JP5508797B2 - 忌避剤 - Google Patents
忌避剤 Download PDFInfo
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- JP5508797B2 JP5508797B2 JP2009219300A JP2009219300A JP5508797B2 JP 5508797 B2 JP5508797 B2 JP 5508797B2 JP 2009219300 A JP2009219300 A JP 2009219300A JP 2009219300 A JP2009219300 A JP 2009219300A JP 5508797 B2 JP5508797 B2 JP 5508797B2
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- essential oil
- pinene
- impregnated
- copolymer
- lactide
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- 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.)
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- 239000005871 repellent Substances 0.000 title claims description 31
- 230000002940 repellent Effects 0.000 title claims description 31
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 122
- 239000000341 volatile oil Substances 0.000 claims description 70
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 62
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims description 61
- 229920001577 copolymer Polymers 0.000 claims description 32
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims description 25
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 24
- 239000004626 polylactic acid Substances 0.000 claims description 24
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 16
- VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 claims description 8
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LMTDPKYREUZYAO-UHFFFAOYSA-N 1,4-dioxepane Chemical compound C1COCCOC1 LMTDPKYREUZYAO-UHFFFAOYSA-N 0.000 claims 2
- 238000005470 impregnation Methods 0.000 description 39
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 35
- 229920001432 poly(L-lactide) Polymers 0.000 description 32
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 31
- 239000000463 material Substances 0.000 description 29
- 229920000642 polymer Polymers 0.000 description 25
- 239000007789 gas Substances 0.000 description 24
- 238000000354 decomposition reaction Methods 0.000 description 20
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- 238000013268 sustained release Methods 0.000 description 12
- 239000012730 sustained-release form Substances 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- 239000001569 carbon dioxide Substances 0.000 description 8
- -1 terpene hydrocarbon Chemical class 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- AOLNDUQWRUPYGE-UHFFFAOYSA-N 1,4-dioxepan-5-one Chemical compound O=C1CCOCCO1 AOLNDUQWRUPYGE-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 108010067770 Endopeptidase K Proteins 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000007515 enzymatic degradation Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920009537 polybutylene succinate adipate Polymers 0.000 description 5
- 235000007586 terpenes Nutrition 0.000 description 5
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229920001896 polybutyrate Polymers 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001923 cyclic compounds Chemical class 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000007997 Tricine buffer Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011978 dissolution method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229940094938 stannous 2-ethylhexanoate Drugs 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- XTRAXJOYTUDQJU-YFKPBYRVSA-N (7s)-7-methyl-1,4-dioxepan-5-one Chemical compound C[C@H]1CC(=O)OCCO1 XTRAXJOYTUDQJU-YFKPBYRVSA-N 0.000 description 1
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- VVCGOQDXURYHJV-UHFFFAOYSA-N 3,6-dimethylmorpholine-2,5-dione Chemical compound CC1NC(=O)C(C)OC1=O VVCGOQDXURYHJV-UHFFFAOYSA-N 0.000 description 1
- OVDQEUFSGODEBT-UHFFFAOYSA-N 4-methyl-1,3-dioxan-2-one Chemical compound CC1CCOC(=O)O1 OVDQEUFSGODEBT-UHFFFAOYSA-N 0.000 description 1
- JRFXQKZEGILCCO-UHFFFAOYSA-N 5,5-dimethyl-1,3-dioxan-2-one Chemical compound CC1(C)COC(=O)OC1 JRFXQKZEGILCCO-UHFFFAOYSA-N 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- 241000218691 Cupressaceae Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000000877 Sex Attractant Substances 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229920006125 amorphous polymer Polymers 0.000 description 1
- FPXMWTIQAUOFBN-UHFFFAOYSA-N benzyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)C1(C)COC(=O)OC1 FPXMWTIQAUOFBN-UHFFFAOYSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 229920006167 biodegradable resin Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000001999 effect on insects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- MMHWNKSVQDCUDE-UHFFFAOYSA-N hexanedioic acid;terephthalic acid Chemical compound OC(=O)CCCCC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 MMHWNKSVQDCUDE-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- JMRZMIFDYMSZCB-UHFFFAOYSA-N morpholine-2,5-dione Chemical compound O=C1COC(=O)CN1 JMRZMIFDYMSZCB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004631 polybutylene succinate Substances 0.000 description 1
- 229920002961 polybutylene succinate Polymers 0.000 description 1
- 239000004630 polybutylene succinate adipate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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Description
1.α−ピネンの含浸実験 (表1、2)
2.α−ピネン濃度に対する含浸率の測定 (表3)
3.放出ガス量の測定 (図1)
4.酵素分解試験 (図2)
5.まとめ
ポリ乳酸共重合体からなる基材として、L−ラクチド(以下、LLAと略す。)とε−カプロラクトン(以下、CLと略す。)との共重合体(以下、PLLArCLと略す。)、LLAとδ−バレロラクトン(以下、VLと略す。)との共重合体(以下、PLLArVLと略す。)、LLAとテトラメチレンカーボネート(以下、TEMCと略す。)との共重合体(以下、PLLArTEMCと略す。)、及びLLAと1,5−ジオキセパン−2−オン(以下、DXOと略す。)との共重合体(以下、PLLArDXOと略す。)を用意した。
含浸率に関する因子としてα−ピネン濃度について検討した。なお、ここでは、基材にPLLA(H440)、PLLArCL(91/9)、PLLArVL(85/15)、PLLArTEMC(89/11)、PLLArDXO(90/10)を用いて含浸を行った。
(実施例13)実際に放出されるガス状態の精油量を評価するために、ポリマーの分解過程において、発生したガス量をGC(ガスクロマトグラフ:GC-14B、(株)島津製作所社製)により測定した。ポリマーの分解は、1L容のテトラバックにリン酸緩衝溶液(pH7)50mlと精油を含浸させたポリマーとしてPLLArVL(組成比85/15)(精油含量10.4%)280mgを入れ、37℃で加水分解を行った。所定の日数ごとにバック内のガスを採取し、GCで測定することにより精油の放出ガス量(ppm)を求め、徐放性について評価した。
α−ピネンが含浸された忌避剤とd−リモネンが含浸された忌避剤との分解性及び徐放性の違いを明らかにするために、忌避成分が内部まで含浸しにくいPLLAを基材に用い、PLLAに対して高い分解活性を示す酵素の一つであるプロティナーゼK(PTK)による酵素分解試験を行った。
これらの結果をまとめると、α−ピネンはd−リモネンと同じテルペン系忌避化合物であるが、他の実験条件を全て同じとして実験を行った場合、d−リモネンよりも含浸量を約2倍増加させることができることが分かった。さらに、放出性はd−リモネンを含浸させたものよりもα−ピネンを含浸させた方が安定していた。よって、ポリ乳酸共重合体にα−ピネンを含浸させた忌避剤は、d−リモネンよりも高濃度で忌避成分であるα−ピネンを放出することができ、かつ、長期間の使用に耐えうる優れた徐放性を有する。
Claims (3)
- L−ラクチドとε−カプロラクトンとの共重合体、L−ラクチドとδ−バレロラクトンとの共重合体、L−ラクチドとテトラメチレンカーボネートとの共重合体、及びL−ラクチドと1,5−ジオキセパン−2−オンとの共重合体から選択される少なくとも1種から構成されるポリ乳酸共重合体に、α-ピネンを主成分とする樹木精油を含浸させてなる忌避剤。
- 上記ポリ乳酸共重合体は、L−ラクチドが80〜91モル%の割合で重合されてなる請求項1記載の忌避剤。
- L−ラクチドとε−カプロラクトンとの共重合体、L−ラクチドとδ−バレロラクトンとの共重合体、L−ラクチドとテトラメチレンカーボネートとの共重合体、及びL−ラクチドと1,5−ジオキセパン−2−オンとの共重合体から選択される少なくとも1種から構成されるポリ乳酸共重合体に、α-ピネンを主成分とする樹木精油を含浸させる忌避剤の製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009219300A JP5508797B2 (ja) | 2009-09-24 | 2009-09-24 | 忌避剤 |
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JP2009219300A JP5508797B2 (ja) | 2009-09-24 | 2009-09-24 | 忌避剤 |
Publications (2)
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JP2011068577A JP2011068577A (ja) | 2011-04-07 |
JP5508797B2 true JP5508797B2 (ja) | 2014-06-04 |
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JP2009219300A Expired - Fee Related JP5508797B2 (ja) | 2009-09-24 | 2009-09-24 | 忌避剤 |
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Families Citing this family (1)
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GB201811764D0 (en) * | 2018-07-18 | 2018-08-29 | Flaherty Michael John | Polymer composition |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH08133907A (ja) * | 1994-11-10 | 1996-05-28 | Mikado Kako Kk | 持続性害虫忌避性成形体及びその製造方法 |
JP2001294505A (ja) * | 2000-04-14 | 2001-10-23 | Jukankyo Kojo Jumoku Seibun Riyo Gijutsu Kenkyu Kumiai | 有害生物駆除及び忌避剤並びに徐放材 |
EP2533046A1 (en) * | 2003-04-24 | 2012-12-12 | Tyratech, Inc. | Screening method for compositions for controlling insects |
JP5458261B2 (ja) * | 2006-07-12 | 2014-04-02 | 独立行政法人国立高等専門学校機構 | 徐放剤 |
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