WO2008032840A2 - Method for preparing insect-repellent compound-containing resin pellet - Google Patents
Method for preparing insect-repellent compound-containing resin pellet Download PDFInfo
- 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
Links
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
Abstract
The invention provides 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 in the course of preparing the insect-repellent compound-containing resin pellet. The invention relates to a method for preparing an insect-repellent compound-containing resin pellet, said method 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.%, melt-kneading the resulting composition with a twin-screw extruder, and extruding the composition as a strand, and cutting the strand into pellets of the insect-repellent compound-containing resin, wherein said condition (1) of said ethylene based resin is that the ratio of (η1/η2) is from 1.8 inclusive to 3 inclusive, in which η1 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 η2 is the melt viscosity thereof at 200°C and at a shear rate of 1,200 sec-1.
Description
DESCRIPTION
Method for Preparing Insect-Repellent Compound-Containing
Resin Pellet
Field of the Invention
The present invention relates to a method for preparing an insect-repellent compound-containing resin pellet . Background of the Invention
An insect-repellent compound-containing resin composition obtained by kneading an insect-repellent compound and a resin can be shaped into desired shapes, and the shaped articles are used in various fields since they can maintain insect-repellent performance over a long period of time. For example, 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) . Disclosure of the Invention However, 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.
That is, 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. %, melt-kneading the resulting composition with a twin- screw extruder, and extruding the composition as a strand, and cutting the strand into pellets of the insect- repellent compound-containing resin,
wherein the condition (1) of the ethylene based resin is that the ratio of (ηi/η2) is from 1.8 inclusive to 3 inclusive, in which ηi 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 η2 is the melt viscosity thereof at 200°C and at a shear rate of
1,200 sec"1.
According to the method of the present invention, 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.
Best Modes for Carrying out the Invention
In the method of the present invention, an ethylene based resin and porous particles impregnated with an insect-repellent compound are used.
Examples of the insect-repellent compound include pyrethroid compounds such as permethrin, cyphenothrin, d- phenothrin, 4-resmethrin, fenvalerate, fenpropathrin, etofenprox, tralomethrin, profluthrin, and metofluthrin.
Among such 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.
While there is no particular limit in selection of the kind of the porous particles to be used in the present invention, silica is generally used. The use of porous particles having too small an average particle size tends to cause agglomerate of the porous particles, which makes it hard to form a homogenous dispersion, and makes it easy to fly very fine particles during the preparation. On the other hand, the use of porous particles having too large an average particle size induces the roughening of the surface of a shaped article when used for shaping, or provides fibers which are easy to cut. Therefore, the average particle size of the porous particles is generally from 0.03 to 40 μm, preferably from 0.1 to 20 μm.
In the present invention, the porous particles impregnated with the insect-repellent compound are used. For this reason, preferably, 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. When 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. On the contrary, when 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/cm3 inclusive to less than 0.930 g/cm3, a linear low density polyethylene, a medium density polyethylene having a density of 0.930 g/cm3 inclusive to less than 0.942 g/cm3, a high density polyethylene having a density of 0.942 g/cm3 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 (ηi/η2) is from 1.8 inclusive to 3 inclusive, in which ηi 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 η2 is the melt viscosity thereof at 200°C and at a shear rate of 1,200 sec"1. When the porous particles impregnated with the insect-repellent compound and such a resin are melt-kneaded with a twin- screw extruder, 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. When an ethylene based resin whose ηi/η2 exceeds 3 is used, the ethylene based resin has a higher
temperature within the extruder, which makes it impossible to obtain a pellet containing the insect-repellent compound at a desired concentration. In this regard, 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. On the other hand, when the proportion of the same porous particles exceeds 60 wt.%, it becomes impossible to form pellets. When a thermoplastic resin is mixed with various additives to form pellets, conventionally, the resin and the additives are firstly mixed with a banbury mixer, and the mixture is formed into pellets. However, the use of the banbury mixer is likely to increase the loss of the insect-repellent compound, since the insect-repellent
compound adheres to the inner wall of the apparatus or leaks to an external from the mixer. In the meantime, the use of a single-screw extruder instead of the banbury mixer induces insufficient dispersion of the porous particles. To solve these disadvantages, in the present invention, 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. Preferably, the L/D of the screw segment of the kneading section is from 0.5 to 1.0. In addition, it is better not to use a reverse screw segment in order to suppress heat generation in the kneading section. The kneading temperature within the twin-screw extruder is usually from 150 to 210°C.
In the present invention, 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.
According to the method for preparing the insect- repellent compound-containing resin pellets of the present invention, 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. For example, 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. Although 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. Specifically, 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. For example, 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. Examples
Next, the present invention will be described by way of Examples thereof, which should not be construed as limiting the scope of the present invention in any way. The analyses of the insect-repellent compounds and the measurement of the melt viscosities of 'the ethylene based resins of Examples and Comparative Examples were conducted as follows.
(1) Measurement of Insect-Repellent Compound Content
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 .
Conditions for Gas Chromatography Analysis
Detector: flame ionization detector Column: DB-17 capillary column Column temperature: 225°C Gasification chamber temperature: 270°C Detector temperature: 280°C (2) Measurement of Melt Viscosity
The measurement of the melt viscosity of an ethylene based resin with a capillary rheomether was conducted by the capillary rheometer method according to JIS K 7199, Plastics-Determination of the fluidity of plastics using capillary and slit-die rheometers, under the following conditions :
Instrument: capillary rheometer, Capillograph
IB, manufactured by Toyo Seiki Seisaku-sho, Ltd.
Size of Orifice: 1 mm in inner diameter and
40 mm in length L/D: 40
Measuring temperature: 200°C Melt viscosity: the melt viscosity ηi at an apparent shear rate of 120 sec"1 and the melt viscosity η2 at an apparent shear rate of 1,200 sec'1 were measured (Pa. s in unit) . Example 1
Porous particles (porous silica having an average particle size of 12 μm; oil absorption (JIS K 5101-13-1, the methods of test for pigments, Part 13: oil absorption, Chapter 1: the purified linseed oil method) = 130 ml/100 g) (35.5 wt. parts) and permethrin as an insect-repellent compound (38.1 wt . parts) were mixed with a mixer, and further, BHT (1.1 wt . parts), zinc stearate (21.7 wt . parts) and a blue pigment (ultramarine violet) (3.6 wt . parts) were added thereto to obtain an insect-repellent compound-containing mixture.
This insect-repellent compound-containing mixture (41.5 wt . parts) and a linear low density polyethylene (LLDPE) (Sumikathene L GA807 manufactured by Sumitomo Chemical Company, Limited; density = 0.913 g/cm3, ηi = 280, η2 = 140, and ηi/η2 = 2) (58.5 wt . parts) were mixed, and the mixture was melt-kneaded with a twin-screw extruder at a melt-kneading zone temperature of 200°C, and was then extruded from the die heated at 200°C as a strand thereof. 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, with a size of φ 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
Example 1 was repeated, except that a high density polyethylene (HDPE) (HI-ZEX 5000S manufactured by MITSUI CHEMICALS, INC.; density = 0.950 g/cm3, ηi = 1,900, η2 = 265, and ηi/η2 = 7.2) was used instead of LLDPE. 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
300°C. 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.%.
The major embodiments and the preferred embodiments of the present invention are listed below. [1] A method for preparing an insect-repellent compound-
containing resin pellet, said method 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. %, melt-kneading the resulting composition with a twin- screw extruder, and extruding the composition as a strand, and cutting said strand into pellets of the insect- repellent compound-containing resin, wherein said condition (1) of said ethylene based resin is that the ratio of (ηi/η2) is from 1.8 inclusive to 3 inclusive, in which ηi 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 Ύ\2 is the melt viscosity thereof at 200°C and at a shear rate of 1,200 sec"1.
This application claims Paris Convention priority of Japanese Patent Application No. 2006-245255, the entire contents of which are herein incorporated by reference.
Claims
1. A method for preparing an insect-repellent compound-containing resin pellet, said method 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. %, melt-kneading the resulting composition with a twin- screw extruder, and extruding the composition as a strand, and cutting said strand into pellets of the insect- repellent compound-containing resin, wherein said condition (1) of said ethylene based resin is that the ratio of (ηi/η∑) is from 1.8 inclusive to 3 inclusive, in which ηi 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 η2 is the melt viscosity thereof at 200°C and at a shear rate of 1,200 sec"1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007800336044A CN101511191B (en) | 2006-09-11 | 2007-09-10 | Method for preparing insect-repellent compound-containing resin pellet |
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 (en) | 2008-03-20 |
| WO2008032840A3 WO2008032840A3 (en) | 2008-10-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2007/068003 WO2008032840A2 (en) | 2006-09-11 | 2007-09-10 | Method for preparing insect-repellent compound-containing resin pellet |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN101511191B (en) |
| WO (1) | WO2008032840A2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110432264A (en) * | 2019-08-07 | 2019-11-12 | 华南农业大学 | A kind of medicament-carrying nano-microsphere, slow releasing pharmaceutical expelling parasite Pet neck ring and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4680328A (en) * | 1984-11-29 | 1987-07-14 | The Dow Chemical Company | Insect resistant polyethylene composition suitable for wire and cable applications |
| WO1998007318A2 (en) * | 1996-08-19 | 1998-02-26 | Battelle Memorial Institute | Method of making controlled release devices |
| WO2003068855A1 (en) * | 2002-01-28 | 2003-08-21 | The 54 Group, Ltd. | Polymeric resins impregnated with insect repellents |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58113102A (en) * | 1981-12-26 | 1983-07-05 | Earth Chem Corp Ltd | Method for slowing release of drug |
| JPH0465509A (en) * | 1990-06-29 | 1992-03-02 | Sumitomo Chem Co Ltd | Production of moth-proofing fiber |
| JPH08163950A (en) * | 1994-05-19 | 1996-06-25 | Tokyo Ink Kk | Resin net for controlling pest insect |
| JP3360532B2 (en) * | 1996-06-12 | 2002-12-24 | 住友ベークライト株式会社 | Thermoforming resin composition and sheet |
-
2007
- 2007-09-10 WO PCT/JP2007/068003 patent/WO2008032840A2/en active Application Filing
- 2007-09-10 CN CN2007800336044A patent/CN101511191B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO1998007318A2 (en) * | 1996-08-19 | 1998-02-26 | Battelle Memorial Institute | Method of making controlled release devices |
| WO2003068855A1 (en) * | 2002-01-28 | 2003-08-21 | The 54 Group, Ltd. | Polymeric resins impregnated with insect repellents |
Non-Patent Citations (4)
| Title |
|---|
| DATABASE WPI Week 198332 Thomson Scientific, London, GB; AN 1983-732715 XP002491081 & JP 58 113102 A (EARTH SEIYAKU KK) 5 July 1983 (1983-07-05) * |
| DATABASE WPI Week 199215 Thomson Scientific, London, GB; AN 1992-120589 XP002491080 & JP 04 065509 A (SUMITOMO CHEM CO LTD) 2 March 1992 (1992-03-02) cited in the application * |
| DATABASE WPI Week 199635 Thomson Scientific, London, GB; AN 1996-348939 XP002485371 & JP 08 163950 A (TOKYO INK KK) 25 June 1996 (1996-06-25) * |
| DATABASE WPI Week 199811 Thomson Scientific, London, GB; AN 1998-113505 XP002491082 & JP 09 328584 A (SUMITOMO BAKELITE CO LTD) 22 December 1997 (1997-12-22) * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101511191A (en) | 2009-08-19 |
| WO2008032840A3 (en) | 2008-10-23 |
| CN101511191B (en) | 2012-10-10 |
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