CN107251902A - 二溴丙二酰胺的组合物及其作为杀生物剂的用途 - Google Patents
二溴丙二酰胺的组合物及其作为杀生物剂的用途 Download PDFInfo
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- CN107251902A CN107251902A CN201710538261.2A CN201710538261A CN107251902A CN 107251902 A CN107251902 A CN 107251902A CN 201710538261 A CN201710538261 A CN 201710538261A CN 107251902 A CN107251902 A CN 107251902A
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Classifications
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Abstract
二溴丙二酰胺的组合物及其作为杀生物剂的用途。一种用于控制水性或含水体系中的微生物的杀生物组合物，该组合物包含：2,2‑二溴丙二酰胺和选自下组的含亲电子试剂的杀生物剂：溴硝基苯乙烯、二硫氰基甲烷和1,2‑二溴‑2,4‑二氰基丁烷，以及该组合物在控制水性和含水体系中的微生物方面的用途。
Description
本发明专利申请是申请号为201510500505.9、申请日为2010年9月30日、名称为“二溴丙二酰胺的组合物及其作为杀生物剂的用途”的发明专利申请的分案申请，上述发明专利申请又是国际申请号为PCT/US2010/050880，国际申请日为2010年9月30日，进入中国国家阶段的申请号为201080069381.9，名称为“二溴丙二酰胺的组合物及其作为杀生物剂的用途”的发明专利申请的分案申请。
技术领域
本发明涉及杀生物组合物及其在水性和含水体系中用于控制微生物的方法。所述组合物包括2,2-二溴丙二酰胺和包含至少一个亲电子部分的杀生物化合物。
背景技术
水体系为藻类、细菌、病毒和真菌(其中一些可为致病性的)提供肥沃的繁殖地。微生物污染可产生各种问题，包括美观性差(例如泥泞的绿色水)、严重的健康风险(例如真菌、细菌或病毒感染)以及机械性问题(包括堵塞、设备的腐蚀以及传热的减少)。
在水性体系和含水体系中，通常使用杀生物剂来消毒并控制微生物的生长。然而，并非所有的杀生物剂对各种微生物和/或温度有效，并且一些杀生物剂与其它化学处理添加剂不相容。另外，一些杀生物剂不能提供足够长时间的微生物控制。
尽管通过使用较大量的杀生物剂可以克服上述缺点中的一部分，该方法会带来自身的问题，包括成本增加、浪费增加以及增加了杀生物剂将干扰所处理介质的所需性质的可能性。另外，由于许多市售的杀生物剂化合物对某些类型的微生物的活性弱或者某些微生物对这些化合物具有抗性，因此即使使用较大量的杀生物剂，这些杀生物剂化合物仍不能提供有效的控制。
本领域中提供这样一种用于水体系处理的杀生物剂组合物将是一项重大进步，该组合物能产生一种或多种以下益处：在较低浓度下效力提高；与物理条件和所处理介质中的其它添加剂相容；对宽范围的微生物有效；和/或能够同时提供对微生物的短期控制和长期控制。
发明内容
在一个方面，本发明提供了一种杀生物组合物。该组合物可用于控制水性或含水体系中的微生物。该组合物包含：2,2-二溴丙二酰胺和包含至少一个亲电子部分的杀生物化合物(“含亲电子试剂的杀生物剂”)，其中，所述含亲电子试剂的杀生物剂选自下组：2-溴-2-硝基丙烷-1,3-二醇、溴硝基苯乙烯、二硫氰基甲烷和1,2-二溴-2,4-二氰基丁烷。
在第二个方面，本发明提供一种控制水性或含水体系中的微生物的方法。该方法包括使用有效量的本文所述的杀生物组合物来处理所述体系。
发明详述
如上所述，本发明提供了一种杀生物组合物以及使用该化合物来控制微生物的方法。该组合物包含：2,2-二溴丙二酰胺和选自下组的含亲电子试剂的杀生物剂：2-溴-2-硝基丙烷-1,3-二醇、溴硝基苯乙烯、二硫氰基甲烷和1,2-二溴-2,4-二氰基丁烷。我们令人惊讶地发现，当以一定的重量比将2,2-二溴丙二酰胺和本文所述的含亲电子试剂的杀生物剂的组合用于水性或含水介质中的微生物控制时，这两种物质的组合具有协同作用。也就是说，所述组合材料的杀生物性质比基于其单独的性能所预期的杀生物性质得到改进。该协同作用使得用来实现所需杀生物性能效果的材料量减少，因此，减少了由工业处理水中微生物生长所造成的问题，同时可能降低了环境影响和材料成本。
出于本发明的目的，术语“微生物”包括但不限于：细菌、真菌、藻类和病毒。术语“控制”应广义地被解释为包括但不限于以下含义：抑制微生物的生长或繁殖，杀死微生物、消毒、和/或防腐。在一些优选的实施方式中，“控制”指的是抑制微生物的生长或繁殖。在其它实施方式中，“控制”指的是杀死微生物。
术语“2,2-二溴丙二酰胺”指的是由以下化学式表示的化合物：
2,2-二溴丙二酰胺和本发明的含亲电子试剂的杀生物剂均市售可得，和/或可容易地由本领域技术人员使用熟知的技术制备得到。
在本发明的一些实施方式中，2,2-二溴丙二酰胺与所述含亲电子试剂的杀生物剂的重量比约为100:1至1:100。
在一些实施方式中，2,2-二溴丙二酰胺与所述含亲电子试剂的杀生物剂的重量比约为40:1至1:30。
在一些实施方式中，2,2-二溴丙二酰胺与所述含亲电子试剂的杀生物剂的重量比约为32:1至1:20。
在一些实施方式中，所述含亲电子试剂的杀生物剂是2-溴-2-硝基丙烷-1,3-二醇，2,2-二溴丙二酰胺与2-溴-2-硝基丙烷-1,3-二醇的重量比约为100:1至1:20，或者约为70:1至1:10，或者约为40:1至1:5，或者约为32:1至1:2。在一些实施方式中，该重量比约为9:1至3:1。
在一些实施方式中，所述含亲电子试剂的杀生物剂是溴硝基苯乙烯，2,2-二溴丙二酰胺与溴硝基苯乙烯的重量比约为100:1至1:20，或者约为70:1至1:10，或者约为40:1至1:5，或者约为32:1至1:2。
在一些实施方式中，所述含亲电子试剂的杀生物剂是二硫氰基甲烷，2,2-二溴丙二酰胺与二硫氰基甲烷的重量比约为40:1至1:10，或者约为32:1至1:1，或者约为32:1至4:1。
在一些实施方式中，所述含亲电子试剂的杀生物剂是1,2-二溴-2,4-二氰基丁烷，2,2-二溴丙二酰胺与1,2-二溴-2,4-二氰基丁烷的重量比约为20:1至1:10，或者约为10:1至1:1，或者约为8:1至2:1。
本发明的组合物可用于控制各种水性和含水体系中的微生物。此类体系的例子包括但不限于：油漆和涂料、水性乳液、胶乳、黏合剂、油墨、颜料分散体、家用和工业清洁剂、去污剂、餐具洗涤剂、矿物浆液、聚合物乳液、填缝剂和粘合剂、带条接缝配混物、消毒剂、杀菌剂、金属加工流体、建筑产品、个人护理产品、纺织流体(例如纺丝油剂)、工业处理水(例如油田水、纸浆和纸张水、冷却水)、油田功能流体(例如钻井泥浆和压裂液)、燃料、空气洗涤剂、废水、压舱水、过滤系统以及游泳池和温泉水。优选的水性体系是金属加工流体、个人护理、家用和工业清洁剂、工业处理水以及油漆和涂料。特别优选的是工业处理水、油漆和涂料、金属加工流体以及纺织流体(例如纺丝油剂)。
本领域普通技术人员不需要过多的实验就很容易确定任意具体应用中为提供微生物控制而应使用的所述组合物的有效量。作为说明，以所述水性或含水体系的总重量为基准计，合适的活性物质浓度(2,2-二溴丙二酰胺和含亲电子试剂的杀生物剂的总计)通常至少约为1ppm，或者至少约为3ppm，或者至少约为7ppm，或者至少约为10ppm，或者至少约为30ppm，或者至少约为100ppm。在一些实施方式中，以所述水性或含水体系的总重量为基准计，活性物质浓度的合适上限约为1000ppm，或者约500ppm，或者约100ppm，或者约50ppm，或者约30ppm，或者约15ppm，或者约10ppm，或者约7ppm。
可将所述组合物的组分分别添加至所述水性或含水体系中，或者在添加前进行预混。本领域普通技术人员很容易能确定合适的添加方法。所述组合物可与其它添加剂联用于所述系统中，所述添加剂例如但不限于：表面活性剂、离子/非离子聚合物和水垢和腐蚀抑制剂、氧清除剂、和/或其它杀生物剂。
以下实施例用于说明本发明，而不是用来限制其范围。除非另有说明，本文使用的比值、百分比、份数等以重量计。
实施例
实施例中提供的结果是使用生长抑制试验或杀灭试验产生的。各试验的细节如下。
杀灭试验。该试验用作所述活性物质之间的协同作用的初步评价。该方法如下：用等量(约100CFU/ml)的铜绿假单胞菌(Pseudomonas aeruginosa)ATCC 10045和金黄色葡萄球菌(Staphylococcus aureus)ATCC 6538的混合物对矿物盐溶液(0.2203克CaCl2、0.1847克MgSO4和0.2033克NaHCO3在1L水中，pH约为8)进行接种。然后使用2,2-二溴丙二酰胺("DBMAL")、含亲电子试剂的杀生物剂以及它们以各种浓度含量的组合对等份的所述细胞悬液进行处理。在37℃条件下孵育2小时后，基于完全杀死等份样中细菌细胞所需的最小杀生物剂浓度(MBC)来确定杀生物效力。然后使用该MBC值来计算协同指数(SI)值。
所述杀灭试验结果的总结如各实施例所示。各表中，列出测试的各杀生物剂和混合物的MBC值。同样，列出了所述组合的协同指数("SI")值。使用下式计算SI：
协同指数＝MDBMAL/CDBMAL+MB/CB
式中，
CDBMAL：单独使用DBMAL时抑制细菌生长所需的DBMAL的浓度；
CB：单独使用杀生物剂(B)时抑制细菌生长所需的杀生物剂(B)的浓度；
MDBMAL：DBMAL与杀生物剂(B)联用时抑制细菌生长所需的DBMAL的浓度；
MB：杀生物剂(B)与DBMAL联用时抑制细菌生长所需的杀生物剂(B)的浓度。
所述SI值解释如下：
SI<1：协同性组合
SI＝1：相加性组合
SI>1：对抗性组合
生长抑制试验。实施例中使用的生长抑制试验测量了微生物聚生体的生长抑制(或缺乏生长)。生长的抑制可为以下情况的结果：细胞被杀死(因此不发生生长)；大量大部分细胞群被杀死因而再生长需要很长的时间；或者抑制了生长而没有杀死(静态)。无论是何作用机理，杀生物剂(或杀生物剂的组合)的影响可基于群落尺寸的增加随时间进行测量。
该实验测量了在稀释矿物盐培养基中一种或多种杀生物剂在防止细菌聚生体的生长上的效力。所述培养基包含(以毫克/升计)以下组分：FeCl3.6H2O(1)；CaCl2.2H2O(10)；MgSO4.7H2O(22.5)；(NH4)2SO4(40)；KH2PO4(10)；K2HPO4(25.5)；酵母提取物(10)；以及葡萄糖(100)。待将所有的组分添加至去离子水中后，将该培养基的pH调节至7.5。过滤灭菌之后，将100微升量的等分样分配至无菌微孔板孔中。然后将DBMAL和/或“杀生物剂B”的稀释液添加至该微孔板中。待制备如下所示的活性物质的组合后，用100微升的细胞悬液对各孔进行接种，该细胞悬液中每毫升的铜绿假单胞菌、肺炎杆菌(Klebsiella pneumoniae)、金黄色葡萄球菌和芽孢杆菌(Bacillus subtilis)的混合物包含约1x100个细胞。各孔中培养基的最终总体积为300微升。如表1所示，当如本文所述进行制备后，各活性物质的浓度为25至0.19ppm。所得培养基可以测试每个活性物质的8种浓度，即以(活性物质的)不同比例的活性物质的64种组合。
表1.显示各活性物质浓度的基于微孔板的协同作用试验的模板。各活性物质的比例以重量(ppm)计。
对照样(未显示)包含未添加杀生物剂的培养基。待制备如上所示的活性物质的组合后，用100微升的细胞悬液对各孔进行接种，该细胞悬液中每毫升的铜绿假单胞菌、肺炎杆菌、金黄色葡萄球菌和芽孢杆菌的混合物包含约1x100个细胞。各孔中培养基的最终总体积为300微升。
待微孔板预备好后，立即在580纳米下测量各孔的光密度(OD)读数，然后使该板在37℃下孵育24小时。孵育期后，在OD580值被采集之前，对该板进行温和搅拌。用T24处的OD580值减去T0处的OD580值以确定发生的生长(或缺乏生长)的总量。这些值被用于计算由于存在各杀生物剂和各64种组合而导致的生长抑制百分数。结合下式，使用90％生长抑制作为计算协同指数(SI)值的阈值：
协同指数＝MDBMAL/CDBMAL+MB/CB
式中，
CDBMAL：单独使用DBMAL时抑制约90％的细菌生长所需的DBMAL浓度；
CB：单独使用杀生物剂(B)时抑制约90％的细菌生长所需的杀生物剂(B)的浓度；
MDBMAL：DBMAL与杀生物剂(B)联用时抑制约90％的细菌生长所需的DBMAL的浓度；
MB：杀生物剂(B)与DBMAL联用时抑制约90％的细菌生长所需的杀生物剂(B)的浓度。
所述SI值解释如下：
SI<1：协同性组合
SI＝1：相加性组合
SI>1：对抗性组合
在以下实施例中，溶液中杀生物剂的量以毫克/升(mg/l)的溶液为单位计量。由于溶液密度约为1.0，因此毫克/升度量对应于重量ppm。因此，在实施例中两种单位可互换使用。
实施例1
DBMAL和溴硝丙二醇(bronopol)
杀灭试验结果。表2总结了单独使用DBMAL以及DBMAL与2-溴-2-硝基丙烷-1,3-二醇("溴硝丙二醇"或"BNPD")联用的试验的结果。该结果表明了活性物质之间的协同作用(表2)。
表2.DBMAL、溴硝丙二醇及其组合的MBC。
抑制生长试验结果。表3显示了DBMAL、THPS及其组合的抑制生长试验结果。在该试验中，聚生体的生长比对照样至少低90％所需的DBMAL的最小浓度(I90值)为12.5毫克/升。溴硝丙二醇的I90值为6.25毫克/毫升。
表3.24小时孵育期后，由单独的溴硝丙二醇(BNPD)、单独的DBMAL以及这两种活性物质的组合产生的物种限定的微生物聚生体中的生长抑制百分数。数值表示与时间为0时的光密度测量值相比，时间为24小时时的光密度测量值(580纳米)所测得的生长抑制百分数。
表4显示了在生长抑制试验下，发现具有协同作用的DBMAL和溴硝丙二醇(BNPD)的比值。
表4.
实施例2
DBMAL和BNS
抑制生长试验结果。表5显示了DBMAL、溴硝基苯乙烯("BNS")及其组合的抑制生长试验结果。DBMAL和BNS的I90值分别为12.5毫克/升和6.25毫克/升。
表5.24小时孵育期后，由单独的BNS、单独的DBMAL以及这两种活性物质的组合产生的物种限定的微生物聚生体中的生长抑制百分数。数值表示与时间为0时的光密度测量值相比，时间为24小时时的光密度测量值(580纳米)所测得的生长抑制百分数。
表6显示了在生长抑制试验下，发现具有协同作用的DBMAL和BNS的浓度。该比值基于活性物质的浓度。
表6
实施例3
DBMAL和MBT
抑制生长试验结果。表7显示了DBMAL、二硫氰基甲烷("MBT")及其组合的抑制生长试验结果。DBMAL和MBT的I90值分别为12.5毫克/升和0.78毫克/升。
表7.24小时孵育期后，由单独的DBMAL、单独的MBT以及这两种活性物质的组合产生的物种限定的微生物聚生体中的生长抑制百分数。数值表示与时间为0时的光密度测量值相比，时间为24小时时的光密度测量值(580纳米)所测得的生长抑制百分数。
表8显示了发现具有协同作用的DBMAL和MBT的浓度。该比值基于活性物质的浓度。
表8
实施例4
DBMAL和DBDCB
抑制生长试验结果。表9显示了DBMAL、1,2-二溴-2,4-二氰基丁烷("DBDCB")及其组合的抑制生长试验结果。DBMAL和DBDCB的I90值为6.25毫克/升。
表9.24小时孵育期后，由单独的DBMAL、单独的DBDCB以及这两种活性物质的组合产生的物种限定的微生物聚生体中的生长抑制百分数。数值表示与时间为0时的光密度测量值相比，时间为24小时时的光密度测量值(580纳米)所测得的生长抑制百分数。
表10显示了发现具有协同作用的DBMAL和DBDCB的浓度。
表10
尽管已根据本发明优选的实施方式对本发明进行了以上描述，可对本发明作出修改并且这些修改包括在本发明的精神和范围内。因此该申请旨在涵盖使用本文所述的通用原理的本发明的任意变化、应用或改动。另外，本申请旨在涵盖属于本发明所属领域的已知或常规实践以及落入所附权利要求书的限定内的与本发明相偏离之处。
Claims (8)
1.一种用于控制水性或含水体系中的微生物的杀生物组合物，该组合物包含：2,2-二溴丙二酰胺和选自下组的含亲电子试剂的杀生物剂：二硫氰基甲烷。
2.如权利要求1所述的组合物，其特征在于，2,2-二溴丙二酰胺与所述含亲电子试剂的杀生物剂的重量比约为100:1至1:100。
3.如权利要求1所述的组合物，其特征在于，所述含亲电子试剂的杀生物剂是二硫氰基甲烷，并且2,2-二溴丙二酰胺与二硫氰基甲烷的重量比约为32:1至4:1。
4.如权利要求1-3中任一项所述的组合物，该组合物是：油漆、涂料、水性乳液、胶乳、黏合剂、油墨、颜料分散体、家用或工业清洁剂、去污剂、餐具洗涤剂、矿物浆液聚合物乳液、填缝剂、粘合剂、带条接缝配混物、消毒剂、杀菌剂、金属加工流体、建筑产品、个人护理产品、纺织流体、纺丝油剂、工业处理水、油田功能流体、燃料、空气洗涤剂、废水、压舱水、过滤系统、游泳池或温泉水。
5.一种控制水性或含水体系中微生物生长的方法，该方法包括使用有效量的如权利要求1-4中任一项所述的组合物来处理所述水性或含水体系。
6.如权利要求5所述的方法，其特征在于，所述水性或含水体系是油漆、涂料、水性乳液、胶乳、黏合剂、油墨、颜料分散体、家用或工业清洁剂、去污剂、餐具洗涤剂、矿物浆液聚合物乳液、填缝剂、粘合剂、带条接缝配混物、消毒剂、杀菌剂、金属加工流体、建筑产品、个人护理产品、纺织流体、纺丝油剂、工业处理水、油田功能流体、燃料、空气洗涤剂、废水、压舱水、过滤系统、游泳池或温泉水。
7.如权利要求5-6中任一项所述的方法，其特征在于，所述组合物抑制所述水性或含水体系中微生物的生长。
8.如权利要求5-6中任一项所述的方法，其特征在于，所述组合物杀死所述水性或含水体系中的微生物。
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| CN201710538261.2A CN107251902A (zh) | 2010-09-30 | 2010-09-30 | 二溴丙二酰胺的组合物及其作为杀生物剂的用途 |
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| PCT/US2010/050880 WO2012044301A1 (en) | 2010-09-30 | 2010-09-30 | Compositions of dibromomalonamide and their use as biocides |
| CN201710538261.2A CN107251902A (zh) | 2010-09-30 | 2010-09-30 | 二溴丙二酰胺的组合物及其作为杀生物剂的用途 |
| CN201080069381.9A CN103200818B (zh) | 2010-09-30 | 2010-09-30 | 二溴丙二酰胺的组合物及其作为杀生物剂的用途 |
| CN201510500505.9A CN105165829A (zh) | 2010-09-30 | 2010-09-30 | 二溴丙二酰胺的组合物及其作为杀生物剂的用途 |
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| CN201710538261.2A Pending CN107251902A (zh) | 2010-09-30 | 2010-09-30 | 二溴丙二酰胺的组合物及其作为杀生物剂的用途 |
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| EP (1) | EP2621271B1 (zh) |
| JP (1) | JP5703381B2 (zh) |
| CN (2) | CN103200818B (zh) |
| BR (1) | BR112013007734A2 (zh) |
| MX (1) | MX342968B (zh) |
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| AR098357A1 (es) | 2013-11-25 | 2016-05-26 | Dow Global Technologies Llc | Composiciones de dibromomalonamida y su uso como biocidas |
| CN112868650A (zh) * | 2021-02-03 | 2021-06-01 | 山东华特水处理科技有限公司 | 一种杀菌剂及其制备方法和应用 |
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- 2010-09-30 US US13/876,534 patent/US9288983B2/en not_active Expired - Fee Related
- 2010-09-30 JP JP2013531547A patent/JP5703381B2/ja not_active Expired - Fee Related
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Also Published As
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| EP2621271B1 (en) | 2014-08-27 |
| US20160165893A1 (en) | 2016-06-16 |
| RU2561527C2 (ru) | 2015-08-27 |
| US20130184341A1 (en) | 2013-07-18 |
| MX342968B (es) | 2016-10-19 |
| US9288983B2 (en) | 2016-03-22 |
| RU2013119817A (ru) | 2014-11-10 |
| EP2621271A1 (en) | 2013-08-07 |
| WO2012044301A1 (en) | 2012-04-05 |
| US20160150780A1 (en) | 2016-06-02 |
| CN103200818A (zh) | 2013-07-10 |
| US20160165884A1 (en) | 2016-06-16 |
| US9439420B2 (en) | 2016-09-13 |
| US9433210B2 (en) | 2016-09-06 |
| BR112013007734A2 (pt) | 2017-09-26 |
| US9439419B2 (en) | 2016-09-13 |
| JP5703381B2 (ja) | 2015-04-15 |
| JP2013538850A (ja) | 2013-10-17 |
| CN103200818B (zh) | 2015-07-22 |
| MX2013003156A (es) | 2013-05-30 |
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