JP2013159667A - 表面改質方法及び表面改質弾性体 - Google Patents
表面改質方法及び表面改質弾性体 Download PDFInfo
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- JP2013159667A JP2013159667A JP2012021228A JP2012021228A JP2013159667A JP 2013159667 A JP2013159667 A JP 2013159667A JP 2012021228 A JP2012021228 A JP 2012021228A JP 2012021228 A JP2012021228 A JP 2012021228A JP 2013159667 A JP2013159667 A JP 2013159667A
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- Prior art keywords
- modification method
- surface modification
- polymer chain
- modified
- group
- Prior art date
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- 239000000178 monomer Substances 0.000 claims abstract description 42
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 33
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- 230000000977 initiatory effect Effects 0.000 claims abstract description 7
- -1 benzophenone compound Chemical class 0.000 claims description 43
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- 238000012986 modification Methods 0.000 claims description 29
- 239000012965 benzophenone Substances 0.000 claims description 26
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- 239000003504 photosensitizing agent Substances 0.000 claims description 15
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- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 39
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Abstract
【解決手段】加硫ゴム又は熱可塑性エラストマーを改質対象物とする表面改質方法であって、前記改質対象物の表面に重合開始点を形成する工程1と、前記重合開始点を起点にして、モノマーをラジカル重合させ、前記改質対象物の表面にポリマー鎖を成長させる工程2と、前記ポリマー鎖を機能化処理する工程3とを含む表面改質方法に関する。
【選択図】なし
Description
前記還元剤又は抗酸化物質として、リボフラビン、アスコルビン酸、α−トコフェロール、β−カロテン及び尿酸からなる群より選択される少なくとも1種を使用することが好ましい。
例えば、前記ポリマー鎖の側鎖を、アルカリ金属塩又は抗菌性金属塩を用いて塩転換すること、前記ポリマー鎖の側鎖を、アンモニア水に接触させた後に塩転換すること、前記ポリマー鎖の側鎖を、アルカリ性塩を用いて塩転換すること、前記ポリマー鎖の側鎖を、硝酸塩、炭酸塩又はハロゲン化塩を用いて塩転換すること、前記ポリマー鎖の側鎖を、硝酸銀、炭酸銀又は塩化銀を用いて塩転換することで機能性基を導入することにより、前記工程3を実施できる。
また、前記アミン化合物として、下記式で示される化合物を使用することが好ましい。
CF3(CF2)n−(CX2)p−NH2−m((CF2)nCF3)m
(式中、Xは水素又はフッ素を表す。nは同一又は異なって1〜10の整数を表す。mは0〜2の整数を表す。pは0〜4の整数を表す。)
前記ポリマー鎖の長さは、10〜50000nmであることが好ましい。
本発明は、前記記載の表面改質方法により得られる水存在下又は乾燥状態での摺動性、低摩擦又は水の低抵抗が要求される表面改質弾性体に関する。
本発明は、前記記載の表面改質方法により得られる抗菌性が要求される表面改質弾性体に関する。
ここで、前記表面改質弾性体は、ポリマーブラシであることが好ましい。
本発明は、前記記載の表面改質方法により改質された表面を少なくとも一部に有するカテーテルに関する。
本発明はまた、前記記載の表面改質方法により改質されたタイヤの溝表面を少なくとも一部に有するタイヤに関する。
上記加硫ゴム、上記熱可塑性エラストマーとしては、二重結合に隣接する炭素原子(アリル位の炭素原子)を有するものが好適に使用される。
モノマーは、工程2〜3で作製するポリマー鎖に付与する性能や機能に応じて、適宜選択すればよく、例えば、置換基や側鎖などにイオン性基を有するイオン性モノマーが挙げられる。この場合、工程2でイオン性モノマーに起因する摺動性などの機能を発揮するポリマー鎖が作製されるとともに、更に工程3で抗菌性、疎水性などの機能も容易に追加できる。
エルゴカルシフェロール、コレカルシフェロール、1,2,5−ジヒドロキシ−コレカルシフェロールなどのビタミンD類、それらの誘導体及びそれらの塩;α−トコフェロール、β−トコフェロール、γ−トコフェロール、δ−トコフェロール、α−トコトリエノール、β−トコトリエノール、γ−トコトリエノール、δ−トコトリエノール、酢酸トコフェロール、ニコチン酸トコフェロールなどのビタミンE類、それらの誘導体及びそれらの塩;トロロックス、その誘導体及びそれらの塩;ジヒドロキシトルエン、ブチルヒドロキシトルエン、ブチルヒドロキシアニソール、ジブチルヒドロキシトルエン、α−リポ酸、デヒドロリポ酸、グルタチオン、その誘導体及びそれらの塩;尿酸、エリソルビン酸、エリソルビン酸ナトリウムなどのエリソルビン酸、その誘導体及びそれらの塩;没食子酸、没食子酸プロピルなどの没食子酸、その誘導体及びそれらの塩;ルチン、α−グリコシル−ルチンなどのルチン、その誘導体及びそれらの塩;トリプトファン、その誘導体及びそれらの塩;ヒスチジン、その誘導体及びそれらの塩;N−アセチルシステイン、N−アセチルホモシステイン、N−オクタノイルシステイン、N−アセチルシステインメチルエステルなどのシステイン誘導体及びそれらの塩;N,N’−ジアセチルシスチンジメチルエステル、N,N’−ジオクタノイルシスチンジメチルエステル、N,N’−ジオクタノイルホモシスチンジメチルエステルなどのシスチン誘導体及びそれらの塩;カルノシン、その誘導体及びそれらの塩;ホモカルノシン、その誘導体及びそれらの塩;アンセリン、その誘導体及びそれらの塩;カルシニン、その誘導体及びそれらの塩;ヒスチジン及び/又はトリプトファン及び/又はヒスタミンを含むジペプチド又はトリペプチド誘導体及びそれらの塩;フラバノン、フラボン、アントシアニン、アントシアニジン、フラボノール、クエルセチン、ケルシトリン、ミリセチン、フィセチン、ハマメリタンニン、カテキン、エピカテキン、ガロカテキン、エピガロカテキン、エピカテキンガレート、エピガロカテキンガレートなどのフラボノイド類;タンニン酸、コーヒー酸、フェルラ酸、プロトカテク酸、カルコン、オリザノール、カルノソール、セサモール、セサミン、セサモリン、ジンゲロン、クルクミン、テトラヒドロクルクミン、クロバミド、デオキシクロバミド、ショウガオール、カプサイシン、バニリルアミド、エラグ酸、ブロムフェノール、フラボグラシン、メラノイジン、リボフラビン、リボフラビン酪酸エステル、フラビンモノヌクレオチド、フラビンアデニンヌクレオチド、ユビキノン、ユビキノール、マンニトール、ビリルビン、コレステロール、エブセレン、セレノメチオニン、セルロプラスミン、トランスフェリン、ラクトフェリン、アルブミン、スーパーオキシドジスムターゼ、カタラーゼ、グルタチオンペルオキシダーゼ、メタロチオネイン、O−ホスホノ−ピリドキシリデンローダミンなどが挙げられる。これらは単独又は2種以上を併用して用いてもよい。
また、ラジカル重合性モノマーの使用量は、形成するポリマー鎖の長さ、その鎖により発揮される性能などにより、適宜設定すればよい。更に、還元剤、抗酸化物質の使用量も系内の酸素の補足などの点から、適宜設定すればよい。
CF3(CF2)n−(CX2)p−NH2−m((CF2)nCF3)m
(式中、Xは水素又はフッ素を表す。nは同一又は異なって1〜10の整数を表す。mは0〜2の整数を表す。pは0〜4の整数を表す。)
図2〜3において、中央縦溝3a(溝深さD1)、ショルダー縦溝3b(溝深さD2)は、タイヤ周方向に直線状にのびるストレート溝で構成される。このようなストレート溝は、排水抵抗を小さくし、直進走行時に高い排水性能を発揮しうる。
イソプレンユニットを含むクロロブチルゴム(不飽和度:1〜2%)をトリアジンで架橋した加硫ゴム(180℃で10分加硫)をベンゾフェノンの1wt%アセトン溶液に浸漬して、加硫ゴム表面にベンゾフェノンを吸着させた。その後、加硫ゴムを取り出し乾燥した。次いで、加硫ゴム表面に365nmの波長を持つLEDライトを10分照射し、ベンゾフェノンを化学結合させた後、未反応のベンゾフェノンを除くために表面をアセトンで洗浄した。
乾燥した加硫ゴムをアクリル酸水溶液(2.5M:18gのアクリル酸を100mLの水に溶解)の入ったガラス反応容器に浸漬し、その上にリボフラビン水溶液(濃度0.0093mmol/L)を入れた。水溶液はモノマー液と混ざらず、かつ水溶液はモノマー液のより比重が軽いことから上層に分離した状態になった。そして365nmの波長を持つLEDライトで、紫外線を1時間照射してラジカル重合を行ってゴム表面にポリマー鎖を成長させた。
得られたポリマー鎖が表面に形成された加硫ゴムを、硝酸銀水溶液(0.01M)に5時間浸漬した後、水で洗浄して、乾燥させ、表面改質弾性体(ポリマーブラシ)を作製した。
得られたポリマー鎖が表面に形成された加硫ゴムを、アンモニア水に2時間浸漬して、水洗したのち、硝酸銀水溶液に浸漬した以外は実施例1と同様にして表面改質弾性体(ポリマーブラシ)を作製した。
硝酸銀水溶液を、炭酸銀のアンモニア・希硝酸水溶液に変更した以外は実施例1と同様にして表面改質弾性体(ポリマーブラシ)を作製した。
硝酸銀水溶液を、塩化銀のアンモニア水溶液に変更した以外は実施例1と同様にして表面改質弾性体(ポリマーブラシ)を作製した。
イソプレンユニットを含むクロロブチルゴム(不飽和度:1〜2%)をトリアジンで架橋した加硫ゴム(180℃で10分加硫)をベンゾフェノンの1wt%アセトン溶液に浸漬して、加硫ゴム表面にベンゾフェノンを吸着させた。その後、加硫ゴムを取り出し乾燥した。次いで、加硫ゴム表面に365nmの波長を持つLEDライトを10分照射し、ベンゾフェノンを化学結合させた後、未反応のベンゾフェノンを除くために表面をアセトンで洗浄した。
乾燥した加硫ゴムをアクリル酸水溶液(2.5M:18gのアクリル酸を100mLの水に溶解)の入ったガラス反応容器に浸漬し、その上にリボフラビン水溶液(濃度0.0093mmol/L)を入れた。水溶液はモノマー液と混ざらず、かつ水溶液はモノマー液のより比重が軽いことから上層に分離した状態になった。そして365nmの波長を持つLEDライトで、紫外線を1時間照射してラジカル重合を行ってゴム表面にポリマー鎖を成長させた。
得られたポリマー鎖が表面に形成された加硫ゴムにおいて、重合表面のアクリル酸の側鎖のカルボキシル基(COOH基)に、1H,1H−パーフルオロヘプチルアミン(CF3(CF2)5CH2NH2)を、硫酸の存在下でアミド化反応させ(6時間)、その後、洗浄して、表面改質弾性体(ポリマーブラシ)を作製した。
クロロブチルゴムをトリアジンで架橋した加硫ゴム(180℃で10分加硫)を使用した。
(ポリマー鎖の長さ)
加硫ゴム表面に形成されたポリマー鎖の長さは、ポリマー鎖が形成された改質ゴム断面を、SEMを使用し、加速電圧15kV、1000倍で測定した。撮影されたポリマー層の厚みをポリマー鎖の長さとした。
表面改質弾性体の表面の静摩擦係数、動摩擦係数、及びそれぞれに水を200μL滴下したサンプル表面の静摩擦係数、動摩擦係数を、ASTM D1894に規定された方法に準拠して測定した。また、サンプルは、ホウケイ酸ガラスと接触させて、ホウケイ酸ガラスとの間の摩擦力を測定した。なお、摩擦係数の測定のための荷重は200g、引張速度は600mm/min、ロード距離は10cmの条件で測定した。装置は、ヘイドンtype14(新東科学(株)製)を使用した。
実施例で作製したポリマーブラシについて、銀が導入されていることをSEM−EDXによる元素分析で調べた。
11a、11b、11c 環状突起部
13 底面部の表面
2 トレッド部
3a 中央縦溝
3b ショルダー縦溝
5 細溝
6 中間傾斜溝
7 継ぎ溝
8、8a、8b ショルダー横溝
Claims (28)
- 加硫ゴム又は熱可塑性エラストマーを改質対象物とする表面改質方法であって、
前記改質対象物の表面に重合開始点を形成する工程1と、
前記重合開始点を起点にして、モノマーをラジカル重合させ、前記改質対象物の表面にポリマー鎖を成長させる工程2と、
前記ポリマー鎖を機能化処理する工程3とを含む表面改質方法。 - 前記工程1は、前記改質対象物の表面に300〜400nmのLED光を照射し、前記表面上の光増感剤から重合開始点を形成させるものであり、
前記工程2は、前記重合開始点を起点にして、モノマーを300〜400nmのLED光を照射してラジカル重合させてポリマー鎖を成長させるものである請求項1記載の表面改質方法。 - 前記加硫ゴム又は熱可塑性エラストマーが二重結合に隣接する炭素原子であるアリル位の炭素原子を有する請求項1又は2記載の表面改質方法。
- 前記工程2は、前記モノマーのラジカル重合時に、還元剤又は抗酸化物質が添加される請求項1〜4のいずれかに記載の表面改質方法。
- 前記還元剤又は抗酸化物質は、リボフラビン、アスコルビン酸、α−トコフェロール、β−カロテン及び尿酸からなる群より選択される少なくとも1種である請求項5記載の表面改質方法。
- 前記光照射時又は照射前に反応容器及び反応液に不活性ガスを導入し、不活性ガス雰囲気に置換して重合させる請求項1〜6のいずれかに記載の表面改質方法。
- 前記工程3は、前記ポリマー鎖の側鎖を塩転換する請求項1〜7のいずれかに記載の表面改質方法。
- 前記工程3は、前記ポリマー鎖の側鎖を、アルカリ金属塩又は抗菌性金属塩を用いて塩転換する請求項1〜7のいずれかに記載の表面改質方法。
- 前記工程3は、前記ポリマー鎖の側鎖を、アンモニア水に接触させた後に塩転換する請求項1〜7のいずれかに記載の表面改質方法。
- 前記工程3は、前記ポリマー鎖の側鎖を、アルカリ性塩を用いて塩転換する請求項1〜7のいずれかに記載の表面改質方法。
- 前記工程3は、前記ポリマー鎖の側鎖を、硝酸塩、炭酸塩又はハロゲン化塩を用いて塩転換する請求項1〜7のいずれかに記載の表面改質方法。
- 前記工程3は、前記ポリマー鎖の側鎖を、硝酸銀、炭酸銀又は塩化銀を用いて塩転換する請求項1〜7のいずれかに記載の表面改質方法。
- 前記工程3は、前記ポリマー鎖の側鎖におけるカルボン酸基とアミン化合物とを反応させてアミド結合を形成し、機能性基を導入する請求項1〜7のいずれかに記載の表面改質方法。
- 前記工程3は、前記ポリマー鎖の側鎖におけるカルボン酸基と水酸基含有化合物とを反応させてエステル結合を形成し、機能性基を導入する請求項1〜7のいずれかに記載の表面改質方法。
- 前記機能性基は、フルオロアルキル基である請求項14又は15記載の表面改質方法。
- 前記アミン化合物は、下記式で示される化合物である請求項14又は16記載の表面改質方法。
CF3(CF2)n−(CX2)p−NH2−m((CF2)nCF3)m
(式中、Xは水素又はフッ素を表す。nは同一又は異なって1〜10の整数を表す。mは0〜2の整数を表す。pは0〜4の整数を表す。)
改質方法。 - 前記ラジカル重合性モノマー(液体)又はその溶液が重合禁止剤を含むもので、該重合禁止剤の存在下で重合させる請求項1〜17のいずれかに記載の表面改質方法。
- 前記重合禁止剤が4−メチルフェノールである請求項18記載の表面改質方法。
- 前記ポリマー鎖の長さは、10〜50000nmである請求項1〜19のいずれかに記載の表面改質方法。
- 請求項1〜20のいずれかに記載の表面改質方法により得られる表面改質弾性体。
- 請求項1〜20のいずれかに記載の表面改質方法により得られる水存在下又は乾燥状態での摺動性、低摩擦又は水の低抵抗が要求される表面改質弾性体。
- 請求項1〜20のいずれかに記載の表面改質方法により得られる抗菌性が要求される表面改質弾性体。
- 請求項1〜20のいずれかに記載の表面改質方法により三次元形状の固体表面の少なくとも一部が改質された表面改質弾性体。
- ポリマーブラシである請求項21〜24のいずれかに記載の表面改質弾性体。
- 請求項1〜20のいずれかに記載の表面改質方法により改質された表面を少なくとも一部に有する注射器用ガスケット。
- 請求項1〜20のいずれかに記載の表面改質方法により改質された表面を少なくとも一部に有するカテーテル。
- 請求項1〜20のいずれかに記載の表面改質方法により改質されたタイヤの溝表面を少なくとも一部に有するタイヤ。
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EP2623335A2 (en) | 2013-08-07 |
US20130203883A1 (en) | 2013-08-08 |
CN103242487B (zh) | 2017-08-08 |
US9321872B2 (en) | 2016-04-26 |
EP2623335B1 (en) | 2018-03-14 |
EP2623335A3 (en) | 2014-01-22 |
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CN103242487A (zh) | 2013-08-14 |
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