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WO2008032840A2 - Procédé de préparation de granulé de résine contenant un composé insectifuge - Google Patents

Procédé de préparation de granulé de résine contenant un composé insectifuge Download PDF

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Publication number
WO2008032840A2
WO2008032840A2 PCT/JP2007/068003 JP2007068003W WO2008032840A2 WO 2008032840 A2 WO2008032840 A2 WO 2008032840A2 JP 2007068003 W JP2007068003 W JP 2007068003W WO 2008032840 A2 WO2008032840 A2 WO 2008032840A2
Authority
WO
WIPO (PCT)
Prior art keywords
insect
repellent compound
ethylene based
based resin
repellent
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.)
Ceased
Application number
PCT/JP2007/068003
Other languages
English (en)
Other versions
WO2008032840A3 (fr
Inventor
Masayoshi Nitta
Hiroaki Takahata
Masakazu Miyakado
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to CN2007800336044A priority Critical patent/CN101511191B/zh
Publication of WO2008032840A2 publication Critical patent/WO2008032840A2/fr
Publication of WO2008032840A3 publication Critical patent/WO2008032840A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • A01N25/08—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 solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • 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

Definitions

  • the present invention relates to a method for preparing an insect-repellent compound-containing resin pellet .
  • JP-A-4-65509/1992 discloses a method for obtaining fibers by shaping an insect-repellent compound-containing resin composition, in which the insect- repellent compound and the resin are kneaded with a banbury mixer to form insect-repellent compound-containing resin pellets, which are further kneaded with a resin with the banbury mixer to form pellets, which are then used for melt-spinning (cf . JP-A-4-65509/1992) .
  • the conventional method for preparing the insect-repellent compound-containing resin pellet, using the banbury mixer has a problem in that the insect- repellent compound is decomposed or volatilizes in the course of the preparation of the pellet, which makes it hard to obtain a resin pellet containing the insect- repellent compound at a desired concentration.
  • An object of the present invention is therefore to provide a method for preparing a resin pellet which contains an insect-repellent compound at a desired concentration, by reducing the loss of the insect-repellent compound during the preparation of the pellet.
  • the present invention provides a method for preparing an insect-repellent compound-containing resin pellet, and this method comprises the steps of mixing porous particles impregnated with an insect- repellent compound with an ethylene based resin satisfying the following condition (1) so that the ratio of the porous particles impregnated with the insect-repellent compound/the ethylene based resin is 20 to 60 wt.%/40 to 80 wt.
  • the condition (1) of the ethylene based resin is that the ratio of ( ⁇ i/ ⁇ 2) is from 1.8 inclusive to 3 inclusive, in which ⁇ i is the melt viscosity of the ethylene based resin at 200°C and at a shear rate of 120 sec "1 , measured with a capillary rheometer, and ⁇ 2 is the melt viscosity thereof at 200°C and at a shear rate of
  • the loss of the insect-repellent compound during the preparation of the pellet can be reduced so that a resin pellet which contains the insect-repellent compound at a desired concentration can be prepared.
  • an ethylene based resin and porous particles impregnated with an insect-repellent compound are used.
  • insect-repellent compound examples include pyrethroid compounds such as permethrin, cyphenothrin, d- phenothrin, 4-resmethrin, fenvalerate, fenpropathrin, etofenprox, tralomethrin, profluthrin, and metofluthrin.
  • insect-repellent compounds compounds which can be in liquid states at 25°C are preferably used. It is also possible to use an insect-repellent compound other than pyrethroid compounds. In the present invention, a single kind of insect-repellent compound may be used, or two or more kinds of insect-repellent compounds may be used in combination.
  • the average particle size of the porous particles is generally from 0.03 to 40 ⁇ m, preferably from 0.1 to 20 ⁇ m.
  • the porous particles impregnated with the insect-repellent compound are used.
  • the oil absorption of the porous particles is from 100 to 180 ml/100 g determined by the purified linseed oil method according to JIS K 5101-13- 1, the methods of test for pigments, Part 13.
  • the oil absorption of the porous particles is too small, it becomes difficult to impregnate the porous particles with a required amount of the insect-repellent compound.
  • the oil absorption thereof is too large, the adsorption of the insect-repellent compound becomes so strong to make it hard to release the insect-repellent compound. As a result, the obtained shaped article can not exhibit a desired insect-repellent effect.
  • the ratio of the porous particles to the insect- repellent compound may be appropriately selected according to the oil absorption of the porous particles. Generally, 50 to 200 wt. parts of the porous particles are used per 100 wt . parts of the insect-repellent compound. While there is no limit in selection of the method for impregnating the porous particles with the insect-repellent compound, preferably, the insect-repellent compound in a liquid state or a solution of the insect-repellent compound in a solvent is gradually added to the porous particles which are being stirred.
  • Examples of the ethylene based resin to be used in the present invention include a low density polyethylene having a density of 0.850 g/cm 3 inclusive to less than 0.930 g/cm 3 , a linear low density polyethylene, a medium density polyethylene having a density of 0.930 g/cm 3 inclusive to less than 0.942 g/cm 3 , a high density polyethylene having a density of 0.942 g/cm 3 or more, copolymers of ethylene and at least one monomer selected from the group consisting of vinyl carboxylates and unsaturated carboxylates .
  • Such copolymers include an ethylene-vinyl carboxylate copolymer and an ethylene-unsaturated carboxylate copolymer.
  • the ethylene-vinyl carboxylate copolymer may be an ethylene- vinyl acetate copolymer (or EVA) .
  • the ethylene-unsaturated carboxylate copolymer may be an ethylene-methyl methacrylate copolymer (or EMMA) , an ethylene-methyl acrylate copolymer (or EMA) , an ethylene-ethyl acrylate copolymer (or EEA), etc. Any of such ethylene based resins may be used singly, or two or more kinds of ethylene based resins may be used in combination.
  • the ethylene based resin to be used in the present invention satisfies the following condition: that is, the ratio of ( ⁇ i/ ⁇ 2) is from 1.8 inclusive to 3 inclusive, in which ⁇ i is the melt viscosity of the ethylene based resin at 200°C and at a shear rate of 120 sec "1 , measured with a capillary rheometer, and ⁇ 2 is the melt viscosity thereof at 200°C and at a shear rate of 1,200 sec "1 .
  • the loss of the insect-repellent compound can be reduced, and a resin pellet which contains the insect-repellent compound at a desired concentration can be prepared.
  • the temperature for kneading the ethylene based resin with the extruder is generally from about 150 to about 210°C.
  • the shear rate herein referred to means an apparent shear rate found when measured with a capillary rheometer.
  • the mixing ratio of the porous particles impregnated with the insect-repellent compound to the ethylene based resin is as follows: when the total of the ethylene based resin and the porous particles impregnated with the insect- repellent compound is 100 wt.%, the ratio of the porous particles impregnated with the insect-repellent compound/the ethylene based resin is 20 to 60 wt.%/40 to 80 wt.%, preferably 30 to 60 wt.%/40 to 70 wt.%. When the proportion of the porous particles impregnated with the insect-repellent compound is less than 20 wt.%, pellets which contain the insect-repellent compound at a high concentration can not be obtained.
  • a twin-screw extruder is used to knead the ethylene based resin and the porous particles impregnated with the insect- repellent compound.
  • the twin-screw extruder to be used is not limited. However, usually, a twin-screw extruder whose L/D is from about 20 to about 60 is used.
  • the L/D of the screw segment of the kneading section is from 0.5 to 1.0.
  • the kneading temperature within the twin-screw extruder is usually from 150 to 210°C.
  • an antioxidant such as an antioxidant, UV absorber, antistatic agent, lubricant, anti-blocking agent, pigment, nucleitor, metal soap, antibacterial and antifungi component, etc. may be optionally added, when the porous particles impregnated with the insect-repellent compound and the ethylene based resin are melt-kneaded in the twin- screw extruder.
  • the mixture of the ethylene based resin with the porous particles impregnated with the insect-repellent compound is melt-kneaded with the twin-screw extruder, and is extruded as a strand thereof, which is then cut to obtain pellets of the insect-repellent compound-containing resin.
  • the strand extruded from the extruder is usually allowed to pass through cooling water and cooled, and is then cut with a pelletizer.
  • the loss of the insect-repellent compound during the preparation of the pellets can be reduced.
  • the method of the present invention is therefore suitable for the preparation of pellets which contain the insect-repellent compound at a high concentration.
  • the method of the present invention makes it possible to prepare pellets which contain 15 wt . % or more of the insect- repellent compound, while reducing the loss of the insect- repellent compound during the preparation.
  • the insect-repellent compound-containing resin pellets which contain the insect-repellent compound at such a high concentration can be directly shaped into a desired shape, such pellets are particularly suitable for use as a master batch of the insect-repellent compound.
  • a resin and the insect-repellent compound-containing resin pellets are mixed so that the concentration of the insect- repellent compound can be a desired value after the mixing, and the resulting mixture is used for shaping.
  • the shaping method and the shape of a shaped article are not limited.
  • the mixture is extruded into a film to provide an insect-repellent film; the mixture is injection-shaped to provide an insect-repellent collar or an ear tag for animals; the mixture is melt-spun to provide insect- repellent fibers; and further, such insect-repellent fibers are woven or knitted to provide a mosquito net or the like.
  • a sample (about 0.25 g) was put in a flat bottom flask and precisely weighed. Then, an internal standard liquid (6,000 ppm of di-n-octyl phthalate/xylene) (5 ml) was added, and xylene (45 ml) was further added. The flask was set on a refluxing apparatus to extract the sample at 75°C for 2 hours. Then, the extract was cooled and analyzed by gas chromatography .
  • an internal standard liquid 6,000 ppm of di-n-octyl phthalate/xylene
  • Measuring temperature 200°C
  • Melt viscosity the melt viscosity ⁇ i at an apparent shear rate of 120 sec "1 and the melt viscosity ⁇ 2 at an apparent shear rate of 1,200 sec '1 were measured (Pa. s in unit) .
  • LLDPE linear low density polyethylene
  • the strand was cut with a pelletizer to obtain pellets of the insect-repellent compound-containing resin, with a size of ⁇ 2mm X 3 mm in length.
  • the insect-repellent compound content in the pellet was measured, and it was found to be 15.8 wt . % .
  • the theoretical value of the insect-repellent compound in the pellet, calculated from the charged amounts of the raw materials, was 15.8 wt.%, and thus, it was confirmed that the insect-repellent compound was contained in the pellet in accordance with the formulation. Comparative Example 1
  • HDPE high density polyethylene
  • the resulting mixture was extruded with the melt-kneading zone temperature of the twin-screw extruder set at 200°C and the die temperature thereof, at 200°C. However, the heat generation was vigorous, and the temperature was raised to
  • the extruded strand was allowed to pass through a cooling water tank and cooled. Then, the strand was cut with a pelletizer to obtain pellets of the insect-repellent compound-containing resin.
  • the pellets included many bubbles. It was supposed that the insect-repellent compound foamed to cause the bubbles.
  • the insect-repellent compound content in the pellet was measured, and it was 14.7 wt.%.
  • a method for preparing an insect-repellent compound- containing resin pellet comprising the steps of mixing porous particles impregnated with an insect- repellent compound with an ethylene based resin satisfying the following condition (1) so that the ratio of said porous particles impregnated with said insect-repellent compound/said ethylene based resin is 20 to 60 wt.%/40 to 80 wt.
  • said condition (1) of said ethylene based resin is that the ratio of ( ⁇ i/ ⁇ 2) is from 1.8 inclusive to 3 inclusive, in which ⁇ i is the melt viscosity of the ethylene based resin at 200°C and at a shear rate of 120 sec "1 , measured with a capillary rheometer, and ⁇ 2 is the melt viscosity thereof at 200°C and at a shear rate of 1,200 sec "1 .

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)

Abstract

L'invention concerne un procédé de préparation d'un granulé de résine qui contient un composé insectifuge dans une concentration souhaitée, par réduction de la perte du composé insectifuge au cours de la préparation du granulé de résine contenant un composé insectifuge. L'invention concerne un procédé de préparation d'un granulé de résine contenant un composé insectifuge, ledit procédé comprenant les étapes consistant à mélanger des particules poreuses imprégnées d'un composé insectifuge avec une résine à base d'éthylène satisfaisant la condition suivante (1), de sorte que le rapport desdites particules poreuses imprégnées dudit composé insectifuge/de ladite résine à base d'éthylène est de 20 à 60% en poids/40 à 80% en poids, à malaxer à l'état fondu la composition ainsi obtenue à l'aide d'une extrudeuse à double vis, et à extruder la composition sous forme d'un fil de base, ainsi qu'à découper le fil de base en granulés de résine contenant un composé insectifuge, ladite condition (1) de ladite résine à base d'éthylène étant que le rapport de (η1/η2) est compris entre 1,8 et 3, où η1 représente la viscosité à l'état fondu de la résine à base d'éthylène à 200°C et à un taux de cisaillement de 120 sec-1, mesuré à l'aide d'un rhéomètre capillaire, et η2 représente la viscosité à l'état fondu de ladite résine à 200°C et à un taux de cisaillement de 1200 sec-1.
PCT/JP2007/068003 2006-09-11 2007-09-10 Procédé de préparation de granulé de résine contenant un composé insectifuge Ceased WO2008032840A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2007800336044A CN101511191B (zh) 2006-09-11 2007-09-10 含驱虫性化合物的树脂丸粒的制备方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006245255 2006-09-11
JP2006-245255 2006-09-11

Publications (2)

Publication Number Publication Date
WO2008032840A2 true WO2008032840A2 (fr) 2008-03-20
WO2008032840A3 WO2008032840A3 (fr) 2008-10-23

Family

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Application Number Title Priority Date Filing Date
PCT/JP2007/068003 Ceased WO2008032840A2 (fr) 2006-09-11 2007-09-10 Procédé de préparation de granulé de résine contenant un composé insectifuge

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CN (1) CN101511191B (fr)
WO (1) WO2008032840A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110432264A (zh) * 2019-08-07 2019-11-12 华南农业大学 一种载药纳米微球、缓释药物驱虫宠物项圈及其制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58113102A (ja) * 1981-12-26 1983-07-05 Earth Chem Corp Ltd 薬剤の徐放化材
US4680328A (en) * 1984-11-29 1987-07-14 The Dow Chemical Company Insect resistant polyethylene composition suitable for wire and cable applications
US6852328B1 (en) * 1989-09-01 2005-02-08 Battelle Memorial Institute K1-53 Method and device for protection of wooden objects proximate soil from pest invasion
JPH0465509A (ja) * 1990-06-29 1992-03-02 Sumitomo Chem Co Ltd 防虫繊維の製造法
JPH08163950A (ja) * 1994-05-19 1996-06-25 Tokyo Ink Kk 害虫防除用樹脂ネット
US5856271A (en) * 1995-06-07 1999-01-05 Battelle Memorial Institute Method of making controlled released devices
JP3360532B2 (ja) * 1996-06-12 2002-12-24 住友ベークライト株式会社 熱成形用樹脂組成物及びシート
US20020165297A1 (en) * 2001-02-02 2002-11-07 The 54 Group, Ltd. Polymeric resins impregnated with insect repellants

Also Published As

Publication number Publication date
WO2008032840A3 (fr) 2008-10-23
CN101511191B (zh) 2012-10-10
CN101511191A (zh) 2009-08-19

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