JP7061241B1 - 塗料用組成物 - Google Patents
塗料用組成物 Download PDFInfo
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- JP7061241B1 JP7061241B1 JP2022505638A JP2022505638A JP7061241B1 JP 7061241 B1 JP7061241 B1 JP 7061241B1 JP 2022505638 A JP2022505638 A JP 2022505638A JP 2022505638 A JP2022505638 A JP 2022505638A JP 7061241 B1 JP7061241 B1 JP 7061241B1
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- siloxane
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- 239000000178 monomer Substances 0.000 claims abstract description 124
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims abstract description 92
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- 125000003118 aryl group Chemical group 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
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- 125000002252 acyl group Chemical group 0.000 claims description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 229920001519 homopolymer Polymers 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
[1]シロキサン基含有ポリマー(A)および架橋剤(B)を含む塗料用組成物であり、
前記シロキサン基含有ポリマー(A)が、AブロックとBブロックとを含むブロック共重合体であり、Aブロックに少なくともシロキサン基含有ビニルモノマー(a)に由来する構造単位を含み、Bブロックに水酸基含有ビニルモノマー(b)に由来する構造単位ならびに必要に応じて、前記ビニルモノマー(a)および(b)と共重合可能な他のビニルモノマー(c)に由来する構造単位を含み、
かつ、分子量分布(Mw/Mn)が2.0以下であり、リビングラジカル重合により重合された共重合体である、
塗料用組成物を提供する。また、本発明は、更に以下の態様を提供する:
[3]前記シロキサン基含有ポリマー(A)の重量平均分子量(Mw)が、5,000~100,000である、[1]または[2]の塗料用組成物。
[4]前記リビングラジカル重合が下記式(1):
で表される有機テルル化合物を用いて重合する方法である、[1]~[3]のいずれかに記載の塗料用組成物。
[5]更に、水酸基含有ポリマー(C)を含む、[1]~[4]のいずれかに記載の塗料用組成物。
[6]前記シロキサン基含有ポリマー(A)と前記水酸基含有ポリマー(C)との配合割合が、シロキサン基含有ポリマー(A):水酸基含有ポリマー(C)の重量比で15:85~80:20の割合である[1]~[5]のいずれかに記載の塗料用組成物。
[7]前記シロキサン基含有ビニルモノマー(a)の数平均分子量(Mn)が、500~50,000である、[1]~[6]のいずれかに記載の塗料用組成物。
[8]前記架橋剤(B)が、イソシアネート系架橋剤である、[1]~[7]のいずれかに記載の塗料用組成物。
上記シロキサン基含有ポリマー(A)は、AブロックとBブロックとを含むブロック共重合体であり、Aブロックに少なくともシロキサン基含有ビニルモノマー(a)に由来する構造単位を含み、Bブロックに水酸基含有ビニルモノマー(b)ならびに必要に応じて、前記ビニルモノマー(a)および(b)と共重合可能な他のビニルモノマー(c)に由来する構造単位を含み、
かつ、分子量分布(Mw/Mn)が2.0以下であり、リビングラジカル重合により重合された共重合体である。
本明細書中で「ビニルモノマー」とは分子中にラジカル重合可能な炭素-炭素二重結合を有するモノマーのことをいう。「ビニルモノマーに由来する構造単位」とは、ビニルモノマーのラジカル重合可能な炭素-炭素二重結合が、重合して炭素-炭素単結合になった構造単位をいう。
で表されるものである。上記式(I)のシロキサン基含有ビニルモノマー(a)は下記式II:
(メタ)アクリル酸、β-カルボキシエチルアクリレートなどのアクリル酸のダイマー酸等のカルボキシル基含有モノマー類;
シクロヘキシル(メタ)アクリレート、シクロヘキシルオキシアルキル(メタ)クリレート、t-ブチルシクロヘキシルオキシエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート等の脂環含有モノマー類;
ポリエチレングリコールモノ(メタ)アクリレートのリン酸エステル、(モノ(プロピレングリコールモノメタクリレート)ホスフェート等のポリプロピレングリコールモノ(メタ)アクリレートのリン酸エステル、リン酸メチレン(メタ)アクリレート、リン酸トリメチレン(メタ)アクリレート、リン酸プロピレン(メタ)アクリレート、リン酸テトラメチレン(メタ)アクリレート等のリン酸アルキレン(メタ)アクリレート等のリン酸基含有(メタ)アクリレート類;
エチレンスルホン酸、アリルスルホン酸、メタアリルスルホン酸等のオレフィンスルホン酸、2-アクリルアミド-2-メチルプロパンスルホン酸、スチレンスルホン酸、スルホン酸基含有モノマー類あるいはその塩;
メトキシメチル(メタ)アクリルアミド、エトキシメチル(メタ)アクリルアミド、プロポキシメチル(メタ)アクリルアミド、イソプロポキシメチル(メタ)アクリルアミド、n-ブトキシメチル(メタ)アクリルアミド、イソブトキシメチル(メタ)アクリルアミドなどのアルコキシアルキル(メタ)アクリルアミド系モノマー、(メタ)アクリロイル
モルホリン、ジメチル(メタ)アクリルアミド、ジエチル(メタ)アクリルアミド、(メタ)アクリルアミドN-メチロール(メタ)アクリルアミド等の(メタ)アクリルアミド系モノマー類;
グリシジルアクリレート、フルフリルアクリレート、テトラヒドロフルフリルアクリレート、グリシジルメタクリレート、フルフリルメタクリレート、テトラヒドロフルフリルメタクリレート、メチルビニルケトン、スチレン、α-メチルスチレン、N-ビニルカプロラクタム、酢酸ビニル等;
が挙げられ、特にイソボルニル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレートは塗膜物性バランスの観点から好ましい。
下記式(1):
式(2):
(R1Te)2 (2)
〔式中、R1は、上記と同じ。〕
本発明の塗料用組成物に配合する架橋剤は、特に限定されるものではないが、シロキサン基含有ポリマー(A)に存在する水酸基と架橋反応するものであり、イソシアネート系架橋剤、エポキシ系架橋剤、アミノプラスト樹脂、グリオキサール等が挙げられる。これら架橋剤は、単独で使用してもよいし、2種以上を併用してもよい。
本発明の塗料用組成物には、必要に応じて水酸基含有ポリマー(C)を配合することができる。水酸基含有ポリマー(C)としては、例えば、アクリル樹脂、シリコーンアクリル樹脂、ポリエステル樹脂、アルキド樹脂、シリコーンポリエステル樹脂、エポキシ樹脂、エポキシエステル樹脂、フッソ樹脂等を挙げることができるが、これらのうちアクリル樹脂、ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、エポキシエステル樹脂が好適に使用できる。水酸基含有ポリマー(C)は、官能基の制御や製造の容易性から、水酸基を含有するアクリル樹脂(以下、「アクリルポリオール樹脂」と呼ぶこともある。)が好ましい。
本発明の塗料用組成物は、上記塗料用組成物を構成する各成分を、通常用いられる手段によって混合することによって、調製することができる。上記塗料用組成物には、必要に応じて、顔料、表面調整剤(消泡剤、レベリング剤等)、顔料分散剤、可塑剤、造膜助剤、紫外線吸収剤、酸化防止剤、難燃剤、帯電防止剤、静電助剤、熱安定剤、光安定剤、溶剤(水、有機溶剤)その他の添加剤を含有してもよい。
本発明の塗料用組成物が塗布される被塗物として、鉄、鋼、ステンレス、アルミニウム、銅、亜鉛、スズなどの金属およびこれらの合金などの鋼板;ポリエチレン樹脂、EVA樹脂、ポリオレフィン樹脂(ポリエチレン樹脂、ポリプロピレン樹脂など)、塩化ビニル樹脂、スチロール樹脂、ポリエステル樹脂(PET樹脂、PBT樹脂などを含む)、不飽和ポリエステル樹脂、ポリカーボネート樹脂、アクリル樹脂、アクリロニトリルブタジエンスチレン(ABS)樹脂、アクリロニトリルスチレン(AS)樹脂、ポリアミド樹脂、アセタール樹脂、フェノール樹脂、フッ素樹脂、メラミン樹脂、ウレタン樹脂、エポキシ樹脂、ポリフェニレンオキサイド(PPO)などの樹脂;および、有機-無機ハイブリッド材などが挙げられる。これらは成形された状態であってもよい。本発明の塗料用組成物は、特にポリエチレン樹脂、ポリオレフィン樹脂(ポリエチレン樹脂、ポリプロピレン樹脂など)、スチロール樹脂、ポリエステル樹脂(PET樹脂、PBT樹脂などを含む)、ポリカーボネート樹脂などの帯電しやすい材料や、FRP、CFRPに用いる不飽和ポリエステル樹脂の時に効果を発揮する。
製造例1 シロキサン基含有ポリマー(A-1)の製造
アルゴンガス導入管、撹拌翼を供えたフラスコに、エチル-2-メチル-2-n-ブチルテラニル-プロピオネート(BTEE)1.49g、ジブチルジテルリド(DBDT)0.92g、メタクリル酸2-ヒドロキシエチル(HEMA)42g、メタクリル酸イソブチル(iBMA)98g、2,2’-アゾビス(イソブチロニトリル)(AIBN)0.33g、酢酸ブチル140gを仕込み(第1モノマー組成物)、60℃で36時間反応させBブロックを重合した。
アルゴンガス導入管、撹拌翼を供えたフラスコに、BTEE 1.49g、DBDT 0.92g、HEMA 42g、iBMA 78g、AIBN 0.33g、酢酸ブチル120gを仕込み(第1モノマー組成物)、60℃で36時間反応させBブロックを重合した。
製造例1のHEMA 42g、iBMA 98gをiBMA 140gに変更したこと以外は同様にし、シロキサン基含有ポリマー(A-3)を得た。得られたシロキサン基含有ポリマー(A-3)の物性、重量平均分子量(Mw)、分子量分布(Mw/Mn)、水酸基価、製造方法(TERP/FRP)、ポリマー形態(ブロックポリマー/ランダムポリマー)、ブロック形態(AB/ABAの区別)およびモノマーの配合を表1に示す。
アルゴンガス導入管、撹拌翼を供えたフラスコに、BTEE 1.49g、DBDT 0.92g、HEMA 42g、iBMA 98g、X-22-174ASX 60g、AIBN 0.33g、酢酸ブチル400gを仕込み(第1モノマー組成物)、60℃で36時間反応させランダム構造のシロキサン基含有ポリマー(A-4)を得た。得られたランダム構造のシロキサン基含有ポリマー(A-4)の物性、重量平均分子量(Mw)、分子量分布(Mw/Mn)、水酸基価、製造方法(TERP/FRP)、ポリマー形態(ブロックポリマー/ランダムポリマー)、ブロック形態(AB/ABAの区別)およびモノマーの配合を表1に示す。
温度調節器、攪拌翼、還流管、窒素導入口を備えた0.2Lのセパラブルフラスコに、酢酸ブチル30gを仕込み、フラスコ内部を窒素雰囲気下にした後、温度を120℃に昇温して一定に保った。一方、HEMA 20.88g、iBMA 49.12g、X-22-174ASX 30gおよびカヤエステルO 0.88gの混合液を滴下ロートに入れて、3時間かけて滴下した。
アルゴンガス導入管、撹拌翼を供えたフラスコに、BTEE 1.49g、DBDT 0.92g、HEMA 42g、iBMA 98g、AIBN 0.33g、酢酸ブチル140gを仕込み(第1モノマー組成物)、60℃で36時間反応させBブロックを重合した。
アルゴンガス導入管、撹拌翼を供えたフラスコに、BTEE 1.49g、DBDT 0.92g、HEMA 42g、iBMA 98g、AIBN 0.33g、酢酸ブチル140gを仕込み(第1モノマー組成物)、60℃で36時間反応させBブロックを重合した。
アルゴンガス導入管、撹拌翼を供えたフラスコに、BTEE 1.49g、DBDT 0.92g、HEMA 42g、メタクリル酸イソボルニル(IBXMA)98g、AIBN 0.33g、酢酸ブチル140gを仕込み(第1モノマー組成物)、60℃で36時間反応させBブロックを重合した。
アルゴンガス導入管、撹拌翼を供えたフラスコに、予めアルゴン置換したシロキサン基含有アクリルモノマー(信越化学社製:X-22-174ASX)60.0g、AIBN 0.33g、酢酸ブチル60gの混合溶液(第1モノマー組成物)を加え、60℃で36時間反応させAブロックを重合した。
[数平均分子量(Mn)、重量平均分子量(Mw)及び分子量分布(Mw/Mn)の測定]
ゲルパーミエーションクロマトグラフィー(GPC)にて、カラムはTSKgel SuperMultipore HZ-H(Φ4.6×150)×2(東ソー(株)製)、移動相としてテトラヒドロフラン、標準物質としてポリスチレン(東ソー(株)製、TSK Standard)を使用して検量線を作成し、重量平均分子量(Mw)、数平均分子量(Mn)を測定した。これらの測定値から分子量分布(Mw/Mn)を算出した。
温度調節器、攪拌翼、還流管、窒素導入口を備えた2Lのセパラブルフラスコに、酢酸ブチル444.27gを仕込み、フラスコ内部を窒素雰囲気下にした後、温度を130℃に昇温して一定に保った。一方、スチレン(ST)255g、メタクリル酸(MAA)8.5g、HEMA 394.4g、アクリル酸2-エチルヘキシル(EHA)117.47g、iBMA 74.72g、およびカヤエステルO 102gの混合液を滴下ロートに入れて、3時間かけて滴下した。
塗料用組成物および塗膜の作成
シロキサン基含有ポリマー(A)(A-1~A-9)、架橋剤(B)としてのN3600(コベストロ社製、NCO%=23)、水酸基含有ポリマー(C)を表1に記載した配合量で配合し、酢酸ブチルを用いて樹脂分を50重量%に希釈した塗料用組成物を、アプリケーターを用いて、乾燥膜厚が30μmになるように、ブリキ板上に塗装し、試験片は、温度20±5℃、相対湿度78%以下の塗装環境下で7分間放置した。尚、比較例4はシロキサン基含有ポリマーを配合していない例である。尚、表1には、シロキサン基含有ポリマー(A)と水酸基含有ポリマー(C)の重量比率(シロキサン基含有ポリマー(A):水酸基含有ポリマー(C))も記載した。
塗膜の表面を目視観察し、下記の基準で評価した。
○:塗膜は透明であり全く異常が認められない
△:塗膜がうっすらと乳白色である。
×:塗膜に白濁が認められる
カーボンブラック(Furnace black(KREMER pigmente)に、松脂、テルピネオール、リモネンを入れ、ディスパーで攪拌させ、黒色のタール状液体を得た。これを油系有機汚染物とした。アプリケーターを用いて、乾燥膜厚が約20μmになるように、実施例で得られた塗膜の上にこれを塗工し、熱風乾燥機を用いて80℃下で、30分間乾燥させたものを下記条件で評価した。
高圧水噴射条件:噴射ノズル(1/4PMEG-2506)、水流(11L/min),水温(50℃)、洗浄時間(1分)、水噴射距離(10cm)
○…水噴射と同時に汚れが吹き飛び、吹き飛んだところの塗膜に黒色の汚れがない
×…汚れがきれいに吹き飛ばない。塗面に黒い汚れが残っている。
実施例で得られた塗膜の上に、エビアン(商品名)を、アトマイザーを用いて噴霧させ、塗膜の上に水滴をのせた。これを熱風乾燥機で60℃下、10分間乾燥させ、水垢を塗膜に固着させた。塗膜を水道水に流しながらスポンジを用い10往復洗浄した後の塗膜に残った水垢を目視により評価した。
◎…水垢が固着していない
○…水垢がほとんどとれている。小さな点状で残っている。
×…水垢がコーヒーリングのように環になって固着している。(外観が悪い)
協和界面科学社製のDMo-701型接触角計を用い、25℃、55%RHの雰囲気下で、約1μLの蒸留水を塗膜表面に着滴させ、10秒後の液滴と塗膜表面とのなす角をθ/2法にて算出した。
◎…接触角が95度以上、
○…接触角が85度以上、
×…接触角が85度未満。
洗車を想定して、コンパウンド剤(#7500番)を電動ポリッシャーで10秒間、ポリッシングし、中性洗剤を用いイオン交換水で塗膜を水洗した後、常温乾燥させたものを測定塗膜とした。
協和界面科学社製のDMo-701型接触角計を用い、25℃、55%RHの雰囲気下で、約1μLの蒸留水を塗膜表面に着滴させ、10秒後の液滴と塗膜表面とのなす角をθ/2法にて算出した。
◎…接触角が95度以上、
○…接触角が85度以上、
×…接触角が85度未満。
得られた塗膜の上にトルエンを2μl滴下し、5分間静置した。5分後にドライウエスでふき取った後の外観を以下の基準で評価した。
○…塗膜外観に異常がみられない。
△…うっすらと液滴のあとが残る。
Claims (6)
- シロキサン基含有ポリマー(A)および架橋剤(B)を含む塗料用組成物であり、
前記シロキサン基含有ポリマー(A)が、AブロックとBブロックとを含むブロック共重合体であり、Aブロックに少なくともシロキサン基含有ビニルモノマー(a)に由来する構造単位を含み、Bブロックに水酸基含有ビニルモノマー(b)に由来する構造単位ならびに必要に応じて、前記ビニルモノマー(a)および(b)と共重合可能な他のビニルモノマー(c)に由来する構造単位を含み、
かつ、分子量分布(Mw/Mn)が2.0以下であり、リビングラジカル重合により重合された共重合体であり、
前記架橋剤(B)が、イソシアネート系架橋剤であり、
前記リビングラジカル重合が、下記式(1):
で表される有機テルル化合物を用いて重合する方法である、
塗料用組成物。 - 前記シロキサン基含有ポリマー(A)が、AB型ジブロック共重合体またはABA型トリブロック共重合体である、請求項1記載の塗料用組成物。
- 前記シロキサン基含有ポリマー(A)の重量平均分子量(Mw)が、5,000~100,000である、請求項1または請求項2に記載の塗料用組成物。
- 更に、水酸基含有ポリマー(C)を含む、請求項1~3のいずれか一項に記載の塗料用組成物。
- 前記シロキサン基含有ポリマー(A)と前記水酸基含有ポリマー(C)との配合割合が、シロキサン基含有ポリマー(A):水酸基含有ポリマー(C)の重量比で15:85~80:20の割合である請求項4に記載の塗料用組成物。
- 前記シロキサン基含有ビニルモノマー(a)の数平均分子量(Mn)が、500~50,000である、請求項1~5のいずれか一項に記載の塗料用組成物。
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