JP5446202B2 - フッ素樹脂粒子用分散剤、フッ素樹脂粒子分散液及びフッ素樹脂塗料 - Google Patents
フッ素樹脂粒子用分散剤、フッ素樹脂粒子分散液及びフッ素樹脂塗料 Download PDFInfo
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- JP5446202B2 JP5446202B2 JP2008264131A JP2008264131A JP5446202B2 JP 5446202 B2 JP5446202 B2 JP 5446202B2 JP 2008264131 A JP2008264131 A JP 2008264131A JP 2008264131 A JP2008264131 A JP 2008264131A JP 5446202 B2 JP5446202 B2 JP 5446202B2
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 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
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
〔式(1)−13で表されるフッ素化合物の合成〕
メチルイソブチルケトン(以下、「MIBK」という。)100gに、式(3)−8で表される化合物78.4g(0.1mol)、式(4)−4で表される化合物(昭和電工株式会社製「カレンズMOI」)15.5g(0.1mol)、メトキノン0.05g及びオクチル酸スズ0.05gを加え、80℃で4時間反応した。減圧下MIBKを留去し、目的物である式(1)−13で表される化合物93.9g(0.1mol)を得た。
〔式(1)−8で表されるフッ素化合物の合成〕
MIBK100gに、式(1)−8で表される化合物58.4g(0.1mol)、式(4)−4で表される化合物(昭和電工株式会社製「カレンズMOI」)15.5g(0.1mol)、メトキノン0.05g及びオクチル酸スズ0.05gを加え、80℃で4時間反応した。減圧下MIBKを留去し、目的物73.9g(0.1mol)を得た。
〔フッ素樹脂粒子用分散剤(1)の合成〕
合成例1で得られた式(1)−13で表されるフッ素化合物36.7質量部及びヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)63.3質量部をMIBK133.3質量部に溶解した後、重合開始剤(日油株式会社製「パーブチルO」)5質量部を加えた。この混合溶液を窒素雰囲気下で、105℃のMIBK100質量部に3時間かけて滴下し、さらに9時間重合反応を行い、フッ素樹脂粒子用分散剤(1)(共重合体30質量%のMIBK溶液)を得た。この共重合体をゲルパーミエーショングラフ(以下、「GPC」という。)により分析した結果、重量平均分子量は、6,900であった。
GPCによる重量平均分子量は、下記の条件により測定した標準ポリスチレン換算の値である。
装置:東ソー株式会社製「HLC8220システム」
分離カラム:東ソー株式会社製「TSKgelSuperH−RC」を2本、東ソー株式会社製「TSKgelGMHHR−N」を4本使用。
カラム温度:40℃
移動層:和光純薬工業株式会社製テトラヒドロフラン
流速:1.0ml/分
試料濃度:0.1質量%
試料注入量:100マイクロリットル
検出器:示差屈折計
〔フッ素樹脂粒子用分散剤(2)の合成〕
合成例1で得られた式(1)−13で表されるフッ素化合物36.7質量部及びヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)63.3質量部をMIBK133.3質量部に溶解した後、重合開始剤(日油株式会社製「パーブチルO」)5質量部を加えた。この混合溶液を窒素雰囲気下で、95℃のMIBK100質量部に4時間かけて滴下し、さらに8時間重合反応を行い、フッ素樹脂粒子用分散剤(2)(共重合体30質量%のMIBK溶液)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、15,600であった。
〔フッ素樹脂粒子用分散剤(3)の合成〕
合成例1で得られた式(1)−13で表されるフッ素化合物61.2質量部及びヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)38.8質量部をMIBK133.3質量部に溶解した後、重合開始剤(日油株式会社製「パーブチルO」)5質量部を加えた。この混合溶液を窒素雰囲気下で、105℃のMIBK100質量部に3時間かけて滴下し、さらに9時間重合反応を行い、フッ素樹脂粒子用分散剤(3)(共重合体30質量%のMIBK溶液)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、4,600であった。
〔フッ素樹脂粒子用分散剤(4)の合成〕
合成例1で得られた式(1)−13で表されるフッ素化合物61.2質量部及びヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)38.8質量部をMIBK133.3質量部に溶解した後、重合開始剤(日油株式会社製「パーブチルO」)5質量部を加えた。この混合溶液を窒素雰囲気下で、95℃のMIBK100質量部に4時間かけて滴下し、さらに8時間重合反応を行い、フッ素樹脂粒子用分散剤(4)(共重合体30質量%のMIBK溶液)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、14,900であった。
〔フッ素樹脂粒子用分散剤(5)の合成〕
合成例2で得られた式(1)−8で表されるフッ素化合物58.8質量部及びヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)41.2質量部をMIBK133.3質量部に溶解した後、重合開始剤(日油株式会社製「パーブチルO」)5質量部を加えた。この混合溶液を窒素雰囲気下で、105℃のMIBK100質量部に3時間かけて滴下し、さらに9時間重合反応を行った。その後、MIBKを減圧留去し、共重合体であるフッ素樹脂粒子用分散剤(5)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、7,600であった。
〔フッ素樹脂粒子用分散剤(6)の合成〕
合成例1で得られた式(1)−13で表されるフッ素化合物43.0質量部及びヒドロキシポリ(オキシエチレン)のモノメタクリレート(新中村化学工業株式会社製「NKエステル M−230G」)57.0質量部をMIBK133.3質量部に溶解した後、重合開始剤(和光純薬工業株式会社製の2,2’−アゾビス(イソ酪酸ジメチル))5質量部を加えた。この混合溶液を窒素雰囲気下で、80℃のMIBK100質量部に4時間かけて滴下し、さらに8時間重合反応を行った。その後、MIBKを減圧留去し、共重合体であるフッ素樹脂粒子用分散剤(6)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、9,700であった。
〔フッ素樹脂粒子用分散剤(7)の合成〕
実施例1で用いた式(1)−13で表されるフッ素化合物36.7質量部を下記式(6)−1で表されるフッ素化合物31.7質量部に代え、ヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)の使用量を63.3質量部から68.3質量部に変更した以外は実施例1と同様にして、フッ素樹脂粒子用分散剤(7)(共重合体30質量%のMIBK溶液)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、7,200であった。
〔フッ素樹脂粒子用分散剤(8)の合成〕
実施例2で用いた式(1)−13で表されるフッ素化合物36.7質量部を前記式(6)−1で表されるフッ素化合物31.7質量部に代え、ヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)の使用量を63.3質量部から68.3質量部に変更した以外は実施例2と同様にして、フッ素樹脂粒子用分散剤(8)(共重合体30質量%のMIBK溶液)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、11,900であった。
〔フッ素樹脂粒子用分散剤(9)の合成〕
実施例3で用いた式(1)−13で表されるフッ素化合物61.2質量部を前記式(6)−1で表されるフッ素化合物52.8質量部に代え、ヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)の使用量を38.8質量部から47.2質量部に変更した以外は実施例3と同様にして、フッ素樹脂粒子用分散剤(9)(共重合体30質量%のMIBK溶液)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、11,900であった。
〔フッ素樹脂粒子用分散剤(10)の合成〕
実施例4で用いた式(1)−13で表されるフッ素化合物61.2質量部を前記式(6)−1で表されるフッ素化合物52.8質量部に代え、ヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)の使用量を38.8質量部から47.2質量部に変更した以外は実施例4と同様にして、フッ素樹脂粒子用分散剤(10)(共重合体30質量%のMIBK溶液)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、14,900であった。
〔フッ素樹脂粒子用分散剤(11)の合成〕
実施例5で用いた式(1)−8で表されるフッ素化合物58.8質量部を下記式(6)−2で表されるフッ素化合物34.6質量部に代え、ヒドロキシポリ(オキシプロピレン)のモノメタクリレート(日油株式会社製「ブレンマーPP−1000」)の使用量を41.2質量部から65.4質量部に変更した以外は実施例5と同様にして、共重合体であるフッ素樹脂粒子用分散剤(11)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、4,200であった。
〔フッ素樹脂粒子用分散剤(12)の合成〕
実施例6で用いた式(1)−13で表されるフッ素化合物43.0質量部を前記式(6)−1で表されるフッ素化合物37.0質量部に代え、ヒドロキシポリ(オキシエチレン)のモノメタクリレート(新中村化学工業株式会社製「NKエステル M−230G」)の使用量を57.0質量部から63.0質量部に変更した以外は実施例6と同様にして、共重合体であるフッ素樹脂粒子用分散剤(12)を得た。この共重合体をGPCにより分析した結果、重量平均分子量は、7,500であった。
実施例1〜6及び比較例1〜6で得られたフッ素樹脂粒子用分散剤(1)〜(12)を用いて、下記の方法でフッ素樹脂粒子用分散剤を調製した。
フッ素樹脂粒子(PTFE微粉末(平均粒子径1〜2μm)、シャムロック社製「SST−1MG」)30質量部、フッ素樹脂粒子用分散剤のMIBK溶液(共重合体30質量%)5.0質量部(共重合体として1.5質量部)及びブチルセロソルブ65.0質量部をガラス製容器に入れ、自転・公転真空ミキサー(株式会社シンキー製「ARE−250」)を用いて2000回転で2分間処理し、フッ素樹脂粒子分散液を得た。なお、フッ素樹脂粒子用分散剤がMIBK溶液でない場合は、フッ素樹脂粒子用分散剤1.5質量部とし、ブチルセロソルブ68.5質量部とした。
フッ素樹脂粒子(PTFE微粉末(平均粒子径1〜2μm)、シャムロック社製「SST−1MG」)30質量部、フッ素樹脂粒子用分散剤(4)のMIBK溶液(共重合体30質量%)を0.5質量部、1.0質量部、2.0質量部、3.0質量部、4.0質量部(共重合体として0.15質量部、0.3質量部、0.6質量部、0.9質量部、1.2質量部)及びブチルセロソルブを各成分の合計が100質量部となるようにガラス製容器に入れ、自転・公転真空ミキサー(株式会社シンキー製「ARE−250」)を用いて2000回転で2分間処理し、フッ素樹脂粒子分散液を得た。また、フッ素樹脂粒子用分散剤(4)を配合しない例として、フッ素樹脂粒子用分散剤(4)を配合せずに、同様にしてフッ素樹脂粒子分散液を得た(比較例13)。
上記で得られたフッ素樹脂粒子分散液の分散安定性を、目視にて観察し、下記の基準で評価した。なお、評価は、フッ素樹脂粒子用分散剤を調製した後、室温で1時間静置後と1日静置後に行った。
4:PTFEが沈降しないもの。
3:PTFEがわずかに沈降しているもの。
2:PTFEが沈降しているもの。
1:ハードケーキ(沈降して再分散できないもの)を生成しているもの。
Claims (7)
- 下記一般式(1)で表されるフッ素化合物と、ポリオキシアルキレン鎖を有するエチレン性不飽和単量体との共重合体からなることを特徴とするフッ素樹脂粒子用分散剤。
- 前記一般式(1)中のR1及びR2が炭素原子数1〜6のパーフルオロアルキル基であり、かつA1及びA2がともにエチレン基である請求項1記載のフッ素樹脂粒子用分散剤。
- 前記一般式(1)中のR1及びR2が炭素原子数1〜5のパーフルオロアルキル基であり、A1及びA2がともに直接結合であり、かつX1及びX2がともに前記一般式(2)で表されるスルホンアミドである請求項1記載のフッ素樹脂粒子用分散剤。
- 前記一般式(1)中のR1が炭素原子数1〜6のパーフルオロアルキル基であり、A1がエチレン基であり、X1が酸素原子又は硫黄原子であり、R2が炭素原子数1〜5のパーフルオロアルキル基であり、A2が直接結合であり、かつX2が前記一般式(2)で表されるスルホンアミドである請求項1記載のフッ素樹脂粒子用分散剤。
- 前記一般式(1)中のA3がエチレン基である請求項1〜4のいずれか1項記載のフッ素樹脂粒子用分散剤。
- 請求項1〜5のいずれか1項記載のフッ素粒子用分散剤を用いて、フッ素樹脂粒子を有機溶剤又は水中で分散させたことを特徴とするフッ素樹脂粒子分散液。
- 請求項6記載のフッ素樹脂粒子分散液を配合したことを特徴とするフッ素樹脂塗料。
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