JP2021059663A - 汚損生物付着抑制剤、汚損生物付着抑制用組成物、防汚塗膜及び防汚塗膜付き基材 - Google Patents
汚損生物付着抑制剤、汚損生物付着抑制用組成物、防汚塗膜及び防汚塗膜付き基材 Download PDFInfo
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Abstract
Description
本実施形態に係る汚損生物付着抑制剤は、2以上の水酸基を有する重合性二重結合含有単量体(以下、「単量体A」ともいう)由来の構造単位Aを有する重合体を含む。重合体における構造単位Aの含有量は、10質量%以上である。
本実施形態に係る汚損生物付着抑制剤は、架橋剤と組み合わせて汚損生物付着抑制用組成物として用いてもよい。すなわち、本実施形態に係る汚損生物付着抑制用組成物は、上述した汚損生物付着抑制剤と、架橋剤と、を含有する。
本実施形態に係る防汚塗膜は、上述した汚損生物付着抑制剤又は汚損生物付着抑制用組成物を含んでなる。本実施形態に係る防汚塗膜を基材上に形成して、基材と、該基材上に設けられた防汚塗膜と、を備える防汚塗膜付き基材とすることにより、基材の防汚性を向上させることができる。
[GLMA(グリセロールモノアクリレート)]
撹拌子を入れた反応容器にガス導入管、温度計、冷却管、及び、留出液受器に繋げたトの字管を付し、アクリル酸メチル230g、2,2−ジメチル−1,3−ジオキソラン−4−メタノール(DOM)70gを仕込み、ガス導入管を通して酸素/窒素混合ガス(酸素濃度7vol%)を吹き込みながら反応溶液を攪拌し、オイルバス(バス温110℃)で加熱を開始した。留出液に水が出てこなくなってから、チタンテトライソプロポキシド4.5gを反応容器に添加し、エステル交換反応を開始させた。生成してくるメタノールをアクリル酸メチルで共沸留去しながら、ガスクロマトグラフィ(GC)分析によりiPGLMA(イソプロピリデングリセリルアクリレート)/DOMの面積比を追跡した。反応開始から7時間後のGC分析で、iPGLMA/DOMの面積比が9/1を超えたのを確認し、反応を終了し、室温まで冷却した。このようにして、GLMA合成の中間体として、1,3―ジオキソラン構造を有する単量体である、iPGLMAを得た。反応液に精製水150gと抽出溶媒として酢酸エチル300gを加え10分撹拌した。チタンテトライソプロポキシドの加水分解により生じた酸化チタンの沈殿を、吸引濾過で除いた濾液を分液漏斗に移し、有機層と水層を分離した。有機層を精製水で2回洗浄したのち、ロータリーエバポレーターに移し、残存アクリル酸メチル及び軽沸成分を留去し、iPGLMA96gを得た。
撹拌子を入れた反応容器にガス導入菅、温度計、冷却管を付し、単量体としてGLMA13.3g、アクリル酸(AA)0.7g、溶媒としてイオン交換水125.0gを仕込み、窒素ガスを流しながら98℃まで昇温した。アゾ系ラジカル重合開始剤0.007g(和光純薬株式会社製、商品名:VA086)をイオン交換水1.0gに溶解した溶液を投入し、重合反応を開始した。温度を99℃以上に保ちながら、反応を7時間継続し、その間、反応開始から1時間後、3時間後、5時間後にそれぞれ、0.0035gのVA086をイオン交換水0.5gに溶解した溶液を投入した。
撹拌子を入れた反応容器にガス導入菅、温度計、冷却管を付し、単量体としてGLMA45.0g、ブチルアクリレート(BA)45.0g、溶媒としてエタノール45g、イオン交換水15gを仕込み、窒素ガスを流しながら80℃まで昇温した。アゾ系ラジカル重合開始剤0.009g(和光純薬株式会社製、商品名:V−601)をエタノール0.5gに溶解した溶液を投入し、重合反応を開始した。温度を80℃以上に保ちながら、反応を10時間継続し、その間、反応開始から1時間後、2時間後、4時間後、6時間後、8時間後にそれぞれ、0.009gのV−601をエタノール0.5gに溶解した溶液を投入した。
単量体としてGLMA3.5g、ヒドロキシエチルアクリレート(HEA)9.8g、AA0.7gを用いた以外は、重合体1と同様にして、重合体3を得た。
上記で得られた重合体1を固形分換算で100質量部、及び架橋剤としてのエポクロスWS−700(オキサゾリン系架橋剤:株式会社日本触媒製)を固形分換算で5質量部配合し、エタノールで希釈して濃度5%に調製した。得られた溶液を、基材としての3cm×3cmの硬質塩化ビニル樹脂板上に、バーコーターを用いて塗布し、室温で乾燥後、熱風乾燥機により120℃で30分間、熱処理し試料サンプルとした。
重合体及び架橋剤の種類及び配合比を下記表1に示すとおりに変更した以外は、実施例1と同様にして、試料サンプルを得た。表1中の商品名又は略語の詳細を以下に示す。
(架橋剤)
WS700:エポクロスWS−700(オキサゾリン基含有架橋剤:株式会社日本触媒製)
V−02:カルボジライト V−02(カルボジイミド基含有架橋剤:日清紡ケミカル株式会社製)
上記で得られた重合体1と、エポクロスWS−700(オキサゾリン系架橋剤;株式会社日本触媒製)を、それぞれエタノール/イオン交換水=75/25(wt/wt)の混合溶媒で希釈して濃度10%の溶液を調製した。まず、エポクロスWS−700の溶液を3cm×3cmの硬質塩化ビニル樹脂板上にバーコーターを用いて塗布し、室温で乾燥してアンダーコートを形成した後、その上から重合体1の溶液を、バーコーターを用いて塗布した。室温で乾燥した後、熱風乾燥機により、120℃で30分間、熱処理し試料サンプルとした。
何も塗装しない3cm×3cmの硬質塩化ビニル樹脂板を準備した。
実施例1〜6及び比較例1の試料サンプルに対し、以下の方法で汚損生物付着試験を実施した。
Claims (9)
- 2以上の水酸基を有する重合性二重結合含有単量体由来の構造単位Aを有する重合体を含み、
前記重合体における前記構造単位の含有量が、10質量%以上である、汚損生物付着抑制剤。 - 前記重合体が、1つの水酸基を有する重合性二重結合含有単量体由来の構造単位Bを更に有する、請求項1に記載の汚損生物付着抑制剤。
- 前記重合体が、アルキル基の炭素数が4〜12であるアルキル(メタ)アクリレート由来の構造単位Cを更に有する、請求項1又は2に記載の汚損生物付着抑制剤。
- 請求項1〜4のいずれか一項に記載の汚損生物付着抑制剤と、
オキサゾリン基を有する架橋剤、エポキシ基を有する架橋剤、カルボジイミド基を有する架橋剤及びメラミン樹脂系架橋剤からなる群より選ばれる少なくとも1種の架橋剤と、を含有する、汚損生物付着抑制用組成物。 - 前記架橋剤の含有量が、前記重合体100質量部に対して、0.5〜10質量部である、請求項5に記載の汚損生物付着抑制用組成物。
- 請求項1〜4のいずれか一項に記載の汚損生物付着抑制剤、若しくは請求項5又は6に記載の汚損生物付着抑制用組成物を含んでなる防汚塗膜。
- 基材と、該基材上に設けられた請求項7に記載の防汚塗膜と、を備える防汚塗膜付き基材。
- 前記基材が、船舶、水中構造物、漁網、漁具、配管、用水路又は取水施設である、請求項8に記載の防汚塗膜付き基材。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05171066A (ja) * | 1991-12-24 | 1993-07-09 | Mitsubishi Rayon Co Ltd | 防汚性塗料組成物 |
JP2002348778A (ja) * | 2001-05-31 | 2002-12-04 | Nof Corp | 繊維用処理剤、処理方法及び被処理繊維 |
JP2003055617A (ja) * | 2001-08-10 | 2003-02-26 | Asahi Glass Co Ltd | 低汚染化剤、該低汚染化剤を含む塗料用組成物および塗装物品 |
JP2017189762A (ja) * | 2016-04-11 | 2017-10-19 | 株式会社日本触媒 | 水処理用膜 |
JP2020502297A (ja) * | 2016-11-11 | 2020-01-23 | ヘンペル エイ/エス | 新規な炭素ベースの加水分解可能ポリマーを含む防汚塗料組成物 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05171066A (ja) * | 1991-12-24 | 1993-07-09 | Mitsubishi Rayon Co Ltd | 防汚性塗料組成物 |
JP2002348778A (ja) * | 2001-05-31 | 2002-12-04 | Nof Corp | 繊維用処理剤、処理方法及び被処理繊維 |
JP2003055617A (ja) * | 2001-08-10 | 2003-02-26 | Asahi Glass Co Ltd | 低汚染化剤、該低汚染化剤を含む塗料用組成物および塗装物品 |
JP2017189762A (ja) * | 2016-04-11 | 2017-10-19 | 株式会社日本触媒 | 水処理用膜 |
JP2020502297A (ja) * | 2016-11-11 | 2020-01-23 | ヘンペル エイ/エス | 新規な炭素ベースの加水分解可能ポリマーを含む防汚塗料組成物 |
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