compounds can be stabilized by suppressing decomposition by the addition of metal nitrates such as calcium nitrate and magnesium nitrate or metal nitrates such as sodium nitrite. and calcium nitrite, to the solutions of the isothiazolone compounds. In Japanese Patent Application Specifications Open to the Public Nos. Showa
61 (1986) -56174 and Showa 61 (1986) -212576, the stabilized solutions of isothiazolone compounds prepared by the addition of metal salts such as copper chloride, sodium chloride, magnesium chloride and copper nitrate to the solutions of the isothiazolone compounds such as 5-chloro-2-methyl-4-isothiazolin-3-one in propylene glycol, 1,5-pentanediol or benzyl alcohol However, the above agents and solutions have disadvantages in that the stability of the Isothiazolone compounds deteriorate noticeably when the agents and solutions are nothing else diluted with water or organic solvents. In the specification of Japanese Patent Application Laid-Open No. Heisei 5 (1993) -124917, a method is proposed for protecting the isothiazolone compounds from decomposition using sulfur-containing compounds such as L-ci.at.ina, in combination with isothiazolone compounds. However, this method has a drawback in that L-cystine has a small solubility in water and in hydrophilic organic solvents and it is difficult to mix the L-cystine with the isothiazolone compounds. Therefore, an antimicrobial compound that suppresses the decomposition of isothiazolone compounds and shows excellent stability has been desired. Isothiazolone compounds often irritate the skin and agents containing isothiazolone compounds should be handled with sufficient care. In the specification of Japanese Patent Application Laid-Open No. Heisei 5 (1993) -246807, compositions containing polycationic compounds such as polylysine and isothiazolone are described. However, it is known that these compositions do not show the effect of suppressing the decomposition of the isothiazolone compounds.
DESCRIPTION OF THE INVENTION
An object of the present invention is to provide an antimicrobial composition comprising an isothiazolone compound, which suppresses the decomposition of the isothiazolone compound and which reduces skin irritation, caused by the isothiazolone compound. As a result of extensive studies to achieve the above objective, it was found that specific aminocarboxylic acids and derivatives thereof show the effect of stabilizing isothiazolone compounds and reducing skin irritation.
^^^ l? ^^ jg ^^^^^ j ^^^^ j ^^^ j ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ isothiazolone compounds. The present invention has been completed based on this knowledge. The present invention provides: (1) An antimicrobial composition comprising an isothiazolone compound, represented by the general formula [1] or the general formula [2] and an ammocarboxylic acid represented by the general formula [3] or an acid derivative to inocarboxyl co: 10
wherein R 1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, X and Y each represent a hydrogen atom, a halogen atom, or form a benzene ring in combination with the carbon atoms in positions 4 and 5 of the isothiazolone compound, M 25 represents a cation of an alkali metal, a metal
^ YH ^ ^^^ x «^ & aÉj & gbjMi ^ £ | É ^^ ***. * < ? ? * k * JL *? ?? bS MMa ± * alkaline earth, a heavy metal or an amine, Z represents an anion which forms, in combination with the cation represented by M a compound having a sufficient solubility to form a complex compound, a represents 1 or 2 and n represents an integer required for the anion represented by Z to satisfy a valence of the cation represented by M;
wherein R 2 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, unsubstituted or substituted with a carboxyl group, R 3
represents a linear or branched alkylene group having from 1 to 5 carbon atoms, R4 represents a hydrogen atom or an alkyl group having from 1 to 5 carbon atoms, unsubstituted or substituted with a carboxyl group, a carbamoyl group , a group
Hydroxyl, a phenyl group, a hydroxyphenyl group, a ureido group, a methylthio group or a 4-imidazolyl group, R 2 and R 4 form a heterocyclic group unsubstituted or substituted by a hydroxyl group or oxo group in combination with N- (R 3 ) bC and b represents 0 or 1; Y
(2) An antimicrobial composition according to (1), wherein the aminocarboxylic acid derivative represented by the general formula [3] is a metal salt of the aminocarboxylic acid represented by the general formula [3J; a compound having a structure in which the aminocarboxylic acids represented by the general formula [3] of one or more types are linked to each other via a peptide bond or a metal salt of the compound; a compound
Having a structure in which the ammocarboxylic acid represented by the general formula [3] is linked to a different aminocarboxylic acid, through a peptide bond, or a metal salt of the compound; an N-acetyl acid compound
ammocarboxylic represented by the general formula [3] or a metal salt of the compound; or an amide of the aminocarboxylic acid represented by the general formula [3]. Preferred embodiments of the present invention include: (3) An antimicrobial composition described in any of (1) and (2), comprising 0.1 to 10% by weight of the isothiazolone compound represented by the general formula [1] or the general formula [2]; and (4) An antimicrobial composition described in
any of (1), (2) and (3), which comprises the acid
ammocarboxylic acid or the derivative thereof represented by the general formula [3] in an amount per mol 0.1 to 50 times the amount per mol of the isothiazolone compound represented by the general formula [1] or the general formula [2].
THE MOST PREFERRED MODALITY TO CARRY OUT THE
INVENTION
The antimicrobial composition of the present invention comprises an isothiazolone compound represented by the general formula [1] or the general formula [2] and an aminocarboxylic acid represented by the general formula [3] or a derivative of the ammocarboxylic acid.
j ^ Ügyhgjj ^^^^^^^^^^^^^^^ and ^^^^^ IU? a ^ JS »t ^ £ jL? s.? kÁ? á.
In the general formula [1] and in the general formula [2], R1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group, X and Y each represent a hydrogen atom or a halogen atom, or form a benzene ring in combination with the carbon atoms at positions 4 and 5 of the isothiazolone compound, M represents a cation of an alkali metal, an alkaline earth metal, a heavy metal or an amine, Z represents an anion that forms, in combination with the cation represented by M, a compound having a sufficient solubility to form a complex compound, represents 1 or 2 and n represents an integer required for the anion represented by Z to satisfy a valence of the cation represented by M;
N- (R3) D-C-COOH (3) R '4 R4
In the general formula [3], R ^ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, unsubstituted or substituted with a carboxyl group, RJ represents a linear or branched alkylene group having from 1 to 5 carbon atoms, R4 represents a hydrogen atom or an alkyl group having from 1 to 5 carbon atoms, unsubstituted or substituted by a carboxyl group, (-COOH), a carbamoyl group (-CONH2), a hydroxyl group (-OH), a phenyl group (-C6H5), a hydroxyphenyl group (-C6H4OH), a ureido group (-NHCONH2), a methylthio group (-SCH3) or a 4-imidazolyl group:
R2 and R4 form a heterocyclic group unsubstituted or substituted by a hydroxyl group or an oxo group, in combination with N- (R3) -C and b represents 0 or 1. Examples of the isothiazolone compound represented by the general formula [1] include 2-methyl-4-? sot? azolm-3-one, 2-ethyl-4-? sot? azolin-3-one, 2-oct? l-4-isot? azolm-3-one, 5-chloro -2-methyl-4-isothiazolin-3-one, 5-clQro-2-octyl-4-? Sthiazolin-3-one, 4,5-d? Chloro-2-met? L-4-? Sotiazolm-3 -one, 4, 5-dichloro-2-octyl-4-isot-azolm-3-one and 1,2-benzoisot-azolin-3-one. Examples of the isothiazolone compound represented by the general formula [2] include the complex compounds of the isothiazolone compounds
^^^^^^^^ § ^ ^ ^ ^ g $ j¡ represented by the general formula [1] with magnesium chloride, magnesium nitrate, copper chloride, copper nitrate and calcium chloride. Examples of the aminocarboxylic acid represented by the general formula [3] include glycine, alanine, β-alanine, valine, leucine, isoleucine, serine, threonine, aspartic acid, glutamic acid, asparagine, glutamine, sarcosine, citrulline, methionine, -aminobutyric acid, ß-aminobutyric acid, α-aminobutyric acid, e-aminocaproic acid, phenylalanine, tyrosine, histidine, proline, 4-hydroxyproline, 2-pyrrolidone-5-carboxylic acid and iminodiacetic acid. As the compound having a structure in which the aminocarboxylic acid represented by the general formula [3] is linked through a peptide bond, the compounds having a structure in which the aminocarboxylic acids represented by the general formula [3] ] of one or more types are linked to each other via a peptide bond, are preferable. Examples of such compounds include glycylglycine, glycylglycylglycine, glycylglycylglycylglycine, glycyl alanine, glycyl paraffin, glycyl-leucine, glycylisoleucine, glycylphenylalanine, glycylproline, glycolsarcosine,
-. ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ Glycyl-serine, glycylthreonine, glycylvaline, glycylglutamine, alanylalanine, alanylapargin, alanylglutamine, alanylglycine, alanylphenylalanine, alanyltyrosine, β-alanylhistidine, polyasparagic acid and polyglutamic acid. Examples of the N-acetyl aminocarboxylic acid compound represented by the general formula [3] include N-acetylglycine, N-acetylalanine, N-acetyl-L-asparagic acid, N-acetyl-L-glutamic acid and N-acetyl tyrosine. Examples of the aminocarboxylic acid amide represented by the general formula [3] include glycinamide. Examples of the metal salt of the compound represented by the general formula [3] and the derivatives thereof include lithium salts, sodium salts, potassium salts, calcium salts and magnesium salts. The ammocarboxylic acids represented by the general formula [3] occasionally include DL-compounds, L-compounds and D-compounds. Any of the compounds DL, L-compounds and D-compounds can be used in the present invention. In the composition of the present invention, glycine and sodium glutamate are preferably used as the aminocarboxylic acid depicted
^^^^. ^. ^^. ^ ^^ -. & A ^, ^^^ m ^^ .. ^^ ,, ^^^ ^ ^ m ^ by the general formula [3] and the derivative thereof. Glycine and sodium glutamate have advantages in that the antimicrobial composition can be prepared rapidly since these compounds have large dissolution rates, that the amounts by weight of these compounds are smaller when these compounds are used in an amount prescribed by mole in relation to an amount per mole of the isothiazolone compound represented by the general formula [1] or the
general formula [2] since these compounds have smaller molecular weights and since these compounds are readily available, since these compounds are industrially produced on a large scale. In the composition of the present invention, the
The concentration of the isothiazolone compound represented by the general formula [1] or the general formula [2] is not particularly limited. It is preferable that the concentration be 0.1 to 10% by weight and more preferably 0.5 to 8% by weight. When the
The concentration of the isothiazolone compound represented by the general formula [1] or the general formula [2] is less than 0.1% by weight, the volume of the antimicrobial composition as a commercial product is increased and there is a possibility that the product is 5 economically disadvantageous in transportation and in
storage. When the concentration of the isothiazolone compound represented by the general formula [1] or the general formula [2] exceeds 10% by weight, there is a possibility that the stability of the antimicrobial composition is adversely affected. In the present invention, the concentration of aminocarboxylic acid represented by the general formula [3] or the derivative thereof is not particularly limited. It is preferable that the aminocarboxylic acid c the derivative thereof be used in an amount per mol 0.1 to 50 times and more preferably 1 to 10 times the amount per mol of the isothiazolone compound represented by the general formula [1] or the general formula [ 2]. When the amount of the ammocarboxylic acid represented in the general formula [3] or the derivative thereof is less than the amount per mol 0.1 times the amount per mol of the isothiazolone compound, there is a possibility that the stability of the antimicrobial composition is insufficient and the decomposition of the isothiazolone compound tends to take place, and the irritation of the skin is increased. It is generally sufficient that the amount per mole of the ammocarboxylic acid represented by the general formula [3] or the derivative thereof is 50 times the amount per mole of the isothiazolone compound
s ^ A ^? & ^ a. £ ^ £ ^ a,. ^ or smaller. The stability of the antimicrobial composition or the effect of reducing the irritation of the skin caused by the isothiazolone compound is no longer improved even when the aminocarboxylic acid represented by the general formula [3] or the derivative thereof is used in an amount per mol exceeding 50 times the amount per mole of the isothiazolone compound. When the aminocarboxylic acid derivative represented by the general formula [3] is a polyamino acid, it is preferable that the concentration of the derivative in the antimicrobial composition is 0.1 to 20% by weight. The solvent used in the composition of the present invention is not particularly limited, as long as the isothiazolone compound represented by the general formula [1] or the general formula [2] and the aminocarboxylic acid represented by the general formula [3] or the derivative thereof is dissolved in the solvent. Because the composition is frequently used in an aqueous system, water or a hydrophilic organic solvent are preferable as the solvent. Examples of the hydrophilic organic solvent include the amides such as dimethylformamide; glycols such as ethylene glycol, propylene glycol, diethylene glycol and dipropylene glycol; glycol esters such as methyl-L-acetyl, phenyl-cellosolve, diethylene glycol monomethyl ether and dipropylene glycol monomethyl ether; alcohols having 8 or less carbon atoms; and esters such as methyl acetate, ethyl acetate, 3-methoxybutyl acetate, 2-ethoxyethyl acetate, 2-ethoxypropyl acetate and propylene carbonate. It is preferable that the pH of the antimicrobial composition of the present invention be 7 or less. It is preferable that the pH of the composition be 2 to 5 to improve the stability of the isothiazolone compound. The antimicrobial composition of the present invention may further comprise corrosion inhibitors, scale inhibitors, antimicrobial agents other than isothiazolone compounds, foam disintegrating agents, surfactants and algaecides where necessary. Examples of the corrosion inhibitor include tolyltriazole, benzotriazole, methylbenzotriazole, molybdic acid, tungstic acid, silicic acid, nitrous acid, 2-phosphonobutan-1,2-tricarboxylic acid, hydroxyethyldendiphosphonic acid, hexametaphosphoric acid, tripolyphosphoric acid, orthophosphoric acid, salts of these compounds, zinc chloride, zinc chloride hydrochloride, zinc sulfate, zinc ligninsulfonate and hydrazine.
Examples of the scale inhibitor include polyacrylic acid, copolymers of acrylic acid and 2-hydroxyethyl methacrylate, copolymers of acrylic acid, 2-hydroxyethyl methacrylate and methyl acrylate 5, copolymers of acrylic acid and allyl glycidyl ether or a derivative of these, copolymers of acrylic acid and 2-hydroxy-3-allyloxy-1-propanesulfonic acid, copolymers of acrylic acid and isoprene sulfonic acid, copolymers of acrylic acid
and vinylsulfonic acid, copolymers of acrylic acid and allylsulfonic acid, polymaleic acid, copolymers of maleic acid or maleic anhydride and isobutylene, copolymers of maleic acid or maleic anhydride and styrenesulfonic acid, copolymers of maleic acid or
maleic anhydride and acrylic acid, copolymers of maleic acid or maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid, copolymers of maleic acid or maleic anhydride and pentenoic acid, copolymers of maleic acid or maleic anhydride and a substance
Fluorescent such as 5-allylbenzosuberenol substituted with an allyl group, polyacrylamide, poly-itaconic acid and salts of these compounds. Examples of the antimicrobial agent other than the isothiazolone compounds include
halogenated nitroaliphatic compounds, such as 2-
bromo-2-nitro-l, 3-propanediol and 2,2-dibromo-2-nitroethanol; esters of these compounds; dibromonitrilopropionamide; alkylene bistiocyanates such as methylene bisthiocyanate; 1,4-bisbromoacetoxy-2-butene; hexabromo-dimethylsulfone; isophthalonitrile compounds such as 5-chloro-2,4,6-trifluoroisophthalonitrile and tetrachloroisophthalonitrile; dimethyl dithiocarbamate; 4, 5-dichloro-l, 2-dithiol-3-one; 3,3,4,4-tetrachloro-tetrahydrothiophen-1-dioxide;
triiodoalyl alcohol; bromonitrostyrene; aldehyde compounds such as glutaraldehyde; phthalaldehyde, isophthalaldehyde and terephthalaldehyde; dichloroglyxime; benzaldoxime compounds such as a-chlorobenzaldoxime acetate and a-chlorobenzaldoxime; and 5,5- 15 dimethylhydantoin. Examples of the foam disintegrating agent include silicone and non-silicone defoaming agents. Examples of the surfactant include anionic, cationic, nonionic surfactants and
amphoteric. Examples of the algicide include triazine compounds such as ametryn. The embodiments of the composition of the present invention include antimicrobial compositions containing 0.1 to 10% by weight of the
Isothiazolone compound represented by the formula
* ES &M ~? -.: * > &.;:: .-. • • '- - «*« - * general [1] or general formula [2], 0.1 to 20% by weight of the aminocarboxylic acid represented by the general formula [3] or the derivative thereof, 0 to 50% by weight of corrosion inhibitors, 0 to 50% by weight of scale inhibitors, 0 to 30% by weight of other antimicrobial agents, or to 10% by weight of foam disintegrating agents, 0 to 10% by weight of surfactants , 0 to 10% by weight of algicides and 30 to 99% by weight of water or a hydrophilic organic solvent. The antimicrobial composition of the present invention can be used in a suitably selected concentration in accordance with the objective and subject matter of the application. For example, when the composition is used for the prevention of the lama in a paper and pulp manufacturing system or in a cooling water system, it is preferable that the concentration of the isothiazolone compound is 0.1 to 25 g / m3. . When the composition is used for the prevention of putrefaction of an emulsion of a synthetic resin, a starch paste, a suspension of starch, a coating material or an oil for working with metals, it is preferable that the concentration of the isothiazolone compound be 1 to 5,000 g / m3.
The antimicrobial composition of the present invention containing the isothiazolone compound and the aminocarboxylic acid or the derivative thereof, shows excellent stabi under heating and for a prolonged time, does not cause decomposition of the isothiazolone compound for a prolonged time, shows the excellent antimicrobial effect derived from the isothiazolone compound and can be easily handled due to the decreased irritation of the skin, caused by the isothiazolone compound.
EXAMPLES
The present invention will be more specifically described in the following with reference to the examples. However, the present invention is not limited to the examples. In the examples and comparative examples, the irritation of the skin by an antimicrobial composition was evaluated according to the following method. The selection test of a prepared antimicrobial composition, with respect to skin irritation, was conducted using three rabbits
whites (New Zealand white strain) for each composition.
A portion of a normal skin of a mouse was used for the test. An antimicrobial composition without dilution in an amount of 0.5 ml was added to a gauze patch and applied to the portion for the test. After the patch was held in the portion for 4 hours, the patch was removed and the portion was washed. Skin irritation was visually observed after 1, 24, 48 and 72 hours, and recorded according to the criteria described below. The numbers with
With respect to erythema and edema were added, and the sums obtained were averaged to obtain a primary index for skin irritation (P1I) that was in the range of 0 to 8. Formation of erythema and eschar 15 0: no erythema 1: very light erythema (barely noticeable) 2 well-defined erythema 3 moderate to severe erythema 20 4 severe erythema (ro or as beet) to light eschar formation (damage in depth) Edemas formation 0: no edema 1: very light edema (barely perceptible)
2: light edema (edge of well defined area by defined eleon) 3: moderate edema (raised approximately 1 mm) 5 4: severe edema (raised more than 1 mm and extending beyond the exposure area)
Example 1 A solution of ethylene glycol (ZONEN-F;
manufactured by ICHIKAWA GOSEI KAGAKU Co. , Ltd.) containing 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one and 1% by weight of 2-methyl-4-isothiazolin-3-one in an amount of 5.0 parts by weight. weight, 0.62 parts by weight of glycine and 94.38 parts by weight of water, were mixed
to form a homogeneous solution and an antimicrobial composition was prepared. The prepared antimicrobial composition contained glycine in an amount per mole twice the total amount per mole of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one. In addition, 25 types of antimicrobial compositions were prepared using, in place of glycine, alanine, β-alanine, DL-serine, DL-threonine, DL-asparagine, L-glutamma, sarcosine, DL-β-aminobutyric acid, acid ? -aminobutyric acid, DL-methionine,
iminodiacetic acid, glycylglycine, glycylglycylglycine, glycylglycylglycylglycine, glycyl-L-glutamine, L-alanyl-L-glutamine, β-alanyl-L-histidine, pyrrolidinecarboxylic acid, N-acetylglycine, N-acetyl-L-tyrosine, L-aspartate sodium, sodium L-glutamate, citrulline, phenylalanine or glycinamide such as the aminocarboxylic acid represented by the general formula [3] or the derive thereof. A solution of ethylene glycol (ZONEN-F; manufactured by ICHIKAWA GOSEI KAGAKU CO., Ltd.) containing 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one and 1% by weight of 2- methyl-4-isothiazolin-3-one in an amount of 5.0 parts by weight and the aminocarboxylic acid represented by the general formula [3] or the derive thereof, in an amount per mole of twice the total amount per mole of -chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and water, in an amount such that the total amount of the composition was 100 parts by weight, were mixed form a homogeneous solution. The 26 types obtained from antimicrobial compositions were allowed to stand at room temperature for one month. The compositions remained as clear liquids and no precipitates were found.
Comparative Example 1 A solution of ethylene glycol (ZONEN-F, manufactured by ICHIKAA GOSEI KAGAKU CO., Ltd.) containing 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one and 1% by weight of 2-methyl-4-isothiazolin-3-one in an amount of 5.0 parts by weight and 95.0 parts by weight of water were mixed to form a homogeneous solution and an antimicrobial composition was prepared. The prepared antimicrobial composition is
of or at rest at room temperature for one month. Yellow-orange precipitates formed in the composition. The results of Example 1 and Comparative Example 1 are shown in Table 1. TABLE 1 Aminocarboxylic acid or derivative thereof Appearance after one month Example 1 No 1 Glycine Clear liquid, no precipitate No 2 Alamine Clear liquid, no precipitate No 3 ß-alaruna Clear liquid, without precipitate No 4 DL-sepna Clear liquid, without precipitate No 5 DL-threonine Clear liquid, without precipitate No 6 DL-aspargina Transparent liquid, without precipitate No 7 L-glutanuna Clear liquid, without precipitate
No. 8 Sarcosine Clear liquid, without precipitate
No 9 Acid Clear liquid, without precipitate
No. 10 Acid? -aminobutyric Clear liquid, sm precipitate
No. 11 DL-metiomna Clear liquid, sm precipitate
No. 12 Minodiacetic acid Clear liquid, without precipitate
No 13 Glycylglycine Clear liquid, no precipitate No. 14 Ghcylglycylgly Clear liquid, without precipitate No. 15 Glycylglycylglycylglycol Clear liquid, without precipitate No. 16 Ghcil-L-glutamine Clear liquid, without precipitate No 17 L-alanyl-L-glutapuna Transparent liquid , no precipitate No 18 ß-alanyl-L-histidine Clear liquid, no precipitate No 19 pyrrolidonecarboxylic acid Clear liquid, no precipitate No 20 N-acetylcholine Clear liquid, no precipitate No 21 N-acetyl-L-tyrosine Clear liquid, no precipitate No. 22 L-aspartate of sodium Clear liquid, sm precipitate No 23 L-glutamate of sodium Clear liquid, sm precipitate No 24 Otruline Clear liquid, sm precipitate No. 25 Phenylalanine Clear liquid, sm precipitate No 26 glicinanuda Clear liquid, no precipitate Comparative Example 1 Yellow-orange precipitates None
As shown by the results in Table 1, precipitates were formed in the antimicrobial composition of Comparative Example 1 containing
-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one but not containing the aminocarboxylic acid represented by the general formula [3] or the derivative thereof after the composition was allowed to stand at room temperature for one month. In contrast, the antimicrobial compositions of Example 1 containing the aminocarboxylic acid represented by the general formula [3] or the derivative thereof showed no change in appearance after the compositions were allowed to stand at room temperature for 1 month and They showed excellent stability for a long time.
Example 2 From the 26 types of antimicrobial compositions prepared in Example 1, 23 types of compositions were selected and allowed to stand in a constant temperature oven maintained at 60 ° C for 48 hours. Then, the content of 5- 0 chloro-2-methyl-4-isothiazolin-3-one was measured according to the high-resolution liquid chromatography and the residue was calculated. The residue of 5-chloro-2-methyl-4-izothiazolin-3-one in the antimicrobial composition containing glycine was 76%. The residues of the other 5 antimicrobial compositions are shown in Table 2.
Comparative Example 2 The antimicrobial composition prepared in Comparative Example 1 was allowed to stand in a constant temperature oven maintained at 60 ° C for 48 hours. Then, the content of 5-chloro-2-methyl-4-isothiazolin-3-one was measured according to high performance liquid chromatography. No peaks of 5-chloro-2-methyl-4-isothiazolin-3-one were found in the chromatogram. This shows that 5-chloro-2-methyl-4-0 isothiazolin-3-one was completely decomposed.
Comparative Example 3 A solution was prepared in ethylene glycol (ZONEN-F, manufactured by ICHIKA A GOSEI KAGAKU CO., Ltd.) containing 11% by weight of 5-chloro-2-methyl-4-isot-azolin-3-one. and 1% by weight of 2-methyl-4-isothiazolin-3-one in an amount of 5.0 parts by weight, 2.0 parts by weight of polylysine and 93.0 parts by weight of water, and mixed to form a homogeneous solution and a antimicrobial composition. The antimicrobial composition prepared above was allowed to stand in a constant temperature oven maintained at 60 ° C for 48 hours. Then, the content of 5-chloro-2-methyl-4-isothiazolin-3-one was measured according to the chromatography
-i ffin ~ ^ «2 > yltíii > l S Sil * and &6aSL * eM¡ * ~, < .a »j ^ jaafejjlj high resolution liquid. No peaks of 5-chloro-2-methyl-4-isothiazolin-3-one were found in the chromatogram. This shows that 5-chloro-2-methyl-4-isothiazolin-3-one was completely decomposed. The results of Example 2 and Comparative Examples 2 and 3 are shown in Table 2.
TABLE 2 Ammocarboxylic acid or derivative thereof 5-chloro-2-methyl-4-isothiazolin-3-one. residual (%)
Example 1 No. 1 Glycine 76 No. 2 Alanine 60 No. 3 β-alanine 58 No. 4 DL-serine 71 No. 5 DL-threonine 76 No. 6 DL-asparagine 67 No. 7 L-glutamine 78 No. 8 Sarcosine 60 No. 9 DL-ß-aminobutyric acid 73 No. 10? -aminobutyric acid 61 o. 11 DL-methionine 45 o. 12 iminodiacetic acid 99 o. 13 glycylglycine 100 o. 14 Glycylglycylglycine 100 No. 15 Glycylglycylglycylglycine 100 No. 16 Glycyl-L-glutamine 100 No. 17 L-alanyl-L-glutamine 100 No. 18 ß-alanyl-L-histidine 88 No. 19 Pyrrolidonecarboxylic acid 52 No. 20 N- acetylglycine 35 No. 21 N-acetyl-L-tyrosine 62 No. 22 L-aspartate sodium No. 23 L-sodium glutamate 74 Comparative Example 2 None 0 Comparative Example 3 Polylysine 0
As shown by the results in Table 2, 5-chloro-2-methyl-4-isothiazolin-3-one was completely decomposed in the antimicrobial composition of Comparative Example 2, which contained 5-chloro-2-met? l-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one but did not contain the aminocarboxylic acid represented by the general formula [3] or the derivative thereof after the composition was left at rest at 60 ° C for 48 hours. In contrast, the antimicrobial compositions of Example 2 containing the aminocarboxylic acid represented by
general formula [3] or the derivative thereof showed a higher residue of 5-chloro-2-methyl-4-isothiazolin-3-one after the compositions were allowed to stand at 60 ° C for 48 hours and showed excellent stability thermal In particular, 5-chloro-2-methyl-4-isot-azolin-3-one did not decompose completely and the residue remained at 100% in the antimicrobial compositions containing glycylglycine, glycylglycylglycine, glycylglycylglycylglycine, glycyl-L-glutamine or L-alanyl-L-glutamine, for example, the compound having a structure in which the ammocarboxylic acids represented by the general formula [3] were linked to each other via a peptide bond. The antimicrobial composition of Comparative Example 3 having a compound having a structure which is similar to ammocarboxylic acid represented by the general formula [3] but in which the group represented by R 4 is an alkyl group substituted with the ammo group, for example , polylysine, showed lower thermal stability and 5-chloro-2-methyl-4-isothiazolin-3-one completely decomposed after the composition was allowed to stand at 60 ° C for 48 hours.
Example 3 An aqueous solution (KATHON-WT; manufactured by ROHM &HAAS Company) containing 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one, 3% by weight of 2-5 methyl 4-isothiazolin-3-one, magnesium chloride and magnesium nitrate, was used in place of the ethylene glycol solution (ZONEN-F, manufactured by ICHIKAWA GOSEI KAGAKU Co., Ltd.) containing 11 wt. -chloro-2-methyl-4-isothiazolin-3-one and 1% by weight of 2-methyl-4-isothiazolin-3-one. Glycylglycine, glycylglycylglycine, glycylglycylglycylglycine, glycyl-L-glutamine or L-alanyl-L-glutamine were used as the aminocarboxylic acid represented by the general formula [3] or the derivative thereof. Five types of 5 antimicrobial compositions were prepared according to the same procedures as those conducted in Example 2. The prepared compositions were allowed to stand in a constant temperature oven maintained at 60 ° C for 48 hours. Then, the content of 5-chloro-2-methyl-4-isothiazolin-3-one was measured according to high performance liquid chromatography. The residue of 5-chloro-2-methyl-4-isothiazolin-3-one was 100% in all compositions. 5
^^^^^ tó »^^^^^« «^^^^ t ^^^^^ Comparative Example 4
An aqueous solution (KATHON-WT; manufactured by ROHM &HAAS Company) containing 11% by weight of 5- 5 chloro-2-methyl-4-isothiazolin-3-one, 3% by weight of 2-methyl 4-isothiazolin-3-one, magnesium chloride and magnesium nitrate in an amount of 5 parts by weight and 95.0 parts by weight of water were mixed to form a homogeneous solution and an antimicrobial composition was prepared. The prepared compositions were allowed to stand in a constant temperature oven maintained at 60 ° C for 48 hours. Then, the content of 5-chloro-2-meth? L-4? -thiazolm-3-one was measured according to the high-resolution liquid chromatography. The residue of 5-chloro-2-met? L-4-? Sot? Azole-3-one was 51%. The results of Example 3 and Comparative Example 4 are shown in Table 3.
twenty
TABLE 3
Aminocarboxylic acid-or denative of the same 5-chloro-2-meth? L-4-isot? Azolm-3-one (%) Example 3 No. 13 Glycylglycine 100 No. 14 Glycylglycylglycine 100 No. 15 Glycylglycylglycylglycine 100 No. 16 Glycyl-L-glutamine 100 No. 17 L-alanyl-L-glutamine 100 Comparative Example 4 None 51
As shown by the results in Table 3, 5-chloro-2-methyl-4-isothiazolin-3-one in the antimicrobial compositions of Example 3 containing glycylglycine, glycylglycylglycine, glycylglycylglycylglycine, glycyl-L-glutamine or L- alanyl-L-glutamine, for example, the compound in which the aminocarboxylic acids represented by the general formula [3] were linked to each other via a peptide bond, did not decompose completely and the residue remained at 100% after that the compositions were allowed to stand at 60 ° C for 48 hours. In contrast, the antimicrobial composition of Example
The comparison 4 which did not contain the aminocarboxylic acid represented by the general formula [3] or the derivative thereof showed lower thermal stability and approximately half of the the amount of 5-chloro-2-methyl-4-isothiazolin-3-one was decomposed after the composition was allowed to stand at 60 ° C for 48 hours.
Example 4 A solution in ethylene glycol (ZONEN-F;
manufactured by ICHIKAA GOSEI KAGAKU Co. , Ltd.) containing 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one and 1% by weight of 2-methyl-4-isothiazolin-3-one in an amount of 5.0 parts by weight. weight, 1.09 parts by weight of glycylglycine and 93.1 parts by weight of water,
mixed to form a homogeneous solution and an antimicrobial composition was prepared. The prepared antimicrobial composition contained glycylglycine in an amount per mole twice the total amount per mole of 5-chloro-2-methyl-4- s -thiazolin-3-one and 2-methyl-4-isothiazolin-3-one. . Using Bacillus subtilis, the prepared composition was examined for the effect of suppressing the development of the bacteria. In a liquid medium containing 1 g / liter of peptone and 1 g / liter of yeast extract and that had
pH of 7, Bacillus subtilis was inoculated in an amount of
106 bacteria / ml. To the inoculated medium, the above antimicrobial composition was added in an amount such that the concentration was 20 mg / liter, 60 mg / liter or 100 mg / liter. The medium obtained was cultivated at 30 ° C for 24 hours while stirring. The effect of suppression of the development of the bacteria was found when the concentration was 60 mg / liter and 100 mg / liter, although the effect was not found when the concentration was 20 mg / liter. After the aforementioned antimicrobial composition was allowed to stand at room temperature for 1 month, the composition was examined for the effect of suppressing bacterial development, according to the same procedures as those conducted above. The effect of suppression of development of the bacteria was found when the concentration was 60 mg / liter and 100 mg / liter, although the effect was not found when the concentration was 20 mg / liter.
Comparative Example 5 A solution in ethylene glycol (ZONEN-F; manufactured by ICHIKAWA GOSEI KAGAKU Co., Ltd.) containing 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one and 1% by weight of 2-methyl-4-isothiazolin-3-one in a
amount of 5.0 parts by weight and 95 parts by weight of water, were mixed to form a homogeneous solution and an antimicrobial composition was prepared. Using Bacillus subtilis, the prepared composition was examined with respect to the effect of suppressing the development according to the same procedures as those conducted in Example 4. The suppression effect of the development of the bacteria was found when the concentration was 60 mg / liter and 100 mg / liter, although
the effect was not found when the concentration was 20 mg / liter. After the aforementioned antimicrobial composition was allowed to stand at room temperature for one month, the composition was
examined with respect to the suppression effect of the development of the bacteria according to the same procedures as those described above. The suppressive effect of the development of the bacteria was not found in any of the cases where the
The concentration was 20 mg / liter, 60 mg / liter and 100 mg / liter. The results of Example 4 and Comparative Example 5 are shown in Table 4.
TABLE 4
Test Time Concentration of the suppression effect of the antimicrobial composition development of the mg / hrtro bacteria Example 4 Immediately after the preparation 20 Not shown 60 Shown 100 Shown After 1 month at room temperature 20 Not Shown 60 Shown 100 Shown Comparative Example 5 Immediately after preparation 20 Not shown 60 Shown 100 Shown After 1 month at room temperature 20 Not shown 60 Not shown 100 Not shown
As shown by the results in Table 4, the antimicrobial composition prepared in Comparative Example 5 lost the effect of suppressing the development of Bacillus subtilis after the composition was left standing at room temperature for 1 month. In contrast, the antimicrobial composition
. ku ^ im? üu *** »,. .. *** .. L .- ^. The preparation prepared in Example 4, which contained glycylglycine, maintained the effect of suppressing the development of bacteria after the composition was removed. let stand at room temperature for 1 month. Thus, it is shown that the antimicrobial composition of the present invention exhibits excellent stability for a long time.
Example 5 Glycine, sodium L-glutamate, iminodiacetic acid or glycylglycine were used as the ammocarboxylic acid represented by the general formula [3] or the derivative thereof. A solution in ethylene glycol (ZONEN-F, manufactured by ICHIKAWA GOSEI KAGAKU Co., Ltd.)
which contained 11% by weight of 5-chloro-2-methyl-4- isothiazolin-3-one and 1% by weight of 2-methyl-4-isothiazolin-3-one in an amount of 5.0 parts by weight, the aminocarboxylic acid represented by the general formula [3] or the derivative thereof in an amount per mol
times the total amount by mol of 5-chloro-2-methyl-4- isothiazolin-3-one and 2-methyl-4-? Sotiazolin-3-one and water in an amount such that the total amount of the composition was of 100 parts by weight, were mixed to form a homogeneous solution and 4 types of
antimicrobial compositions.
^^ ^^^ * KLG Iî fe3W ^^^^^^^^^^^^^ 3J ^ i | &? * ^^^^ ¿í ^ The above test of irritation of skin was conducted using the compositions antimicrobials prepared.
Comparative Example 6 A solution of ethylene glycol (ZONEN-F; manufactured by ICHIKAWA GOSEI KAGAKU Co., Ltd.) containing 11% by weight of 5-chloro-2-methyl-4-isothiazolin-3-one and 1% by weight 2-meth? l-4-isothiazolin-3-one in an amount of 5.0 parts by weight and 95.0 parts by weight of water were mixed to form a homogeneous solution and an antimicrobial composition was prepared. The previous test of skin irritation was conducted using the prepared antimicrobial composition. The results of Example 5 and Comparative Example 6 are shown in Table 5.
Table 5
Amino acid- Number obtained by evaluation Primary carboxylic index Irritation Time (hour) for irritation Example 5 Glycine 2 33 2 33 2 67 3 33 5 67 4 00 3 00 3 00 2 00
^^^^^^^^^? ^^? ^ ^^^^^^ j ^^^ i ^ ^ Total 6.33 5.33 5.67 5.33 L-glutamate Erythema 2.33 2.33 2.67 3.33 3.67 5.67 sodium Edema 4.00 3.00 3.00 2.00 Total 6.33 5 33 5.67 5.33 Acid Erythema 2.33 3.00 2.67 3.33 5 42 iminodiacetic Edema 4 00 2.33 2.00 2.00 Total 6.33 5.33 4.67 5.33 Ghcilghcina Erythema 2.00 2.67 2.67 2.67 5.25 Edema 4.00 2 67 2.33 2.00 Total 6.00 5.34 5.00 4 67 Comparative Example 6 none Erythema 3 33 3 00 3 33 3.33 7.25 Edema 4 00 4 00 4 00 4 00 Total 7.33 7 00 7 33 7.33
The results of Example 5 and Comparative Example 6 in Table 5 were obtained under the same condition, except that the aminocarboxylic acid or derivative thereof was present in Example 5 and absent in Comparative Example 6. When these results are compared , it is shown that the antimicrobial compositions prepared in Example 5, which contained glycine, sodium L-glutamate, acid
^^^ l ^^^^ l ^^^^^^ i ^^^^^^^^^^^^ J ^^^^^^ C ^^^^ ygMj ^^^^^^^^ The iminodiacetic or glycylglycine showed smaller primary ratios of skin irritation than the antimicrobial composition prepared in Comparative Example 6 which did not contain the aminocarboxylic acid 5 or the derivative thereof. Thus, it is shown that the skin irritation caused by the antimicrobial composition containing the isothiazolone compound was reduced when the composition contained the aminocarboxylic acid or the derivative thereof.
INDUSTRIAL APPLICABILITY The antimicrobial composition of the present invention comprising the isothiazolone compound and
The aminocarboxylic acid or the derivative thereof, shows excellent stability for a long time and excellent heat stability, suppresses the decomposition of the isothiazolone compound even after storage for a long time,
shows the excellent antimicrobial effect of the isothiazolone compound, reduces the skin irritation caused by the isothiazolone compound and can be handled easily.
It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Claims (18)
1. An antimicrobial composition comprising an isothiazolone compound represented by the general formula [1] _ or the general formula [2] and a 10 aminocarboxylic acid represented by general formula [3] or an aminocarboxylic acid derivative: Characterized in that R1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkyl group or an aralkyl group, X and Y each represent a hydrogen atom, a halogen atom, or form a ring of 25 benzene in combination with the carbon atoms in the • < ttí. .- & a < fcwt.fc »? -XÉÉ S &? i ^ ujtaai positions 4 and 5 of the isothiazolone compound, M represents a cation of an alkali metal, an alkaline earth metal, a heavy metal or an amine, Z represents an anion that forms, in combination with the cation depicted by M, a compound having sufficient solubility to form a complex compound, a represents 1 or 2 and n represents an integer required for the anion represented by Z to satisfy a valence of the cation represented by M; 0 Wherein R 'represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, unsubstituted or substituted with a carboxyl group, R3 represents a linear or branched alkylene group having from 1 to 5 carbon atoms, R4 represents a hydrogen atom or an alkyl group having from 1 to 5 carbon atoms, unsubstituted or substituted by a carboxyl group, carbamoyl group, hydroxyl group, phenyl group, hydroxyphenyl group, ureido group, methylthio group or group 4 - imidazolyl, R ^ and R4 form a heterocyclic group not substituted or substituted with hydroxyl group or oxo group in combination with N- (R3) b-C and b represents 0 or 1.
2. An antimicrobial composition according to claim 1, characterized in that the aminocarboxylic acid derivative represented by the general formula [3] is a metal salt of the aminocarboxylic acid represented by the general formula [3]; a compound having a structure in which the aminocarboxylic acids represented by the general formula [3] of one or more types are linked to each other via a peptide bond or a metal salt of the compound; a compound having a structure in which the aminocarboxylic acid represented by the general formula [3] is linked to a different aminocarboxylic acid via a peptide bond or a metal salt of the compound; an N-acetyl compound of the aminocarboxylic acid represented by the general formula [3] or a metal salt of the compound; or an amide of the aminocarboxylic acid represented by the general formula [3].
3. An antimicrobial composition according to claim 1, characterized in that it comprises 0.1 to 10% by weight of the compound of ^ ákaCfejt ^ ari || atfufeM £ jgKÉi | ftÉ | O? A? «» L ?? * lltíZ ~ -isotiazolona represented by the general formula [1] or the general formula [2],
4. An antimicrobial composition according to claim 3, characterized in that it comprises 0.5 to 8% by weight of the isothiazolone compound represented by the general formula [1] or the general formula [2].
5. An antimicrobial composition according to claim 1, characterized in that it comprises the aminocarboxylic acid represented by the general formula [3] or the aminocarboxylic acid derivative in an amount per mol 0.1 to 50 times an amount per mol of the isothiazolone compound represented by the general formula [1] or the general formula [2].
6. An antimicrobial composition according to claim 5, characterized in that it comprises the aminocarboxylic acid represented by the general formula [3] or the aminocarboxylic acid derivative in an amount per mole 1 to 10 times an amount per mole of the isothiazolone compound represented by the general formula [1] or the general formula [2].
7. An antimicrobial composition according to claim 1, characterized in that the isothiazolone compound represented by the general formula [1] or the general formula [2] and the aminocarboxylic acid represented by the general formula [3] or the aminocarboxylic acid derivative, they dissolve in water as a solvent.
8. An antimicrobial composition according to claim 1, characterized in that the isothiazolone compound represented by the general formula [1] or the general formula [2] and the aminocarboxylic acid represented by the general formula [3] or the aminocarboxylic acid derivative Dissolve in a mixed solvent of water and a hydrophilic solvent.
9. An antimicrobial composition according to claim 1, characterized in that the isothiazolone compound represented by the general formula [1] is 5-chloro-2-methyl-4-isothiazolin-3-one.
10. An antimicrobial composition "according to claim 1, characterized in that the isothiazolone compound represented by the general formula [2] is a complex compound of 5-chloro-5-methyl-4-isothiazolin-3-one with magnesium chloride or magnesium nitrate.
11. An antimicrobial composition according to claim 1, characterized 10 because the aminocarboxylic acid represented by the general formula [3] is glycine.
12. An antimicrobial composition according to claim 1, characterized 15 because the aminocarboxylic acid represented by the general formula [3] is iminodiacetic acid.
13. An antimicrobial composition according to claim 2, characterized Because the aminocarboxylic acid derivative represented by the general formula [3] is glycylglycine.
14. An antimicrobial composition according to claim 2, characterized 25 by the aminocarboxylic acid derivative represented by the general formula [3] is glycylglycylglycine.
15. An antimicrobial composition of 5 according to claim 2, characterized in that the aminocarboxylic acid derivative represented by the general formula [3] is glycyl-L-glutamine.
16. An antimicrobial composition according to claim 2, characterized in that the aminocarboxylic acid derivative represented by the general formula [3] is L-alanyl-L-glutamine.
17. An antimicrobial composition according to claim 2, characterized in that the aminocarboxylic acid derivative represented by the general formula [3] is β-alanyl-L-20 histidine.
18. An antimicrobial composition according to claim 2, characterized in that the ammocarboxylic acid derivative represented by the General formula [3] is sodium L-glutamate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10/249736 | 1998-09-03 | ||
| JP11/230876 | 1999-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA01002295A true MXPA01002295A (en) | 2001-11-21 |
Family
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