CN1066143C - 稳定侵蚀性系统中的非卤代3－异噻唑酮的方法 - Google Patents
稳定侵蚀性系统中的非卤代3－异噻唑酮的方法 Download PDFInfo
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- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical class O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 title abstract description 20
- 230000006641 stabilisation Effects 0.000 title description 6
- 238000011105 stabilization Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000012530 fluid Substances 0.000 claims description 18
- 238000005555 metalworking Methods 0.000 claims description 18
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 9
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000002497 iodine compounds Chemical class 0.000 claims description 4
- 238000003754 machining Methods 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 abstract description 2
- 230000000087 stabilizing effect Effects 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical group OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 241000872931 Myoporum sandwicense Species 0.000 description 3
- -1 halo 3-isothiazolones Chemical class 0.000 description 3
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 2
- 238000002242 deionisation method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 description 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- 241000717739 Boswellia sacra Species 0.000 description 1
- 235000003717 Boswellia sacra Nutrition 0.000 description 1
- 235000012035 Boswellia serrata Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004863 Frankincense Substances 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 239000003265 pulping liquor Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 229920006174 synthetic rubber latex Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
本发明提供了一种在pH高于8.5的侵蚀性系统中稳定非卤代的3-异噻唑酮的方法。本发明还公开了pH高于8.5，含有非卤代的3-异噻唑酮和有效稳定剂量的含碘的稳定剂的组合物。
Description
本发明涉及在受侵蚀的系统中稳定非卤代的3-异噻唑酮的方法。
已知非卤代的3-异噻唑酮用于许多地方如木材，涂料，粘合剂，嵌缝胶，乳香，乳胶，纸浆和纸浆液，纺织品，皮革，塑料，卡片纸板，润滑剂，化妆品，洗涤剂，家用产品，工业冷却水，金属加工液，颜料浆液，光学的处理液，和石油的防腐。这些地方中，特别是金属加工液，已知由于高pH特别容易侵蚀3-异噻唑酮。由于pH高于8.5时3-异噻唑酮分解，所以金属加工液的防腐很难。因此，希望找到一种在侵蚀性金属加工液pH高于8.5时稳定非卤代的3-异噻唑酮的方法。
本发明包括在pH高于8.5的条件下，不存在5-氯-2-甲基-4-异噻唑啉-3-酮(CMI)的组合物中稳定2-甲基-4-异噻唑啉-3-酮(MI)，2-正辛基-4-异噻唑啉-3-酮(OI)，或它们的混合物的方法，包括引入有效稳定剂量的选自碘酸，高碘酸，和它们的盐的含碘化合物。
本发明和涉及一组合物，它pH高于8.5，含有MI，OI，或它们的混合物和有效稳定剂量的选自碘酸，高碘酸，和它们的盐的含碘化合物，所述组合物不含氯化的3-异噻唑酮。
优选的3-异噻唑酮化合物在溶液中的浓度是750～5000ppm的MI，或100～2500ppm的OI，或它们的混合物，基于系统的总重。
特别优选的3-异噻唑酮化合物在溶液中的浓度是2000～2500ppm的MI，或500～1000ppm的OI，或它们的混合物，基于系统的总重。
优选的稳定剂在溶液中的浓度是100～5000ppm，更优选1000～3000ppm，基于系统的总重。
也有金属盐如硫酸铜作为3-异噻唑酮稳定剂的报道。参见“KathonMWC Bulletin CS-584”，第6页，Rohm和Hass公司，1989。因为环境的规则使用铜作为3-异噻唑酮在金属加工液中的稳定剂是不能被接受的。
日本东京Koho 05-170608，转让给Shinto Paint公司，公开了抗微生物组合物，用于防止合成高聚物如合成橡胶乳胶的水稀释液被微生物污染，它不会引起所述稀释液的聚沉。此组合物含有3-异噻唑酮和一种稳定剂或选自溴酸，碘酸，高碘酸或它们的盐的稳定剂。但这篇参考文献没有指出如何在pH高于8.5的侵蚀性金属加工液中稳定非卤代的3-异噻唑酮。
日本公开东京Koho 05-286815，转让给Takeda Pharmaceutical公司，公开了含有3-异噻唑酮，溴酸或碘酸的碱金属盐，和水的工业杀菌剂。优选溴酸钾作为稳定剂。此发明也未指出如何在pH高于8.5的侵蚀性金属加工液中稳定非卤代的3-异噻唑酮。
在下述实施例中，MI的来源是50％的2-甲基-4-异噻唑啉-3-酮在丙二醇中的溶液。OI的来源是45％的2-正辛基-4-异噻唑啉-3-酮在丙二醇中的溶液。实施例1中CMI的来源3∶1的CMI∶MI混合物的1.5％水溶液。实施例3的CMI的来源是99％的CMI。
实施例1
此实施例证明非氯化的3-异噻唑酮(MI和OI)在1,2-乙二醇/水溶液中是稳定的，二氯化的异噻唑酮(CMI)在同样的溶液中是不稳定的。样品在30ml.带螺旋帽的小瓶中制备。样品1是2.0g.MI，4g.乙二醇，和14.0g.去离子(DI)水。样品2是1.46g.CMI，9.0g.乙二醇，和9.54g.DI水。样品3是2.20g.OI，15.0g.乙二醇，和2.80gDI水。将样品封好震摇，然后在45℃保存4星期。用带UV分析的高压液相色谱(HPLC)检测，结果列于表1。
表1
实施例2
此比较例证明pH对非氯化的3-异噻唑酮在金属加工液中的稳定性的影响。样品在30ml.带螺旋帽的小瓶中制备。低水含量的金属加工液浓缩液可直接测量pH值，而不用间接测量，所以，用5％的水稀释液测量pH值。向1g.金属加工液中加入19g.DI水。测量pH值且计算调节5％稀释液pH所用的盐酸(HCl)的量。相应量的HCl(20X)加入到金属加工液(MWF)本身。金属加工液的初始pH为9.2。向样品1，2，3，4，5，和6中加入19.92g.MWF和0.08g.MI。MWF的pH如下：样品1=9.2，样品2=9.0，样品3=8.5，样品4=8.1，样品5=7.6，样品6=7.0。向样品7，8，9，10，11，和12加入19.91g.MWF和0.09g.OI。MWF的pH如下：样品7=9.2，样品8=9.0，样品9=8.5，样品10=8.1，样品11=7.6，样品12=7.0。将样品封好震摇，然后在室温保存。在0，7，14，21，和28天用HPLC检测，结果列于表2。
表2比较
％MI剩余 ％OI剩余液体 7天 14天 21天 28天 7天 14天 21天 28天pH9.2 8 0 0 0 0 NA NA NA9 64 30 19 16 0 NA NA NA8.5 77 56 43 35 0 NA NA NA8.1 90 76 66 60 74 5 3 NA7.6 99 90 86 81 100 93 91 927 99 94 95 92 100 100 100 99实施例3-本发明稳定剂的作用
此实施例证明了本发明的稳定剂对CMI，MI，和OI在金属加工液中的稳定作用。金属加工液“A”作为本实施例的液体。它是半合成金属加工液具有pH9.22(4％稀释液)。样品在30ml.带螺旋帽的小瓶中制备。向样品1中加入0.04g.CMI和19.96g.MWF“A”。向样品2，3，4，5，和6中加入0.04g.CMI，0.04g.稳定剂和19.92g.MWF“A”。向样品2中加入碘酸钾(KIO3)，向样品3中加入高碘酸钠(NaIO4)，向样品4中加入溴酸钠(NaBrO3)，向样品5中加入碘酸(HIO3)，且向样品6中加入高碘酸(HIO4)。向样品7中加入0.08g.MI和19.92g.MWF“A”。向样品8，9，10，11，和12中加入0.08g.MI，0.02g.稳定剂，和19.90g.MWF“A”。向样品8中加入KIO3，向样品9中加入NaIO4，向样品10中加入NaBrO3，向样品11中加入HIO3，且向样品12中加入HIO4。向样品13中加入0.09g.OI和19.91g.MWF“A”。向样品14，15，16，17，和18中加入0.09g.OI，0.04g.稳定剂，和19.87g.MWF“A”。向样品14中加入KIO3，向样品15中加入NaIO4，向样品16中加入NaBrO3，向样品17中加入HIO3，且向样品18中加入HIO4。将样品封好震摇，然后在40℃保存。在0，1，2，3，和4周用HPLC分析。如果贮存后样品中活性组分的含量大于50％则认为样品过关，结果列于表3和表4。
表3
％CMI ％OI剩余稳定剂 量(ppm) 1周 1周 2周 3周 4周无* 0 0 0 NA NA NAKIO3 2,000 0 83 73 57 62NaIO4 2,000 0 77 76 71 71NaBrO3 * 2,000 0 0 NA NA NAHIO3 2,000 0 89 78 71 75HIO4 2,000 0 93 96 84 73
NA=未分析
表4
％MI剩余稳定剂 量(ppm) 1周 2周 3周无* 0 0 NA NAKIO3 1,000 56 2 NANaBrO3 * 1,000 0 NA NAHIO3 2,000 75 74 53HIO4 2,000 79 76 70*=对比
此实施例还证明碘酸，高碘酸，和它们的盐对于在pH高于8.5的侵蚀性金属加工液中稳定非氯代的3-异噻唑酮是有效的，而溴酸盐是无效的。另外，不管是碘酸，高碘酸，它们的盐，还是溴酸盐对于在此液体中稳定氯代的3-异噻唑酮都是无效的。
Claims (5)
1、一种在pH高于8.5且不含5-氯-2-甲基-4-异噻唑啉-3-酮的金属加工液形式组合物中稳定2-甲基-4-异噻唑啉-3-酮、2-正辛基-4-异噻唑啉-3-酮、或它们的混合物的方法，该方法包括引入有效稳定剂量的选自碘酸、高碘酸、和它们的盐的含碘化合物。
2、一种pH高于8.5的金属加工液形式的组合物，其中含有2-甲基-4-异噻唑啉-3-酮、2-正辛基-4-异噻唑啉-3-酮或它们的混合物，以及选自碘酸、高碘酸和它们的盐的有效稳定量的含碘化合物，而不含5-氯-2-甲基-4-异噻唑啉-3-酮。
3、依据权利要求2的组合物，其含有切削油。
4、依据权利要求2的组合物，其中2-甲基-4-异噻唑啉-3-酮的浓度为750～5000ppm。
5、依据权利要求2的组合物，其中2-正辛基-4-异噻唑啉-3-酮的浓度为100～2500ppm。
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| US6008238A (en) * | 1997-10-28 | 1999-12-28 | Rohm And Haas Company | Stabilization of 3-isothiazolone solutions |
| US5910503A (en) * | 1997-10-28 | 1999-06-08 | Rohm And Haas Company | Stable microbicide formulation |
| US6153633A (en) * | 1998-08-11 | 2000-11-28 | Rohm And Haas Company | Stable 3-isothiazolone compositions |
| US6417211B1 (en) | 1999-08-30 | 2002-07-09 | Rohm And Haas Company | Isothiazolone concentrates |
| US6511673B1 (en) * | 2000-05-10 | 2003-01-28 | Rohm And Haas Company | Microbicidal composition |
| WO2007005195A1 (en) * | 2005-06-29 | 2007-01-11 | Union Carbide Chemicals & Plastics Technology Corporation | Wood preservative composition |
| EP1849362B1 (en) | 2006-04-07 | 2012-09-12 | Rohm and Haas Company | Water treatment method |
| JP4903745B2 (ja) * | 2007-05-08 | 2012-03-28 | ローム アンド ハース カンパニー | 安定化された流体 |
| DE102009048188A1 (de) * | 2009-10-02 | 2011-04-07 | Schülke & Mayr GmbH | Antimikrobiell wirksame Gebrauchslösungen enthaltend Kombinationen von Isothiazolonen und Aminen |
| DE102009048189A1 (de) * | 2009-10-02 | 2011-04-07 | Schülke & Mayr GmbH | Lagerstabile mikrobizide Konzentrate und deren Verwendung als Konservierungsmittel |
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| JPH05170608A (ja) * | 1991-12-24 | 1993-07-09 | Shinto Paint Co Ltd | 殺菌組成物 |
| JPH05286915A (ja) * | 1991-07-25 | 1993-11-02 | Imperial Chem Ind Plc <Ici> | 治療用アミド |
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| US4608183A (en) * | 1985-01-14 | 1986-08-26 | Board Of Governors Of Wayne State University | Synergistic antimicrobial or biocidal mixtures including isothiazolones |
| CA2027241A1 (en) * | 1989-10-24 | 1991-04-25 | Andrew B. Law | Stabilized metal salt/3-isothiazolone combinations |
| US5242893A (en) * | 1990-03-02 | 1993-09-07 | Rohm And Haas Company | Use of hexamethylenetetramine as a stabilizer for 3-isothiazolones |
| US5145501A (en) * | 1991-11-12 | 1992-09-08 | Rohm And Haas Company | Bromate stabilizers for 3-isothiazolones |
| JP3524937B2 (ja) * | 1992-02-10 | 2004-05-10 | 日本エンバイロケミカルズ株式会社 | 工業用殺菌剤 |
| EP0676140B1 (en) * | 1994-04-07 | 1999-09-29 | Rohm And Haas Company | Halogen-free biocide |
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| JPH05170608A (ja) * | 1991-12-24 | 1993-07-09 | Shinto Paint Co Ltd | 殺菌組成物 |
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