CN1149922C - 杀生物剂组合物及其应用 - Google Patents
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- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 230000003115 biocidal effect Effects 0.000 title description 3
- DHVLDKHFGIVEIP-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)pentanedinitrile Chemical compound BrCC(Br)(C#N)CCC#N DHVLDKHFGIVEIP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 230000000845 anti-microbial effect Effects 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 10
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 6
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims description 5
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 5
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 claims description 4
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229940032912 zephiran Drugs 0.000 claims description 4
- 229920001131 Pulp (paper) Polymers 0.000 claims description 3
- 239000000498 cooling water Substances 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 2
- 125000005997 bromomethyl group Chemical group 0.000 claims 2
- 230000002195 synergetic effect Effects 0.000 claims 1
- 150000003868 ammonium compounds Chemical class 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 241000233866 Fungi Species 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
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- -1 DBDCB compound Chemical class 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PNLVGFSEHLOUTK-UHFFFAOYSA-N 2-(bromomethyl)pentanedinitrile Chemical compound BrCC(C#N)CCC#N PNLVGFSEHLOUTK-UHFFFAOYSA-N 0.000 description 1
- OWQGBDSLJUVLKF-UHFFFAOYSA-N 2-dodecylpyridine Chemical compound CCCCCCCCCCCCC1=CC=CC=N1 OWQGBDSLJUVLKF-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000193400 Bacillus simplex Species 0.000 description 1
- 241000589513 Burkholderia cepacia Species 0.000 description 1
- YWWMUOCIAHODNK-UHFFFAOYSA-N CC(C)(C)CCCCCCCCCCCCCCCCl.N Chemical compound CC(C)(C)CCCCCCCCCCCCCCCCl.N YWWMUOCIAHODNK-UHFFFAOYSA-N 0.000 description 1
- 241000866631 Caballeronia glathei Species 0.000 description 1
- 241000990232 Curtobacterium flaccumfaciens pv. flaccumfaciens Species 0.000 description 1
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920002444 Exopolysaccharide Polymers 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- FADYGXGJTNYCHZ-UHFFFAOYSA-M benzyl-dodecyl-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](CC)(CC)CC1=CC=CC=C1 FADYGXGJTNYCHZ-UHFFFAOYSA-M 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- YBNLWIZAWPBUKQ-UHFFFAOYSA-N trichloro(trichloromethylsulfonyl)methane Chemical compound ClC(Cl)(Cl)S(=O)(=O)C(Cl)(Cl)Cl YBNLWIZAWPBUKQ-UHFFFAOYSA-N 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了用于控制含水系统中微生物的生长的抗微生物组合物及方法，所述的组合物包括有效量的2-溴-2-(溴甲基)-戊二腈和季铵化合物。
Description
发明背景
通常微生物在许多含水环境中产生外多糖物质，常称为粘液。这一行为使微生物不仅在天然水系如泻湖、湖泊和池塘中存在，而且在有限水系如游泳池和许多工业系统中存在。工业应用是特别感兴趣的，如冷却水系统、空气洗涤系统和纸浆造纸系统。所有这些环境均具有易于粘液菌生长和繁殖的条件。在封闭系统如造纸厂以及在单程及循环冷却系统中未能控制的粘液的形成是耗费大且经常碰到的问题。
除了控制细菌外，一直需要也能控制水系统中的真菌的毒性较低的物质。目前有几种能控制细菌及真菌的活性物质，包括亚甲基双硫氰酸酯和双(三氯甲基)砜。报道的这些物质的水生环境毒性分布比本发明的物质高。
环境规章越来越强调抗微生物组合物应提供更好的哺乳动物及水生环境毒理学分布。另外，活性物质的环境影响要求也日益严格。
发明详述
已发现杀生物活性剂特别是2-溴-2-(溴甲基)-戊二腈(也称为1，2-二溴-2，4-二氰基丁烷(DBDCB))与季铵化合物(Quats)的混合物能提供比组成混合物的各个单独成分更高程度的抗微生物活性。DBDCB化合物是抗广谱细菌、酵母和真菌特别有效的试剂。
季铵化合物的例子包括但不限于二乙基十二烷基苄基氯化铵、十八烷基二甲基苄基氯化铵、二甲基二癸基氯化铵、二甲基双十二烷基氯化铵、三甲基十四烷基氯化铵、三甲基十八烷基氯化铵、三甲基十六烷基氯化铵、烷基二甲基苄基氯化铵、溴化十六烷基吡啶、氯化十六烷基吡啶、氯化十二烷基吡啶和苄基十二烷基双(B-羟乙基)氯化铵。
由于活性化合物这一混合物的协同性质，因此可以产生一有效的混合物，该混合物因为具备增强的活性因此可以降低处理浓度。因此，可以通过使用降低浓度的每种活性成分来利用这种有效性。
因此，本发明一个方面提供了一种抗微生物组合物，其包括协同有效量的(a)2-溴-2-(溴甲基)-戊二腈和(b)季铵化合物，本发明的组合物中2-溴-2-(溴甲基)-戊二腈和季铵化合物的重量比为3∶1至1∶16。在一个实施方案中，本发明的组合物中季铵化合物选自烷基二甲基苄基氯化铵、月桂基三甲基氯化铵、十六烷基三甲基氯化铵和氯化十六烷基吡啶。
本发明还涉及一种控制含水系统中微生物的生长的方法，包括向所述系统中加入有效量的本发明的组合物。
所述的含水系统包括冷却水系统，纸浆和造纸系统等。
根据本发明，DBDCB：Quat联合处理可以以每百万重量份含水介质中加入0.5-60重量份联合处理的量加入到需进行杀生物处理的含水系统中。优选地，每百万重量份含水介质中加入0.5-50重量份联合处理。
用剂量方案确定活性物质和混合物的效果。在pH值为5.5和8.0的合成的白水中评价活性剂。在含有约相等数量的六株细菌菌株的人工细菌聚生体上测试物质。尽管测试菌株是造纸系统中存在的微生物的代表菌株，但是作用效果不仅限于这些细菌。这些菌株中的两个是肺炎克氏杆菌(ATCC13883)和铜绿假单胞菌(ATCC15442)，其它四株菌株分离自造纸系统并已被鉴定为Curtobacteriumflaccumfaciens，Burkholderia cepacia，Bacillus maroccanus和Pseudomonas glathei。将每株菌于37℃温育过夜，然后悬浮于无菌生理盐水中，合并等体积的每株菌以制备聚生体。将该细菌聚生体分配于微滴定板的各个孔中，各孔中存在各种浓度的活性物质或者不存在活性物质。在37℃保温微滴定板，在保温开始时(t0)以及保温4小时后(t4)读取650nm处的光密度。
根据下述公式将原始数据转化成“抑制百分率”：
抑制％＝[(a-b)÷a]×100
其中a＝(在tn时对照组的光密度(OD))-(在t0时对照组的OD)
b＝(在tn时处理组的OD)-(在t0时处理组的OD)
抑制值可以针对每种活性剂以及特定混合物的剂量绘图，由此产生一剂量应答曲线，从该曲线可计算出达到50％抑制(I50)的剂量。在下述实施例中，I50值以活性物质的百万分数(ppm)表示。
经Kull，F.C.，P.C.Eisman，H.D.Sylwestrowicz and R.L.Mayer(1961)，应用微生物学9，538所述的等式计算协同作用指数(SI)。这些数值是基于达到规定终点所需的量。这一研究所选择的终点是50％抑制。
SI@t4(QA÷Qa)+(QB÷Qb)
其中QA＝在混合物中化合物A的量，
Qa＝化合物A单独作用的量，
QB＝在混合物中化合物B的量，
Qb＝化合物B单独作用的量。
如果SI小于1，则表明有协同作用；如果SI大于1，则表明有拮抗作用；如果SI等于1，则表明是添加行为。
表1
DBDCB和烷基(40％C12，50％C14，10％C18)二甲基苄基氯化铵(ADBAC)
pH 5.5
pH 8.0
I50.ppm. SI I50.ppm SI
DBDCB 2.20 2.30
1DBDCB： 2.06 0.85 2.25 0.94
1ADBAC
ADBAC 2.69 2.69
pH 5.5 pH 8.0
I50.ppm SI I50.ppm SI
DBDCB 3.07 2.79
2DBDCB： 2.77 0.91. 2.05 0.73
1ADBAC
ADBAC 2.69 2.78
表II
DBDCB和月桂基三甲基氯化铵(LTAC)
pH 5.5
pH 8.0
I50，ppm SI I50.ppm SI
DBDCB 2.38 2.39
2DBDCB： 2.28 0.69 2.65 0.88
1LTAC
LTAC 14.12 6.08
表III
DBDCB和十六烷基三甲基氯化铵(CTAC)
pH 5.5
pH 8.0
I50.ppm SI I50.ppm SI
DBDCB 3.19 3.23
2DBDCB： 1.89 0.63 2.06 0.87
1CTAC
CTAC 2.66 1.55
表IV
DBDCB和氯化十六烷基吡啶(CPyrC)
pH 5.5
pH 8.0
I50.ppm SI I50.ppm SI
DBDCB 2.90 1.99
1DBDCB： 1.56 0.79 2.51 1.16
1CPyrC
CPyrC 1.49 2.36
pH 5.3
pH 8.0
I50.ppm SI I50.ppm SI
DBDCB 2.79 2.27
2DBDCB： 1.74 0.86 1.81 0.96
1CPyrC
CPyrC 1.30 1.39
根据上表I-IV，当2-溴-2-(溴甲基)-戊二腈(BBMG)：Quat产品的比率在约2∶1至1∶20之内时，经常发生预想不到的结果。由于所测试的BBMG产品是约98％活性的，且所测试的Quat产品是约80％活性杀生物剂成分，因此这一范围可转变成BBMG∶Quat(100％活性基础)的范围为约3∶1-1∶16。目前，优选地实施本发明的市售产品包括重量比为1∶2的BBMG∶Quat。
尽管本发明已参照特定实施方案进行了描述，但是本发明的各种其它形式和修改对于本领域技术人员是显而易见的。所附权利要求书和本发明通常应被理解为包括在本发明的实质和范围内的所有这些显而易见的形式和修饰。
Claims (7)
1、一种抗微生物组合物，包括协同有效量的(a)2-溴-2-(溴甲基)-戊二腈和(b)季铵化合物，其中(a)和(b)的重量比为3∶1至1∶16。
2、权利要求1的组合物，其中季铵化合物选自烷基二甲基苄基氯化铵、月桂基三甲基氯化铵、十六烷基三甲基氯化铵和氯化十六烷基吡啶。
3、一种控制含水系统中微生物的生长的方法，包括向所述系统中加入有效量的一种组合物，该组合物包括(a)2-溴-2-(溴甲基)-戊二腈和(b)季铵化合物的具有协同作用的混合物，其中加入到所述系统中的所述组合物的量为每百万份所述含水系统0.5-60份，所述组合物中(a)和(b)的重量比为3∶1至1∶16。
4、权利要求3的方法，其中季铵化合物选自烷基二甲基苄基氯化铵、月桂基三甲基氯化铵、十六烷基三甲基氯化铵和氯化十六烷基吡啶。
5、权利要求3的方法，其中所述的含水系统包括冷却水系统。
6、权利要求3的方法，其中所述的含水系统是纸浆和造纸系统。
7、权利要求1的抗微生物组合物，其由协同有效量的(a)2-溴-2-(溴甲基)-戊二腈和(b)季铵化合物组成，其中(a)和(b)的重量比为3∶1至1∶16。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/821,746 US5763482A (en) | 1997-03-20 | 1997-03-20 | Biocidal composition and use |
| US08/821,746 | 1997-03-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1257405A CN1257405A (zh) | 2000-06-21 |
| CN1149922C true CN1149922C (zh) | 2004-05-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB98805311XA Expired - Fee Related CN1149922C (zh) | 1997-03-20 | 1998-02-05 | 杀生物剂组合物及其应用 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5763482A (zh) |
| EP (1) | EP0984685B1 (zh) |
| JP (1) | JP4187272B2 (zh) |
| KR (1) | KR20010005499A (zh) |
| CN (1) | CN1149922C (zh) |
| AT (1) | ATE298503T1 (zh) |
| AU (1) | AU726937B2 (zh) |
| BR (1) | BR9808028B1 (zh) |
| CA (1) | CA2284543C (zh) |
| DE (1) | DE69830724T2 (zh) |
| ES (1) | ES2241128T3 (zh) |
| MY (1) | MY133559A (zh) |
| NO (1) | NO994555L (zh) |
| NZ (1) | NZ337937A (zh) |
| WO (1) | WO1998041088A1 (zh) |
| ZA (1) | ZA98364B (zh) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20020074899A (ko) * | 2001-03-22 | 2002-10-04 | 김용국 | 살균·살충·소독제 조성물 |
| KR20020074903A (ko) * | 2001-03-22 | 2002-10-04 | 김용국 | 농약 조성물 및 그 용도 |
| JP4534051B2 (ja) * | 2001-08-16 | 2010-09-01 | 株式会社片山化学工業研究所 | ウエットパルプの防腐防かび方法およびその防腐防かび組成物 |
| US20060231505A1 (en) * | 2002-08-22 | 2006-10-19 | Mayer Michael J | Synergistic biocidal mixtures |
| US7008545B2 (en) * | 2002-08-22 | 2006-03-07 | Hercules Incorporated | Synergistic biocidal mixtures |
| US7413643B2 (en) * | 2003-03-04 | 2008-08-19 | Volsper Sourcing, Inc. | Treating an electrocoat system with a biosurfactant |
| US8541194B2 (en) * | 2003-03-04 | 2013-09-24 | Valspar Sourcing, Inc. | Detecting micro-organisms in an electrocoating process |
| MXPA05009294A (es) * | 2003-03-04 | 2005-10-05 | Valspar Sourcing Inc | Sistema de manejo de electrorrevestimiento. |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3054678A (en) * | 1958-04-16 | 1962-09-18 | Michener Harold David | Preservation process with quaternary ammonium compounds |
| US3829586A (en) * | 1970-01-02 | 1974-08-13 | Betz Laboratories | Slime control compositions and their use |
| US3833731A (en) * | 1970-12-28 | 1974-09-03 | Merck & Co Inc | Dihalomethylglutaronitriles used as antibacterial and antifungal agents |
| US4655815A (en) * | 1985-03-27 | 1987-04-07 | Calgon Corporation | Admixtures of 2-bromo-2-bromomethylglutaronitrile and a formaldehyde donor |
| US5034405A (en) * | 1985-03-27 | 1991-07-23 | Calgon Corporation | Admixtures of 2-bromo-2-bromomethyl-glutaronitrile, 2-methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4-isothiazolin-3-one |
| GB9009529D0 (en) * | 1990-04-27 | 1990-06-20 | Ici Plc | Biocide composition and use |
| NZ240129A (en) * | 1990-10-15 | 1993-07-27 | Calgon Corp | Synergistic microbiocide |
| US5444088A (en) * | 1993-10-05 | 1995-08-22 | Nalco Chemical Company | Synergistic anti-microbial compositions comprising 2-bromo-2-(bromomethyl)-glutaronitrile and 2-bromo-2-nitro-propane-1,3-diol |
-
1997
- 1997-03-20 US US08/821,746 patent/US5763482A/en not_active Expired - Fee Related
-
1998
- 1998-01-14 MY MYPI98000155A patent/MY133559A/en unknown
- 1998-01-16 ZA ZA98364A patent/ZA98364B/xx unknown
- 1998-02-05 AU AU64339/98A patent/AU726937B2/en not_active Ceased
- 1998-02-05 AT AT98909987T patent/ATE298503T1/de active
- 1998-02-05 JP JP54049098A patent/JP4187272B2/ja not_active Expired - Fee Related
- 1998-02-05 NZ NZ337937A patent/NZ337937A/xx not_active IP Right Cessation
- 1998-02-05 KR KR1019997008556A patent/KR20010005499A/ko not_active Application Discontinuation
- 1998-02-05 WO PCT/US1998/002127 patent/WO1998041088A1/en active IP Right Grant
- 1998-02-05 ES ES98909987T patent/ES2241128T3/es not_active Expired - Lifetime
- 1998-02-05 EP EP98909987A patent/EP0984685B1/en not_active Expired - Lifetime
- 1998-02-05 BR BRPI9808028-8A patent/BR9808028B1/pt not_active IP Right Cessation
- 1998-02-05 DE DE69830724T patent/DE69830724T2/de not_active Expired - Lifetime
- 1998-02-05 CN CNB98805311XA patent/CN1149922C/zh not_active Expired - Fee Related
- 1998-02-05 CA CA002284543A patent/CA2284543C/en not_active Expired - Fee Related
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1999
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Also Published As
| Publication number | Publication date |
|---|---|
| WO1998041088A1 (en) | 1998-09-24 |
| AU726937B2 (en) | 2000-11-23 |
| EP0984685B1 (en) | 2005-06-29 |
| CA2284543A1 (en) | 1998-09-24 |
| DE69830724T2 (de) | 2006-05-04 |
| CN1257405A (zh) | 2000-06-21 |
| NO994555L (no) | 1999-11-02 |
| ATE298503T1 (de) | 2005-07-15 |
| NZ337937A (en) | 2000-07-28 |
| US5763482A (en) | 1998-06-09 |
| AU6433998A (en) | 1998-10-12 |
| BR9808028A (pt) | 2000-03-28 |
| BR9808028B1 (pt) | 2009-05-05 |
| ES2241128T3 (es) | 2005-10-16 |
| EP0984685A1 (en) | 2000-03-15 |
| JP4187272B2 (ja) | 2008-11-26 |
| EP0984685A4 (en) | 2004-08-18 |
| DE69830724D1 (de) | 2005-08-04 |
| ZA98364B (en) | 1998-07-30 |
| MY133559A (en) | 2007-11-30 |
| CA2284543C (en) | 2003-09-30 |
| JP2001517219A (ja) | 2001-10-02 |
| KR20010005499A (ko) | 2001-01-15 |
| NO994555D0 (no) | 1999-09-20 |
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