Resin composition containing ethofenprox, and sustained-release resin molded article for pest control using the same
A resin composition with etofenprox, insect growth regulator, and vinyl chloride resin components addresses the moldability issues of etofenprox, enabling a collar with sustained pest control and no stickiness.
Patent Information
- Application Number
- JP2023209799
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-12-13
- Publication Date
- 2025-06-25
AI Technical Summary
Etofenprox, a pyrethroid compound, tends to solidify at low temperatures and bleed easily at normal temperatures, making it difficult to incorporate into a resin composition and mold into articles like collars without causing stickiness.
A resin composition containing etofenprox, an insect growth regulator, a plasticizer, and a fatty acid in a vinyl chloride resin, specifically using diisononyl adipate, diisodecyl adipate, di(2-ethylhexyl) azelate, sebacic acid, 2-ethylhexyl, and diethylene glycol monoethyl ether as plasticizers, and isostearic acid as the fatty acid, to enhance moldability and pest control.
The composition allows for the production of a molded article, such as a collar, that effectively controls pests with sustained release of active ingredients without surface stickiness.
Smart Images

Figure 2025094338000001 
Figure 2025094338000002
Abstract
Description
Technical Field
[0001] The present invention relates to a resin composition containing etofenprox for controlling pests attached to animals such as pets and livestock. More specifically, the present invention relates to a resin composition containing etofenprox, which has an excellent pest control effect for animals and can be used for collars for pet animals, etc., and a sustained-release pest control resin molded body using the same.
Background Art
[0002] Pests attached to animals that have contact with humans, such as pets or livestock, may transmit diseases that cause serious symptoms in these animals or may cause allergies or harmful effects on humans. For these pests, pest control agents for dripping, spraying, and applying are mainly known on the body surfaces of pets and livestock.
[0003] As active ingredients of such pest control agents, pyrethroid compounds or combinations of pyrethroid compounds and other compounds are widely used (Patent Document 1).
Prior Art Documents
Patent Documents
[0004]
Patent Document 1
Summary of the Invention
Problems to be Solved by the Invention
[0005] Etofenprox, a pyrethroid compound, is known as a pest control agent. On the other hand, etofenprox has the property of being likely to solidify at low temperatures and of bleeding progressing easily at normal temperature or higher. For this reason, it is difficult to incorporate etofenprox into a resin composition and mold it into a collar or the like. That is, it is extremely difficult to produce a good molded article that uses etofenprox and can retain appropriate bleeding without causing stickiness.
[0006] An object of the present invention is to provide a resin composition containing etofenprox, which has a good control effect on animals to be controlled for pests, and a molded article using the same.
Means for Solving the Problems
[0007] As a result of intensive studies to solve this problem, the present inventor has found that by incorporating etofenprox, an insect growth regulator, a plasticizer, and a fatty acid into a vinyl chloride resin, a resin composition excellent in moldability and capable of surely controlling pests can be prepared, and thus the present invention has been completed.
[0008] That is, the present invention provides a resin composition described below. [1] A pest control resin composition comprising etofenprox, an insect growth regulator, a plasticizer, and a fatty acid contained in a vinyl chloride resin, wherein the plasticizer is one or more selected from the group consisting of diisononyl adipate, diisodecyl adipate, di(2-ethylhexyl) azelate, sebacic acid, 2-ethylhexyl, and diethylene glycol monoethyl ether. [2] The pest control resin composition according to [1], wherein the fatty acid is isostearic acid. [3] The pest control resin composition according to [1] or [2], wherein the content of etofenprox is 10% by mass or more and 25% by mass or less in the total composition. [4] The pest control resin composition according to any one of [1] to [3], wherein the content of the plasticizer is 5% by mass or more and 50% by mass or less in the total composition. [5] The pest control resin composition according to any one of [1] to [4], wherein the content of the fatty acid is 0.01% by mass or more and 15% by mass or less in the total composition. [6] The pest control resin composition according to any one of [1] to [5], wherein the insect growth regulator is pyriproxyfen and / or S-methoprene.
[0009] Furthermore, the present invention provides a molded article described below. [7] A sustained-release pest control resin molded article formed by molding the pest control resin composition according to any one of [1] to [6]. [8] The sustained-release pest control resin molded article according to [7], wherein the sustained-release pest control resin molded article is a collar. [9] A method for stably sustainedly releasing etofenprox and an insect growth regulator by coexisting one or more plasticizers selected from the group consisting of etofenprox, an insect growth regulator, diisononyl adipate, diisodecyl adipate, di(2-ethylhexyl) azelate, sebacic acid, 2-ethylhexanol, and diethylene glycol monoethyl ether, and a fatty acid in a vinyl chloride resin.
Effects of the Invention
[0010] According to the present invention, it is possible to provide an excellent resin composition that can be molded into a collar or the like for reliably controlling pests, and a molded article using the same.
Modes for Carrying Out the Invention
[0011] In this specification, the unit of content "mass%" is synonymous with "g / 100g".
[0012] [Resin Composition] The resin composition of the present invention is obtained by incorporating etofenprox, an insect growth regulator, a plasticizer, and a fatty acid into a vinyl chloride resin.
[0013] (Etofenprox) Etofenprox means 2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether. As etofenprox, any active stereoisomer or mixture can be used.
[0014] In the resin composition of the present invention, from the viewpoint of exerting the effects of the present invention, the content of etofenprox relative to the total amount of the resin composition is 10% by mass or more and 25% by mass or less, preferably 11% by mass or more and 22% by mass or less, and more preferably 12% by mass or more and 20% by mass or less.
[0015] (Plasticizer) The plasticizer can be used as a plasticizer for the vinyl chloride resin in the present invention. Among these, one or more selected from the group consisting of diisononyl adipate, diisodecyl adipate, di-2-ethylhexyl azelate, sebacic acid, 2-ethylhexanol, and diethylene glycol monoethyl ether are preferable.
[0016] In the resin composition of the present invention, from the viewpoint of exerting the effects of the present invention, the content of the plasticizer relative to the total amount of the resin composition is preferably 5% by mass or more and 50% by mass or less, and more preferably 10% by mass or more and 40% by mass or less.
[0017] (Fatty acid) The fatty acid can be used as a bleeding promoter in the present invention. Examples of such fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, linoleic acid, oleic acid, arachidic acid, and behenic acid, with isostearic acid being particularly preferable.
[0018] In the resin composition of the present invention, from the viewpoint of exerting the effects of the present invention, the content of the fatty acid relative to the total amount of the resin composition is 0.01% by mass or more and less than 15% by mass, preferably 0.2% by mass or more and 8.0% by mass or less, and more preferably 0.7% by mass or more and 4.0% by mass or less.
[0019] In the resin composition of the present invention, from the viewpoint of exerting the effects of the present invention, the content of isostearic acid relative to the total amount of the resin composition is 0.01% by mass or more and less than 15% by mass, preferably 0.2% by mass or more and 8.0% by mass or less, and more preferably 0.7% by mass or more and 4.0% by mass or less.
[0020] (Insect growth regulator) An insect growth regulator refers to a substance that inhibits the molting and emergence of insects by controlling the balance of hormones that regulate the metamorphosis and molting of insects. Insect growth regulators include chitin synthesis inhibitors typified by benzoylurea compounds such as chlorfluazuron, diflubenzuron, flufenoxuron, lufenuron, novaluron, and teflubenzuron; ecdysteroid and other molting hormone active compounds; and juvenile hormone-like substances selected from the group consisting of hydroprene, kinoprene, phenoxycarb, pyriproxyfen, diofenolan, epofenonan, triprene, methoprene (particularly S-methoprene), and hydroprene. These insect growth regulators can be used alone or in combination of two or more. As these compounds, any active stereoisomer or a mixture thereof can be used. Among these, juvenile hormone-like substances are preferably used, and pyriproxyfen and / or S-methoprene are more preferably used.
[0021] In the resin composition of the present invention, from the viewpoint of exerting the effects of the present invention, the content of the insect growth regulator relative to the total amount of the resin composition is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.1% by mass or more and 7% by mass or less, and even more preferably 0.2% by mass or more and 5% by mass or less.
[0022] In particular, in the resin composition of the present invention, from the viewpoint of exerting the effects of the present invention, the content of pyriproxyfen and / or S-methoprene with respect to the total amount of the resin composition is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.1% by mass or more and 7% by mass or less, and even more preferably 0.2% by mass or more and 5% by mass or less.
[0023] In the resin composition of the present invention, the ratio of the insect growth regulator to etofenprox is preferably 0.0004 parts by mass or more and 1 part by mass or less, more preferably 0.0045 parts by mass or more and 0.65 parts by mass or less, and even more preferably 0.01 parts by mass or more and 0.45 parts by mass or less with respect to 1 part by mass of etofenprox.
[0024] In the resin composition of the present invention, the ratio of pyriproxyfen and / or S-methoprene to etofenprox is preferably 0.0004 parts by mass or more and 1 part by mass or less, more preferably 0.0045 parts by mass or more and 0.65 parts by mass or less, and even more preferably 0.01 parts by mass or more and 0.45 parts by mass or less with respect to 1 part by mass of etofenprox.
[0025] (Vinyl chloride resin) The resin serving as the base material of the resin composition of the present invention is a vinyl chloride resin, which is a polymer having a group represented by -CH2-CHCl-. Such vinyl chloride resins include, in addition to homopolymers of vinyl chloride monomers, copolymers of vinyl chloride monomers and other copolymerizable monomers. Further, a chlorinated vinyl chloride resin may also be used.
[0026] Examples of other monomers copolymerizable with vinyl chloride monomers include, for example, α-olefins; vinyl esters; vinyl ethers; (meth)acrylic acid esters; aromatic vinyls; N-substituted maleimides and the like. These other monomers may be used in combination.
[0027] The resin serving as the base material of the resin composition of the present invention is preferably a vinyl chloride resin composed of a homopolymer. For example, it is also possible to use vinyl chloride monomers of two or more types of homopolymers having different degrees of polymerization.
[0028] From the viewpoint of achieving both moldability and bleed, the average degree of polymerization of the vinyl chloride resin of the present invention preferably includes, at least in part, a homopolymer having a degree of polymerization of 1000 to 1600, and more preferably includes a homopolymer having a degree of polymerization of 1350 to 1500. Here, the average degree of polymerization is the average degree of polymerization measured in accordance with JIS K-6721 "Test Methods for Vinyl Chloride Resins" using, as a sample, the resin obtained by dissolving the polyvinyl chloride resin in tetrahydrofuran (THF), removing the insoluble components by filtration, and then drying and removing the THF in the filtrate.
[0029] As the vinyl chloride resin of the present invention, commercially available ones may be used. For example, polyvinyl chloride "ZEST1400Z" (average degree of polymerization 1450) of Shin-Etsu Vinyl Co., Ltd. and polyvinyl chloride "TK-1400" (average degree of polymerization 1400) of Shin-Etsu Chemical Co., Ltd. can be used.
[0030] Furthermore, in addition to such a resin, it is also possible to use in combination a vinyl chloride resin composed of a homopolymer having different properties. Different properties refer to cases where the average degree of polymerization is different or the particle size is different. For example, it is also preferable to mix a polyvinyl chloride resin in fine powder form (particle size of about 100 μm or less).
[0031] A typical example of use is a combination of polyvinyl chloride "ZEST1400Z" (average degree of polymerization 1450) and "ZESTP24Z" (average degree of polymerization 1200 to 1390) of Shin-Etsu Vinyl Co., Ltd., but it is not limited thereto.
[0032] In particular, in the resin composition of the present invention, from the viewpoint of exerting the effects of the present invention, the content of the vinyl chloride resin relative to the total amount of the resin composition is preferably 40% by mass or more and 65% by mass or less, more preferably 45% by mass or more and 60% by mass or less, and even more preferably 47% by mass or more and 55% by mass or less.
[0033] In the resin composition of the present invention, when containing two or more vinyl chloride resins having different degrees of polymerization, for example, the ratio of ZEST P24Z to ZEST 1400Z is preferably 0.005 parts by mass or more and 0.8 parts by mass or less, more preferably 0.03 parts by mass or more and 0.5 parts by mass or less, and even more preferably 0.05 parts by mass or more and 0.2 parts by mass or less with respect to 1 part by mass of ZEST 1400Z.
[0034] (Pest) The pests referred to in this specification include, but are not limited to, in particular, fleas (including fleas parasitizing dogs, cats, etc.), mites (including ticks, chiggers, spider mites, citrus red mites, rodent mites, etc.), or parasitic or blood-sucking pests such as bedbugs and mosquitoes. Particularly preferred pests to be controlled are fleas, mites, mosquitoes or bedbugs.
[0035] The animals of the present invention include various animals such as various pets, livestock, and poultry. In particular, pets such as dogs, cats, rabbits, hamsters, etc., and livestock and poultry such as cows, horses, pigs, chickens, etc. are mentioned.
[0036] (Other components) As long as the effects of the present invention are not inhibited, the resin composition of the present invention may contain one or more plasticizers selected from the group consisting of etofenprox, insect growth regulators, diisononyl adipate, diisodecyl adipate, di(2-ethylhexyl) azelate, sebacic acid, 2-ethylhexyl, and diethylene glycol monoethyl ether, and any components other than fatty acids in the vinyl chloride resin. By way of example, the optional components include other pest control components other than etofenprox and insect growth regulators, additional plasticizers, stabilizers, pigments, fragrances, etc.
[0037] Examples of additional plasticizers that can be used in the present invention include phosphate esters.
[0038] Examples of stabilizers that can be used in the present invention include, for example, one or more selected from the group consisting of epoxidized soybean oil, barium / zinc-based liquid stabilizers, and barium stearate. It is also desirable to use all of these in combination.
[0039] (Method for producing resin composition and molded article) The resin composition of the present invention can be produced, for example, by the following method, although not limited thereto. First, raw material components other than vinyl chloride resin and pigment are mixed to prepare a mixture. The temperature during stirring can be in the range of 1 to 30°C, and the time can be about 1 to 20 minutes. Then, the vinyl chloride resin and the mixture of raw material components are stirred. After stirring, it is dried at a high temperature. The temperature at this time is not limited, but is preferably about 100°C or higher and 150°C or lower. Stirring and heat drying are repeated until the resin dries up. At this time, for example, a Banbury mixer, a super mixer, etc. can also be used.
[0040] Next, the resin composition thus obtained is made into a resin molded article for pest control. At this time, for example, it can also be melted and molded. As the method for producing the molded article, a method usually used in resin molding processing can be used. Examples of such methods include extrusion molding, injection molding, blow molding, compression molding, powder molding, or press molding, etc. Although not limited, preferably, an injection molding machine can be used to produce the molded article.
[0041] (Uses, etc.) The resin composition of the present invention can be used, for example, as a collar, ear tag, tail tag, limb band, or end rope, etc., although not limited thereto. Among these, in particular, it can be preferably used as a collar for pest control.
[0042] Depending on the application, the resin composition of the present invention can be appropriately selected in terms of shape, size, thickness, etc., and can be molded into a film shape, sheet shape, ring shape, fibrous shape, net shape, etc. For the purpose of using it as a pest control collar, first, it can be molded into a belt shape or band shape, but it is also possible to directly mold it into a shape according to the application after melting the resin with an injection molding machine or the like. For example, it can be poured into a mold in the shape of a collar and cooled to directly mold it into a collar.
[0043] As a non-limiting example, with an injection molding machine, at a temperature setting of 138 to 145 °C, an injection time of 2 to 3 seconds, a cooling time of 8 to 15 seconds, it can be molded into the shape of a collar with a length of 35 cm or 60 cm, a width of about 1.0 cm, and a thickness of about 0.3 cm.
[0044] The resin composition of the present invention can also be used while being exchanged at a frequency of about once every six months or once a year according to the application, etc. In particular, it can be used at these frequencies as collars for medium-sized and large-sized dogs.
[0045] [Stable sustained release method] The present invention also relates to a method for stably sustainedly releasing etofenprox and an insect growth regulator by coexisting one or more plasticizers selected from the group consisting of etofenprox, insect growth regulators, diisononyl adipate, diisodecyl adipate, di(2-ethylhexyl) azelate, sebacic acid, 2-ethylhexyl, and diethylene glycol monoethyl ether, and fatty acids in a vinyl chloride resin. In the sustained release method of the present invention, etofenprox, insect growth regulators, plasticizers, and fatty acids and their contents conform to the contents described in the above resin composition.
Examples
[0046] Next, the present invention will be specifically described by way of examples, but the present invention is not limited to the following examples. In addition, the unit of each component amount in the table is mass% unless otherwise specified in the table.
[0047] A collar made of the resin composition of the example was manufactured by the following method. Raw material components other than the vinyl chloride resin and the pigment shown in Table 1 were mixed at room temperature for about 10 minutes to prepare a mixture.
[0048] Thereafter, the vinyl chloride resin, the pigment, and the mixture of the raw material components were stirred and dried at a high temperature. The temperature at this time was 120°C. Stirring and heat drying were repeated until the resin became brittle.
Table 1
[0049] Next, the resin composition thus obtained was used to manufacture a collar-shaped molded body using an injection molding machine (SE180D). Using an injection molding machine, at a temperature setting of 138 to 145°C, with an injection time of 2 to 3 seconds and a cooling time of 8 to 15 seconds, it was poured into a mold in the shape of a collar with a length of 35 cm, a width of 1.0 cm, and a thickness of 0.3 cm and cooled to directly mold it into a collar.
[0050] [1] Bleeding test Each collar, which is a molded body, was hung in a constant temperature bath at 35°C. From day 0, every 10 days, the chemical liquid oozing out on the surface of the collar was wiped off with a paper wipe (Pro Wipe manufactured by Oji Paper Co., Ltd.) until the chemical liquid disappeared and the surface became dry. The paper wipe after wiping was immersed in a solvent (acetone), and ultrasonic extraction (3510J-DTH) was performed at room temperature for 30 minutes. The obtained solvent was analyzed by HPLC (equipment LC-2010AHT), and the amounts of etofenprox and pyriproxyfen, which are active ingredients, were analyzed.
[0051] The results are shown in Table 2 as the bleeding amount converted per day (μg / cm 2 / day).
[0052]
Table 2
[0053] As a result of the tests, in all of the molded articles obtained from the compositions of the examples, there was no stickiness on the surface, and good sustained release of the active ingredient was exhibited.
Claims
1. A pest control resin composition comprising etofenprox, an insect growth regulator, a plasticizer, and a fatty acid in a vinyl chloride resin, wherein the plasticizer is one or more selected from the group consisting of diisononyl adipate, diisodecyl adipate, di(2-ethylhexyl) azelate, sebacic acid, 2-ethylhexyl, and diethylene glycol monoethyl ether.
2. The pest control resin composition according to claim 1, wherein the fatty acid is isostearic acid.
3. The pest control resin composition according to claim 1, wherein the content of etofenprox is 10% by mass or more and 25% by mass or less in the total composition.
4. The pest control resin composition according to claim 1, wherein the content of the plasticizer is 5% by mass or more and 50% by mass or less in the total composition.
5. The pest control resin composition according to claim 1, wherein the content of the fatty acid is 0.01% by mass or more and 15% by mass or less in the total composition.
6. The pest control resin composition according to claim 1, wherein the insect growth regulator is pyriproxyfen and / or S-methoprene.
7. A sustained-release pest control resin molded article formed by molding the pest control resin composition according to any one of claims 1 to 6.
8. The sustained-release pest control resin molded article according to claim 8, wherein the sustained-release pest control resin molded article is a collar.
9. A method for stably sustainedly releasing etofenprox and an insect growth regulator by coexisting etofenprox, an insect growth regulator, a plasticizer, and a fatty acid in a vinyl chloride resin.
Citation Information
Patent Citations
Animal pest control composition
JP2020007238A