JP2021116397A - 防藻性塗料 - Google Patents
防藻性塗料 Download PDFInfo
- Publication number
- JP2021116397A JP2021116397A JP2020012754A JP2020012754A JP2021116397A JP 2021116397 A JP2021116397 A JP 2021116397A JP 2020012754 A JP2020012754 A JP 2020012754A JP 2020012754 A JP2020012754 A JP 2020012754A JP 2021116397 A JP2021116397 A JP 2021116397A
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- JP
- Japan
- Prior art keywords
- algae
- hydroxybenzoate
- formula
- proof
- hexyl
- 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.)
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- 239000011248 coating agent Substances 0.000 title claims abstract description 42
- 238000000576 coating method Methods 0.000 title claims abstract description 42
- 230000002353 algacidal effect Effects 0.000 title abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 229910052783 alkali metal Chemical group 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 6
- 241000195493 Cryptophyta Species 0.000 claims description 57
- 239000003973 paint Substances 0.000 claims description 26
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 18
- -1 4-hydroxybenzoic acid ester Chemical class 0.000 claims description 17
- WEMCWZGCSRGJGW-UHFFFAOYSA-N [3-fluoro-5-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC(F)=CC(C(F)(F)F)=C1 WEMCWZGCSRGJGW-UHFFFAOYSA-N 0.000 claims description 17
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- SRINDXMUNIMKQR-UHFFFAOYSA-N octan-3-yl 4-hydroxybenzoate Chemical compound CCCCCC(CC)OC(=O)C1=CC=C(O)C=C1 SRINDXMUNIMKQR-UHFFFAOYSA-N 0.000 claims description 8
- SJNCMISSTSMUFF-UHFFFAOYSA-N hexadecyl 4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC=C(O)C=C1 SJNCMISSTSMUFF-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 abstract description 11
- 230000002401 inhibitory effect Effects 0.000 description 9
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 8
- 241000238586 Cirripedia Species 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
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- 241000588266 Kamptonema laetevirens Species 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 229940116318 copper carbonate Drugs 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
- BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical compound [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 2
- 229940112669 cuprous oxide Drugs 0.000 description 2
- GMMXJVUYXPXLPY-UHFFFAOYSA-N decyl 4-hydroxybenzoate Chemical compound CCCCCCCCCCOC(=O)C1=CC=C(O)C=C1 GMMXJVUYXPXLPY-UHFFFAOYSA-N 0.000 description 2
- BAYSQTBAJQRACX-UHFFFAOYSA-N dodecyl 4-hydroxybenzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=C(O)C=C1 BAYSQTBAJQRACX-UHFFFAOYSA-N 0.000 description 2
- 230000002063 effect on algae Effects 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- SNYRYVGRFMTVGK-UHFFFAOYSA-N heptadecyl 4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCOC(=O)C1=CC=C(O)C=C1 SNYRYVGRFMTVGK-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 2
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 2
- MBNSKHJDYXPONL-UHFFFAOYSA-N nonyl 4-hydroxybenzoate Chemical compound CCCCCCCCCOC(=O)C1=CC=C(O)C=C1 MBNSKHJDYXPONL-UHFFFAOYSA-N 0.000 description 2
- ITYCRFXTOMEQFF-UHFFFAOYSA-N octadecyl 4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=C(O)C=C1 ITYCRFXTOMEQFF-UHFFFAOYSA-N 0.000 description 2
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- 229960001763 zinc sulfate Drugs 0.000 description 2
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- 239000004408 titanium dioxide Substances 0.000 description 1
- AKVYEIVWNCVUPZ-UHFFFAOYSA-N tridecyl 4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=C(O)C=C1 AKVYEIVWNCVUPZ-UHFFFAOYSA-N 0.000 description 1
- VNHZHSYTJBADIV-UHFFFAOYSA-N undecyl 4-hydroxybenzoate Chemical compound CCCCCCCCCCCOC(=O)C1=CC=C(O)C=C1 VNHZHSYTJBADIV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
Abstract
Description
〔1〕式(1)
で表される4−ヒドロキシ安息香酸エステルを含む防藻性塗料。
〔2〕前記式(1)中、R1は水素原子を示す、〔1〕に記載の防藻性塗料。
〔3〕R2は炭素原子数5〜22のアルキル基またはアリール基である、〔1〕または〔2〕に記載の防藻性塗料。
〔4〕前記式(1)中、R2は炭素原子数6〜18のアルキル基またはアリール基を示す、〔1〕〜〔3〕のいずれかに記載の防藻性塗料。
〔5〕前記式(1)中、R2はアルキル基を示す、〔1〕〜〔4〕のいずれかに記載の防藻性塗料。
〔6〕式(1)で表される4−ヒドロキシ安息香酸エステルは、4−ヒドロキシ安息香酸ヘキシル、4−ヒドロキシ安息香酸エチルヘキシルおよび4−ヒドロキシ安息香酸ヘキサデシルからなる群から選択される1種以上である、〔1〕〜〔5〕のいずれかに記載の防藻性塗料。
〔7〕藻類が生育可能な被処理域または被処理体に、〔1〕〜〔6〕のいずれかに記載の防藻性塗料を適用し、藻類を防除または藻類の発生を予防する方法。
ユーグレナ・グラシリス(Euglena gracilis)などのユーグレナ(Euglena)属などを含むミドリムシ藻類。
実施例および比較例に用いた防藻成分A〜D、および試験対象藻類1〜5と使用培地を以下に示す。
防藻成分A:4−ヒドロキシ安息香酸ヘキシル(上野製薬株式会社製)
防藻成分B:4−ヒドロキシ安息香酸エチルヘキシル(上野製薬株式会社製)
防藻成分C:4−ヒドロキシ安息香酸ヘキサデシル(上野製薬株式会社製)
防藻成分D:4−ヒドロキシ安息香酸ブチル(上野製薬株式会社製)
防藻成分E:フェノキシエタノール(試薬:富士フイルム和光純薬株式会社製)
藻類1:クロレラ・ヴルガリス:Chlorella vulgaris NIES−2170(使用培地:C培地)
藻類2:ノストック・コミュン:Nostoc commune NIES−24(使用培地:MDM培地)
藻類3:オシラトリア・ラエテヴイレンス:Oscillatoria laetevirens NIES−31(使用培地:MDM培地)
藻類4:エオリムナ・ミニマ:Eolimna minima NIES−2720(使用培地:CSi培地)
藻類5:ゴンフォネマ・パルブルム:Gomphonema parvulum NIES−2723(使用培地:CSi培地)
最小発育阻止濃度は、日本化学療法学会標準法において、菌を藻に変更して測定した。
4−ヒドロキシ安息香酸ヘキシル0.04g、ジメチルスルホシキド(DMSO)500μL、培地9.46mLをサンプル管へ投入し、ボルテックスミキサーにて1分間撹拌し、前調製液(4−ヒドロキシ安息香酸ヘキシル濃度4000μg/mL)を作製した。各試験対象藻類に対し、試験管を12本準備し、左端の試験管へ前調製液を3mL、それ以外の試験管へは培地1.5mLを採取した。
4−ヒドロキシ安息香酸ヘキシルを4−ヒドロキシ安息香酸エチルヘキシルに変更した以外は実施例1と同様にして最小発育阻止濃度を算出した。結果を表1に示す。
4−ヒドロキシ安息香酸ヘキシルを4−ヒドロキシ安息香酸ヘキサデシルに変更した以外は実施例1と同様にして最小発育阻止濃度を算出した。結果を表1に示す。
4−ヒドロキシ安息香酸ヘキシルを4−ヒドロキシ安息香酸ブチルに変更した以外は実施例1と同様にして最小発育阻止濃度を算出した。結果を表1に示す。
4−ヒドロキシ安息香酸ヘキシルをフェノキシエタノールに変更した以外は実施例1と同様にして最小発育阻止濃度を算出した。結果を表1に示す。
4−ヒドロキシ安息香酸ヘキシル1.0gをウレタン塗料(和信ペイント株式会社製)9.0gに添加し、4−ヒドロキシ安息香酸ヘキシル10質量%の防藻性塗料を調製した。調製した塗料を、540×430×0.4(mm)のポリプロピレン製試験片の表面に刷毛で塗布し、乾燥後の塗膜状態を観察したが、4−ヒドロキシ安息香酸ヘキシルの粒子や分離層は確認されず、塗膜として問題ないものであった。このように、藻類を防除しまたは藻類の発生を予防することができる塗膜を得ることができた。
塗料中の4−ヒドロキシ安息香酸ヘキシル濃度を5質量%に変更した以外は実施例5と同様にして塗膜状態を観察したが、4−ヒドロキシ安息香酸ヘキシルの粒子や分離層は確認されず、塗膜として問題ないものであった。このように、藻類を防除しまたは藻類の発生を予防することができる塗膜を得ることができた。
塗料中の4−ヒドロキシ安息香酸ヘキシル濃度を2質量%に変更した以外は実施例5と同様にして塗膜状態を観察したが、4−ヒドロキシ安息香酸ヘキシルの粒子や分離層は確認されず、塗膜として問題ないものであった。このように、藻類を防除しまたは藻類の発生を予防することができる塗膜を得ることができた。
塗料中の4−ヒドロキシ安息香酸ヘキシル濃度を0.5質量%に変更した以外は実施例5と同様にして塗膜状態を観察したが、4−ヒドロキシ安息香酸ヘキシルの粒子や分離層は確認されず、塗膜として問題ないものであった。このように、藻類を防除しまたは藻類の発生を予防することができる塗膜を得ることができた。
塗料中の4−ヒドロキシ安息香酸ヘキシルを4−ヒドロキシ安息香酸エチルヘキシルに変更した以外は実施例5と同様にして塗膜状態を観察したが、分離層は確認されず、塗膜として問題ないものであった。このように、藻類を防除しまたは藻類の発生を予防することができる塗膜を得ることができた。
塗料中の4−ヒドロキシ安息香酸ヘキシルを4−ヒドロキシ安息香酸ヘキサデシルに変更した以外は実施例5と同様にして塗膜状態を観察したが、4−ヒドロキシ安息香酸ヘキサデシルの粒子や分離層は確認されず、塗膜として問題ないものであった。このように、藻類を防除しまたは藻類の発生を予防することができる塗膜を得ることができた。
塗料中の4−ヒドロキシ安息香酸ヘキシルを4−ヒドロキシ安息香酸ブチルに変更した以外は実施例5と同様にして塗膜状態を観察したが、4−ヒドロキシ安息香酸ブチルの粒子や分離層は確認されず、塗膜として問題ないものであった。このように、藻類を防除しまたは藻類の発生を予防することができる塗膜を得ることができた。
4−ヒドロキシ安息香酸ヘキシルをフェノキシエタノールに変更した以外は実施例5と同様にして塗膜状態を観察したところ、塗膜に分離層が確認された。このように、藻類を防除しまたは藻類の発生を予防することができる塗膜を得ることができなかった。
Claims (7)
- 前記式(1)中、R1は水素原子を示す、請求項1に記載の防藻性塗料。
- R2は炭素原子数5〜22のアルキル基またはアリール基である、請求項1または2に記載の防藻性塗料。
- 前記式(1)中、R2は炭素原子数6〜18のアルキル基またはアリール基を示す、請求項1〜3のいずれかに記載の防藻性塗料。
- 前記式(1)中、R2はアルキル基を示す、請求項1〜4のいずれかに記載の防藻性塗料。
- 式(1)で表される4−ヒドロキシ安息香酸エステルは、4−ヒドロキシ安息香酸ヘキシル、4−ヒドロキシ安息香酸エチルヘキシルおよび4−ヒドロキシ安息香酸ヘキサデシルからなる群から選択される1種以上である、請求項1〜5のいずれかに記載の防藻性塗料。
- 藻類が生育可能な被処理領域または被処理体に、請求項1〜6のいずれかに記載の防藻性塗料を適用し、藻類を防除または藻類の発生を予防する方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4992136A (ja) * | 1972-10-23 | 1974-09-03 | ||
JPS5169533A (ja) * | 1975-11-06 | 1976-06-16 | Toa Gosei Chem Ind | Bootoryososeibutsu |
JPH06340504A (ja) * | 1993-06-01 | 1994-12-13 | Yoshitomi Pharmaceut Ind Ltd | 水中防汚剤 |
JP2002053409A (ja) * | 2000-08-14 | 2002-02-19 | Daiichi Seimou Co Ltd | 殺藻殺菌剤 |
JP2018172347A (ja) * | 2017-03-31 | 2018-11-08 | 上野製薬株式会社 | ペレット |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4992136A (ja) * | 1972-10-23 | 1974-09-03 | ||
JPS5169533A (ja) * | 1975-11-06 | 1976-06-16 | Toa Gosei Chem Ind | Bootoryososeibutsu |
JPH06340504A (ja) * | 1993-06-01 | 1994-12-13 | Yoshitomi Pharmaceut Ind Ltd | 水中防汚剤 |
JP2002053409A (ja) * | 2000-08-14 | 2002-02-19 | Daiichi Seimou Co Ltd | 殺藻殺菌剤 |
JP2018172347A (ja) * | 2017-03-31 | 2018-11-08 | 上野製薬株式会社 | ペレット |
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