CN1200875A - 受控释放组合物 - Google Patents
受控释放组合物 Download PDFInfo
- Publication number
- CN1200875A CN1200875A CN98109336A CN98109336A CN1200875A CN 1200875 A CN1200875 A CN 1200875A CN 98109336 A CN98109336 A CN 98109336A CN 98109336 A CN98109336 A CN 98109336A CN 1200875 A CN1200875 A CN 1200875A
- Authority
- CN
- China
- Prior art keywords
- methyl
- composition
- isothiazolone
- chloro
- phenyl
- 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.)
- Granted
Links
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- 238000013270 controlled release Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
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- 238000000576 coating method Methods 0.000 claims abstract description 20
- 230000000975 bioactive effect Effects 0.000 claims description 49
- 239000000126 substance Substances 0.000 claims description 32
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- 238000000034 method Methods 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- PHXZQPLQBTYCFV-UHFFFAOYSA-N 4-chloro-2-octyl-1,2-thiazol-3-one Chemical class CCCCCCCCN1SC=C(Cl)C1=O PHXZQPLQBTYCFV-UHFFFAOYSA-N 0.000 claims description 17
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000012530 fluid Substances 0.000 claims description 13
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 10
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- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 10
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 9
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
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- 239000011737 fluorine Substances 0.000 claims description 6
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 claims description 5
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- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 4
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 4
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 3
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 3
- 229960002447 thiram Drugs 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- FHXRXZOSNIASHH-UHFFFAOYSA-N 1-(iodomethylsulfonyl)-4-methylbenzene Chemical class CC1=CC=C(S(=O)(=O)CI)C=C1 FHXRXZOSNIASHH-UHFFFAOYSA-N 0.000 claims description 2
- PNLVGFSEHLOUTK-UHFFFAOYSA-N 2-(bromomethyl)pentanedinitrile Chemical compound BrCC(C#N)CCC#N PNLVGFSEHLOUTK-UHFFFAOYSA-N 0.000 claims description 2
- ABBGMXMPOCXVNL-UHFFFAOYSA-N 2-bromo-2-cyanoacetamide Chemical class NC(=O)C(Br)C#N ABBGMXMPOCXVNL-UHFFFAOYSA-N 0.000 claims description 2
- LHQKXYCMFLDMDH-UHFFFAOYSA-N 2-bromo-2-nitropropane-1,1-diol Chemical class OC(O)C(Br)(C)[N+]([O-])=O LHQKXYCMFLDMDH-UHFFFAOYSA-N 0.000 claims description 2
- QRNATDQRFAUDKF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate Chemical compound NC(=S)SCCSC(N)=S QRNATDQRFAUDKF-UHFFFAOYSA-N 0.000 claims description 2
- JMZRZEXRYJUHEB-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;zinc Chemical compound [Zn].NC(=S)SCCSC(N)=S JMZRZEXRYJUHEB-UHFFFAOYSA-N 0.000 claims description 2
- PZOGAKOZVSTZSO-UHFFFAOYSA-N 2-methyl-5,6-dihydro-4h-cyclopenta[d][1,2]thiazol-3-one Chemical compound C1CCC2=C1SN(C)C2=O PZOGAKOZVSTZSO-UHFFFAOYSA-N 0.000 claims description 2
- ZVPQMESWKIQHGS-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC(Cl)=C1Cl ZVPQMESWKIQHGS-UHFFFAOYSA-N 0.000 claims description 2
- UZIRFBMYVLTOHJ-UHFFFAOYSA-N 3-(2,4,6-trichlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C1=CC(=O)NC1=O UZIRFBMYVLTOHJ-UHFFFAOYSA-N 0.000 claims description 2
- WVMWFSJEDURTRX-UHFFFAOYSA-N 4-[(2-hydroxy-5-methylphenyl)methyl]benzene-1,3-diol Chemical class CC1=CC=C(O)C(CC=2C(=CC(O)=CC=2)O)=C1 WVMWFSJEDURTRX-UHFFFAOYSA-N 0.000 claims description 2
- RUQYQUHBSPKBEU-UHFFFAOYSA-N 6-cyclopropyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C2CC2)=N1 RUQYQUHBSPKBEU-UHFFFAOYSA-N 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
- 241000195493 Cryptophyta Species 0.000 claims description 2
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- REEQPVJLQQIULO-UHFFFAOYSA-N NC([Zn])=O Chemical compound NC([Zn])=O REEQPVJLQQIULO-UHFFFAOYSA-N 0.000 claims description 2
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- SUPAZVZLWKYRON-UHFFFAOYSA-N S(=O)(=O)(O)C=1SC2=C(N1)C(=C(C(=C2)C#N)C)S(=O)(=O)O Chemical compound S(=O)(=O)(O)C=1SC2=C(N1)C(=C(C(=C2)C#N)C)S(=O)(=O)O SUPAZVZLWKYRON-UHFFFAOYSA-N 0.000 claims description 2
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- PQRDTUFVDILINV-UHFFFAOYSA-N bcdmh Chemical compound CC1(C)N(Cl)C(=O)N(Br)C1=O PQRDTUFVDILINV-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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Abstract
本发明涉及缓慢释放生物活性化合物的含有生物活性化合物的组合物。这些组合物可以直接参入到要保护的场所或者可以施用于涂有涂料的结构物。
Description
本发明概括来说涉及控制生物活性化合物释放的组合物。特别地,本发明涉及使用一些多酚化合物来控制生物活性化合物的释放。
生物活性化合物在要保护的场所控制释放的能力在生物活性化合物领域是重要的。一般来说,当将生物活性化合物加到要保护的场所时,不管是否需要,该化合物都快速释放。受控释放组合物以更密切适应化合物所需的方式运送生物活性化合物。通过该方式,只有需要量的生物活性化合物释放到要保护的场所。受控释放提供减少成本,降低毒性和提高药效的优点。
已知多种受控释放方法。这样的方法包括,将生物活性化合物制成胶囊,将生物活性化合物吸附在一种惰性载体上,惰性载体例如硅胶,以及包合该生物活性化合物。
所有这些方法在广泛的商业应用中具有缺陷,例如昂贵的起始材料,受控释放方法对于要释放的化合物或要保护的场所的有限相容性,以及释放生物活性化合物的有限控制。例如,不管包合形式是否是溶剂依赖性的,它都限制可利用的溶剂选择范围。包合带来的另一个问题是除了所期望的生物活性化合物外,有时向混合物中参入溶剂。
例如,EP 709358A(Suzuki等)公开了使用四酚化合物包合异噻唑酮(isothiazolone)的包合物。尽管这些组合物提供一些异噻唑酮的释放控制,但是控制量是有限的,而且用来制备包合物的四酚化合物是很贵的。Suzuki等没有讨论除四酚之外的多酚化合物。
Kurita申请的JP 07003191A公开了一种用5,5’-二氯-2,2’-二羟基二苯基甲烷包合异噻唑酮的包合物,用于海上防污漆。这些组合物的成功是有限的,因为在一些国家5,5’-二氯-2,2’-二羟基二苯基甲烷是被禁止的。
因此还是需要受控释放的生物活性组合物,其不贵,与宽范围要保护的场所相容,并且与目前可获得的组合物相比,控制释放生物活性化合物更有效。
本发明涉及一种受控释放组合物,其含有一种生物活性化合物和一种下式多酚化合物:
其中A=CR4R5,二环戊二烯;R1=H,(C1-C8)烷基;R2,R3,R4,R5,R6各自独立地选自R1,OR1,SR1,NO2,CN,CO2R1,卤素,苯基,取代的苯基,苯氧基,取代的苯氧基,(C1-C4)烷氧基苯基,取代的(C1-C4)烷氧基苯基;m=0或1;n=0-100;前提条件是当m=0时,n=0;且其中多酚化合物是任选交联的。
本发明也涉及控制或抑制一些场所处微生物生长的方法,包括向所述要保护场所处或场所上引入有效量的上述组合物。
本发明进一步涉及一种减小或抑制海水生物在一个结构物上生长的方法,包括向要保护的该结构物上或其中引入有效量的上述组合物。
本发明进一步涉及一种减小或抑制真菌,植物和昆虫生长的方法,包括向要保护的场所引入有效量的上述组合物。
除非另有说明,说明书前后所使用的下面的术语具有下面的意义。
术语“生物活性化合物”指杀微生物剂,海上防污剂,和农业杀虫剂。“杀微生物剂”指一种能抑制或控制微生物在一些场所生长的化合物。术语“微生物”包括但不限于真菌,细菌和藻类。
“海上防污剂”包括杀藻剂和杀软体动物剂。“海上防污活性”意指包括减少和抑制海上微生物的生长的活性。适用于本发明的被海上防污剂控制的海上生物包括硬体和软体污物生物。一般来说,术语“软体污物生物”指植物和无脊椎动物,例如粘液,海藻,海草,软体珊瑚虫,被囊类动物,螅体,寄生虫,和海葵,而术语“硬体污物生物”指具有一些类型硬外壳的无脊椎动物,例如藤壶,管虫(tubeworm),和软体动物。
“农业杀虫剂”包括农业杀真菌剂,除草剂和杀虫剂。“农业杀真菌剂”指农业应用中能抑制或控制真菌生长的化合物,农业应用例如处理植物和土壤;“除草剂”指能抑制或控制一些植物生长的化合物;“杀虫剂”指能控制害虫的化合物。
“烷基”指直链,支链,环状,或者其任何组合;“卤原子”和“卤素”指氟,氯,溴,或碘。“取代的苯基”,“取代的苯氧基”,“取代的(C1-C4)烷氧基苯基”指芳香环上的一个或几个氢被其它取代基置换,其它取代基例如氰基,羟基,(C1-C4)烷基,硝基,巯基,(C1-C4)烷硫基,卤素,和(C1-C4)烷氧基。除非另有说明,所有的量以重量百分比计(“wt%”),而且所有wt%范围首尾也包括在内。说明书自始至终使用下面的缩写:g=克;mg=毫克;mL=毫升;分子量=分子量;IR=红外;rpm=每分钟转速;HPLC=高效液相色谱;ppm=每百万份数;AWPA=美国木材防腐协会。
本发明中,有用的生物活性化合物是氢键受体化合物。即这些化合物是具有一个或几个选自氮,氧,氟原子或其混合的那些化合物。这些氮原子或氧原子可以具有单键或多键,例如存在于羰基,亚胺,腈,羟基,酰胺,烷氧基,酯,醚或氨基中。
本发明合适的杀微生物剂包括但不限于5-氯-2-甲基-3-异噻唑酮;2-甲基-3-异噻唑酮;2-正辛基-3-异噻唑酮;4,5-二氯-2-正辛基-3-异噻唑酮;氨基甲酸3-碘-2-丙炔基丁酯;1,2-二溴-2,4-二氰基丁烷;亚甲基双硫代氰酸酯;2-硫代氰基甲基硫代苯并噻唑;四氯间苯二氰;5-溴-5-硝基-1,3-二噁烷;2-溴-2-硝基丙二醇;2,2-二溴-3-次氮基丙酰胺;N,N’-二甲基羟基-5,5’-二甲基乙内酰脲;溴氯二甲基乙内酰脲;1,2-苯异噻唑啉-3-酮;4,5-三亚甲基-2-甲基-3-异噻唑酮;5-氯-2-(2,4-二氯苯氧基)苯酚和3,4,4’-三氯对称二苯脲。
本发明合适的海上防污剂包括但不限于:亚乙基双二硫代氨基甲酸锰;二甲基二硫代氨基甲酸锌;2-甲基-4-叔丁基氨基-6-环丙基氨基-s-三嗪;2,4,5,6-四氯间苯二氰;N,N-二甲基二氯苯基脲;亚乙基双二硫代氨基甲酸锌;硫代氰酸铜;4,5-二氯-2-正辛基-3-异噻唑酮;N-(氟二氯甲基硫代)-邻苯二甲酰亚胺;N,N-二甲基-N’-苯基-N’-氟二氯甲基硫代-硫酰胺;锌的2-吡啶硫醇-1-氧化物;二硫化四甲基秋兰姆;2,4,6-三氯苯基马来酰亚胺;2,3,5,6-四氯-4-(甲基磺酰基)-吡啶;氨基甲酸3-碘-2-丙炔基丁酯;二碘代甲基对甲苯基砜;双二甲基二硫代氨基甲酰基锌亚乙基双二硫代氨基甲酸盐;苯基(双吡啶基)铋二氯化物;2-(4-噻唑基)苯并咪唑;吡啶三苯基甲硼烷;苯基酰胺;卤代炔丙基化合物;或2-卤代烷氧基芳基-3-异噻唑酮。合适的2-卤代烷氧基芳基-3-异噻唑酮包括但不限于2-(4-三氟甲氧基苯基)-3-异噻唑酮;2-(4-三氟甲氧基苯基)-5-氯-3-异噻唑酮;和2-(4-三氟甲氧基苯基)-4,5-二氯-3-异噻唑酮。
本发明合适的农业杀真菌剂包括但不限于:二硫代氨基甲酸酯和衍生物,例如福美铁,福美锌,代森锰,代森锰锌,代森锌,丙森锌,威百亩,福美双,代森锌与二硫化多亚乙基秋兰姆的配合物,棉隆,以及这些和铜盐的混合物;硝基苯酚衍生物,例如二硝巴豆酸酯,乐杀螨,和碳酸2-仲丁基-4,6-二硝基苯基异丙酯;杂环结构,例如克菌丹,灭菌丹,果绿定,二噻农,克杀螨,苯菌灵,噻菌灵,乙烯菌核利,异菌脲,腐霉利,三唑醇,三唑酮,双苯三唑醇,氟代酰亚胺,triarimol,放线菌酮,乙嘧酚,十二环吗啉,烯酰吗啉,thifluzamide,和灭螨猛;混杂的卤化的杀真菌剂,例如:四氯对醌,二氯萘醌,地茂散,tricamba,氯硝胺,和多氯硝基苯;杀真菌抗生素例如:灰黄霉素,春雷霉素和链霉素;混杂的杀真菌剂例如:二苯基砜,多果定,甲氧基,1-硫代氰基-2,4-二硝基苯,1-苯基硫代氨基脲,四氢噻吩甲酯(thiophanate-methyl),和霜脲氰;以及酰基丙氨酸,例如呋霜灵,酯菌胺,甲呋酰胺,苯霜灵,噁霜灵;氟定胺,fluazinam,苯基苯甲酰胺衍生物,例如EP578586A1公开的那些,氨基酸衍生物,例如EP550788中公开的氨酸衍生物,甲氧基丙烯酸酯类,例如(E)-2-(2-(6-(2-氰基苯氧基)嘧啶-4-基氧)苯基)-3-甲氧基丙烯酸甲酯;苯并(1,2,3)噻二唑-7-硫代羧酸S-甲酯:丙酰胺;抑霉唑,多菌灵,腈菌唑;fenbuconazole;十三吗啉;吡嘧磷;氯苯嘧啶醇;拌种咯;和pyrimethanil。
本发明合适的除草剂包括但不限于:羧酸衍生物,包括苯甲酸及其盐;苯氧基和苯基取代的羧酸及其盐;和三氯乙酸及其盐;氨基甲酸衍生物,包括N,N-二(正丙基)硫代氨基甲酸乙酯和戊炔草胺;取代的脲,取代的三嗪,二苯基醚衍生物例如乙氧氟草醚和乙羧氟草醚,酰苯胺类,例如敌稗,氧苯氧除草剂,脲嘧啶类,腈类,和其它有机除草剂例如氟硫草定和thiazopyr。
本发明合适的杀虫剂包括但不限于乙酰甲胺磷;涕灭威;甲体氯氰菊酯;保棉磷;氟氯菊酯;乐杀螨;噻嗪酮;甲萘威;克百威;杀螟丹;甲基毒死稗(chlorpyrifos,chlorpyrifos-methyl);四螨嗪;氟氯氰菊酯;三环锡;氯氰菊酯;苯醚氰菊酯;溴氰菊酯;内吸磷(demeton,demeton-S);甲基内吸磷(demeton-S-methyl,demeton-O-methyl);亚砜吸磷;田乐磷(demephion-S,demephion-O);氯亚胺硫磷;二嗪磷;三氯杀螨醇;百治磷;除虫脲;乐果;二硝巴豆酸酯;硫丹;因毒磷;高氰戊菊酯;乙硫苯威;乙硫磷;益果;灭线磷;乙嘧硫磷;抗螨唑;苯丁锡;杀螟硫磷;双氧威;线虫磷;倍硫磷;氰戊菊酯;氟螨脲;氟虫脲;氟胺氰菊酯;地虫硫磷;丁苯硫磷;呋线威;噻螨酮;氯唑磷;异丙胺磷;噁唑磷;甲胺磷;杀扑磷;灭梭威;灭多威;甲基对硫磷;速灭磷;兹克威;久效磷;烟碱;氧乐果;杀线威;对硫磷;氯菊酯;甲拌磷;伏杀硫磷;亚胺硫磷;磷胺;抗芽威;嘧啶磷;丙溴磷;猛杀威克螨特;哒螨酮;苄呋菊酯;鱼藤酮;tebufenozide;双硫磷;TEPP;特丁磷;硫双威;甲基立枯磷;triazamate;三唑磷;和芽灭多。
生物活性化合物优选杀微生物剂或海上防污剂。特别优选的是2-甲基-3-异噻唑酮,5-氯-2-甲基-3-异噻唑酮,2-正辛基-3-异噻唑酮,4,5-二氯-2-正辛基-3-异噻唑酮,苯并异噻唑酮,4,5-三亚甲基-3-异噻唑酮,氨基甲酸3-碘-2-丙炔基丁酯;5-氯-2-(2,4-二氯苯氧基)苯酚和3,4,4’-三氯对称二苯脲。
用于本发明的多酚化合物包括但不限于2,6-双(2’,4’-二羟基苄基)-4-甲基苯酚;4,4’-双酚;二环戊二烯-苯酚树脂;苯酚-甲醛缩聚物;交联的苯酚-甲醛缩聚物;甲酚-甲醛缩聚物,例如2,6-双[(2-羟基-5-甲基苯基)甲基]-4-甲基苯酚;和交联的甲酚-甲醛缩聚物。苯酚-甲醛缩聚物一般具有600-8000的分子量。甲酚-甲醛缩聚物一般具有450-20000的分子量。甲酚-甲醛缩聚物可以从邻-,间-,或对-甲酚或其混合物制备。当交联时,用于本发明的多酚化合物与亚甲基桥键联。
用于本发明的多酚化合物是抗光蚀剂和离子交换剂领域公知的而且一般可以购得。例如,苯酚-甲醛缩合物可以以phenol Novolac树脂商品名购得;甲酚-甲醛缩聚物可以以cresol Novolac树脂商品名购得;二环戊二烯-苯酚树脂商品名是Durite树脂,所有这些都从Borden Chemical,Inc.(Louisville,KY)购得。交联的苯酚-甲醛缩聚物可以以DuoliteXAD树脂商品名从Haas Company(Philadelphia,PA)购得。
本发明组合物通过将生物活性化合物的溶液与多酚化合物溶液混合而制备。或者,将单一生物活性化合物或多酚化合物加入到另一种成分的溶液中。例如一种多酚化合物可以加入到生物活性化合物溶液中。可以通过任何方法去除溶剂,例如减压法,得到固体或油状组合物。用来溶解生物活性化合物的溶剂可以相同或不同于用来溶解多酚化合物的溶剂。当使用不同溶剂来溶解生物活性化合物和多酚化合物时,优选这些溶剂彼此混容。也可以使用溶剂混合物。合适的溶剂包括甲醇,乙醇,和丙醇;酯类,例如乙酸乙酯和乙酸丁酯;酮类,例如丙酮和甲基异丁基酮;腈类,例如乙腈;等等。或者生物活性化合物或多酚化合物之一或者两者可以熔融混合。本发明组合物是固体或者油。
一般是加入本发明多酚化合物中的生物活性化合物为0.1wt%-95wt%,以多酚化合物重量为准计。因此,组合物中生物活性化合物与多酚化合物重量比通常是0.1∶99.9-95∶5。优选该重量比是1∶10-9∶1,更优选3∶10-6∶10。
本发明组合物中可以使用多于一种的生物活性化合物,只要这些化合物之间不反应(否则不稳定),而且与多酚化合物相容。其优点在于控制释放多种生物活性化合物,其提供比单独一种化合物更广范围的控制。而且,这可以降低必须使用多种生物活性化合物时的处理费用。当使用多于一种的生物活性化合物时,生物活性化合物与多酚化合物总量之比一般是0.1∶99.9-95∶5。
本发明组合物可以进一步含有一种载体·例如水,有机溶剂或其混合物。合适的有机溶剂载体包括但不限于:乙腈,乙酸乙酯,乙酸丁酯,甲苯,二甲苯,甲醇,乙醇,丙酮,甲基乙基酮,甲基异丁基酮,乙二醇,二乙二醇,丙二醇,二丙二醇,和乙二醇醚。当本发明组合物要应用于农业上时,优选载体是农业可接受的载体。
无论在哪里,只要生物活性化合物是有用的,则本发明组合物有用。当生物活性化合物是一种杀微生物剂时,本发明组合物用于控制或抑制一场所处的微生物例如细菌和真菌的生长。本发明组合物适用于任何需要保护不受微生物侵害的场所。合适的场所包括但不限于:冷却塔;空气滤清器;矿物泥浆;纸浆和纸加工液;纸涂料;游泳池;spas;粘合剂;胶粘水泥;堵塞物;密封剂;农业助剂防腐剂;建筑材料;化妆品和厕卫用品;香波;消毒剂和抗菌剂;配制的工业和消费品;肥皂;洗衣房喷淋水;皮革和皮革制品;木材,包括制材,栋木,纤维板,胶合板和复合木材;塑料,润滑剂;水利系统用流体;医药装置;金属加工液;乳液和分散液;漆,包括海上用漆;清漆,包括海上用清漆;胶乳;控制气味的液体;涂料,包括海上用涂料;石油加工液;燃料;石油领域用流体;照相化学品;印刷流体;清洁剂;洗涤剂;纺织原料;和纺织品。
当本发明组合物含有一种杀微生物剂时,可以直接将其加到要保护的场所或者作为进一步含有一种合适的载体的组合物加到要保护的场所。用于杀微生物应用的合适的载体包括但不限于水;有机溶剂,例如乙二醇,二乙二醇,丙二醇,二丙二醇,二甲苯,甲苯,丙酮,甲基异丁基酮,或酯类;或其混合物。组合物也可以配制成微型乳剂,可微乳化油,乳剂,乳油,糊剂,或者可以制成胶囊。具体的制剂取决于要保护的场所和使用的具体杀微生物剂。这些制剂的制备有公知的标准方法。
当组合物含有一种杀微生物剂时,控制或抑制微生物生长所必需的本发明组合物的量取决于要保护的场所,但是一般情况下,如果向要保护的场所提供0.5-2500ppm杀微生物剂则足够了。杀微生物剂经常用于需要进一步稀释的场所。例如,本发明组合物可以加入到金属加工液浓缩物中,然后进一步稀释。如果在最终稀释物中一般提供5-50ppm的杀微生物剂,则在最终金属加工液稀释物中控制微生物生长所必需的本发明组合物的量足够了。在不用进一步稀释的场所例如漆中,如果一般提供500-2500ppm的杀微生物剂,则控制微生物生长所必需的本发明组合物的量足够了。
当本发明生物活性化合物是一种海上防污剂时,可以通过将组合物施用到海上要保护的结构物上或之中、来使用本发明组合物抑制海上微生物的生长。根据要保护的海上结构物,本发明组合物可以直接参入海上结构物中,直接施用于海上结构物,或者参入到涂料中,然后将涂料应用到海上结构物。
合适的海上结构物包括但不限于:小船,轮船,采油平台,码头,桩基,船坞,高弹橡胶,和渔网。本发明组合物一般在生产过程中直接被参入到结构物例如高弹橡胶或渔网纤维中。对于例如渔网或木桩这样的结构物,一般直接应用本发明组合物。本发明组合物也可以直接参入到海上用涂料中,例如海上用漆或清漆。
当本发明组合物含有抑制海上防污剂时,根据要保护的结构物的重量或根据要施用的涂料的重量,如果提供0.1-30wt%的单一的海上防污剂,则抑制或防止海上微生物生长所必需的本发明组合物的量一般足够了。当本发明组合物直接参入进或直接施用到一个结构物上时,根据要保护的结构物的重量,如果提供0.1-30wt%的单一的海上防污剂,则抑制海上微生物生长所必需的本发明组合物的量一般足够了。优选提供0.5-20wt%的单一的海上防污剂,则本发明组合物的量足够;更优选1-15wt%。当参入到涂料中时,根据所述涂料的重量,提供0.1-30wt%的单一的海上防污剂,则适于抑制海上微生物生长的本发明组合物的量一般足够了。本发明组合物的量优选提供0.5-15wt%单一的海上防污剂;更优选1-10wt%。
总之,含有一种海上防污剂的本发明组合物参入到一种载体中,所述载体例如水;有机溶剂,例如二甲苯,甲基异丁基酮,和甲基异戊基酮;或其混合物。
本发明组合物的直接施用可以通过任何常规的方法,例如浸渍,喷施,或涂敷。例如渔网也可以通过将渔网浸入含有本发明组合物和一种载体的组合物中或者通过用所述组合物对渔网喷施来保护。
象木桩和渔网这样的结构物可以通过直接将本发明组合物参入到该结构物中来保护。例如进一步含有一种载体的本发明组合物可以通过加压处理或真空浸渍的方法施用于用作桩的木料中。这些组合物也可以在生产过程中参入到渔网纤维中。
海上涂料含有一种粘合剂和溶剂以及任选的其它成分。溶剂可以是有机溶剂或水。本发明组合物适用于以溶剂和水两者为基础的海上涂料。优选以溶剂为基础的海上涂料。
任何常规粘合剂可以用于参入本发明组合物的海上防污涂料。合适的粘合剂包括但不限于:溶剂体系中的聚氯乙烯;溶剂体系中的氯化橡胶;溶剂或水体系中的丙烯酸树脂;作为水分散液或溶剂体系的乙酸氯乙烯酯-乙酸乙烯酯共聚物;丁苯橡胶;丁二烯-丙烯腈橡胶;丁二烯-苯乙烯-丙烯腈橡胶;无水油例如亚麻子油;沥青;环氧树脂,硅氧烷等。
本发明海上涂料任选地含有一种或几种下列成分:无机颜料,有机颜料,或染料,和受控释放材料,例如松香。以水为基础的涂料也可以任选地含有:聚结剂,分散剂,表面活性剂,流变学调节剂,或促粘合剂。以溶剂为基础的涂料也可以任选地含有:增充剂,增塑剂,或流变学调节剂。
典型的海上涂料含有2-20wt%粘合剂,最多15wt%松香/改性松香,0.5-5wt%增塑剂,0.1-2wt%抗沉降剂,5-60wt%溶剂/稀释剂,最多70wt%氧化亚铜,最多30wt%颜料(除氧化亚铜之外),和最多15wt%海上防污剂。
含有本发明组合物的海上涂料可以通过任何常规方法施用于要保护的结构物。合适的施用方法包括但不限于喷施;滚压;刷涂;或浸涂。
当生物活性化合物是一种农业除草剂时,本发明组合物可以施用于植物或土壤,或者可以用作种子处理剂。组合物可以直接使用或者配制成细粉剂,颗粒剂,流动剂,乳油,微型乳油,溶剂,微溶剂,或可以制成胶囊。
下面的实施例是为了详细说明本发明的各个方面而不是为了在任何方面限制本发明范围。
实施例1
下面是根据下面通用方法之一制备的本发明组合物的实施例。
A.溶液方法
将生物活性化合物的甲醇溶液加入到烧瓶中。向该溶液中加入多酚化合物的甲醇或乙醇溶液。使用的生物活性化合物的量使终产物含有以多酚化合物重量计为31-56wt%的生物活性化合物。然后在50℃下真空去除甲醇或乙醇,得到一种固体或油状物。
B.熔融方法
生物活性化合物置于烧瓶中并熔融。将熔融的生物活性化合物加入到多酚化合物的甲醇或乙醇的溶液或悬浮液中。使用的生物活性化合物的量使终产物含有以多酚化合物重量计为13-79wt%值的生物活性化合物。然后在50℃下真空去除甲醇或乙醇,得到一种固体或油状物。
表1中给出了制备的组合物以及配合的异噻唑酮羰基的IR频率。记录的组合物中生物活性化合物的量是以多酚化合物重量为基础的wt%。表1中使用的缩写如下。
多酚化合物
A1=2,6-双(2’4’-二羟基苄基)-4-甲基苯酚
A2=分子量=2000的苯酚-甲醛缩聚物(Phenyl Novolac SD-1711)
A3=分子量=1000的苯酚-甲醛缩聚物(Phenyl Novolac SD-1731A)
A4=羟基官能度是4-5的苯基-甲醛树脂(Phenyl Novolac SD-3418)
A5=羟基官能度是6-7的苯基-甲醛树脂(Phenyl Novolac SD-838A)
A6=2,6-双[(2-羟基-5-甲基苯基)甲基]-4-甲基苯酚
A7=交联的苯酚-甲醛缩聚物(Duolite XAD-761)
生物活性化合物
B1=4,5-二氯-2-正辛基-3-异噻唑酮
B2=5-氯-2-甲基-3-异噻唑酮与2-甲基-3-异噻唑酮的3∶1的混合物
B3=2-甲基-3-异噻唑酮
B4=2-正辛基-3-异噻唑酮
B5=3,4,4’-三氯对称二苯脲
表1:本发明组合物
样品 | 多酚化合物 | 生物活性化合物(wt%) | 制备方法 | IRcm-1 | 物理状态 |
1 | A1 | B1(43) | A | 1642 | 油 |
2 | A2 | B1(38) | B | 1640 | 油 |
3 | A3 | B1(36) | B | 1642 | 油 |
4 | A4 | B1(39) | B | 1642 | 油 |
5 | A5 | B1(37) | B | 1640 | 油 |
6 | A6 | B1(56) | A | 1639 | 固体 |
7 | A2 | B2(30) | A | 固体 | |
8 | A6 | B2(31) | A | 固体 | |
9 | A2 | B3(40) | B | 1582 | 油 |
1 | A2 | B4(40) | B | 1588 | 油 |
11 | A2 | B5(45) | A | 固体 | |
12 | A2 | B1(79) | B | 油 | |
13 | A2 | B1(13) | B | 油 | |
14 | A7 | B1(49) | B | 固体 | |
对照 | - | B1 | - |
实施例2
根据下面的方法评估实施例1的组合物释放生物活性化合物的速度。
将称重的样品放入100ml样品瓶中。然后向该样品瓶中加入含有0.2wt%辛基磺基琥珀酸钠的100ml水。然后小心搅拌该溶液以保证没有泡沫生成。在各不同时间点取等份(0.5ml)并转移到微离心试管中。然后每一等份以14000rpm离心3分钟。然后移取上清液并通过HPLC分析生物活性化合物的量。然后用含有0.2wt%辛基磺基琥珀酸钠的0.5ml水洗涤微离心试管,并将洗涤液加到样品瓶中。这保证在取样的过程中没有样品损失,样品瓶中的体积保持不变。表2给出了释放的4,5-二氯-2-正辛基-3-异噻唑酮的累计百分比。
表2:释放的4,5-二氯-2-正辛基-3-异噻唑酮的百分率
时间(分钟) | 样品1 | 样品2 | 样品4 | 样品5 | 样品12 | 样品14 |
2460 | 2.8 | |||||
2640 | 3.4 | |||||
3840 | 12.2 | |||||
4200 | 1.3 | 0.6 | 1.0 | |||
5520 | 5.8 | |||||
5580 | 6.2 | |||||
7080 | 2.1 | 1.1 | 1.5 | |||
9840 | 8.4 | |||||
9960 | 8.8 | 23.3 | ||||
10140 | 2.8 | 1.5 | 2.0 | |||
16800 | 33.2 |
上面的数据清楚地表明,本发明组合物提供4,5-二氯-2-正辛基-3-异噻唑酮的受控释放。
实施例3
评估实施例1的组合物对生物活性化合物在木料中的释放的控制。
将足够量的样品13(表1)溶解于乙醇中,提供以基于4,5-二氯-2-正辛基-3-异噻唑酮计为1300ppm的处理液。通过将4,5-二氯-2-正辛基-3-异噻唑酮自身溶解于乙中、得到1300ppm溶液来制备对照样品。根据AWPAStandard M11-87用两种样品处理Southern Yellow Pine木块。用样品13处理液加压处理8块木块,并用对照处理液处理8块木块。让每组木块中的6块干燥3星期,然后再用水加压。称重木块,确定被木块吸收的4,5-二氯-2-正辛基-3-异噻唑酮的标称重量。用样品13处理液处理的木块含有总标称重量为26727μg的4,5-二氯-2-正辛基-3-异噻唑酮,而用对照处理液处理的木块含有总标称重量为26985μg的4,5-二氯-2-正辛基-3-异噻唑酮。因此,相同量的4,5-二氯-2-正辛基-3-异噻唑酮浸入了木块。然后将每个处理组中的6块木块浸入水中一定时间。然后去除水并通过HPLC分析测定从木块中沥出的4,5-二氯-2-正辛基-3-异噻唑酮的量。然后向木块加入新鲜的水并重复试验。结果见表3。
表3:沥出的4,5-二氯-2-正辛基-3-异噻唑酮
时间(小时) | 样品13(ppm) | 对照(ppm) |
4 | 0.51 | 2.19 |
22 | 0.58 | 2.24 |
72 | 0.59 | 2.27 |
164 | 0.55 | 2.03 |
218 | 0.53 | 1.91 |
267 | 0.48 | 1.61 |
339 | 0.47 | 1.63 |
386 | 0.44 | 1.47 |
506.5 | 0.34 | 1.07 |
沥出的总的ppm | 4.49 | 16.42 |
上面的数据清楚地表明,与常规处理的木材(对照)相比,本发明组合物大大减少从木材(样品13)中沥出的4,5-二氯-2-正辛基-3-异噻唑酮的量。
Claims (10)
2.权利要求1的组合物,其中生物活性化合物选自:5-氯-2-甲基-3-异噻唑酮;2-甲基-3-异噻唑酮;2-正辛基-3-异噻唑酮;4,5-二氯-2-正辛基-3-异噻唑酮;1,2-二溴-2,4-二氰基丁烷;亚甲基双硫代氰酸酯;2-硫代氰基甲基硫代苯并噻唑;四氯间苯二氰;5-溴-5-硝基-1,3-二噁烷;2-溴-2-硝基丙二醇;2,2-二溴-3-次氮基丙酰胺;N,N’-二甲基羟基-5,5’-二甲基乙内酰脲;溴氯二甲基乙内酰脲;1,2-苯异噻唑啉-3-酮;4,5-三亚甲基-2-甲基-3-异噻唑酮;5-氯-2-(2,4-二氯苯氧基)苯酚;3,4,4’-三氯对称二苯脲,亚乙基双二硫代氨基甲酸锰;二甲基二硫代氨基甲酸锌;2-甲基-4-叔丁基氨基-6-环丙基氨基-s-三嗪;2,4,5,6-四氯间苯二氰;N,N-二甲基二氯苯基脲;亚乙基双二硫代氨基甲酸锌;硫代氰酸铜;N-(氟二氯甲基硫代)-邻苯二甲酰亚胺;N,N-二甲基-N’-苯基-N’-氟二氯甲基硫代-硫酰胺;锌的2-吡啶硫醇-1-氧化物;二硫化四甲基秋兰姆;2,4,6-三氯苯基马来酰亚胺;2,3,5,6-四氯-4-(甲基磺酰基)-吡啶;氨基甲酸3-碘-2-丙炔基丁酯;二碘代甲基对甲苯基砜;双二甲基二硫代氨基甲酰基锌亚乙基双二硫代氨基甲酸盐;苯基(双吡啶基)铋二氯化物;2-(4-噻唑基)苯并咪唑;吡啶三苯基甲硼烷;苯基酰胺;卤代炔丙基化合物;和2-卤代烷氧基芳基-3-异噻唑酮。
3.权利要求2的组合物,其中生物活性化合物选自:2-甲基-3-异噻唑酮,5-氯-2-甲基-3-异噻唑酮,2-正辛基-3-异噻唑酮,4,5-二氯-2-正辛基-3-异噻唑酮,苯并异噻唑酮,4,5-三亚甲基-3-异噻唑酮,氨基甲酸3-碘-2-丙炔基丁酯;5-氯-2-(2,4-二氯苯氧基)苯酚和3,4,4’-三氯对称二苯脲。
4.权利要求1的组合物,其中多酚化合物选自2,6-双(2’,4’-二羟基苄基)-4-甲基苯酚;4,4’-双酚;二环戊二烯-苯酚树脂;苯酚-甲醛缩聚物;交联的苯酚-甲醛缩聚物;甲酚-甲醛缩聚物,和交联的甲酚-甲醛缩聚物。
5.权利要求1的组合物,其中生物活性化合物与多酚化合物的重量比是0.1∶99.9-95∶5。
6.权利要求5的组合物,其中的重量比是1∶10-9∶1。
7.权利要求1的组合物,其进一步含有一种载体,载体选自水,乙腈,乙酸乙酯,乙酸丁酯,甲苯,二甲苯,甲醇,乙醇,丙酮,甲基乙基酮,甲基异丁基酮,乙二醇,二乙二醇,丙二醇,二丙二醇。
8.一种控制或抑制真菌,细菌,藻类,海上污物生物,植物,和害虫生长的方法,包括将一种权利要求1的组合物引入要保护的场所。
9.权利要求8的方法,其中要保护的场所选自:冷却塔;空气滤清器;矿物泥浆;纸浆和纸加工液;纸涂料;游泳池;spas;粘合剂;胶粘水泥;堵塞物;密封剂;农业助剂防腐剂;建筑材料;化妆品和厕卫用品;香波;消毒剂和抗菌剂;配制的工业和消费品;肥皂;洗衣房喷淋水;皮革和皮革制品;木材;塑料,润滑剂;水利系统用流体;医药装置;金属加工液;乳液和分散液;漆;清漆;胶乳;控制气味的液体;涂料;石油加工液;燃料;油田用流体;照相化学品;印刷流体;清洁剂;洗涤剂;纺织原料;和纺织品;海上结构物;植物;土壤;和种子。
10.权利要求9的方法,其中海上结构物选自小船,轮船,采油平台,码头,桩基,船坞,高弹橡胶,和渔网。
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JP2002020203A (ja) * | 2000-06-29 | 2002-01-23 | Yokohama Rubber Co Ltd:The | ゴム製品に防汚性を付与する方法 |
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MXPA03009304A (es) | 2001-04-11 | 2004-11-12 | Int Paper Co | Articulos de papel que exhiben capacidad de almacenamiento a largo plazo. |
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US20090227452A1 (en) * | 2001-09-14 | 2009-09-10 | Birthisel Timothy D | Spent fermented grain soil additive |
US7087106B2 (en) * | 2003-02-20 | 2006-08-08 | University Of Florida | Materials and methods for inhibiting fouling of surfaces exposed to aquatic environments |
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US7906463B2 (en) * | 2006-08-02 | 2011-03-15 | Kemira Chemicals Inc. | Biocide for well stimulation and treatment fluids |
CN101857768B (zh) * | 2010-06-18 | 2012-11-07 | 上海纳米技术及应用国家工程研究中心有限公司 | 一种用于铝合金型材的超声波改性纳米隔热粉末涂料及其制备方法 |
US9363993B2 (en) * | 2011-02-15 | 2016-06-14 | Toyo Seikan Group Holdings, Ltd. | Antibacterial resin composition |
AU2012271948B2 (en) | 2011-06-21 | 2015-10-15 | Akzo Nobel Coatings International B.V. | Biocidal foul release coating systems |
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PT3174950T (pt) * | 2014-08-01 | 2019-01-22 | Buckman Laboratories Int Inc | Microbicidas e sua utilização |
WO2017095335A1 (en) | 2015-11-30 | 2017-06-08 | Aquafil S.P.A. | Microencapsulated biocides, coating compositions with microencapsulated biocides and use of coating compositions for fishing nets |
US20210130678A1 (en) * | 2016-01-15 | 2021-05-06 | Ambrish Kamdar | Compositions Useful for Diverting or Stopping Fluids in Subterranean Operations |
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JP4587341B2 (ja) | 2010-11-24 |
CN1214716C (zh) | 2005-08-17 |
EP0880892A1 (en) | 1998-12-02 |
CA2238230A1 (en) | 1998-11-28 |
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