CN1042642A - 杀虫气雾剂 - Google Patents
杀虫气雾剂 Download PDFInfo
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- CN1042642A CN1042642A CN89108472A CN89108472A CN1042642A CN 1042642 A CN1042642 A CN 1042642A CN 89108472 A CN89108472 A CN 89108472A CN 89108472 A CN89108472 A CN 89108472A CN 1042642 A CN1042642 A CN 1042642A
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- 241000238631 Hexapoda Species 0.000 title claims description 5
- 230000000361 pesticidal effect Effects 0.000 claims abstract description 18
- 235000007516 Chrysanthemum Nutrition 0.000 claims abstract description 14
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 13
- 239000003350 kerosene Substances 0.000 claims abstract description 12
- -1 imidazolidine-3-ylmethyl Chemical group 0.000 claims abstract description 6
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 241000723353 Chrysanthemum Species 0.000 claims description 13
- 239000003599 detergent Substances 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 6
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000003380 propellant Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 claims description 2
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 claims description 2
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 claims description 2
- 229940024113 allethrin Drugs 0.000 claims description 2
- 229960001591 cyfluthrin Drugs 0.000 claims description 2
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 2
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229950001327 dichlorvos Drugs 0.000 claims description 2
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960000490 permethrin Drugs 0.000 claims description 2
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 2
- SMKRKQBMYOFFMU-UHFFFAOYSA-N prallethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(CC#C)C(=O)C1 SMKRKQBMYOFFMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 238000003197 gene knockdown Methods 0.000 description 4
- 239000003915 liquefied petroleum gas Substances 0.000 description 4
- 241000255925 Diptera Species 0.000 description 3
- 101100172132 Mus musculus Eif3a gene Proteins 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229960003536 phenothrin Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- FJDPATXIBIBRIM-QFMSAKRMSA-N (1R)-trans-cyphenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 FJDPATXIBIBRIM-QFMSAKRMSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 238000012856 packing Methods 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000004504 smoke candle Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
Classifications
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- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
- A01N25/06—Aerosols
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
一种用于气雾剂的杀虫组合物，包括活性组分2，4-二氧-1-)2-丙炔基)咪唑烷-3-基甲基菊酸酯和一种含有至少一种C12-20芳烃和煤油的有机溶剂(芳烃和煤油的重量比为1∶20-4∶1)。本发明的烟雾剂具有优秀的杀虫活性。
Description
本发明涉及一种用制备气雾剂的杀虫组合物。2，4-二氧-1-（2-丙炔基）-咪唑烷-3-基甲基菊酸酯（以下通式所示，以下简称化合物A）在USO No.4176189中被公开。该化合物是已知的用于杀虫气雾剂的活性组分。但是由于含有该化合物的气雾剂的杀虫活性总是不那么令人满意，所以它至今还未用于实际中。
根据本发明，提供了一种杀虫组合物，其中含有：
（A）作为杀虫活性组分的2，4-二氧-1-（2-丙炔基）咪唑烷-3-基甲基菊酸酯。
（B）含有至少一种C12-20芳香烃和煤油的有机溶剂，芳烃和煤油的重量比是1∶10～4∶1。
本发明还提供了含和几何体构体有该组合物的气雾剂，用于本发明的化合物A具有多个旋光异构体。因此具有杀虫活性的任何一种异构体和含有这些异构体的混合物都可以用于本发明。在本发明的组合物中化合物A的含量不是太严格，但较好为0.0001-2.0%（重），最好为0.01-1.0%（重）（以杀虫组合物的总重为基准）。
用作溶剂的芳烃是C12-20的芳烃。其具体例子为辛基苯、十二烷基苯、苯基二甲苯基乙烷等。
“煤油”指沸点在100-350℃之间的烃的混合物，是原油精馏中得到的介于汽油和燃料油之间的馏份。
通常，用作气雾剂溶剂的煤油的沸点为180-280℃。
在本发明的杀虫组合物中，芳烃和煤油的重量比为1∶20-4∶1，最好为1∶12-4∶1。
本发明的杀虫组合物可以进一步与化合物A之外的杀虫剂、增效剂、芳香剂、杀菌剂等混合。该杀虫剂的具体例子有3-烯丙基-2-甲基-4-氧环戊-2-烯基菊酸酯（allethrin）、3，4，5，6-四氢苯邻二甲酰亚胺甲基菊酸酯（tetramethrin）2-甲基-4-氧-3-（2-丙炔基）环戊-2-烯基菊酸酯（pralle thrin）、菊酸3-苯氧基苄酯（phenothrin）5-苄基-3-呋喃基甲基菊酸酯（resmethhrin）、2-氰基-3-苯氧基苄基菊酸酯（cyphenothrin）、3-（2，2-二氯乙烯基）-2，2-二甲基环丙烷羧酸3-苯氧基苄基酯（permethrin）、3-（2，2-二氯乙烯基）-2，2-二甲基环丙烷羧酸2-氰基-3-苯氧基苄基酯（cypermethein）3-（2，2-二氯乙烯基）-2，2-二甲基环丙烷羧酸2-氰基-4-氟-3-苯氧基苄基酯（cyfluthrin）、propoxur dichlorvos、fenitrotion等。
本发明的杀虫组合物的制备是将化合物A、至少一种C12-20芳烃、煤油以及根据情况选择的化合物A之外的杀虫剂、增效剂、芳香剂、杀菌剂等在室温或加热条件下混合起来。
本发明的杀虫组合物宜用作制作气雾剂的杀虫组合物，即将组合物加入一个装有一个阀的烟雾罐中，并通过该阀在压力下向罐中加入推进剂。
推进剂的具体例子是液化石油气、二甲醚、二氧化碳气、氮气等。其中以液化石油气和二甲醚为最好。
本发明的杀虫组合物中的推进剂的数量不太严格，但最好为20-60%（重）（以组合物的总重为基准）。
本发明的杀虫组合物不仅仅可以用于触发喷雾器，可以用于新型喷雾器，例如EXXEL（一种美国Container Industries制造的通过橡胶弹性粉末将杀虫溶液驱出的系统）和PROZON（一种由西德Oeco-tech制造的通过电力泵注入空气而使杀虫溶液喷出的系统）。
本发明将参考下列实施例和参考例来进行更具体的说明，但它并不仅仅限于此。
在下列实施例中，份数是重量份。
实施例1
在加热情况下将0.3份含有d-反式酸部分的化合物A、5.0份十二烷基苯和54.7份煤油混合在一起制备一种杀虫组合物。将得到的组合物放入气雾剂罐中，罐上装有一个阀，并且在加压下通过该阀注入40.0份液化石油气，以得到一种气雾剂。
表1 列出了以上述同样的方式得到的气雾剂组合物。
用在实施例1-8和比较例1-5中得到的气雾剂通过CSMA气雾剂测定方法（Peet grady′s chamber method）来测定对于苍蝇和蚊子的Knock-down效率（50%Knock-down时间。结果列于表2。
实施例9
将0.3份含有d-反式酸部分的化合物A、0.1份phenothrin、20.0份十二烷基苯和39.6份煤油在加热下混合起来以制备一种杀虫组合物。将如此得到的组合物加入一个气雾剂罐中，罐上装有一个阀，通过该阀在加压下装入40.0份液化石油气，得到一种气雾剂。
表3 列出了以上述同样方式得到的烟雾剂杀虫组合物的组成。
通过CSMA气雾剂试定法测定在实施例9-14中得到的气雾剂对苍蝇和蚊子的Knock-down效率。结果列于表4。
表5 列出了以实施例1同样的方式得到的用于气雾剂的杀虫组合物的组成。
通过CSMA烟雾剂测定法测试在实施例15和比较例6-9中得到的气雾剂对苍蝇和蚊子的Knock-down效率。结果列于表6。
Claims (10)
1、一种杀虫组合物，其中包括：
(A)作为活性组分的2，4-二氧-1-(2-丙炔基)咪唑烷-3-基甲基菊酸酯。
(B)含有至少一种C12-20芳烃和煤油的有机溶剂，芳烃和煤油的重量比为1∶20-4∶1。
2、权利要求1的组合物，其中该组合物还含有至少一种选自下列的杀虫剂：3-烯丙基-2-甲基-4-氧环戊-烯基菊酸酯（allethrin）、3，4，5，6-四氢苯邻二甲酰亚胺甲基菊酸酯（tetrametirin）、2-甲基-4-氧-5（2-丙炔基基）环戊-2-烯基菊酸酯（prallethrin）、3-苯氧基苄基菊酸酯（phnothrin）、5-苄基-3-呋喃基甲基菊酸酯（cyphenochrin）、3-（2，2-二氯乙烯基）-2，2-二甲基环丙烷羧酸3-苯氧基苄基酯（permethrin）、3-（2，2-二氯乙烯基）-2，2-二甲基环丙烷羧酸α-氰基-3-苯氧基苄基酯（cypermechrin）、3-（2，2-二氯乙烯基）-2，2-二甲基环丙烷羧酸α-氰基-4-氟-3-苯氧基苄基酯（cyfluthrin）、propoxur、dichlorvos和fenitrothion。
3、一种杀虫气雾剂，其中主要含有一种权利要求1的杀虫组合物和一种推进剂。
4、一种杀虫气雾剂，其中主要含有一种权利要求2的杀虫组合物和一种推进剂。
5、权利要求3的气雾剂，其中杀虫活性成分的数量为组合物总重的0.0001-2.0%。
6、权利要求4的气雾剂，其中杀虫活性成分的数量为组合物总重的0.0001-2.0%。
7、权利要求1的组合物，其中芳烃选自辛基苯、十二烷基苯和苯基二甲苯基乙烷。
8、权利要求2的组合物，其中芳烃选自辛基苯、十二烷基苯和苯基二甲苯基乙烷。
9、权利要求3的气雾剂，其中的芳烃选自辛基苯、十二烷基苯和苯基二甲苯基乙烷。
10、权利要求4的气雾剂，其中的芳烃选自辛基苯、十二烷基苯和苯基二甲苯基乙烷。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28636888 | 1988-11-11 | ||
| JP286368/88 | 1988-11-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1042642A true CN1042642A (zh) | 1990-06-06 |
| CN1040498C CN1040498C (zh) | 1998-11-04 |
Family
ID=17703482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN89108472A Expired - Lifetime CN1040498C (zh) | 1988-11-11 | 1989-11-10 | 含2,4－二氧－1－(2－丙炔基)咪唑烷－3－基甲基菊酸酯的杀虫气雾剂 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5137713A (zh) |
| EP (1) | EP0370321B1 (zh) |
| KR (1) | KR0132427B1 (zh) |
| CN (1) | CN1040498C (zh) |
| AU (1) | AU611590B2 (zh) |
| BR (1) | BR8905776A (zh) |
| CH (1) | CH679825A5 (zh) |
| DE (1) | DE68905149T2 (zh) |
| DK (1) | DK564189A (zh) |
| EG (1) | EG18877A (zh) |
| ES (1) | ES2018736A6 (zh) |
| FR (1) | FR2638941A1 (zh) |
| GB (1) | GB2224654B (zh) |
| GR (1) | GR1002530B (zh) |
| HK (1) | HK105992A (zh) |
| HU (1) | HU205822B (zh) |
| ID (1) | ID804B (zh) |
| IT (1) | IT1237477B (zh) |
| LT (1) | LT3605B (zh) |
| LV (1) | LV10021B (zh) |
| MD (1) | MD400C2 (zh) |
| MX (1) | MX18151A (zh) |
| MY (1) | MY104219A (zh) |
| NZ (1) | NZ230699A (zh) |
| RU (1) | RU2027365C1 (zh) |
| SG (1) | SG107592G (zh) |
| TR (1) | TR24625A (zh) |
| YU (1) | YU47941B (zh) |
| ZA (1) | ZA897350B (zh) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5190745A (en) * | 1990-04-24 | 1993-03-02 | Sumitomo Chemical Company, Limited | Insecticidal compositions |
| JPH0764687B2 (ja) * | 1990-04-24 | 1995-07-12 | 住友化学工業株式会社 | 殺虫組成物 |
| CA2040370C (en) * | 1990-04-24 | 2000-11-14 | Kazunobu Dohara | Insecticidal compositions |
| JP3855311B2 (ja) * | 1996-08-07 | 2006-12-06 | 住友化学株式会社 | エアゾール組成物 |
| KR100471016B1 (ko) * | 1996-08-07 | 2005-07-12 | 스미또모 가가꾸 가부시키가이샤 | 살충성에어로졸조성물및이를제조하기위한살충조성물 |
| JP2009235040A (ja) * | 2008-03-28 | 2009-10-15 | Sumitomo Chemical Co Ltd | ハエ類の防除方法 |
| US10405552B2 (en) | 2017-05-22 | 2019-09-10 | S. C. Johnson & Son, Inc. | Composite insecticidal composition |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1598711A (zh) * | 1968-01-23 | 1970-07-06 | ||
| US3979324A (en) * | 1975-09-08 | 1976-09-07 | Monsanto Company | Dye solvents for pressure-sensitive copying systems |
| JPS5391139A (en) * | 1977-01-18 | 1978-08-10 | Chugai Pharmaceut Co Ltd | Insectcide composition |
| JPS609715B2 (ja) * | 1977-06-20 | 1985-03-12 | 住友化学工業株式会社 | カルボン酸エステル、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
| IT1202862B (it) * | 1978-06-02 | 1989-02-15 | Elche Ltd | Procedimento per la depurazione di salamoie |
| JPS5921140B2 (ja) * | 1979-06-26 | 1984-05-17 | 松下電工株式会社 | 回路しや断器の引外し装置 |
| JPS568001A (en) * | 1979-06-30 | 1981-01-27 | Kohkoku Chem Ind | Shoe bottom * core material for shoe bottom and injection molding of shoe bottom |
| US4826674A (en) * | 1984-09-10 | 1989-05-02 | United Industries Corporation | Air freshener preparations |
| FR2575086B1 (fr) * | 1984-12-20 | 1987-02-20 | Rhone Poulenc Spec Chim | Complexe platine-alcenylcyclohexene comme catalyseur de reaction d'hydrosilylation et son procede de preparation |
| FR2575085B1 (fr) * | 1984-12-20 | 1987-02-20 | Rhone Poulenc Spec Chim | Complexe platine-triene comme catalyseur de reaction d'hydrosilylation et son procede de preparation |
| US4904464A (en) * | 1985-03-04 | 1990-02-27 | United Industries Corporation | Insecticide and air freshener preparations |
| JPH0676281B2 (ja) * | 1986-01-17 | 1994-09-28 | 住友化学工業株式会社 | 安定化された水中油型懸濁状農薬組成物 |
| LU86429A1 (fr) * | 1986-05-16 | 1987-12-16 | Oreal | Compositions cosmetiques renfermant un polymere cationique et un polymere anionique comme agent epaississant |
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1989
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- 1989-10-10 KR KR1019890014525A patent/KR0132427B1/ko not_active IP Right Cessation
- 1989-10-11 EG EG48289A patent/EG18877A/xx active
- 1989-10-12 FR FR8913324A patent/FR2638941A1/fr active Granted
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- 1989-11-06 HU HU895680A patent/HU205822B/hu not_active IP Right Cessation
- 1989-11-07 GR GR890100734A patent/GR1002530B/el unknown
- 1989-11-09 DE DE8989120785T patent/DE68905149T2/de not_active Expired - Fee Related
- 1989-11-09 EP EP89120785A patent/EP0370321B1/en not_active Expired - Lifetime
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- 1989-11-09 IT IT04853689A patent/IT1237477B/it active IP Right Grant
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- 1989-11-10 DK DK564189A patent/DK564189A/da not_active Application Discontinuation
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1992
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1993
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1994
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Granted publication date: 19981104 |