CN114428132A - 一种基于分子探针的异噻唑啉酮检测方法 - Google Patents
一种基于分子探针的异噻唑啉酮检测方法 Download PDFInfo
- Publication number
- CN114428132A CN114428132A CN202111614046.9A CN202111614046A CN114428132A CN 114428132 A CN114428132 A CN 114428132A CN 202111614046 A CN202111614046 A CN 202111614046A CN 114428132 A CN114428132 A CN 114428132A
- Authority
- CN
- China
- Prior art keywords
- molecular probe
- isothiazolinone
- sample
- detecting
- detection
- 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.)
- Pending
Links
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000001514 detection method Methods 0.000 title claims abstract description 25
- 239000003068 molecular probe Substances 0.000 title claims abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000000523 sample Substances 0.000 claims abstract description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 18
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims abstract description 18
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000003480 eluent Substances 0.000 claims abstract description 9
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims abstract description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 6
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 15
- 239000012071 phase Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 238000000504 luminescence detection Methods 0.000 abstract description 2
- 230000001376 precipitating effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 230000004044 response Effects 0.000 abstract description 2
- 238000007142 ring opening reaction Methods 0.000 abstract description 2
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 6
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 description 6
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 6
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 4
- VUWCWMOCWKCZTA-UHFFFAOYSA-N 1,2-thiazol-4-one Chemical class O=C1CSN=C1 VUWCWMOCWKCZTA-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 108010001949 Algal Proteins Proteins 0.000 description 2
- 108010077805 Bacterial Proteins Proteins 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 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
- 239000003139 biocide Substances 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002332 oil field water Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/062—Preparation extracting sample from raw material
Landscapes
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
本发明提供了一种基于分子探针的异噻唑啉酮检测方法。该技术方案摒弃了常规的发光检测路线,采用亚硫酸氢钠与异噻唑啉酮反应,从N‑S键处实现开环,所得产物可作为分子探针,从而进行定量检测。具体来看,本发明首先利用甲醇溶解待测样品,而后与特定量的碳酸钠溶液混合,并通过搅拌充分沉淀杂质;在此基础上,与亚硫酸氢钠混合并在加压低温条件下充分反应,反应产物与聚乙二醇混合后过WCX固相萃取柱,得到初步纯化,对所得的洗脱液,采用C8柱进行HPLC检测。本发明检测方法操作简便,检测速度快,响应灵敏,检出浓度低,具有良好的推广前景和突出的技术优势。
Description
技术领域
本发明涉及分析化学技术领域,具体涉及一种基于分子探针的异噻唑啉酮检测方法。
背景技术
异噻唑啉酮是一种杀虫剂,化学式为C8H9ClN2O282,主要由5-氯-2-甲基-4-异噻唑啉-3-酮(CIT)和2-甲基-4-异噻唑啉-3-酮(MIT)组成。异噻唑啉酮是通过断开细菌和藻类蛋白质的键而起杀生作用的。异噻唑啉酮与微生物接触后,能迅速地不可逆地抑制其生长,从而导致微生物细胞的死亡,故对常见细菌、真菌、藻类等具有很强的抑制和杀灭作用。异噻唑啉酮类杀菌剂在钢铁冶炼、油田注水、炼油厂、火力发电厂、大型化肥厂、造纸厂、轻纺、水涂涂料、工业清洗等领域也广泛应用。
常见的异噻唑啉酮类杀菌剂有:1,2-苯并异噻唑啉-3-酮(BIT)、-n-辛基-4-异噻唑啉-3-酮(OIT)、2-甲基-4-异噻唑啉-3-酮(MIT)、5-氯-2-甲基-4-异噻唑琳-3-酮(CMIT)。它们的共同特点是抗菌能力强、应用剂量小、相容性好、毒性低等优点,并且它对多种细菌、真菌都具有很强的抗菌作用。具有它们高效性、较好的配伍性、较宽的pH适用范围、能够自然生物降解。
异噻唑啉酮主要由5-氯-2-甲基-4-异噻唑啉-3-酮(CIT)和2-甲基-4-异噻唑啉-3-酮(MIT)组成。异噻唑啉酮是通过断开细菌和藻类蛋白质的键而起杀生作用的。异噻唑啉酮与微生物接触后,能迅速地不可逆地抑制其生长,从而导致微生物细胞的死亡,故对常见细菌、真菌、藻类等具有很强的抑制和杀灭作用。杀生效率高,降解性好,具有不产生残留、操作安全、配伍性好、稳定性强、使用成本低等特点。能与氯及大多数阴、阳离子及非离子表面活性剂相混溶。高剂量时,异噻唑啉酮对生物粘泥剥离有显著效果。
作为广泛使用的杀菌防腐剂,异噻唑啉酮的检测分析是确保食品安全的重要手段。对异噻唑啉酮的检测是利用其衍生物与亚硫酸氢钠定量反应,过量的亚硫酸氢钠与碘反应,用硫代硫酸钠标准滴定溶液滴定过量的碘。这种方法虽然能实现对苯并三唑的检测,但检测流程较为复杂,准确性较低,不利于保证检测效率。
发明内容
本发明旨在针对现有技术的技术缺陷,提供一种基于分子探针的异噻唑啉酮检测方法,以解决常规检测方法操作繁琐、准确性较低的技术问题。
为实现以上技术目的,本发明采用以下技术方案:
一种基于分子探针的异噻唑啉酮检测方法,包括以下步骤:取待测样品溶解于甲醇中,而后与浓度为1.2mol/L的碳酸钠溶液混合,而后搅拌20~30min,弃去沉淀物;向其中加入亚硫酸氢钠,将容器密封并加压至2.2个大气压,在8℃下静置反应2h,启封后向其中加入聚乙二醇;而后过WCX固相萃取柱,再用乙醚-氯仿洗脱,收集洗脱液,稀释,而后以如下条件进行HPLC检测:色谱柱为C8柱,柱温30℃,流动相A为甲醇,流动相B为乙醚,流速为0.35mL/min,进样量为15μL。
作为优选,待测样品溶解于甲醇后,其浓度为0.02~0.6mg/mL。
作为优选,待测样品的甲醇溶液与碳酸钠溶液为等体积混合。
作为优选,在搅拌20~30min的过程中,持续超声震荡。
作为优选,加入亚硫酸氢钠后,体系中亚硫酸氢钠的浓度为0.2g/mL。
作为优选,WCX固相萃取柱是由甲醇或乙醇活化的。
作为优选,流动相A与流动相B的体积比为1.5∶2~1.5∶4。
作为优选,对洗脱液稀释的体积倍数为3~8倍。
本发明提供了一种基于分子探针的异噻唑啉酮检测方法。该技术方案摒弃了常规的发光检测路线,采用亚硫酸氢钠与异噻唑啉酮反应,从N-S键处实现开环,所得产物可作为分子探针,从而进行定量检测。具体来看,本发明首先利用甲醇溶解待测样品,而后与特定量的碳酸钠溶液混合,并通过搅拌充分沉淀杂质;在此基础上,与亚硫酸氢钠混合并在加压低温条件下充分反应,反应产物与聚乙二醇混合后过WCX固相萃取柱,得到初步纯化,对所得的洗脱液,采用C8柱进行HPLC检测。本发明检测方法操作简便,检测速度快,响应灵敏,检出浓度低,具有良好的推广前景和突出的技术优势。
具体实施方式
以下将对本发明的具体实施方式进行详细描述。为了避免过多不必要的细节,在以下实施例中对属于公知的结构或功能将不进行详细描述。以下实施例中所使用的近似性语言可用于定量表述,表明在不改变基本功能的情况下可允许数量有一定的变动。除有定义外,以下实施例中所用的技术和科学术语具有与本发明所属领域技术人员普遍理解的相同含义。
实施例1
一种基于分子探针的异噻唑啉酮检测方法,包括以下步骤:取待测样品溶解于甲醇中,而后与浓度为1.2mol/L的碳酸钠溶液混合,而后搅拌20~30min,弃去沉淀物;向其中加入亚硫酸氢钠,将容器密封并加压至2.2个大气压,在8℃下静置反应2h,启封后向其中加入聚乙二醇;而后过WCX固相萃取柱,再用乙醚-氯仿洗脱,收集洗脱液,稀释,而后以如下条件进行HPLC检测:色谱柱为C8柱,柱温30℃,流动相A为甲醇,流动相B为乙醚,流速为0.35mL/min,进样量为15μL。
实施例2
一种基于分子探针的异噻唑啉酮检测方法,包括以下步骤:取待测样品溶解于甲醇中,而后与浓度为1.2mol/L的碳酸钠溶液混合,而后搅拌20~30min,弃去沉淀物;向其中加入亚硫酸氢钠,将容器密封并加压至2.2个大气压,在8℃下静置反应2h,启封后向其中加入聚乙二醇;而后过WCX固相萃取柱,再用乙醚-氯仿洗脱,收集洗脱液,稀释,而后以如下条件进行HPLC检测:色谱柱为C8柱,柱温30℃,流动相A为甲醇,流动相B为乙醚,流速为0.35mL/min,进样量为15μL。其中,待测样品溶解于甲醇后,其浓度为0.02~0.6mg/mL。待测样品的甲醇溶液与碳酸钠溶液为等体积混合。在搅拌20~30min的过程中,持续超声震荡。加入亚硫酸氢钠后,体系中亚硫酸氢钠的浓度为0.2g/mL。WCX固相萃取柱是由甲醇或乙醇活化的。流动相A与流动相B的体积比为1.5∶2~1.5∶4。对洗脱液稀释的体积倍数为3~8倍。
以上对本发明的实施例进行了详细说明,但所述内容仅为本发明的较佳实施例,并不用以限制本发明。凡在本发明的申请范围内所做的任何修改、等同替换和改进等,均应包含在本发明的保护范围之内。
Claims (8)
1.一种基于分子探针的异噻唑啉酮检测方法,其特征在于包括以下步骤:取待测样品溶解于甲醇中,而后与浓度为1.2mol/L的碳酸钠溶液混合,而后搅拌20~30min,弃去沉淀物;向其中加入亚硫酸氢钠,将容器密封并加压至2.2个大气压,在8℃下静置反应2h,启封后向其中加入聚乙二醇;而后过WCX固相萃取柱,再用乙醚-氯仿洗脱,收集洗脱液,稀释,而后以如下条件进行HPLC检测:色谱柱为C8柱,柱温30℃,流动相A为甲醇,流动相B为乙醚,流速为0.35mL/min,进样量为15μL。
2.根据权利要求1所述的一种基于分子探针的异噻唑啉酮检测方法,其特征在于,待测样品溶解于甲醇后,其浓度为0.02~0.6mg/mL。
3.根据权利要求1所述的一种基于分子探针的异噻唑啉酮检测方法,其特征在于,待测样品的甲醇溶液与碳酸钠溶液为等体积混合。
4.根据权利要求1所述的一种基于分子探针的异噻唑啉酮检测方法,其特征在于,在搅拌20~30min的过程中,持续超声震荡。
5.根据权利要求1所述的一种基于分子探针的异噻唑啉酮检测方法,其特征在于,加入亚硫酸氢钠后,体系中亚硫酸氢钠的浓度为0.2g/mL。
6.根据权利要求1所述的一种基于分子探针的异噻唑啉酮检测方法,其特征在于,WCX固相萃取柱是由甲醇或乙醇活化的。
7.根据权利要求1所述的一种基于分子探针的异噻唑啉酮检测方法,其特征在于,流动相A与流动相B的体积比为1.5∶2~1.5∶4。
8.根据权利要求1所述的一种基于分子探针的异噻唑啉酮检测方法,其特征在于,对洗脱液稀释的体积倍数为3~8倍。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111614046.9A CN114428132A (zh) | 2021-12-27 | 2021-12-27 | 一种基于分子探针的异噻唑啉酮检测方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111614046.9A CN114428132A (zh) | 2021-12-27 | 2021-12-27 | 一种基于分子探针的异噻唑啉酮检测方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN114428132A true CN114428132A (zh) | 2022-05-03 |
Family
ID=81311208
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111614046.9A Pending CN114428132A (zh) | 2021-12-27 | 2021-12-27 | 一种基于分子探针的异噻唑啉酮检测方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114428132A (zh) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1179152A (zh) * | 1995-03-17 | 1998-04-15 | 曾尼卡有限公司 | 1,2-苯并异噻唑啉-3-酮类化合物的制备方法 |
CN101050005A (zh) * | 2006-04-07 | 2007-10-10 | 罗门哈斯公司 | 水处理方法 |
US20170233585A1 (en) * | 2014-09-02 | 2017-08-17 | Thor Gmbh | Products preserved with 5-chloro-2-methyl-4-isothiazolin-3-one |
CN108169371A (zh) * | 2017-12-21 | 2018-06-15 | 上海微谱化工技术服务有限公司 | 一种涂料中杀菌剂的定量测定方法 |
-
2021
- 2021-12-27 CN CN202111614046.9A patent/CN114428132A/zh active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1179152A (zh) * | 1995-03-17 | 1998-04-15 | 曾尼卡有限公司 | 1,2-苯并异噻唑啉-3-酮类化合物的制备方法 |
CN101050005A (zh) * | 2006-04-07 | 2007-10-10 | 罗门哈斯公司 | 水处理方法 |
US20170233585A1 (en) * | 2014-09-02 | 2017-08-17 | Thor Gmbh | Products preserved with 5-chloro-2-methyl-4-isothiazolin-3-one |
CN108169371A (zh) * | 2017-12-21 | 2018-06-15 | 上海微谱化工技术服务有限公司 | 一种涂料中杀菌剂的定量测定方法 |
Non-Patent Citations (2)
Title |
---|
郦和生: "异噻唑啉酮杀生剂及其分析方法", 净水技术, no. 04, 31 December 1995 (1995-12-31) * |
郭墨琴: "防腐杀菌剂中有效成分异噻唑啉酮的测定方法", 面向2049年北京日化工业发展与环境保护学术研讨会, 2 September 2000 (2000-09-02) * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Wang et al. | Removal of Microcystis aeruginosa by UV-activated persulfate: performance and characteristics | |
US6096225A (en) | Method of controlling biofouling in aqueous media using antimicrobial emulsions | |
CN105010387B (zh) | 一种改进型油田复合型杀菌剂的配制工艺 | |
Thamke et al. | Evaluation of risk assessment of new industrial pollutant, ionic liquids on environmental living systems | |
US20200123396A1 (en) | Products preserved with 5-chloro-2-methyl-4-isothiazolin-3-one | |
EA017866B1 (ru) | Применение производных лактамида в составе препаратов для снижения токсичности | |
FR2655150A1 (fr) | Methode pour determiner la concentration d'une substance active dans un milieu aqueux. | |
WO2012019360A1 (en) | Biocidal composition | |
KR960013330B1 (ko) | 재순환 물 시스템의 미생물 퇴적 제어 방법 | |
CN107880863A (zh) | 一种采油用缓蚀阻垢清蜡剂及其制备方法 | |
JP7478445B2 (ja) | 安定な殺微生物剤組成物 | |
KR20010077985A (ko) | 안정화된 살균 배합물 | |
CN114428132A (zh) | 一种基于分子探针的异噻唑啉酮检测方法 | |
US3629465A (en) | Preservatives for aqueous systems | |
CN102986669A (zh) | 稳定的杀菌剂组合物 | |
JPH02134302A (ja) | 抗菌組成物及びその使用方法 | |
RU2573322C2 (ru) | Защищенные антимикробные соединения, предназначенные для применения при высокой температуре | |
EP1393628A1 (en) | Liquid deodorant killing microorganism and method of microorganism-killing deodorization | |
AU630599B2 (en) | 1-methyl-3,5,7,-triaza-1-azonia-tricyclodecane compounds, a method for preparing these compounds their use and the control of microorganisms, and their use in the inhibition of corrosion | |
FI111167B (fi) | Menetelmä lietteen säilyvyyden parantamiseksi | |
JP2007031299A (ja) | 工業用防腐防黴剤組成物 | |
JP3916216B2 (ja) | 新規ジブロモニトロアルコール誘導体及びその用途 | |
JP5643117B2 (ja) | 殺藻・殺菌剤及び殺藻・殺菌方法 | |
CN115448432B (zh) | 一种卤水体系中杀菌除污剂及其制备方法 | |
AU597968B2 (en) | Micro biocidal propargyl thiocyanate derivatives |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |