JP2005517790A - 改良された傷耐性および酸耐性を有する粉末コーティング組成物 - Google Patents
改良された傷耐性および酸耐性を有する粉末コーティング組成物 Download PDFInfo
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- JP2005517790A JP2005517790A JP2003569730A JP2003569730A JP2005517790A JP 2005517790 A JP2005517790 A JP 2005517790A JP 2003569730 A JP2003569730 A JP 2003569730A JP 2003569730 A JP2003569730 A JP 2003569730A JP 2005517790 A JP2005517790 A JP 2005517790A
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Abstract
Description
(1.発明の分野)
本発明は、ビニルモノマーのコポリマーを含む熱硬化性組成物に一般に関する。より具体的には、本発明は、イソブチレン型モノマーを含む官能性コポリマーを含む共反応性(co−reactable)固体粒子混合物熱硬化性組成物に関する。
特に、使用中に揮発性有機物の空気中への放出に関連したコーティング組成物の環境への影響を少なくすることは、近年、研究開発中の領域であった。従って、粉末コーティングにおける関心が、一部には、それらに固有の低揮発性有機含量(VOC)塗布工程での空気への放出を著しく低下させることに起因して、高まっている。熱可塑性および熱硬化性の両方のコーティング組成物が市販されているが、熱硬化性コーティングは、典型的には、物理的特性(例えば、硬度および溶媒耐性)が優れているので、望ましい。
本発明は、以下の共反応性固体の粒子状混合物を含む熱硬化性組成物に関する:
(a)官能基を含むフィルム形成材料;および
(b)以下の交互構造単位:
−[DM−AM]−
(ここでDMは、以下の構造(I)を有するドナーモノマーに由来の残基を表す:
操作実施例以外、または特に明記しない限り、本明細書および特許請求の範囲で使用される成分の量、反応条件などを示す全ての数値または表現は、いずれの場合にも、「約(およそ)」との用語により修飾されることが理解できるはずである。本特許出願では、種々の数値範囲が開示されている。これらの範囲は、連続しているので、これらは、その最低値と最高値との間のいずれの値をも含む。特に明記しない限り、本願で特定した種々の数値範囲は、概算値である。
の交互モノマー残基単位を有するドナーモノマー−アクセプターモノマー対の交互配列由来のコポリマーの残基の、少なくとも30モル%、多くの場合に少なくとも40モル%、代表的に少なくとも50モル%、いくつかの場合に少なくとも60モル%、その他の場合に少なくとも75モル%を有する官能基含有コポリマーを含むコポリマー組成物であり得、ここで、DMは、ドナーモノマー由来の残基を表し、そしてAMは、アクセプターモノマー由来の残基を表す。コポリマーは、DMおよびAMの100%交互コポリマーであり得る。さらに特に、少なくとも15モル%のコポリマーが、ドナーモノマーを含み、これはイソブチレン型モノマーであり、以下の構造(I)を有する:
選択モノマーのAlfrey−Price e値
モノマー e値
構造1のモノマー
イソブチレン −1.201
ジイソブチレン 0.492
アクリルモノマー
アクリル酸 0.881
アクリルアミド 0.541
アクリロニトリル 1.231
アクリル酸メチル 0.641
アクリル酸エチル 0.551
アクリル酸ブチル 0.851
アクリル酸ベンジル 1.131
アクリル酸グリシジル 1.281
1 Polymer Handbook,第4版(1999)
2 Rzaevら、Eur.Polym.J.,Vol.24,No.7,pp.981−985(1998)。
(IV)−AA−DIIB−AA−DIIB−AA−DIIB−AA−DIIB−AA−DIIB−AA−DIIB−AA−
しかしながら、大抵の場合、本発明のコポリマー架橋剤は、構造Vで示すように、交互セグメントおよびランダムセグメントを含み、DIIB、AAおよび他のモノマーMのコポリマーである:
(VII) H2C=C(R10)−CH2−
ここで、R10は、水素、ハロゲン、またはC1〜C4アルキル基である。最も一般的には、R10は、水素またはメチルであり、結果的に、一般式VIIは、非置換(メタ)アリルラジカルを表わし、これは、アリルラジカルおよびメタリルラジカルの両方を包含する。アリルモノマーの例には、(メタ)アリルアルコール;(メタ)アリルエーテル(例えば、メチル(メタ)アリルエーテル);カルボン酸のアリルエステル(例えば、酢酸(メタ)アリル、酪酸(メタ)アリル、3,4−ジメトキシ安息香酸(メタ)アリルおよび安息香酸(メタ)アリル)が挙げられるが、これらに限定されない。
−[DM−AM]−
(ここでドナーモノマーは、イソブチレン、ジイソブチレン、ジペンテン、イソプレン、イソプレノール、1−オクテン、およびその混合物から選択され、そしてアクリルアクセプターモノマーは、アクリル酸およびメタクリル酸から選択される)を有する残基を少なくとも30mol%含む。
(A)該基板に熱硬化性組成物を塗布する工程;
(B)該熱硬化性組成物を融合して、実質的に連続なフィルムを形成する工程;および
(C)該熱硬化性組成物を硬化する工程。
(a)着色フィルム形成組成物から堆積されるベースコート;および
(b)このベースコート上に塗布される透明トップコート
を含有する多成分複合コーティング構成物に関する。ここで、このベースコートもしくは透明トップコートのいずれか、またはこれらの両方は、本発明の熱硬化性組成物を含有するクリアフィルム形成熱硬化性組成物から堆積される。本明細書中に記載されるような多成分複合コーティング構成物は、通常、着色透明(color−plus−clear)コーティング構成物と称される。
(a)カソードおよびアノードを含む電気回路においてカソードとして作用する導電性基材を電気コーティングすることによって堆積されるプライマーコートであって、このカソードおよびアノードは、このカソードとアノードとの間に電流を通して、実質的に連続したフィルムとしてこの基材上に電気コーティング組成物を堆積させることによって、水性電気コーティング組成物中に液浸される、プライマーコート;
(b)このプライマーコート上に塗布されるベースコートであって、着色フィルム形成組成物から堆積される、ベースコート;および
(c)このベースコート上に塗布される透明トップコート
を含有し、ここで、このベースコートもしくは透明トップコートまたはこれらの両方は、本発明の熱硬化性組成物を含有するクリアフィルム形成熱硬化性組成物から堆積される。
表1の成分を、交互コポリマー(ジイソブチレン−alt−アクリル酸/ブチルアクリレート(実施例A))を合成するために使用した。
16LUPEROX 575,ATOFINA,Paris,France
チャージ1を、攪拌器、熱電対、およびN2注入口を備えた反応フラスコに添加し、N2ブランケット下に配置し、そして103℃で加熱した。チャージ2を反応フラスコに、4時間にわたって、添加した。15分後、チャージ3を、4時間にわたって、反応フラスコに添加した。モノマーを添加する間、温度を103℃で維持した。チャージ2およびチャージ3を、反応フラスコに添加後、反応混合物を2時間保持した。次いで、反応フラスコを25℃に冷却した。反応混合物のガスクロマトグラフィー(GC)分析は、全てのアクリレートが反応したことを示した。次いで、反応フラスコに、単純減圧蒸留器を備え付け、そして反応混合物を80℃に過熱して、未反応のジイソブチレンおよび溶媒を除去した。生じたポリマー溶液の固体を、110℃、1時間乾燥後、98.3重量%として決定した。コポリマーは、数平均分子量、Mn=1430および多分散性Mw/Mn=1.8(ポリスチレン標準を用いるゲル浸透クロマトグラフィーにより決定される)を有した。粉末の酸価は、207.1であった。
16LUPEROX 575,ATOFINA,Paris,France
チャージ1を、撹拌器、熱電対、およびN2入口を備える反応フラスコに添加し、N2のブランケット下に配置し、そして103℃に加熱した。チャージ2を、この反応フラスコに、4時間かけて添加した。15分後、チャージ3を、この反応フラスコに、4時間かけて添加した。モノマーの添加の間、温度を103℃に維持した。チャージ2およびチャージ2を反応フラスコに入れた後に、この反応混合物を2時間維持した。次いで、この反応フラスコを25℃に冷却した。この反応混合物のGC分析は、全てのアクリレートが反応したことを示した。次いで、この反応フラスコを、単純な減圧蒸留のために取り付け、そしてこの反応混合物を80℃に加熱して、未反応のジイソブチレンおよび溶媒を除去した。得られたポリマーの固形物は、110℃で1時間にわたって、98.52重量%であることが決定された。このコポリマーは、1310のMnおよび1.9のMw/Mnを有した(ポリスチレン標準を使用するゲル濾過クロマトグラフィーによって決定した)。この粉末の酸価は、196.8であった。
18 脂肪酸アミド(エチレンビス−ステアロイルアミド)、Hoechst−Celanese,Summerville,NJから入手可能。
19 2−tert−ブチル−2−(4−ヒドロキシ−3,5−ジ−tert−ブチルベンジル)[ビス(メチル−2,2,6,6−テトラメチル−4−ピペリジニル)]ジプロピオネート)、Ciba Specialty Chemicals,Basel,Switzerlandから入手可能な紫外光安定化剤。
20 (2−[4−((2−ヒドロキシ−3−(2−エチルヘキシルオキシ)プロピル)−オキシ]−2−ヒドロキシフェニル)−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン)、Ciba Specialty Chemicalsから入手可能な紫外光安定化剤。
21 Sanko Chemical Corp.,Fukuoka,Japanから入手可能な抗黄変剤(抗酸化剤)。
22 Akzo−Nobel Corp.,Arnhem,Netherlandsから入手可能なメチルジココアミン。
23 米国特許第6,197,883号B1。
表7の成分を使用して、交互コポリマーの、ジイソブチレン−alt−ヒドロキシエチルアクリレート/メチルアクリレート/イソボルニルアクリレート(実施例J)を合成した。
16 LUPEROX 575、ATOFINA、Paris、France
チャージ1を、攪拌子、熱電対およびN2入口を備える反応フラスコに添加し、N2ブランケット下に置き、そして103℃に加熱した。チャージ2を、4時間にわたってこの反応フラスコに添加した。15分後、チャージ3を、4時間にわたってこの反応フラスコに添加した。モノマー添加の間、温度を103℃に維持した。この反応フラスコ中にチャージ2およびチャージ3を入れた後、この反応混合物を2時間維持した。次いで、この反応フラスコを25℃に冷却した。反応混合物のGC分析により、全てのアクリレートが反応したことが示された。この反応フラスコに、次いで、簡単な減圧蒸留を取付け、この反応混合物を80℃まで加熱して、未反応のジイソブチレンおよび溶媒を除去した。得られたポリマーの固形分を、110℃で1時間にわたって決定して、97.8重量%であることを決定した。コポリマーは、Mn=1700およびMw/Mn=5.1を有した(ポリスチレン基準を使用するゲル透過クロマトグラフィーによって決定)。粉末のヒドロキシル価は、142.6であった。
26 Ti Pure R−706、E.I.du Pont de Nemours and Company,Wilmington,DEから入手可能。
27 Butaflow BT−71、Estron Chemical,Inc.,Calvert City,KYから入手可能。
Claims (36)
- 熱硬化性組成物であって、該熱硬化性組成物が、以下:
(a)官能基を含むフィルム形成材料;および
(b)少なくとも2つの官能基を有する架橋剤であって、該官能基は、該フィルム形成材料(a)における官能基と反応性であり、以下の交互構造単位:
−[DM−AM]−
を有する少なくとも30mol%の残基を含むコポリマー組成物を含む、架橋剤、
の共反応可能な固体の粒子状混合物を含み、
ここで、DMは、以下の構造(I):
ここで、R1は、直鎖または分枝鎖のC1〜C4アルキルであり;R2は、メチル、直鎖、環状または分枝鎖のC1〜C20アルキル、アルケニル、アリール、アルカアリールおよびアラルキルからなる群より選択され;そして、AMは、1つ以上のアクリルアクセプターモノマー由来の残基を表す、熱硬化性組成物。 - 前記官能基を含むフィルム形成材料(a)が、アクリレートモノマー、メタクリレートモノマー、およびこれらの混合物の残基からなるポリマーを含む、請求項1に記載の熱硬化性組成物。
- 請求項1に記載の熱硬化性組成物であって、前記フィルム形成材料(a)の官能基が、エポキシ、カルボン酸、ヒドロキシ、チオール、イソシアネート、キャップ化イソシアネート、アミド、アミン、アセトアセテート、メチロール、メチロールエーテル、オキサゾリンカルバメート、およびβ−ヒドロキシアルキルアミドからなる群より選択され;前記架橋剤(b)の官能基が、エポキシ、カルボン酸、ヒドロキシ、チオール、アミド、アミン、オキサゾリン、アセトアセテート、メチロール、メチロールエーテル、イソシアネート、キャップ化イソシアネート、β−ヒドロキシアルカミドおよびカルバメートからなる群より選択され;そして、ここで該フィルム形成材料(a)の官能基が、該架橋剤(b)における官能基と反応性である、熱硬化性組成物。
- 前記(a)におけるポリマーが、エポキシ官能基を含むモノマーの残基を含み、前記架橋剤(b)におけるアクリルアクセプターモノマーが、1つ以上のカルボン酸官能性アクリルモノマーを含む、請求項2に記載の熱硬化性組成物。
- 前記カルボン酸官能性アクリルモノマーが、アクリル酸を含む、請求項2に記載の熱硬化性組成物。
- 前記ドナーモノマーが、イソブチレン、ジイソブチレン、イソプレン、およびこれらの混合物からなる群より選択される、請求項1に記載の熱硬化性組成物。
- 前記(b)におけるコポリマーが、500〜30,000の数平均分子量および4未満の多分散性指数を有する、請求項6に記載の熱硬化性組成物。
- 前記(a)におけるポリマーが、500〜30,000の数平均分子量および4未満の多分散性指数を有する、請求項6に記載の熱硬化性組成物。
- 前記(b)におけるコポリマーが、100〜5,000グラム/当量の官能基当量を有する、請求項6に記載の熱硬化性組成物。
- 前記(a)におけるポリマーが、100〜5,000グラム/当量の官能基当量を有する、請求項6に記載の熱硬化性組成物。
- 前記(a)におけるポリマーの官能基当量に対する、前記架橋剤(b)のコポリマーにおける官能基当量の当量比が、1:3〜3:1の範囲内である、請求項6に記載の熱硬化性組成物。
- 前記架橋剤(b)が、樹脂固体の全重量に基づいて、1〜45重量%の量で存在し、前記フィルム形成材料(a)が、樹脂固体の全重量に基づいて、55〜99重量%の量で存在する、請求項6に記載の熱硬化性組成物。
- 前記架橋剤(b)が、C4〜C20脂肪族カルボン酸、ポリマー性ポリ無水物、カルボン酸官能性ポリエステル、およびカルボン酸官能性ポリウレタンからなる群より選択される1つ以上のポリカルボン酸官能性材料をさらに含む、請求項6に記載の熱硬化性組成物。
- 前記C4〜C20脂肪族カルボン酸が、ドデカン二酸、アゼライン酸、アジピン酸、1,6−ヘキサン二酸、コハク酸、ピメリン酸、セバシン酸、マレイン酸、クエン酸、イタコン酸、アコニット酸、およびこれらの混合物からなる群より選択される、請求項13に記載の熱硬化性組成物。
- 請求項6に記載の熱硬化性組成物であって、前記アクリルアクセプターモノマーが、構造式(III):
ここで、Yは、−NR3 2、−O−R5−O−C(=O)−NR3 2、および−OR4からなる群より選択され、R3は、H、直鎖または分枝鎖のC1〜C20アルキル、ならびにエポキシ、カルボン酸、ヒドロキシ、チオール、アミド、アミン、オキサゾリン、アセトアセテート、メチロール、メチロールエーテル、イソシアネート、キャップ化イソシアネート、β−ヒドロキシアルカアミドおよびカルバメートからなる群より選択される1つ以上の官能基を含む直鎖または分枝鎖のC1〜C20アルキル、アリール、およびアラルキルからなる群より選択され;R4は、H、エポキシ、カルボン酸、ヒドロキシ、チオール、アミド、アミン、オキサゾリン、アセトアセテート、メチロール、メチロールエーテル、イソシアネート、キャップ化イソシアネート、β−ヒドロキシアルカミドおよびカルバメートからなる群より選択される1つ以上の官能基を含む直鎖または分枝鎖のC1〜C20アルキル、アリール、およびアラルキルからなる群より選択され;そして、R5は、二価の直鎖または分枝鎖のC1〜C20アルキル連結基である、熱硬化性組成物。 - 請求項15に記載の熱硬化性組成物であって、前記アクリルアクセプターモノマーが、ヒドロキシエチルアクリレート、ヒドロキシプロピルアクリレート、アクリル酸、ジメチルアミノエチルアクリレート、アクリルアミド、グリシルアクリレート、グリシジルメタクリレート、n−ブトキシメチルアクリルアミド、ヒドロキシエチルメタクリレート、ヒドロキシプロピルメタクリレート、メタクリル酸、メタクリルアミド、2−カルバモイルオキシエチルアクリレート、2−カルバモイルオキシエチルメタクリレート、2−カルバモイルオキシプロピルアリレート、2−カルバモイルオキシプロピルメタクリレート、2−イソシアナトエチルアクリレート、2−シソシアナトエチルメタクリレート、2−イソシアナトプロピルアクリレート、2−イソシアナトプロピルメタクリレート、2−オキサゾリンエチルアクリレート、2−オキサゾリンエチルメタクリレート、2−オキサゾリンプロピルアクリレート、2−オキサゾリンプロピルメタクリレート、ヒドロキシエチルアクリレートのアセト酢酸エステル、ヒドロキシエチルメタクリレートのアセト酢酸エステル、ヒドロキシプロピルメタクリレートのアセト酢酸エステル、およびヒドロキシプロピルアクリレートのアセト酢酸エステルからなる群より選択される1つ以上である、熱硬化性組成物。
- 熱硬化性組成物であって、該熱硬化性組成物が、以下:
(a)フィルム形成材料であって、該フィルム形成材料は、グリシジルアクリレート、グリシジルメタクリレート、アリルグリシジルエーテル、ビニルグリシジルエーテル、およびこれらの混合物からなる群より選択されるエポキシ官能性モノマーの残基;ならびにアクリル酸の直鎖および分枝鎖C1〜C20アルキル、アリール、アルカアリール、およびアラルキルエステル、およびメタクリル酸のC1〜C20のアルキルエステル、アリールエステル、アルカアリールエステル、およびアラルキルエステルおよびこれらの混合物からなる群より選択されるアクリレートモノマーおよびメタクリレートモノマーの残基から構成されるアクリルコポリマーを含む、フィルム形成材料;ならびに
(b)該フィルム形成材料(a)における官能基と反応性である少なくとも2つの官能基を有する、架橋剤であって、該架橋剤は、以下の交互構造単位:
−[DM−AM]−
を有する少なくとも30mol%の残基からなるコポリマーを含む、架橋剤、
の共反応可能な固体の粒子状混合物を含み、
ここで、DMは、イソブチレン、ジイソブチレン、ジペンテン、イソプレン、イソプレノール、1−オクテン、およびこれらの混合物からなる群より選択されるドナーモノマー由来の残基を表し;そして、AMは、アクリル酸およびメタクリル酸からなる群より選択される1つ以上のアクリルアクセプターモノマー由来の残基を表す、熱硬化性組成物。 - 基材をコーティングする方法であって、以下:
(A)該基材に請求項1の熱硬化性組成物を塗布する工程;
(B)該熱硬化性組成物を合着して、実質的に連続なフィルムを形成する工程;および
(C)該熱硬化性組成物を硬化する工程、
を包含する、方法。 - 基材をコーティングする方法であって、以下:
(A)該基材に請求項17の熱硬化性組成物を塗布する工程;
(B)該熱硬化性組成物を合着して、実質的に連続なフィルムを形成する工程;および
(C)該熱硬化性組成物を硬化する工程、
を包含する、方法。 - 請求項18に記載の方法を使用してコーティングされた、基材。
- 請求項19に記載の方法を使用してコーティングされた、基材。
- 多成分複合コーティング構成物であって、以下:
(a)着色フィルム形成組成物から堆積されたベースコーティング;および
(b)該ベースコーティング上に塗布される透明トップコーティング、
を含み、ここで、該ベースコーティングもしくは該透明トップコーティングのいずれか、またはこれら両方は、請求項6に記載の熱硬化性組成物から堆積される、多成分複合コーティング構成物。 - 前記トップコーティング(b)が、請求項6に記載の熱硬化性組成物を含むフィルム形成熱硬化性組成物から堆積される、請求項22に記載の多成分コーティング構成物。
- 多成分複合コーティング構成物であって、以下:
(a)着色フィルム形成組成物から堆積されたベースコーティング;および
(b)該ベースコーティング上に塗布される透明トップコーティング、
を含み、ここで、該ベースコーティングもしくは該透明トップコーティングのいずれか、またはこれら両方は、請求項17に記載の熱硬化性組成物から堆積される、多成分複合コーティング構成物。 - 前記透明トップコーティング(b)が、請求項17に記載の熱硬化性組成物から堆積される、請求項24に記載の多成分コーティング構成物。
- 多成分複合コーティング構成物であって、以下:
(a)プライマーコーティングであって、カソードおよびアノードを備える電気回路においてカソードとして機能する導電性基材を電気コーティングすることによって堆積され、該カソードおよびアノードは、水性電気コーティング組成物中に浸漬され、該電気コーティングは、該カソードとアノードとの間に電流を通過させて、該基材上に、実質的に連続なフィルムとして該電気コーティング組成物の堆積を引き起こすことによる、プライマーコーティング;
(b)該プライマーコーティング上に塗布されるベースコーティングであって、ここで、該ベースコーティングは、着色フィルム形成組成物から堆積される、ベースコーティング;ならびに
(c)該ベースコーティング上に塗布される透明トップコーティングであって、該ベースコーティングもしくは該透明トップコーティング、またはこれら両方は、請求項6に記載の熱硬化性組成物を含むクリアフィルム形成熱硬化性組成物から堆積される、透明トップコーティング、
を含む、多成分複合コーティング構成物。 - 前記トップコーティング(c)が、請求項6に記載の熱硬化性組成物から堆積される、請求項26に記載の多成分コーティング構成物。
- 多成分複合コーティング構成物であって、以下:
(a)プライマーコーティングであって、カソードおよびアノードを備える電気回路においてカソードとして機能する導電性基材を電気コーティングすることによって堆積され、該カソードおよびアノードは、水性電気コーティング組成物中に浸漬され、該電気コーティングは、該カソードとアノードとの間に電流を通過させて、該基材上に、実質的に連続なフィルムとして該電気コーティング組成物の堆積を引き起こすことによる、プライマーコーティング;
(b)該プライマーコーティング上に塗布されるベースコーティングであって、ここで、該ベースコーティングは、着色フィルム形成組成物から堆積される、ベースコーティング;ならびに
(c)該ベースコーティング上に塗布される透明トップコーティングであって、該ベースコーティングもしくは該透明トップコーティング、またはこれら両方は、請求項17に記載の熱硬化性組成物を含むクリアフィルム形成熱硬化性組成物から堆積される、多成分複合コーティング構成物。 - 前記トップコーティング(c)が、請求項17に記載の熱硬化性組成物から堆積される、請求項28に記載の多成分コーティング構成物。
- 前記(a)におけるプライマーコーティングが、塗布された後で、かつ、前記(b)におけるベースコーティングが、塗布される前に、プライマー表面が、該プライマーコーティング上に塗布される、請求項28に記載の多成分コーティング構成物。
- 前記プライマー表面が、スプレー塗布される、請求項30に記載の多成分コーティング構成物。
- 請求項22に記載の多成分複合コーティング構成物によりコーティングされた、基材。
- 請求項24に記載の多成分複合コーティング構成物によりコーティングされた、基材。
- 請求項26に記載の多成分複合コーティング構成物によりコーティングされた、基材。
- 請求項28に記載の多成分複合コーティング構成物によりコーティングされた、基材。
- 請求項30に記載の多成分複合コーティング構成物によりコーティングされた、基材。
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2007023300A (ja) * | 2002-02-15 | 2007-02-01 | Ppg Ind Ohio Inc | イソブチレン型モノマーの交互コポリマーを含有する熱硬化性組成物 |
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