TW201333126A - 可固化塗料組合物 - Google Patents
可固化塗料組合物 Download PDFInfo
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- TW201333126A TW201333126A TW102102107A TW102102107A TW201333126A TW 201333126 A TW201333126 A TW 201333126A TW 102102107 A TW102102107 A TW 102102107A TW 102102107 A TW102102107 A TW 102102107A TW 201333126 A TW201333126 A TW 201333126A
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- curable coating
- coating composition
- curing agent
- resin
- thiol
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- 239000008199 coating composition Substances 0.000 title claims abstract description 64
- 238000000576 coating method Methods 0.000 claims abstract description 86
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- 239000011248 coating agent Substances 0.000 claims abstract description 74
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 66
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- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 49
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/04—Epoxynovolacs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/66—Mercaptans
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
-
- C—CHEMISTRY; METALLURGY
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Abstract
本發明係關於一種可固化塗料組合物，其包含：(a)可固化塗料樹脂，其包含硫醇反應基，(b)用於可固化塗料樹脂之巰基化降冰片烯固化劑，該巰基化降冰片烯固化劑包含平均至少1.0個硫醇基/分子，及(c)用於促進該可固化塗料樹脂上之硫醇反應基與該巰基化降冰片烯固化劑上之硫醇基間之反應之促進劑。此等塗料組合物可在環境溫度下固化，並提供一種僅在數小時後即可在上面行走之經塗佈之表面。該等塗料組合物通常具有低於250 g/L之VOC。可將該等塗料組合物用於保護大型鋼結構，諸如船隻、建築物、橋樑、工業廠房及石油生產裝置。
Description
本發明係關於一種可固化塗料組合物。此等組合物通常包含樹脂、用於該樹脂之固化劑、及視情況之用於固化反應之觸媒，視情況連同溶劑、顏料及填充劑及提供所需最終使用性能所必須之其他添加劑。當要在環境溫度條件下儲存及使用此等可固化塗料組合物時，通常需分開包裝樹脂及固化劑。所謂環境溫度，吾人意指不對塗料採用人工加熱，且該塗料一經塗佈後即在當時環境條件下固化。可視需要在最適宜包裝中併入其他成份。在將塗料塗佈至基板前不久混合該兩種包裝，尤其係若該塗料需要快速固化時。
一般而言，活化期(亦即在塗料黏度之增加超過可噴射稠度內之時間)需盡可能地長，而該塗料在基板上固化所耗費時間需盡可能地短。在實踐中，若塗料在此過程中迅速固化，則一般不會採用此種噴塗試驗來確定活化期，以免噴塗設備受到損毀。取而代之地，活化期通常係作為反應塗料組合物在環境溫度或所欲溫度範圍下黏度加倍之時間來測量。
環境溫度固化塗料尤其被用於塗佈無法便捷地在建造期間及後續維護期間進行加熱之大型結構，例如船隻、建築物、橋樑、工業廠房及石油生產裝置。塗佈塗料之環境溫度可根據季節及地點而在0℃
或更低至25℃或更高之間變化。需要可利用非專家單一組件進行塗佈，且在25℃下具有相當長活化期(諸如至少半小時或更長)，但將在基板上固化至甚至在0℃或更低溫度下，在一天或更短(較佳8小時或更短)時間內可於其上行走而不會對塗料造成實質損傷之程度的塗料。
在本申請案中，活化期為反應塗料組合物在環境溫度(25℃)下黏度加倍之時間。
根據本發明之第一態樣，提供一種可固化塗料組合物，其包含：(a)可固化塗料樹脂，其包含硫醇反應基，(b)用於使該可固化塗料樹脂固化之巰基化降冰片烯固化劑，該巰基化降冰片烯固化劑包含至少1.0個硫醇基/分子，及(c)用於促進該可固化塗料樹脂上之硫醇反應基與該巰基化降冰片烯固化劑上之硫醇基間之反應之促進劑。
有利地，可固化塗料組合物可具有小於或等於250 g/公升之VOC。
巰基化降冰片烯固化劑之硫醇基之當量數(b)對可固化塗料樹脂之硫醇反應官能基之當量數(a)之比例[(b)/(a)]可在0.5至2.0之範圍內。
在本申請案之框架內，「塗料樹脂」為當塗佈至基板時，其本身或與巰基化降冰片烯固化劑之組合能形成連續薄膜層之樹脂或樹脂混合物。
在本申請案之框架內，應將提及降冰片烯視為係指包含降冰片烯基團之化合物類別。下圖顯示降冰片烯基團。
其中R1至R10可為H、C1至C10烷基(飽和或不飽和、含官能團或
無官能團)、芳基、芳烷基(飽和或不飽和、含官能團或無官能團)、羥基、羧基、醛、胺基或烷基化烷氧基矽烷。若不存在R6與R8(或R5與R7)，則得到降冰片二烯。Q可為碳、氮或氧。當Q=氧時，不存在R9與R10，而當Q=氮時，不存在R10。為清楚起見，不應將術語降冰片烯視為特定指代二環[2.2.1]庚-2-烯(其有時被稱為降冰片烯，且係當R1=R2=R3=R4=R5=R6=R7=R8=R9=R10及Q=碳時得到)。應注意，二環[2.2.1]庚-2-烯為上述降冰片烯類之一成員。在本申請案之框架內，將降冰片二烯視為降冰片烯類之成員。
如本文進一步所述，應將按照本發明之巰基化降冰片烯固化劑視為係指已經巰基化之降冰片烯。
一經巰基化後，巰基化降冰片烯固化劑在降冰片烯之雙環中僅具有低水平之殘餘不飽和性，其如下圖所描繪係實質上飽和。
巰基化降冰片烯固化劑包含一個(及有時二或更多個)巰基化降冰片烯基團。巰基化降冰片烯固化劑包含平均超過一個硫醇基，及平均少於一個烯烴鍵。
促進劑為在塗佈及形成連續薄膜層過程期間，當添加至可固化塗料組合物時，或當藉由使所添加促進劑與該可固化塗料組合物之其他組分進行化學相互作用而於原位形成時，可促進塗料樹脂與巰基化降冰片烯間之化學反應的化合物或化合物之混合物。使用促進劑之目的在於促進可固化塗料樹脂上之硫醇反應基與巰基化降冰片烯固化劑上之硫醇基間之反應。
在WO 00/22025中，揭示環境溫度可固化塗料組合物，其包含環氧樹脂、用於該環氧樹脂之巰基官能固化劑及觸媒。除此之外，此等組合物亦包含短效延遲劑，其可抑制組合物於主體中之固化。較佳不
使用短效延遲劑，因其通常係揮發性液體有機化合物。於此公開案中並未提及巰基化降冰片烯化合物。
在US3553283中，揭示可固化塗料組合物，其包含環氧樹脂、用於該環氧樹脂之巰基官能固化劑及觸媒。此等組合物之所有實例皆包含高含量之有機溶劑。使用高含量之溶劑甚為不佳，且根據此文件之塗料組合物一般具有超過250 g/l之VOC。由於環境及持續性的原因，明確需要具有低於250 g/l之VOC之塗料。於此公開案中並未提及巰基化降冰片烯化合物。
GB 1352527係關於某些聚(S-縮水甘油基)化合物、其合成及此等聚(S-縮水甘油基)化合物在各種應用中(尤其係在塗料及塗漆中)之用途。於此公開案中並未提及巰基化降冰片烯化合物。
EP1477511揭示一種可固化組合物，其包含具有巰基及烯反應組分之化合物。各反應組分(烯及巰基)之官能度必須平均大於一，且全部官能度較佳為四或更高。EP1477511之組合物係經設計，以使烯及巰基反應組分能夠彼此交聯。相對地，本發明之巰基化降冰片烯固化劑並非經設計為與自身交聯，而是與另一包含硫醇反應基之可固化塗料樹脂交聯，以形成塗料。
WO95/00869揭示一種UV可固化組合物，其包含含有超過2個硫醇基/分子之多硫醇、末端為二降冰片烯之聚四亞甲基氧化物聚合物及光引發劑。未提及按照本發明之巰基化降冰片烯固化劑，該巰基化降冰片烯固化劑係用以固化另一可固化塗料樹脂。
已發現，按照本發明之塗料組合物提供許多益處，諸如在高固體調配物中在低溫下之短乾燥時間，同時仍維持可接受的活化期、在未著色(及著色)塗料調配物中之良好耐腐蝕性、在浸漬下對鋼之良好黏著性、以及可接受的氣味、及低成本。
根據本發明之組合物中之塗料樹脂可選自包括下列之群：烯烴
樹脂、不飽和聚胺基甲酸酯樹脂、烯烴-官能樹脂、環硫樹脂、環氧樹脂、環氧丙烷樹脂、異氰酸酯樹脂、醇酸樹脂、不飽和聚酯樹脂、不飽和丙烯酸系樹脂、具有α,β-不飽和羰基之樹脂、苯并噁嗪樹脂、伸乙亞胺樹脂、氮雜環丁烷樹脂、炔樹脂、鹵素官能樹脂、巰基官能樹脂及包含任何以上官能團之聚硫樹脂。在適當時可使用樹脂混合物，且將術語「塗料樹脂」視為適用於單一樹脂系統或混合樹脂系統。塗料樹脂亦可包含具有以上官能團之化合物，例如，三羥甲基丙烷三丙烯酸酯或新戊四醇三烯丙基醚。
在一實施例中，塗料樹脂為環氧樹脂、環氧樹脂之混合物或者一或多種環氧樹脂與任何其他上述樹脂之混合物。環氧樹脂為一般包含約2或更多個1,2-環氧基/分子之聚環氧化合物。Y.Tanaka在C.A.五月版Epoxy Resins Chemistry and Technology(Marcel Dekker,1988)之「Synthesis and Characteristics of Epoxides」中，以及H Lee及K Neville在「Handbook of Epoxy Resins」(McGraw-Hill,1967,1982年再發證)中描述此等環氧化物，其以引用的方式併入。適宜環氧樹脂之實例為雙酚之縮水甘油醚(諸如雙酚A、雙酚F或雙酚S之二縮水甘油醚)或雙酚之縮合或伸展縮水甘油醚。此等衍生自雙酚之縮水甘油醚通常具有2或稍小之環氧官能度，例如，1.5至2。或者，環氧樹脂可為多元酚之縮水甘油醚，例如環氧酚醛樹脂，在此情況中，環氧官能度通常大於2。環氧樹脂亦可為胺或胺基苯酚之縮水甘油衍生物，例如二縮水甘油基苯胺、四縮水甘油基間二甲苯二胺、四縮水甘油基二胺基二苯基甲烷、對胺基苯酚之三縮水甘油化合物或間胺基苯酚之三縮水甘油化合物。可利用根據本發明之固化劑固化之環氧樹脂之其他實例包括脂族環氧樹脂(諸如氫化雙酚A環氧樹脂及氫化縮合之雙酚之縮水甘油醚)、間苯二酚二縮水甘油醚、多元醇之聚縮水甘油醚(諸如三羥甲基丙烷三縮水甘油醚、新戊四醇四縮水甘油醚、二新戊四醇聚
縮水甘油醚、丁二醇二縮水甘油醚及己二醇二縮水甘油醚)、山梨糖醇縮水甘油醚、環氧化油(諸如植物油或堅果油)、衍生自烯烴之環氧化合物(諸如二環氧辛烷、環氧化環十二碳三烯及環氧化聚丁二烯)。其他環氧化物包括異氰尿酸三縮水甘油酯、縮水甘油基三嗪及縮水甘油基胺基甲酸酯。亦可使用環氧化硫醇(諸如本發明巰基化降冰片烯固化劑與表氯醇之反應產物)或環氧化聚硫樹脂。亦可使用環氧官能矽氧烷，諸如縮水甘油氧基丙基三乙氧基矽烷、縮水甘油氧基丙基三甲氧基矽烷及其縮合物。亦可使用縮水甘油酯，諸如(甲基)丙烯酸縮水甘油酯、二縮水甘油基對苯二甲酸酯及三縮水甘油基偏苯三酸酯之(共)聚合物，但並非較佳。當塗料樹脂為環氧樹脂時，若需更進一步減少塗料之溶劑含量，則亦可在樹脂中併入一定量環氧官能稀釋劑。此等環氧稀釋劑之實例包括(但不限於)丁基縮水甘油醚、己基縮水甘油醚、2-乙基己基縮水甘油醚、苯基縮水甘油醚、4-第三丁基苯基縮水甘油醚、甲苯酚基縮水甘油醚、腰果酚(cardanol)縮水甘油醚、乙二醇二縮水甘油醚、丁二醇二縮水甘油醚、己二醇二縮水甘油醚、環己烷二甲醇二縮水甘油醚、新戊二醇二縮水甘油醚、氫化雙酚A二縮水甘油醚及山梨糖醇聚縮水甘油醚。
塗料樹脂可視情況作為含於適宜溶劑中之溶液供應。
塗料樹脂與固化劑較佳係分開包裝，並在將塗料塗佈至基板前不久進行混合，以容許本發明之可固化塗料組合物在環境溫度條件下迅速固化。
根據本發明之可固化塗料組合物亦包含促進劑。促進劑通常將與本發明之固化劑包裝在一起，但此可有所不同。適宜促進劑為胺化合物或胺化合物之混合物，例如第三胺。適宜的第三胺包括N,N-二甲基苯胺、吡啶及其衍生物、喹啉及其衍生物、N,N-二甲基苄胺、N,N-二乙基苄胺、三甲胺、三乙胺、三異丙胺、三丁胺、二氮雜二環辛烷
(三伸乙基二胺，DABCO)、四甲基胍、椰油基二甲胺、N-甲基嗎啉、N-甲基六氫吡啶、N,N'-二甲基六氫吡嗪、N-甲基吡咯啶、N,N-二甲基胺基丙胺、N,N-二乙基胺基丙胺、2,4,6-參(二甲基胺基甲基)苯酚、2,4-雙(二甲基胺基甲基)苯酚、2,6-雙(二甲基胺基甲基)苯酚、2-二甲基胺基甲基苯酚、4-二甲基胺基甲基苯酚、2,4,6-參(二甲基胺基甲基)苯酚與N,N-二甲基胺基丙胺或N,N-二乙基胺基丙胺之反應產物、N-甲基-咪唑、2-乙基-4-甲基咪唑、1,5,7-三氮雜二環[4.4.0]癸-5-烯、7-甲基-1,5,7-三氮雜二環[4.4.0]癸-5-烯、二氮雜二環十一碳烯、金雀花鹼(sparteine)、參[2-(二甲基胺基)乙基]胺、五甲基二伸乙基三胺及其混合物，視情況與其他胺組合。亦可使用第二或甚至第一胺，諸如六氫吡啶或間二甲苯二胺。
或者，可將膦鹼(諸如三苯基膦)或醇用作根據本發明之塗料組合物中之適宜促進劑。醇之實例包括苄醇或正丁醇。亦可使用胺基醇，諸如N,N-二甲基乙醇胺、三乙醇胺、三-異丙醇胺、2-羥乙基六氫吡嗪、雙(2-羥乙基)六氫吡嗪或羥乙基六氫吡啶。應將術語促進劑視為適用於單一促進劑系統或促進劑之混合物。
本發明之塗料組合物尤其適於無法實施熱固化之情況。例如，其極其適合作為用於大型結構(諸如船隻、建築物、橋樑、工業廠房及石油生產裝置)之塗料組合物，其中不可能對塗料及/或基板施加額外加熱。該可固化組合物適於在低於40℃，及尤其低於25℃，或甚至低於10℃下至-5℃、-10℃或甚至-20℃之溫度下固化。該組合物通常在10℃下(及通常在0℃下)迅速地充分硬化，以便在塗佈後24小時內可於一層厚度通常為100-400 μm之薄膜上行走，且通常在塗佈後8小時內不會對該薄膜造成顯著損傷。因此，該可固化組合物適於在寒冷條件或氣候中塗佈及形成薄膜。
或者，本發明之可固化塗料組合物可在高溫下固化，例如在40
至50℃上至100或130℃之溫度範圍，或若要求極其迅速地固化則甚至更高。
根據本發明之可固化塗料組合物可具有在0至340 g/l之範圍內，較佳更小在0至250 g/l之範圍內，甚至更佳在0至200 g/l之範圍內之VOC。可根據EPA Federal Method 24來確定塗料組合物之VOC。當塗料樹脂係作為含於適宜溶劑中之溶液供應時，可加入至可固化塗料組合物之溶劑之量可減少存在於塗料樹脂溶液中之量，以確保可固化塗料組合物滿足所指定之VOC範圍。
可固化塗料組合物可包含一或多種其他成份，諸如一或多種顏料。適宜顏料之實例為二氧化鈦(白色顏料)、彩色顏料(諸如黃色氧化鐵及紅色氧化鐵)、酞菁顏料、補強顏料(諸如雲母氧化鐵及結晶二氧化矽)、防鏽顏料(諸如金屬鋅、磷酸鋅、矽灰石、鉻酸鹽、鉬酸鹽及膦酸鹽)及填充顏料(諸如重晶石、滑石及碳酸鈣)。組合物亦可包含一或多種屏蔽顏料(諸如玻璃薄片、鋁薄片或雲母)及增稠劑(諸如微粒二氧化矽、膨潤土、氫化蓖麻油或聚醯胺蠟。組合物亦可包含一或多種增塑劑、顏料分散劑、穩定劑、助流劑或稀釋溶劑。
根據本發明之可固化塗料組合物可用作底漆塗料及/或飾面塗料組合物。因此，本發明之一態樣為包含如本文所述組分之底漆塗料及/或飾面塗料組合物。
本發明之另一態樣為藉由將包含如本文所述之組分之塗料組合物塗佈至基板，以形成可固化塗覆層，接著使該可固化塗覆層固化，以於該基板上形成塗層所製備得的(底漆及/或飾面)塗料。
此等底漆塗料組合物尤其適於鋼表面(例如在橋樑、管道、工業廠房或建築物、石油及天然氣裝置或船隻之建造中)且較佳係在環境溫度條件下固化。此等底漆塗料組合物可用作不完美表面(諸如老化磨蝕鋼鐵或「薑(ginger)」(已經磨蝕且在小地方開始生銹之鋼)、手工
製風化鋼鐵及老化塗層)之維護及修復塗料。可於底漆塗料組合物上塗佈之飾面塗料包括醇酸樹脂及其他聚酯塗料、環氧塗料、聚胺基甲酸酯塗料、聚矽氧烷塗料、防污黏結層(tie-coat)系統、防污塗料、熱塑性乙烯基塗料及丙烯酸系塗料。此等飾面塗料可係溶劑型、無溶劑型或水性。
可將飾面塗料組合物塗佈於各種底漆塗料上，包括根據本發明之底漆。其他底漆塗料包括(例如)無機矽酸鋅或有機富鋅矽酸鹽底漆及含鋅金屬、防腐蝕性、金屬薄片或屏蔽顏料之有機(例如環氧樹脂)底漆。亦可將飾面塗料組合物直接塗佈於鋁或鋅「金屬噴鍍」塗層上，或鍍鋅鋼、不鏽鋼、鋁或塑料表面(諸如玻璃纖維增強聚酯或聚酯凝膠塗層)上。可將固化劑(例如)用於塗佈在建築物、鋼結構、汽車、飛機及其他車輛及一般工業機械及配件上之飾面塗料組合物中。飾面塗料組合物可係有色，或其可係透明(無色)組合物，尤其係在汽車或遊艇上。可將塗料組合物直接塗佈至所製備的碳鋼作為底漆/飾面。
可藉由任何適宜方法來製備巰基化降冰片烯固化劑。所謂降冰片烯，吾人係指包含降冰片烯基團之化合物類別。術語降冰片烯亦意指所有異構形式，包括所有幾何及立體異構體，例如5-外-乙烯基降冰片-2-烯。
一種製造方法與GB 1352527中所述之方法類似，其中巰基化降冰片烯化合物可藉由使母體降冰片烯化合物與式R'COSH之硫羥酸反應來製備，其中R'表示脂族或芳族基團。在此反應後，利用任何適宜方法使R'CO-基團在水解階段中被氫替代。US 3984456中描述一種方法，其中利用過量氫氧化鈉使硫酯產物在水中沸騰三小時。以鹽酸進行酸化後，藉由萃取至醚中，接著藉由蒸餾移除溶劑來分離硫醇產物。可將關於製備巰基化降冰片烯2-巰乙基降冰片烷硫醇之此方法示
意如下：
另一方法為在自由基引發劑存在下使用過量硫化氫(H2S)。可將關於製備1-巰乙基降冰片烷硫醇之此方法示意如下：
術語「巰基化降冰片烯」包括該物質之所有異構形式，包括所有幾何、立體異構及對映異構形式，無論是否為消旋性。亦可同等地使用術語「硫醇化的降冰片烯」。適宜作為用於製備巰基化降冰片烯化合物之起始材料之降冰片烯化合物之實例包括
- 5-乙烯基-降冰片-2-烯
- 5-亞乙基降冰片-2-烯
亦可將此等材料統稱為巰基化乙烯基降冰片烯或者硫醇化乙烯基降冰片烯。
存在許多其他可用以製備適於硫醇化反應之不飽和降冰片烯之方法。例如，環戊二烯與多官能親二烯體(諸如亞甲基雙丙烯醯胺、1,3,5-三丙烯醯基六氫-1,3,5-三嗪、1,4-苯并醌或馬來酸酐)之狄爾斯-阿爾德反應(Diels Alder reaction)將產生適宜降冰片烯。在狄爾斯-阿爾德反應中使用呋喃或官能呋喃亦可產生適用於硫醇化反應之側氧基-降冰片烯。同樣地，多官能丙烯酸酯亦將產生多官能降冰片烯。
由於降冰片烯不飽和之反應性，有可能使降冰片烯之烯烴鍵直接與元素硫反應，產生三硫環戊烷。三硫環戊烷之後續還原作用將產生作為鄰二硫醇之巰基化降冰片烯，如下所示：
可藉由習知技術使5-乙烯基-降冰片烯之三硫環戊烷聚合，產生多官能三硫環戊烷，接著可將其還原，形成更高度官能之巰基化降冰片烯。
在本申請案之框架內，降冰片二烯亦屬於降冰片烯之類別內，且其自身亦可輕易地藉由任何適宜技術來硫醇化。例如，在與元素硫之反應中，降冰片二烯自身將產生雙(三硫環戊烷)，其經還原將產生如下之四硫醇。
其他可用以形成巰基化降冰片烯之降冰片烯基質包括具有除烯烴基外之官能基的降冰片烯，例如5-降冰片烯-2-甲醇、5-降冰片烯-2,2-二甲醇、5-降冰片烯-2-醇、5-降冰片烯-2-羧酸、5-降冰片烯-2,3-二羧酸及5-降冰片烯-2-羧醛。所有此等物質可經由非烯烴官能團以任何適宜方式反應形成適於硫醇化反應以形成巰基化降冰片烯固化劑之更高度官能之降冰片烯。
據信，取決於反應條件及硫醇化劑對降冰片烯化合物之莫耳比，所得巰基化降冰片烯可具有超過一個/分子之平均硫醇官能度，較佳大約兩個/分子或更多，其取決於存在於降冰片烯化合物上之可硫醇化基團之數目。
巰基化降冰片烯固化劑包含平均(意指數量平均)至少1.0個硫醇基/分子，較佳超過1.0，更接近2.0個硫醇基/分子(例如1.5至2.5個硫醇基/分子或1.8至2.2個硫醇基/分子)。
不希望受理論約束，此平均值來自作為不含硫醇官能之化合物、單硫醇化合物及所有許多可在反應期間形成之可能異構體(例如，二硫醇/三硫醇官能化合物或具有較高官能度之化合物)之混合物之固化劑。平均硫醇官能度為固化劑之平均分子量對硫醇當量重之比例。
為確保巰基化降冰片烯固化劑具有超過1.0之平均硫醇官能度及低於1.0之平均烯烴官能度，在第一步驟中使較諸存在的總不飽和度過量之硫醇化劑與降冰片烯反應，接著藉由以任何適宜方法移除過量硫醇化劑而分離最終產物。
出人意料地，頃發現，諸如彼等上文所給定之巰基化降冰片烯固化劑之組合物雖然具有典型的硫醇型氣味，但此氣味之強度不及其他具有類似分子量之硫醇。含該固化劑之塗料組合物之氣味之強度不至於阻礙該物質被使用在開放、無法提取的區域中，諸如可於製造工廠或造船廠中所見者。
若需要較高分子量之巰基化降冰片烯固化劑，則一種可藉以製得其等之方法係藉由選擇降冰片烯與任何試劑之適宜比例，及用於進行降冰片烯之硫醇化反應之反應條件，並允許發生一定程度之寡聚合反應。此等較高分子量之巰基化降冰片烯可能具有降低的氣味。
或者，較高分子量之巰基化降冰片烯固化劑可藉由與任何可與巰基化降冰片烯固化劑之硫醇基起反應之化合物加合而製得。此等化合物將具有與彼等上文給定之塗料樹脂之清單中者相同的官能團。雖然可使巰基化降冰片烯與僅具有1個官能團之化合物加合，並得到較高分子量之巰基化降冰片烯固化劑，但此種加合作用將具有降低固化劑之硫醇官能度之效應。雖然並不排除單官能加合化合物，但加合化合物較佳具有超過1個能與巰基化降冰片烯之硫醇基反應之官能團。使此種多官能化合物與巰基化降冰片烯固化劑反應不僅將增加分子
量，而且取決於該加合化合物之官能度及所採用巰基化降冰片烯之官能度，亦可增加每個分子之平均官能團數目。例如，該化合物可為雙官能烯烴，諸如二乙烯基苯、二-異丙烯基苯、乙烯基降冰片烯、乙烯基環己烯、辛二烯、環辛二烯、三羥甲基丙烷二烯丙醚、或任何其他適宜的二烯烴。可使用二烯烴與單烯烴之摻合物，只要單烯烴之量不過大即可。例如，市售二乙烯基苯係以具有約20重量%乙基乙烯基苯來供應，且此化合物之混合物導致令人滿意之加合物。或者，該化合物可為雙官能環氧樹脂，諸如彼等上文所列之實例。可使用二異氰酸酯化合物，諸如異佛爾酮二異氰酸酯、六亞甲基二異氰酸酯或甲苯二異氰酸酯。製造此等加合固化劑之反應條件將取決於該等化合物官能團之性質。就烯烴而言，由偶氮或過氧化合物(諸如偶氮-二異丁腈、2,2'-偶氮雙(2-甲基丁腈)或過氧化二-第三丁基)所引發之自由基過程將係合適。就環氧化合物而言，簡單加熱組分應當足矣。異氰酸酯亦同。當然可視情況使用各種加合反應之促進劑。一般而言，平均具有約兩個硫醇基/分子之巰基化降冰片烯當與雙官能試劑加合時將產生平均官能度不改變的新穎巰基化降冰片烯。
一般而言，若塗料樹脂具有高官能度，例如環氧化酚醛樹脂，則巰基化降冰片烯固化劑之官能度可能較低，但仍然形成適當聚合物網絡。
在一些情況中，可能需將本發明之固化劑與所選擇之塗料樹脂之其他固化劑混合，其中此種摻合將促使可固化塗料組合物之一或多種性質提升。例如，在環氧塗料樹脂之情況中，可有利地混合巰基化降冰片烯固化劑與習知胺固化劑，諸如彼等由C Hare在「Protective Coatings：Fundamentals of Chemistry and Composition」(SSPC,1994)中、由W Ashcroft在「Chemistry and Technology of Epoxy Resins」,Ed.B Ellis(Blackie 1993)中、由T S Mika及R S Bauer在C.A.May,ed.,
Epoxy Resins Chemistry and Technology(Marcel Dekker,1988)中、以及由H Lee及K Neville在「Handbook of Epoxy Resins」(McGraw-Hill,1967,1982年再發證)中所述者，並全部以引用的方式併入。亦可能期望巰基化降冰片烯固化劑與其他硫醇物質(諸如可由Bruno Bock獲得之新戊四醇四巰基丙酸酯，或可由Showa Denko獲得之KarenzMT PE-1)之混合物，其中同樣地，此種摻合將促使可固化塗料組合物之一或多種性質提升。
熟習此項技術者相當瞭解，組合良好固化速率或塗料乾燥速度與適於利用習知無氣噴槍之塗佈應用之活化期，尤其係在溶劑含量低的調配物中，係成問題。通常此等反應性塗料必須藉由雙面進料(twin-feed)或複數組件應用技術進行塗佈。出人意料地，已發現，利用本發明之巰基化降冰片烯，經由適宜地選擇恰當促進劑，可於環氧樹脂-硫醇固化組合物中達到活化期與可接受固化速率之良好平衡。
藉由審慎選擇環氧化合物、促進劑及反應條件，可獲得適於利用習知無氣噴射之塗佈應用之活化期，同時仍然保持良好固化速率。
在本發明可固化塗料組合物中所使用之塗料樹脂、固化劑及促進劑之量將依據所使用之特定塗料樹脂之當量重、固化劑之當量重、固化反應之期望化學計量比、期望活化期、期望固化速率及期望的最終使用性能特性而改變。化學計量比係定義為巰基化降冰片烯固化劑之硫醇基之當量數(b)與可固化塗料樹脂之硫醇反應官能基之當量數(a)之比例。化學計量比((b)/(a))通常將係於0.3至2.0之範圍內，更佳0.5-2.0，更佳0.5至1.5，甚至更佳0.6至1.2，最佳於0.7至1.0之範圍內。在彼等使用硫醇固化劑之摻合物或巰基化降冰片烯與習知胺固化劑之摻合物之情況中，在計算化學計量比時，必須將硫醇混合物之硫醇基之當量數或所採用胺固化劑之硫醇基當量數加活性氫原子之當量數考慮在內。
在一實施例中，就基於當量重範圍為170至190 g/莫耳(基於無溶劑塗料樹脂)之環氧塗料樹脂及忽視所有其他成份(諸如顏料、填料、溶劑及其他添加劑)之防腐蝕底漆而言，根據本發明之塗料組合物最佳包含
- 30至80 wt.%塗料樹脂
- 20至70 wt.%巰基化降冰片烯固化劑，及
- 0至4 wt.%促進劑。
現將參考下列實例闡明本發明。此等實例意在說明本發明而不應視為以任何方式限制其範圍。
製備一種經設計以模擬根據本發明之無顏料環氧塗料組合物之反應性的典型環氧調配物，其包含- 70.1 wt.%環氧酚醛樹脂(可由Huntsman獲得之EPN1180X80)，- 29.5 wt.% 2-巰乙基降冰片烷硫醇，及- 0.4 wt.%第三胺(Ancamine K54)。
(wt.%係基於組合物之總重量計算)。
利用300μm下引棒，將混合塗料塗佈至已經噴砂處理為SA2½標準之6x4英寸2mm厚軟鋼板。將經塗佈的板置於設定為0℃及50%相對濕度(RH)之培養箱中。在0℃下，塗料在8小時內硬乾。經過24小時後，將第二塗層施加至該第一塗層，並允許塗料在0℃下再多靜置24小時。薄膜在0℃下如期地在8小時後再次硬乾。薄膜完整性及硬度良好。將經塗佈的板置於室溫及30℃的清水中。4週後，在任一板上皆不存在任何腐蝕跡象。同樣地，在曝露至鹽水4週後對鋼之黏著性良好。
在低溫(10℃)下製備一種經設計以模擬根據本發明之無顏料塗料組合物之反應性的典型環氧調配物，其包含- 60.0 wt.% 3-苯氧基-1,2-環氧丙烷，- 38.7 wt.% 2-巰乙基降冰片烷硫醇，- 1.3 wt.% 2,4,6-參(二甲基胺基甲基)苯酚。
(wt.%係基於組合物之總重量計算)。
將此組合物置於保持在10±1℃之溫度受控環境室中。黏度在第一小時期間保持不變。在10℃下，反應在10小時內完成。
此組合物具有良好活化期(>1hr)，及相對短的反應時間。
在低溫(10℃)下製備一種經設計以模擬根據本發明之無顏料塗料組合物之反應性的典型環氧調配物，其包含- 60.8 wt.% 3-苯氧基-1,2-環氧丙烷，- 38.0 wt.% 2-巰乙基降冰片烷硫醇，- 1.2 wt.%三苯基膦。
(wt.%係基於組合物之總重量計算)。
將此組合物置於保持在10±1℃之溫度受控環境室中。在10℃下，反應在20小時內完成，而黏度在最初若干小時期間保持不變。
此組合物具有極佳活化期，且出乎意料地在低於室溫的條件(10℃)下亦具有相對短的反應時間。
由如下之兩種組分A及B製備塗料組合物：
在25℃下，以4.3：1之重量比混合組分A及組分B，從而得到一種塗料組合物，其具有：- 80%之固體體積，- 87.0%之固體重量，及- 173.9 g/公升之揮發性有機含量(VOC)。
接著在23℃下利用錐板黏度計測量此混合物之黏度隨時間之變化，以得到混合塗料之活化期測量值。黏度在80分鐘後才開始上升。
此等結果顯示，利用本發明之巰基化降冰片烯，甚至在高固體環氧-硫醇調配物中亦可保持良好活化期。
利用BK乾燥追蹤記錄儀(dry track recorder)測量塗料在0℃下之乾燥時間。塗料在6½至7小時內乾透。
此數據證實，利用巰基化降冰片烯固化劑之高固體塗料組合物亦出乎意料地具有長活化期及快速乾燥時間。
Claims (13)
- 一種可固化塗料組合物，其包含：(a)包含硫醇反應基之可固化塗料樹脂，(b)用於該可固化塗料樹脂之巰基化降冰片烯固化劑，該巰基化降冰片烯固化劑包含平均至少1.0個硫醇基/分子，及(c)用於促進該可固化塗料樹脂上之硫醇反應基與該巰基化降冰片烯固化劑上之硫醇基間之反應之促進劑。
- 如請求項1之可固化塗料組合物，其中該巰基化降冰片烯固化劑包含平均1.5-2.5個硫醇基/分子。
- 如請求項1或2之可固化塗料組合物，其中該巰基化降冰片烯固化劑為巰基化降冰片烯固化劑與具有至少1個能夠與該巰基化降冰片烯固化劑之硫醇基起反應之官能團之化合物的加合物。
- 如請求項1或2之可固化塗料組合物，其中該塗料薄膜可在-20℃至50℃之溫度範圍內形成於基板上，而無需對該塗料組合物及/或該基板進行任何額外加熱。
- 如請求項1或2之可固化塗料組合物，其中該可固化塗料樹脂為環氧樹脂或環氧樹脂溶液。
- 如請求項1或2之可固化塗料組合物，其中該促進劑為第三胺、醇類或膦鹼。
- 如請求項6之可固化塗料組合物，其中該塗料組合物在25℃下具有至少30分鐘之活化期。
- 如請求項1或2之可固化塗料組合物，其中該可固化塗料組合物具有小於或等於250g/公升之VOC。
- 如請求項1或2之可固化塗料組合物，其中該可固化塗料組合物在0℃下具有小於10小時之乾燥時間。
- 如請求項1或2之可固化塗料組合物，其中該巰基化降冰片烯固化劑之硫醇基之當量數對該可固化塗料樹脂之硫醇反應官能基之當量數之比例((b)/(a))係在0.5至2.0之範圍內。
- 如請求項1或2之可固化塗料組合物，其包含：(a)30至80 wt.%之該可固化塗料樹脂(b)20至70 wt.%之該巰基化降冰片烯固化劑，及(c)0至4 wt.%之該促進劑，其中所有wt%皆係基於存在於該可固化塗料組合物中之該塗料樹脂、該巰基化降冰片烯固化劑及該促進劑之總重量。
- 一種塗佈基板之方法，其係藉由將如請求項1至11中任一項之可固化塗料組合物塗佈於該基板上，並使該可固化塗料組合物固化，以於該基板上形成塗層。
- 一種經如請求項1至11中任一項之塗料組合物塗佈之基板。
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| KR101629712B1 (ko) * | 2014-10-28 | 2016-06-13 | 가부시키가이샤 도우페 | 프라이머 조성물 및 도장품의 제조방법 |
| BR112017011336B1 (pt) * | 2014-12-05 | 2021-09-08 | Dow Global Technologies Llc | Composição de resina epóxi curável |
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| TWI506085B (zh) * | 2014-12-31 | 2015-11-01 | Ind Tech Res Inst | 樹脂組合物與應用其之塗料 |
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