JP4195536B2 - Surface treatment method for civil engineering base materials - Google Patents
Surface treatment method for civil engineering base materials Download PDFInfo
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- JP4195536B2 JP4195536B2 JP24227399A JP24227399A JP4195536B2 JP 4195536 B2 JP4195536 B2 JP 4195536B2 JP 24227399 A JP24227399 A JP 24227399A JP 24227399 A JP24227399 A JP 24227399A JP 4195536 B2 JP4195536 B2 JP 4195536B2
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- Prior art keywords
- civil engineering
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- base material
- meth
- Prior art date
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Description
【０００１】
【発明の属する技術分野】
本発明は、木材、金属、セラミック、コンクリート、モルタル、アスファルト等の土木建築用基材の表面を保護するために施される表面処理方法に関するものである。
【０００２】
【従来の技術】
床、屋上、壁面、歩道等の基材となるコンクリート、モルタル、アスファルト等は、防水、防蝕、防塵、美観その他の目的で各種液状樹脂を塗布施工し、施工後に硬化させることによりこれら基材の表面を被覆する処理を施すことが多い。例えば、末端にイソシアネート基を有するウレタンプレポリマーは、シーリング材、あるいは、塗料、防水材、床材、舗装材等の土木建築用基材の被覆材として広く利用されている。ウレタンプレポリマー自体は粘度が高く、通常は、塗布作業性の点から、キシレン等の有機溶剤をウレタンプレポリマーに混合して粘度を下げて用いることが多い。ウレタンプレポリマーは、分子の末端にイソシアネート基を有しており、これが、空気中の水分、さらには基材に吸着する水分と反応して高分子量化するものであり、この反応は室温下でも充分に進む。しかしながら、実際には、低粘度化のために混合する有機溶剤が大気に揮散しなければ、硬化は不十分であり、表面にべたつきが残る。よって、ウレタンプレポリマーの硬化速度は、この有機溶剤の揮散速度に依存しており、特に、冬場では、硬化が遅いとの問題があった。
【０００３】
一方、速い硬化速度を有する液状樹脂として、ウレタン（メタ）アクリレートが知られている。これは、ウレタンプレポリマーとヒドロキシ基を有する（メタ）アクリル酸エステルを反応させたものであり、分子末端にラジカル重合性基を有し、ラジカル重合開始剤を添加することにより硬化する。ラジカル重合開始剤を選択することにより、例えば、０℃の雰囲気温度でも硬化することができるが、被覆材として用いた場合、基材との密着性はウレタンプレポリマーより劣る。
【０００４】
【発明が解決しようとする課題】
本発明は、低粘度で硬化が速く、基材との密着性に優れた樹脂組成物を用いて土木建築用基材を被覆する方法を提供することを課題とするものである。
【０００５】
【課題を解決するための手段】
上記課題を解決するため、本発明では、土木建築用基材の表面に、（ａ）ラジカル重合性不飽和基含有化合物、（ｂ）湿気硬化性ウレタンプレポリマー、および、（ｃ）ラジカル重合開始剤を、（ａ）成分１００重量部に対して、（ｂ）成分８０〜２５０重量部、（ｃ）成分０．５〜５．０重量部の割合で含有する樹脂組成物を硬化してなる被覆層を形成し、その後、前記被覆層の上にさらに樹脂層を設ける、土木建築用基材の表面処理方法を提供する。
【０００６】
【発明の実施の形態】
本発明で用いる樹脂組成物について説明する。
（ａ）成分のラジカル重合性不飽和基含有化合物としては、ラジカル種により連鎖重合する化合物であれば特に限定なく使用できる。ただし、（ａ）成分として水酸基を有する化合物を用いた場合、（ｂ）成分の湿気硬化性ウレタンプレポリマーと混合することによって、（ｂ）成分が有するイソシアネート基と反応して樹脂組成物の粘度が上がる場合がある。また、密着性に有用なイソシアネート基の濃度が下がり、基材との密着性が悪くなる場合がある。従って、本発明では、水酸基を有しない（ａ）成分を用いることが好ましいが、本発明の効果である低粘度、速硬化、密着性を損なわない限り、水酸基を有する（ａ）成分を用いてもよく、その量は（ｂ）成分のイソシアネート基１当量に対し、（ａ）成分が有する水酸基が０．５当量以下、さらには０．２当量以下であることが好ましい。
【０００７】
（ａ）成分の具体的な例としては、（メタ）アクリル酸メチル、（メタ）アクリル酸ブチル、（メタ）アクリル酸２−エチルヘキシル、( メタ) アクリル酸シクロヘキシル等の( メタ) アクリル酸アルキル；( メタ) アクリル酸ベンジル、( メタ) アクリル酸フェニル等の芳香族環を有する( メタ) アクリル酸エステル；( メタ) アクリル酸メトキシエトキシエチル、( メタ) アクリル酸エトキシエトキシエチル、ジシクロペンテニルオキシエチル（メタ）アクリレート等のモノアルコールのアルキレンオキシド付加体と( メタ) アクリル酸のエステル化物；( メタ) アクリル酸ヒドロキシエチル、( メタ) アクリル酸ヒドロキシプロピル等の水酸基を有する化合物；スチレン、ビニルトルエン、ジビニルベンゼン等の芳香族ビニル化合物類；ブチルビニルエーテル、トリエチレングリコールジビニルエーテル等のビニルエーテル類等が挙げられる。また、ラジカル重合性不飽和基を一分子中に２個以上有する化合物も使用でき、例えば、エチレングリコールジ（メタ）アクリレート、１．４−ブチレングリコールジ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート等の多価アルキルアルコールと（メタ）アクリル酸のエステル化物；ジエチレングリコールジ（メタ）アクリレート、テトラエチレングリコールジ（メタ）アクリレート等の多価アルキルアルコールのアルキレンオキシド付加体と（メタ）アクリル酸のエステル化物；エポキシ化合物と（メタ）アクリル酸の反応体であるエポキシ（メタ）アクリレート類；多塩基酸と多価アルコールの縮合物である水酸基末端のポリエステルポリオールと（メタ）アクリル酸の反応体であるポリエステルポリ（メタ）アクリレート等が挙げられる。（ａ）成分としては、これらの１種、あるいは２種以上を用いることができる。特に、硬化速度を速くするためには、ラジカル重合性不飽和基を１分子中に２個以上有する化合物を含むことが好ましい。
【０００８】
（ｂ）成分の湿気硬化型ウレタンプレポリマーは、イソシアネート化合物と多価アルコールの反応により得られる。
イソシアネート化合物としては、通常のポリウレタン樹脂の製造に用いられるものを用いることができ、例えば、２，４−トルエンジイソシアネート、２，６−トルエンジイソシアネート、フェニレンジイソシアネート、キシレンジイソシアネート、ジフェニルメタンジイソシアネート、ポリフェニルメタンポリイソシアネート、テトラメチレンジイソシアネート、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート等が挙げられ、これらの１種、あるいは２種以上を用いることができる。
【０００９】
多価アルコールとしては、通常のポリウレタン樹脂の製造に用いるものが挙げられ、例えば、エチレングリコール、プロピレングリコール、１，６−ヘキサンジオール、トリメチロールプロパン、グリセリン等のアルキレンポリオール；ポリエチレングリコール、ポリプロピレングリコール等のポリエーテルポリオール；水酸基を有するポリブタジエン、水酸基を有するポリ（メタ）アクリレート等の水酸基含有の重合体；多塩基酸と多価アルコールとの縮合により得られるエステルポリオール等が挙げられる。また、エステルポリオールを構成する多塩基酸としては、後述の不飽和基を有する多塩基酸の他、例えば、コハク酸、アジピン酸、フタル酸、トリメリット酸、ピロメリット酸等の多塩基酸、及びこれらの無水物が挙げられる。エステルポリオールを構成する多価アルコールとしては、例えば、前述の多価アルコールが挙げられ、エチレンオキシド、プロピレンオキシド等のアルキレンオキシドも用いることができる。
【００１０】
特に、硬化速度を上げるためには、（ｂ）成分の湿気硬化型ウレタンプレポリマーが不飽和結合を有することが好ましく、具体的には多価アルコールとして不飽和結合を有する多価アルコールを使用することが好ましい。不飽和結合を有する多価アルコールとしては、(1) アリルエーテル基を有する多価アルコール、(2) 動植物油あるいは動植物油から誘導される多価アルコール、(3) 不飽和基を有する多塩基酸と多価アルコールとの縮合により得られるエステルポリオール、から選ばれる少なくとも１種の多価アルコールを用いることが好ましい。
【００１１】
アリルエーテル基を有する多価アルコールとしては、例えば、トリメチロールプロパンモノアリルエーテル、ペンタエリスリトールジアリルエーテル、アリルグリシジルエーテルの開環付加重合体等が挙げられる。
動植物油あるいは動植物油から誘導される多価アルコールとしては、ひまし油、動植物油と多価アルコールのエステル交換生成物が挙げられる。
【００１２】
不飽和基を有する多塩基酸と多価アルコールとの縮合により得られるエステルポリオールを構成する多塩基酸としては、脂肪族の炭素二重結合を有する多塩基酸であり、例えば、マレイン酸、フマル酸、イタコン酸、テトラヒドロフタル酸、エンドメチレンテトラヒドロフタル酸、メチルテトラヒドロフタル酸、ダイマー酸、及びこれらの無水物等が挙げられ、多価アルコールとしては前述の多価アルコール等やアルキレンオキシド化合物が挙げられる。
【００１３】
イソシアネート化合物と多価アルコールとの反応は、通常の湿気硬化型ウレタンプレポリマーと同様の反応方法を用いることができ、イソシアネート基と水酸基のモル比がＮＣＯ／ＯＨ＝１．２〜３．０の範囲で仕込み、４０〜１００℃で加熱混合することが好ましく、反応の終点は粘度の増加がほぼ見られない点で決めることもできるが、所定の反応時間が経過した時点を終点とすることができる。なお、イソシアネート化合物と多価アルコールとの反応において、周知のウレタン化触媒を用いることができ、例えば、ジブチル錫ジラウレート、ジブチル錫ジクロライド、ジブチル錫オキサイド等の錫化合物；トリエチルアミン、１，４−ジアザビシクロ［２，２，２］オクタン等のアミン化合物が挙げられる。
【００１４】
また、溶剤の存在下で反応させることもでき、イソシアネートと水酸基に対して不活性な溶剤が用いられ、例えば、トルエン、キシレン、酢酸ブチル等がある。さらに、本発明の（ａ）成分を溶剤として用いることもできる。
（ｃ）成分のラジカル重合開始剤としては、不飽和ポリエステル樹脂、エポキシアクリレート等のラジカル重合性樹脂の硬化に使用する重合開始剤が用いられ、例えば、ベンゾイルパーオキシド、メチルエチルケトンパーオキシド、クメンハイドロパーオキシド、ｔ−ブチルパーベンゾエート、アゾビスイソブチロニトリル等が挙げられ、さらに紫外線等の光照射で硬化させる場合は、ベンゾフェノン、ベンゾインイソブチルエーテル、ベンゾインイソプロピルエーテル、ベンジルジメチルケタール、２，２−ジエトキシアセトフェノン、１−ヒドロキシシクロヘキシルフェニルケトン、エチルフェニルグリオキシレート、２−クロロチオキサントン、２，４−ジイソプロピルチオキサン、２，４，６−トリメチルベンゾイルジフェノイルホスフィンオキシド等が挙げられ、これらの１種、あるいは、２種以上を用いることができる。
【００１５】
前記樹脂組成物における、（ａ），（ｂ），（ｃ）の各成分の混合量比は、得られる樹脂組成物の粘度、ゲル化までの可使時間の設定によって適宜選ぶことができるが、（ａ）成分１００重量部に対し、（ｂ）成分が５０〜４００重量部、（ｃ）成分が０．１〜１０重量部の範囲で混合することが好ましく、（ａ）成分１００重量部に対し、（ｂ）成分が８０〜２５０重量部、（ｃ）成分が０．５〜５．０重量部の範囲で混合することがより好ましい。（ａ）成分が不足すると、硬化が遅くなり、また粘度が高くなる。（ｂ）成分が不足すると、基材との密着性が劣る。（ｃ）成分が不足すると、硬化が遅く、作業性に劣るものとなる。
【００１６】
前記樹脂組成物中で、上記（ａ）、（ｂ）、（ｃ）成分の合計が占める割合は１０〜１００重量％が好ましく、より好ましくは２０〜１００重量％であり、さらに好ましくは３０〜１００重量％である。
前記樹脂組成物は、さらに、硬化促進剤、充填剤、揺変性付与剤、乾燥性向上剤、着色剤等を含むことができる。
【００１７】
硬化速度を速くするためには、（ｄ）成分として、有機カルボン酸の金属塩類からなる硬化促進剤を用いることが好ましい。有機カルボン酸の金属塩類としては、例えば、コバルト、マンガン、鉛、ニッケル、マグネシウム、亜鉛、錫、銅、鉄、ジルコニウム等の金属とオクチル酸、ナフテン酸、酢酸等の有機カルボン酸との金属塩が挙げられる。
【００１８】
さらに（ｄ）成分の有機カルボン酸の金属塩類以外の硬化促進剤として、３級アミン類を用いることができ、例えば、ジメチルアニリン、ジメチルトルイジン、Ｎ，Ｎ−ジヒドロキシエチルトルイジン等の芳香族３級アミン類；トリエチルアミン、Ｎ−メチルモルホリン、トリエチレンジアミン、ジメチルエタノールアミン、メチルジエタノールアミン、トリエタノールアミン等の脂肪族３級アミン類が挙げられる。さらには、硬化促進剤として前記のウレタン化触媒を用いることができる。
【００１９】
（ｄ）成分の有機カルボン酸の金属塩類は、（ａ）成分１００重量部に対し、金属分の重量で、０．００１重量部〜１．０重量部の範囲で混合することが好ましい。３級アミン類あるいは、ウレタン化触媒を混合する場合では、（ａ）成分１００重量部に対し、０．０５重量部〜１０重量部の範囲で混合することが好ましい。
【００２０】
充填剤としては、水酸化アルミ、タルク、珪砂、砕石、炭酸カルシウム、酸化アンチモン、ガラスフレーク等が挙げられる。
揺変性付与剤としては、無水微粉末シリカ、アスベスト、クレー、脂肪酸アミド化合物等が挙げられる。
乾燥性向上剤としては、パラフィン、ワックス、乾性油等が挙げられる。
【００２１】
着色剤としては、有機顔料、無機顔料、染料等が挙げられる。
土木建築用基材の表面に前記樹脂組成物を硬化してなる被覆層を形成するには、炭素繊維、ガラス繊維、ポリアミド繊維等の補強材に前記樹脂組成物を含浸させて被覆材として、基材に密着させて硬化してもよいし、あるいは前記樹脂組成物を基材に塗布した後硬化せしめてもよい。本発明の処理方法において、被覆層を形成させる好ましい形態は、上述のように、前記樹脂組成物を含浸や塗布、被覆させた後、硬化させ、被覆層を形成させることである。このように処理することで基材と被覆層との密着性が良好になる。
【００２２】
土木建築用基材としては特に限定されるものではなく、床、屋上、壁面、歩道等の基材が挙げられる。その材質も特に限定されず、木材、金属、セラミック、コンクリート、モルタル、アスファルト等が挙げられるが、本発明において用いる樹脂組成物は低粘度であることから、基材へ含浸しやすく、基材との密着性を高めるので、特にコンクリート、モルタル、アスファルト等の多孔質表面を有する土木建築用基材の表面を処理する場合に有効である。
【００２３】
本発明では、これらの土木建築用基材を直接被覆してもよいし、これらの土木建築用基材がすでに樹脂等で被覆された状態でも、その上に重ねて被覆してもよい。また、前記樹脂組成物で被覆した後、不飽和ポリエステル樹脂、エポキシ樹脂、エポキシアクリレート、ウレタンアクリレート、アクリルシロップ等の熱硬化性樹脂や溶剤型樹脂塗料、エマルション樹脂塗料等の樹脂をその上に重ねて塗布することにより、多層構造からなる強靭な被覆層を形成することができる。
【００２４】
もちろん、上述の被覆層の形態としては、土木建築用基材の表面に形成される層であれば、特にその形態は限定されない。例えばプライマー層や中間層やトップコート層等である。
前記樹脂組成物の硬化は外気温度雰囲気下で行っても良いし、あるいは加熱下、さらには紫外線等の光照射で硬化してもよい。
【００２５】
本発明の表面処理方法は、土木建築用基材の防水、防蝕、防塵、美観その他の目的に有効であるが、特に防水の目的に有効である。
また、前記樹脂組成物は土木建築用基材の被覆だけではなく、他の基材の被覆にも用いることができる。
【００２６】
【実施例】
（製造例１）
冷却管、攪拌機、温度計、ガス導入管、滴下ロートを備えたフラスコに、トルエンジイソシアネート２６４ｇ、ジエチレエングリコールジメタクリレート５４６ｇ、ベンゾキノン０．１２ｇを仕込み、窒素ガスを吹き込みながら加熱し、６０℃で水酸基当量３４７のひまし油５５５ｇを２時間かけて滴下した。滴下終了後、ジブチル錫ジラウレート０．２４ｇを添加し、さらに６０℃で４時間加熱し、２５℃での粘度が５ストークスの樹脂（１）を得た。
（製造例２）
冷却管、攪拌機、温度計、ガス導入管、滴下ロートを備えたフラスコに、トルエンジイソシアネート５５６ｇ、キシレン２０７ｇを仕込み、窒素ガスを吹き込みながら加熱し、６０℃でトリメチロールプロパン５４ｇ、ポリプロピレングリコール（分子量４００）４８０ｇの混合物を２時間かけて滴下した。滴下終了後、ジブチル錫ジラウレート０．３３ｇを添加し、さらに６０℃で４時間加熱し、冷却後、ジエチレングリコールジメタクリレート５２０ｇ、ベンゾキノン０．１２ｇを添加して、２５℃での粘度が７ストークスの樹脂（２）を得た。
（製造例３）
冷却管、攪拌機、温度計、ガス導入管、滴下ロートを備えたフラスコに、トルエンジイソシアネート３４０ｇ、ジエチレングリコールジメタクリレート６００ｇ、ベンゾキノン０．１５ｇを仕込み、窒素ガスを吹き込みながら加熱し、６０℃で水酸基当量３３３のダイマー酸エチレンオキサイド付加物６６０ｇを２時間かけて滴下した。滴下終了後、ジブチル錫ジラウレート０．３０ｇを添加し、さらに６０℃で４時間加熱し、冷却後、トリメチロールプロパントリメタクリレート７０ｇを添加して、２５℃での粘度が８ストークスの樹脂（３）を得た。
（製造例４）
冷却管、攪拌機、温度計、ガス導入管、滴下ロートを備えたフラスコに、トルエンジイソシアネート３４８ｇ、ジエチレングリコールジメタクリレート４００ｇ、メチルメタクリレート２１３ｇ、ベンゾキノン０．１５ｇを仕込み、窒素ガスを吹き込みながら加熱し、６０℃でトリメチロールプロパンモノアリルエーテル１７２ｇ、ポリプロピレングリコール（分子量４００）４００ｇの混合物を２時間かけて滴下した。滴下終了後、ジブチル錫ジラウレート０．２８ｇを添加し、さらに６０℃で４時間加熱し、２５℃での粘度が６ストークスの樹脂（４）を得た。
（製造例５）
冷却管、攪拌機、温度計、ガス導入管、滴下ロートを備えたフラスコに、トルエンジイソシアネート５５６ｇ、キシレン５００ｇを仕込み、窒素ガスを吹き込みながら加熱し、６０℃でトリメチロールプロパン５４ｇ、ポリプロピレングリコール（分子量４００）４８０ｇの混合物を２時間かけて滴下した。滴下終了後、ジブチル錫ジラウレート０．３３ｇを添加し、さらに６０℃で４時間加熱し、２５℃での粘度が７ストークスのウレタンプレポリマー（５）を得た。
（製造例６）
冷却管、攪拌機、温度計、ガス導入管、滴下ロートを備えたフラスコに、トルエンジイソシアネート４８７ｇ、スチレン６２６ｇ、ベンゾキノン０．１４ｇを仕込み、窒素ガスを吹き込みながら加熱し、６０℃でジエチレングリコール８７ｇを３０分間で滴下した。滴下終了後、さらに１時間加熱し、その後、ヒドロキシエチルメタクリレート３６４ｇを１時間で滴下した。滴下終了後、ジブチル錫ジラウレート０．２８ｇを添加し、さらに２時間加熱して、２５℃での粘度が５ストークスのウレタンメタクリレート（６）を得た。
（実施例１〜４、比較例１、２）
製造例１〜６で得られた各樹脂に、表１に示すラジカル重合開始剤、硬化促進剤を混合し、樹脂組成物を得た。
【００２７】
混合後、直ちに、この樹脂組成物６．４ｇを５ｃｍ角の４５０番ガラス繊維マット１枚に含浸し、コンクリート板上に密着させてコンクリートを被覆した。２５℃雰囲気下に放置し、密着後から、表面が硬化して指触によるべたつきがなくなるまでの時間を表面硬化時間とし、表面硬化性を評価した。
さらにこの試験体を１日放置した後、硬化表面に４ｃｍ角の鉄製ジグをエポキシ系接着剤で接着し、建研式接着力試験器で被覆層とコンクリート層間の接着力を測定した。
【００２８】
表１に結果を示す。
（実施例５、６、比較例３）
製造例１、４、５で得られた各樹脂に表２に示すラジカル重合開始剤、硬化促進剤を混合し、樹脂組成物を得た。
混合後、直ちに、コンクリート板に３００ｇ／ｍ2 の量を塗布した。３０℃雰囲気下で１日放置した後、その表面に、１００重量部のエポラックＮ−４２３ＰＷ（( 株) 日本触媒製）、１重量部の５５％メチルエチルケトンパーオキシドを混合した不飽和ポリエステル樹脂６．４ｇを３８０番ガラス繊維マットの５ｃｍ×５ｃｍに含浸させて、ライニングした。さらに３０℃で１日放置した後、ライニング表面に４ｃｍ角の鉄製ジグをエポキシ系接着剤で接着し、建研式接着力試験器で被覆層とコンクリート層間の接着力を測定した。
【００２９】
表２に結果を示す。
（実施例７）
水系エポキシプライマーであるＪＣプライマー（（株）日本触媒製）をコンクリート板に２００ｇ／ｍ2 の量を塗布した。２５℃で１日放置後、製造例４で得られた樹脂１００重量部、酸化チタン５重量部、８％金属分オクチル酸コバルト１．０重量部、硬化剤３２８Ｅ（化薬アクゾ( 株) 製）１．０重量部を混合した樹脂組成物をプライマー処理した表面に３００ｇ／ｍ2 の量を塗布した。２時間後、塗布面は乾燥、硬化しており、均一で光沢のある外観を有していた。
【００３０】
【表１】
【表２】
【発明の効果】
本発明によると、低粘度で硬化が速く、基材との密着性に優れた樹脂組成物を用いて土木建築用基材を被覆することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a surface treatment method applied to protect the surface of a civil engineering and building base material such as wood, metal, ceramic, concrete, mortar, and asphalt.
[0002]
[Prior art]
Concrete, mortar, asphalt, etc., which are base materials for floors, rooftops, wall surfaces, sidewalks, etc., are coated with various liquid resins for waterproofing, corrosion resistance, dustproofing, aesthetics and other purposes, and cured after construction by applying these liquid resins. In many cases, the surface is coated. For example, a urethane prepolymer having an isocyanate group at a terminal is widely used as a sealing material or a covering material for a base material for civil engineering and construction such as a paint, a waterproofing material, a flooring material, and a paving material. Urethane prepolymer itself has a high viscosity. Usually, from the viewpoint of coating workability, an organic solvent such as xylene is often mixed with the urethane prepolymer to lower the viscosity. Urethane prepolymers have an isocyanate group at the end of the molecule, which reacts with moisture in the air and further with moisture adsorbed on the base material, resulting in a high molecular weight. Proceed well. However, in practice, if the organic solvent to be mixed for lowering the viscosity does not evaporate into the atmosphere, the curing is insufficient and the surface remains sticky. Therefore, the curing rate of the urethane prepolymer depends on the volatilization rate of the organic solvent, and there is a problem that the curing is slow particularly in winter.
[0003]
On the other hand, urethane (meth) acrylate is known as a liquid resin having a high curing rate. This is a product obtained by reacting a urethane prepolymer and a (meth) acrylic acid ester having a hydroxy group, has a radical polymerizable group at the molecular end, and is cured by adding a radical polymerization initiator. By selecting a radical polymerization initiator, for example, it can be cured even at an atmospheric temperature of 0 ° C., but when used as a coating material, the adhesion to the substrate is inferior to that of a urethane prepolymer.
[0004]
[Problems to be solved by the invention]
This invention makes it a subject to provide the method of coat | covering the base material for civil engineering and architecture using the resin composition excellent in adhesiveness with a base material with low viscosity and quick hardening.
[0005]
[Means for Solving the Problems]
To solve the above problems, the present invention, the surface of the civil engineering and construction for the base material, (a) a radical polymerizable unsaturated group-containing compound, (b) moisture-curable urethane prepolymer, and, (c) radical polymerization initiator (B) component 80 to 250 parts by weight, and (c) component 0.5 to 5.0 parts by weight of a resin composition cured with 100 parts by weight of component (a) Provided is a surface treatment method for a civil engineering and building base material, in which a coating layer is formed and then a resin layer is further provided on the coating layer .
[0006]
DETAILED DESCRIPTION OF THE INVENTION
The resin composition used in the present invention will be described.
The radically polymerizable unsaturated group-containing compound of component (a) can be used without particular limitation as long as it is a compound that undergoes chain polymerization with radical species. However, when a compound having a hydroxyl group is used as the component (a), the viscosity of the resin composition reacts with the isocyanate group of the component (b) by mixing with the moisture-curable urethane prepolymer of the component (b). May go up. Moreover, the density | concentration of the isocyanate group useful for adhesiveness falls, and adhesiveness with a base material may worsen. Therefore, in the present invention, it is preferable to use the component (a) having no hydroxyl group, but the component (a) having a hydroxyl group is used as long as the effects of the present invention, such as low viscosity, rapid curing, and adhesion, are not impaired. The amount of the hydroxyl group of the component (a) is preferably 0.5 equivalents or less, more preferably 0.2 equivalents or less with respect to 1 equivalent of the isocyanate group of the component (b).
[0007]
Specific examples of the component (a) include (meth) alkyl acrylates such as methyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate; (Meth) acrylic acid ester having an aromatic ring such as (meth) benzyl acrylate, (meth) phenyl acrylate; (meth) methoxyethoxyethyl acrylate, (meth) ethoxyethoxyethyl acrylate, dicyclopentenyloxyethyl (Meth) acrylate and other monoalcohol alkylene oxide adducts and (meth) acrylic acid esterified compounds; (meth) hydroxyethyl acrylate, (meth) hydroxypropyl acrylate and other hydroxyl group compounds; styrene, vinyltoluene, Aromatic vinyl compounds such as divinylbenzene; butyl vinyl Examples thereof include vinyl ethers such as ether and triethylene glycol divinyl ether. A compound having two or more radically polymerizable unsaturated groups in one molecule can also be used. For example, ethylene glycol di (meth) acrylate, 1.4-butylene glycol di (meth) acrylate, trimethylolpropane tri (meta) ) Esterified products of polyhydric alkyl alcohols such as acrylate and (meth) acrylic acid; alkylene oxide adducts of polyhydric alkyl alcohols such as diethylene glycol di (meth) acrylate and tetraethylene glycol di (meth) acrylate and (meth) acrylic acid An esterified product of: an epoxy (meth) acrylate that is a reaction product of an epoxy compound and (meth) acrylic acid; a hydroxyl-terminated polyester polyol that is a condensate of a polybasic acid and a polyhydric alcohol and a reaction product of (meth) acrylic acid Polyester poly (meta Acrylate, and the like. As the component (a), one or more of these can be used. In particular, in order to increase the curing rate, it is preferable to include a compound having two or more radically polymerizable unsaturated groups in one molecule.
[0008]
The moisture curable urethane prepolymer (b) is obtained by the reaction of an isocyanate compound and a polyhydric alcohol.
As an isocyanate compound, what is used for manufacture of a normal polyurethane resin can be used, for example, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, phenylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, polyphenylmethane polyisocyanate. Isocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate and the like can be mentioned, and one or more of these can be used.
[0009]
Examples of the polyhydric alcohol include those used for the production of ordinary polyurethane resins, such as alkylene polyols such as ethylene glycol, propylene glycol, 1,6-hexanediol, trimethylolpropane, glycerin; polyethylene glycol, polypropylene glycol, etc. Polyether polyols; hydroxyl group-containing polybutadienes, hydroxyl group-containing polymers such as poly (meth) acrylates; ester polyols obtained by condensation of polybasic acids and polyhydric alcohols, and the like. Further, as the polybasic acid constituting the ester polyol, in addition to the polybasic acid having an unsaturated group described later, for example, polybasic acids such as succinic acid, adipic acid, phthalic acid, trimellitic acid, pyromellitic acid, And anhydrides thereof. Examples of the polyhydric alcohol constituting the ester polyol include the aforementioned polyhydric alcohols, and alkylene oxides such as ethylene oxide and propylene oxide can also be used.
[0010]
In particular, in order to increase the curing rate, the moisture curable urethane prepolymer of component (b) preferably has an unsaturated bond, and specifically, a polyhydric alcohol having an unsaturated bond is used as the polyhydric alcohol. It is preferable. The polyhydric alcohol having an unsaturated bond includes (1) a polyhydric alcohol having an allyl ether group, (2) a polyhydric alcohol derived from animal or vegetable oil or animal or vegetable oil, and (3) a polybasic acid having an unsaturated group. It is preferable to use at least one polyhydric alcohol selected from ester polyols obtained by condensation of polyhydric alcohol with polyhydric alcohol.
[0011]
Examples of the polyhydric alcohol having an allyl ether group include trimethylolpropane monoallyl ether, pentaerythritol diallyl ether, allyl glycidyl ether ring-opening addition polymer, and the like.
Animal and vegetable oils or polyhydric alcohols derived from animal and vegetable oils include castor oil and transesterification products of animal and vegetable oils and polyhydric alcohols.
[0012]
The polybasic acid constituting the ester polyol obtained by the condensation of a polybasic acid having an unsaturated group and a polyhydric alcohol is a polybasic acid having an aliphatic carbon double bond, such as maleic acid, fumaric acid. Examples include acids, itaconic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid, methyltetrahydrophthalic acid, dimer acid, and anhydrides thereof. Examples of the polyhydric alcohol include the above-described polyhydric alcohols and alkylene oxide compounds. It is done.
[0013]
For the reaction between the isocyanate compound and the polyhydric alcohol, the same reaction method as that for a normal moisture-curable urethane prepolymer can be used, and the molar ratio of isocyanate group to hydroxyl group is NCO / OH = 1.2 to 3.0. It is preferable to mix in a range and heat at 40 to 100 ° C. The end point of the reaction can be determined by the point that almost no increase in viscosity is seen, but the end point of the predetermined reaction time may be the end point. it can. In the reaction of an isocyanate compound with a polyhydric alcohol, a well-known urethanization catalyst can be used. For example, tin compounds such as dibutyltin dilaurate, dibutyltin dichloride, and dibutyltin oxide; triethylamine, 1,4-diazabicyclo [ And amine compounds such as 2,2,2] octane.
[0014]
The reaction can also be carried out in the presence of a solvent, and a solvent inert to isocyanate and hydroxyl group is used, and examples thereof include toluene, xylene, butyl acetate and the like. Furthermore, the component (a) of the present invention can also be used as a solvent.
As the radical polymerization initiator of component (c), polymerization initiators used for curing radical polymerizable resins such as unsaturated polyester resins and epoxy acrylates are used. For example, benzoyl peroxide, methyl ethyl ketone peroxide, cumene hydroper Oxide, t-butyl perbenzoate, azobisisobutyronitrile, and the like, and when cured by irradiation with light such as ultraviolet rays, benzophenone, benzoin isobutyl ether, benzoin isopropyl ether, benzyl dimethyl ketal, 2,2-di- Ethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, ethyl phenylglyoxylate, 2-chlorothioxanthone, 2,4-diisopropylthioxan, 2,4,6-trimethylbenzoyldiphenoylphenol Fin oxide and the like, these one or may be used two or more kinds.
[0015]
The mixing ratio of the components (a), (b), and (c) in the resin composition can be appropriately selected depending on the viscosity of the resin composition to be obtained and the setting of the pot life until gelation. The component (b) is preferably mixed in an amount of 50 to 400 parts by weight and the component (c) in an amount of 0.1 to 10 parts by weight, and the component (a) is 100 parts by weight. On the other hand, it is more preferable to mix the component (b) in the range of 80 to 250 parts by weight and the component (c) in the range of 0.5 to 5.0 parts by weight. When the component (a) is insufficient, curing is delayed and the viscosity is increased. When the component (b) is insufficient, the adhesion with the substrate is inferior. When the component (c) is insufficient, curing is slow and workability is poor.
[0016]
In the resin composition, the ratio of the total of the components (a), (b), and (c) is preferably 10 to 100% by weight, more preferably 20 to 100% by weight, and still more preferably 30 to 30%. 100% by weight.
The resin composition may further contain a curing accelerator, a filler, a thixotropic agent, a drying improver, a colorant, and the like.
[0017]
In order to increase the curing rate, it is preferable to use a curing accelerator made of a metal salt of an organic carboxylic acid as the component (d). Examples of metal salts of organic carboxylic acids include metal salts of metals such as cobalt, manganese, lead, nickel, magnesium, zinc, tin, copper, iron and zirconium with organic carboxylic acids such as octylic acid, naphthenic acid and acetic acid. Is mentioned.
[0018]
Furthermore, tertiary amines can be used as curing accelerators other than the metal salt of the organic carboxylic acid of component (d), for example, aromatic tertiary such as dimethylaniline, dimethyltoluidine, N, N-dihydroxyethyltoluidine and the like. Amines: Aliphatic tertiary amines such as triethylamine, N-methylmorpholine, triethylenediamine, dimethylethanolamine, methyldiethanolamine, triethanolamine and the like. Furthermore, the above urethanization catalyst can be used as a curing accelerator.
[0019]
The metal salt of the organic carboxylic acid of component (d) is preferably mixed in the range of 0.001 to 1.0 part by weight with respect to 100 parts by weight of component (a) in terms of the weight of metal. When mixing tertiary amines or a urethanization catalyst, it is preferable to mix in the range of 0.05 weight part-10 weight part with respect to 100 weight part of (a) component.
[0020]
Examples of the filler include aluminum hydroxide, talc, silica sand, crushed stone, calcium carbonate, antimony oxide, and glass flakes.
Examples of the thixotropic agent include anhydrous fine powder silica, asbestos, clay, and fatty acid amide compounds.
Examples of the drying improver include paraffin, wax, and drying oil.
[0021]
Examples of the colorant include organic pigments, inorganic pigments, dyes, and the like.
In order to form a coating layer formed by curing the resin composition on the surface of the civil engineering and construction substrate, the resin composition is impregnated into a reinforcing material such as carbon fiber, glass fiber, and polyamide fiber as a coating material. The resin composition may be cured by being in close contact with the substrate, or may be cured after the resin composition is applied to the substrate. In the treatment method of the present invention, a preferred form for forming the coating layer is to form the coating layer by impregnating, coating, and coating the resin composition as described above, and then curing the resin composition. By treating in this way, the adhesion between the substrate and the coating layer is improved.
[0022]
It does not specifically limit as a base material for civil engineering construction, Base materials, such as a floor, a rooftop, a wall surface, a sidewalk, are mentioned. The material is not particularly limited, and examples thereof include wood, metal, ceramic, concrete, mortar, and asphalt. However, since the resin composition used in the present invention has a low viscosity, it is easily impregnated into the substrate, Therefore, it is particularly effective when treating the surface of a civil engineering / building base material having a porous surface such as concrete, mortar, and asphalt.
[0023]
In the present invention, these civil engineering and construction base materials may be directly coated, or even in a state where these civil engineering and construction base materials are already coated with a resin or the like, they may be overlaid thereon. In addition, after coating with the resin composition, a thermosetting resin such as unsaturated polyester resin, epoxy resin, epoxy acrylate, urethane acrylate, acrylic syrup, or resin such as solvent-type resin paint or emulsion resin paint is laminated thereon. By applying these, a tough coating layer having a multilayer structure can be formed.
[0024]
Of course, as a form of the above-mentioned covering layer, the form is not particularly limited as long as it is a layer formed on the surface of the civil engineering base material. For example, a primer layer, an intermediate layer, a top coat layer, and the like.
The resin composition may be cured in an ambient temperature atmosphere, or may be cured by heating and further irradiation with light such as ultraviolet rays.
[0025]
The surface treatment method of the present invention is effective for waterproofing, corrosion prevention, dustproofing, aesthetics and other purposes of civil engineering and construction substrates, but is particularly effective for waterproofing purposes.
Moreover, the said resin composition can be used not only for the coating | covering of the base material for civil engineering construction, but for the coating | covering of another base material.
[0026]
【Example】
(Production Example 1)
A flask equipped with a condenser, stirrer, thermometer, gas inlet tube, and dropping funnel was charged with 264 g of toluene diisocyanate, 546 g of diethylene glycol dimethacrylate, and 0.12 g of benzoquinone, and heated while blowing nitrogen gas at 60 ° C. 555 g of castor oil having a hydroxyl group equivalent of 347 was added dropwise over 2 hours. After completion of the dropwise addition, 0.24 g of dibutyltin dilaurate was added and further heated at 60 ° C. for 4 hours to obtain a resin (1) having a viscosity of 5 Stokes at 25 ° C.
(Production Example 2)
A flask equipped with a condenser, stirrer, thermometer, gas inlet tube, and dropping funnel was charged with 556 g of toluene diisocyanate and 207 g of xylene, heated while blowing nitrogen gas, and 54 g of trimethylolpropane and polypropylene glycol (molecular weight 400) at 60 ° C. ) 480 g of the mixture was added dropwise over 2 hours. After completion of dropping, 0.33 g of dibutyltin dilaurate is added, and further heated at 60 ° C. for 4 hours. After cooling, 520 g of diethylene glycol dimethacrylate and 0.12 g of benzoquinone are added, and the viscosity at 25 ° C. is 7 Stokes resin. (2) was obtained.
(Production Example 3)
A flask equipped with a condenser, stirrer, thermometer, gas inlet tube, and dropping funnel was charged with 340 g of toluene diisocyanate, 600 g of diethylene glycol dimethacrylate, and 0.15 g of benzoquinone, heated while blowing nitrogen gas, and hydroxyl equivalent 333 at 60 ° C. Of dimer acid ethylene oxide adduct was added dropwise over 2 hours. After completion of the addition, 0.30 g of dibutyltin dilaurate was added, and further heated at 60 ° C. for 4 hours. After cooling, 70 g of trimethylolpropane trimethacrylate was added, and the viscosity at 25 ° C. was 8 Stokes resin (3) Got.
(Production Example 4)
A flask equipped with a cooling tube, a stirrer, a thermometer, a gas introduction tube, and a dropping funnel was charged with 348 g of toluene diisocyanate, 400 g of diethylene glycol dimethacrylate, 213 g of methyl methacrylate, and 0.15 g of benzoquinone, and heated while blowing nitrogen gas at 60 ° C. Then, a mixture of 172 g of trimethylolpropane monoallyl ether and 400 g of polypropylene glycol (molecular weight 400) was added dropwise over 2 hours. After completion of the dropwise addition, 0.28 g of dibutyltin dilaurate was added and further heated at 60 ° C. for 4 hours to obtain a resin (4) having a viscosity at 25 ° C. of 6 Stokes.
(Production Example 5)
A flask equipped with a condenser, stirrer, thermometer, gas inlet tube, and dropping funnel was charged with 556 g of toluene diisocyanate and 500 g of xylene, heated while blowing nitrogen gas, and 54 g of trimethylolpropane and polypropylene glycol (molecular weight 400) at 60 ° C. ) 480 g of the mixture was added dropwise over 2 hours. After completion of the dropwise addition, 0.33 g of dibutyltin dilaurate was added and further heated at 60 ° C. for 4 hours to obtain a urethane prepolymer (5) having a viscosity at 25 ° C. of 7 Stokes.
(Production Example 6)
A flask equipped with a condenser, stirrer, thermometer, gas inlet tube, and dropping funnel was charged with 487 g of toluene diisocyanate, 626 g of styrene and 0.14 g of benzoquinone, heated while blowing nitrogen gas, and 87 g of diethylene glycol at 60 ° C. for 30 minutes. It was dripped at. After completion of dropping, the mixture was further heated for 1 hour, and then 364 g of hydroxyethyl methacrylate was added dropwise over 1 hour. After completion of the dropwise addition, 0.28 g of dibutyltin dilaurate was added and further heated for 2 hours to obtain urethane methacrylate (6) having a viscosity at 25 ° C. of 5 Stokes.
(Examples 1-4, Comparative Examples 1 and 2)
The resins obtained in Production Examples 1 to 6 were mixed with the radical polymerization initiator and curing accelerator shown in Table 1 to obtain resin compositions.
[0027]
Immediately after mixing, 6.4 g of this resin composition was impregnated into one 450 cm glass fiber mat of 5 cm square, and was adhered to a concrete plate to cover the concrete. It was allowed to stand in an atmosphere of 25 ° C., and the time until the surface was cured and no stickiness due to finger touches was determined after the adhesion, and the surface curability was evaluated.
Furthermore, after leaving this test body for one day, a 4 cm square iron jig was adhered to the cured surface with an epoxy adhesive, and the adhesion between the coating layer and the concrete layer was measured with a Kenken-type adhesion tester.
[0028]
Table 1 shows the results.
(Examples 5 and 6, Comparative Example 3)
The resins obtained in Production Examples 1, 4, and 5 were mixed with the radical polymerization initiator and curing accelerator shown in Table 2 to obtain a resin composition.
Immediately after mixing, an amount of 300 g / m 2 was applied to the concrete plate. 5. Unsaturated polyester resin in which 100 parts by weight of Epolac N-423PW (manufactured by Nippon Shokubai Co., Ltd.) and 1 part by weight of 55% methyl ethyl ketone peroxide are mixed on the surface after being left for 1 day in an atmosphere of 30 ° C. 4 g was impregnated into 5 cm × 5 cm of No. 380 glass fiber mat and lined. Further, after being left at 30 ° C. for 1 day, a 4 cm square iron jig was adhered to the lining surface with an epoxy adhesive, and the adhesion between the coating layer and the concrete layer was measured with a Kenken-type adhesion tester.
[0029]
Table 2 shows the results.
(Example 7)
JC primer is an aqueous epoxy primer (KK Nippon Shokubai) was coated with an amount of 200 g / m 2 concrete plate. After standing at 25 ° C. for 1 day, 100 parts by weight of the resin obtained in Production Example 4, 5 parts by weight of titanium oxide, 1.0 part by weight of 8% metal cobalt octylate, curing agent 328E (manufactured by Kayaku Akzo Co., Ltd.) ) An amount of 300 g / m 2 was applied to the surface of the primer-treated resin composition mixed with 1.0 part by weight. After 2 hours, the coated surface was dried and cured, and had a uniform and glossy appearance.
[0030]
[Table 1]
[Table 2]
【The invention's effect】
ADVANTAGE OF THE INVENTION According to this invention, the base material for civil engineering and construction can be coat | covered using the resin composition which is low-viscosity, quick hardening, and was excellent in adhesiveness with a base material.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24227399A JP4195536B2 (en) | 1999-08-27 | 1999-08-27 | Surface treatment method for civil engineering base materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24227399A JP4195536B2 (en) | 1999-08-27 | 1999-08-27 | Surface treatment method for civil engineering base materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001062389A JP2001062389A (en) | 2001-03-13 |
| JP4195536B2 true JP4195536B2 (en) | 2008-12-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24227399A Expired - Fee Related JP4195536B2 (en) | 1999-08-27 | 1999-08-27 | Surface treatment method for civil engineering base materials |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5245352B2 (en) * | 2007-10-24 | 2013-07-24 | Ｄｉｃ株式会社 | Primer composition, civil engineering structure and construction method of civil engineering structure |
| KR102271405B1 (en) * | 2014-03-26 | 2021-06-30 | 세키스이가가쿠 고교가부시키가이샤 | Light-/moisture-curable resin composition, electronic component adhesive, and display element adhesive |
| KR102553303B1 (en) * | 2020-07-08 | 2023-07-07 | 주식회사 아이센스 | Functionalized thermoplastic polyurethane, method for preparing the same, method for preparing high performance composite in medical application and medical device comprising the same |
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| JP2001062389A (en) | 2001-03-13 |
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