JP5916008B2 - 高固形分防汚塗料組成物 - Google Patents
高固形分防汚塗料組成物 Download PDFInfo
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- JP5916008B2 JP5916008B2 JP2011240635A JP2011240635A JP5916008B2 JP 5916008 B2 JP5916008 B2 JP 5916008B2 JP 2011240635 A JP2011240635 A JP 2011240635A JP 2011240635 A JP2011240635 A JP 2011240635A JP 5916008 B2 JP5916008 B2 JP 5916008B2
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- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 4
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003450 sulfenic acids Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RJSZFSOFYVMDIC-UHFFFAOYSA-N tert-butyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C)C RJSZFSOFYVMDIC-UHFFFAOYSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- XNFIRYXKTXAHAC-UHFFFAOYSA-N tralopyril Chemical compound BrC1=C(C(F)(F)F)NC(C=2C=CC(Cl)=CC=2)=C1C#N XNFIRYXKTXAHAC-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- AKUNSPZHHSNFFX-UHFFFAOYSA-M tributyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC AKUNSPZHHSNFFX-UHFFFAOYSA-M 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Application Of Or Painting With Fluid Materials (AREA)
- Paints Or Removers (AREA)
Description
従来の技術に鑑みるに、代替となる高固形分の防汚組成物が依然として必要とされている。
上述したように、本発明は防汚塗料組成物に関する。この塗料組成物は2種以上の成分を含み、そのうちの一方はプレポリマー、特にはヒドロキシ官能性プレポリマーを含むベース成分であり、成分bは、硬化剤及び/又は硬化触媒、特には1種以上のポリイソシアネートを含む又はそれから成る。実用という観点からすると一般には好ましくはないものの、この塗料組成物は更なる成分を含み得る。塗料組成物のこの2種以上の成分は、以下でより詳細に説明するように、典型的には、塗料組成物を目的とする基体に塗布する直前に組み合わされ混合される。
塗料組成物のベース成分は、(i)少なくとも1つのアルコキシシリル官能基を有し並びに/又は(ii)硬化剤及び/若しくは硬化触媒(成分b)の存在下で硬化性であるプレポリマーを含み、このプレポリマーは、一般式(I):
−Si(OR)n(R)m
の基を意味すると意図され、式中、Rは直鎖又は分岐C1-6アルキル基(例えば、メチル、エチル、1−プロピル、2−プロピル、1−ブチル、イソブチル、tert−ブチル、シクロヘキシル等)であり、nは1〜3の整数であり、mは0〜2の整数であり、n+mは3である。
Y−(CH(RA)−CH(RB)−O)p−Z (III)
(式中、ZはC1-20アルキル基又はアリール基であり、Yはアクリロイルオキシ基、メタクリロイルオキシ基、マレイノイルオキシ基又はフマロイルオキシ基であり、RA及びRBは独立して水素、C1-20アルキル及びアリールから成る群から選択され、pは1〜25の整数である)の第2のモノマーBと組み合わせて含む。
塗料組成物は、硬化剤及び/又は硬化触媒を含む又はそれから成る成分bも含み、成分bは好ましくは1種以上のポリイソシアネートを含む。
Desmodur N3900(かつてのVP2410)、Bayer社(ドイツ)
Desmodur N3600、Bayer社(ドイツ)
Desmodur N3800、Bayer社(ドイツ)
Tolonate HDT−LV2、Rhodia社(フランス)
Desmodur N3390、Bayer社(ドイツ)
Tolonate HDT90、Rhodia社(フランス)
Basonat HI 190 B/S、BASF社(ドイツ)
Desmodur N75、Bayer社(ドイツ)
Bayhydur VP LS 2319、Bayer社(ドイツ)
Tolonate IDT 70B、Rhodia社(フランス)
Desmodur H、Bayer社(ドイツ)
Desmodur L67 BA(Bayer Material Science社)
Desmodur E21(Bayer Material Science社)
Desmodur VL(Bayer Material Science社)
Voratron EC 112(Dow Chemicals社)
Desmodur E23(Bayer Material Science社)
Desmodur E 1660(Bayer Material Science社)
Suprasec 2495(Huntsman Advanced Materials社)
本発明のベース成分は通常、塗料組成物(塗料)を製造するための慣用の装置(ボールミル、パールミル、スリーロールミル、ハイスピードディスパーサー等)を使用して上記の成分を一度に全て又は分割して混合及び分散することによって調製される。本発明のベース成分は(任意で繊維を含む)、バッグフィルタ、パトロンフィルタ、ワイヤギャップフィルタ、ウェッジワイヤフィルタ、メタルエッジフィルタ、EGLMターノクリーン(turnoclean)フィルタ(Cuno社)、DELTAストレインフィルター(Cuno社)及びJenagストレイナフィルタ(Jenag社)を使用して又は振動濾過によって濾過され得る。塗布前に、ベース成分は成分bと混合される。促進剤が別個の成分として提示される場合、ベース成分は、塗布に先立って成分b及び1種以上の促進剤と混合される。
本発明は更に、表面の少なくとも一部に本明細書で定義の防汚塗料組成物の塗膜を有する海洋構造物に関する。この海洋構造物には、塗料組成物が1層又は数層、特には連続層でコーティングされ得る。
好ましい一実施形態において、塗料組成物全体は(すなわち、ベース成分及び成分b)、少なくとも40%、例えば少なくとも50%、例えば60〜99%、80〜100%、更には70〜98%又は85〜100%の固形分質量比を有する。
「酸価」は、1グラムのポリマー(例えば、プレポリマー)の中和に必要な水酸化カリウム(KOH;Mw=56.1g/mol)のミリグラム数(mg)として定義される。本発明の目的において、酸価は、シリル基が加水分解で除去されてシリルエステル基の代わりに遊離酸性基を有するプレポリマーに関係する。
ヒドロキシ価(OHV)は原則的に酸価と同じやり方で計算され、ポリマー(例えば、プレポリマー(非加水分解))1グラムあたりのヒドロキシル含有量に等しいKOHのミリグラム数を表し、すなわち単位「mgKOH/g(固形分)」となる。
直径1mの円筒形ドラムの曲率に対応する曲率を有するステンレススチール製の試験板(13.5x7cm2)にまず150μm(DFT)のエポキシプライマー(Hempadur Primer 45141、Hempel A/S社)をコーティングする。24時間後、その試験板に、エアスプレー塗装により100μm(DFT)の市販のエポキシタイコート(HEMPADUR 45182、Hempel A/S社)をコーティングする。
試験板を直径1mの円筒形ドラムの凸面に固定し、海水中で回転させる。海水の塩分は、北緯34度東経134度に位置する日本の直島の試験場で、平均温度24℃で31〜35ppthの範囲である。
試験板を直径1mの円筒形ドラムの凸面に固定し、海水中で回転させる。海水の塩分は、北緯41.13度東経1.43度に位置するスペイン北東部のヴィラノヴァ・イ・ラ・ジェルトル(Vilanova i la Geltru)の試験場で、平均温度17〜18℃で37〜38ppthの範囲である。
塗膜の接着を促進するために片面にサンドブラスト加工を施したアクリル製試験板(10x45cm2)にまず、エアスプレー塗装により市販のビニルタールプライマー(Hempanyl 16280、Hempel’s Marine Paints A/S社)を80ミクロン(DFT)でコーティングする。室温の実験室での最低でも24時間の乾燥後、試験塗料をエアスプレー塗装でDFT90〜100ミクロンで塗布する。少なくとも72時間に亘る乾燥後、試験板をラックに固定し、海水に浸漬する。
研磨及び浸出特性を、Kiilらが記載の回転装置と同様の回転装置を使用して測定する(Kiil,S,Weinell,CE,Yebra,DM,Dam−Johansen,K,“Marine biofouling protection:design of controlled release antifouling paints.”In:Ng,KM,Gani,R,Dam−Johansen,K(eds.)Chemical Product Design;Towards a Perspective Through Case Studies,23IDBN−13:978−0−444−52217−7.Part II(7),Elsevier.(2006))。この装置はロータリーリグから成り、2個の同心円状のシリンダを有し、内方シリンダ(ロータ、直径0.3m、高さ0.17m)は回転可能である。このシリンダ対を約400〜500リットルの人工海水が入ったタンクに浸漬する。
試験板の準備
アクリル板(155x100x5mm)にまず、エアスプレー塗装により市販のビニルタールプライマー(Hempanyl 16280、Hempel´s Marine Paints社)を80pm(乾燥膜厚、DFT)でコーティングする。室温の実験室での最低でも24時間の乾燥後、防汚塗料(モデル塗料又は市販の塗料)を、ドクターブレードアプリケータ(間隙サイズ:500μm)を使用して塗布する。試験前に、アクリル板を最低でも7日間に亘って室温の実験室で乾燥させる。
試験板を、クリーブランド結露試験機(QCT、Q−Panel社)において結露及びドライオフモードで試験する。QCT試験機は、ASTM標準試験法DI735−92に記載されている(霧状の水を発生させる装置を使用して塗膜の耐水性を試験する)。コーティングを施した試料を密閉したチャンバ内に置き、霧状の水の噴霧(8時間)/乾燥(4時間)のサイクルに供する。チャンバ内の温度は60℃に維持される。霧状の水を噴霧している間、水は塗膜内に浸透し、乾燥中、水は塗膜から「抜ける(escape)」。
プレポリマー1〜13のプレポリマー合成の手順:モノマー(トリイソプロピルシリルアクリレート、メチルメタクリレート、ブチルアクリレート、2−ヒドロキシエチルメタクリレート、メトキシエチルアクリレート)、アゾビス−メチルブチロニトリル及びキシレンのプレミックスを規定の割合(表1を参照のこと)で調製し、攪拌機、還流凝縮器、窒素注入口及びプレミックス供給口を備えた温度制御反応槽に装入した。反応槽を加熱し、125℃で維持し、プレミックスを反応槽に一定速度で4時間に亘って窒素雰囲気下で装入した。更に30分後、開始剤及びキシレンのプレミックスを反応槽に一定速度で1時間に亘って装入した。更に30分後、反応槽の温度を低下させた。
モデル塗料1〜28及び参考塗料1(表2を参照のこと)を、以下の手順に従って調製した。各ケースにおいて、モデル塗料を、全原材料(ベース成分)をガラスビーズの入った閉鎖された缶内で30分間に亘って混合及び粉砕することによって調製した。得られた粒度は約50μmであった。
研磨率及び浸出率を、本明細書で定義される試験方法に従って本発明のモデル塗料配合物について求めた。結果を表3、表4及び表5に示す。
本発明のまた別の態様は、以下のとおりであってもよい。
〔1〕自己研磨型防汚塗料組成物であって、
(a)(i)少なくとも1つのアルコキシシリル官能基を有し並びに/又は(ii)硬化剤及び/若しくは硬化触媒(成分b)の存在下で硬化性であるプレポリマーを含むベース組成物であって、前記プレポリマーが、一般式(I):
(b)硬化剤及び/若しくは硬化触媒を含む又はそれから成る成分bと
を含むことを特徴とする、前記組成物。
〔2〕前記一般式(I)の末端基が、一般式(II):
〔3〕前記プレポリマーが少なくとも1つのヒドロキシ官能基を更に有する、前記〔1〕〜〔2〕のいずれかに記載の組成物。
〔4〕前記硬化剤及び/又は硬化触媒が1種以上のポリイソシアネートを含む、前記〔1〕〜〔3〕のいずれかに記載の塗料組成物。
〔5〕前記1種以上のポリイソシアネートのイソシアネート当量が50〜3000の範囲である、前記〔4〕に記載の組成物。
〔6〕(a)一般式I:
(b)1種以上のポリイソシアネートを含む硬化剤と
を含む、前記〔1〕〜〔5〕のいずれかに記載の組成物。
〔7〕前記プレポリマーのヒドロキシ価が5〜300mgKOH/g(固形分)の範囲である、前記〔3〕〜〔6〕のいずれかに記載の組成物。
〔8〕シリルエステル基の完全な加水分解後の前記プレポリマーの酸価が5〜500mgKOH/g(固形分)の範囲である、前記〔1〕〜〔7〕のいずれかに記載の組成物。
〔9〕前記プレポリマーの重量平均分子量が1,000〜120,000g/molの範囲である、前記〔1〕〜〔8〕のいずれかに記載の組成物。
〔10〕前記プレポリマーのガラス転移温度T g が−10〜100℃の範囲である、前記〔1〕〜〔9〕のいずれかに記載の組成物。
〔11〕全体で少なくとも40%の固形分質量比を有する、前記〔1〕〜〔10〕のいずれかに記載の組成物。
〔12〕前記プレポリマーが少なくとも1つのアルコキシシリル官能基、及び少なくとも1つの一般式(I)の末端基を有する少なくとも1つの側鎖を有する、前記〔1〕〜〔11〕のいずれかに記載の組成物。
〔13〕本明細書で定義の研磨率試験に従って求められる研磨率が10000海里あたり少なくとも1μmである、前記〔1〕〜〔12〕のいずれかに記載の組成物。
〔14〕前記〔1〕〜〔13〕のいずれかで定義の防汚塗料組成物を含むキットであって、
第1容器にベース成分が、第2容器に成分bが入っていることを特徴とする、キット。
〔15〕防汚塗料組成物用のベース成分であって、
一般式I:
前記プレポリマーのヒドロキシ価が2〜400mgKOH/g(固形分)の範囲であるベース成分を含む
ことを特徴とする、ベース成分。
〔16〕前記〔1〕〜〔13〕のいずれかに記載の防汚塗料組成物から形成される塗膜をその表面の少なくとも一部に有する海洋構造物。
〔17〕構造物をコーティングする方法であって、
構造物の少なくとも一部に前記〔1〕〜〔12〕のいずれかで定義の防汚塗料組成物の層を塗布する工程を含むことを特徴とする、方法。
〔18〕前記層が多層塗膜系の最終層である、前記〔17〕に記載の方法。
Claims (14)
- 自己研磨型防汚塗料組成物であって、
(a)(i)少なくとも1つのアルコキシシリル官能基を有し並びに/又は(ii)硬化剤及び/若しくは硬化触媒(成分b)の存在下で硬化性であるプレポリマーを含むベース成分であって、前記プレポリマーが、一般式(I):
前記プレポリマーのヒドロキシ価が2〜400mgKOH/g(固形分)の範囲である、前記ベース成分と、
(b)1種以上のポリイソシアネートを含む、硬化剤及び/若しくは硬化触媒を含む又はそれから成る成分bと
を含むことを特徴とする、前記塗料組成物。 - 前記1種以上のポリイソシアネートのイソシアネート当量が50〜3000の範囲である、請求項1又は2のいずれかに記載の塗料組成物。
- 前記プレポリマーのヒドロキシ価が5〜300mgKOH/g(固形分)の範囲である、請求項1〜3のいずれかに記載の塗料組成物。
- シリルエステル基の完全な加水分解後の前記プレポリマーの酸価が5〜500mgKOH/g(固形分)の範囲である、請求項1〜4のいずれかに記載の塗料組成物。
- 前記プレポリマーの重量平均分子量が1,000〜120,000g/molの範囲である、請求項1〜5のいずれかに記載の塗料組成物。
- 前記プレポリマーのガラス転移温度Tgが−10〜100℃の範囲である、請求項1〜6のいずれかに記載の塗料組成物。
- 全体で少なくとも40%の固形分質量比を有する、請求項1〜7のいずれかに記載の塗料組成物。
- 前記プレポリマーが少なくとも1つのアルコキシシリル官能基、及び少なくとも1つの一般式(I)の末端基を有する少なくとも1つの側鎖を有する、請求項1〜8のいずれかに記載の塗料組成物。
- 請求項1〜9のいずれかで定義の防汚塗料組成物を含むキットであって、
第1容器にベース成分が、第2容器に成分bが入っていることを特徴とする、キット。 - 請求項1〜9のいずれかに記載の防汚塗料組成物から形成される塗膜をその表面の少なくとも一部に有する海洋構造物。
- 構造物をコーティングする方法であって、
構造物の少なくとも一部に請求項1〜9のいずれかで定義の防汚塗料組成物を塗布する工程を含むことを特徴とする、方法。 - 前記防汚塗料組成物から形成された塗膜が多層塗膜系の最終層である、請求項13に記載の方法。
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