CN101778914A - 具有多重固化机理的热固性涂料组合物 - Google Patents
具有多重固化机理的热固性涂料组合物 Download PDFInfo
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- CN101778914A CN101778914A CN200880100112A CN200880100112A CN101778914A CN 101778914 A CN101778914 A CN 101778914A CN 200880100112 A CN200880100112 A CN 200880100112A CN 200880100112 A CN200880100112 A CN 200880100112A CN 101778914 A CN101778914 A CN 101778914A
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- coating composition
- anhydride
- carbamate
- compound
- curable coating
- Prior art date
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- 229920001187 thermosetting polymer Polymers 0.000 title description 4
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- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 11
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 239000004971 Cross linker Substances 0.000 claims abstract description 7
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- -1 cyclic carboxylic acids Chemical class 0.000 claims description 48
- 230000002378 acidificating effect Effects 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
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- 239000000463 material Substances 0.000 claims description 16
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- BSBQJOWZSCCENI-UHFFFAOYSA-N 3-hydroxypropyl carbamate Chemical compound NC(=O)OCCCO BSBQJOWZSCCENI-UHFFFAOYSA-N 0.000 claims description 5
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- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 4
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
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- 238000004566 IR spectroscopy Methods 0.000 description 5
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- 125000000524 functional group Chemical group 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
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- 150000008064 anhydrides Chemical group 0.000 description 4
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- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/068—Copolymers with monomers not covered by C09D133/06 containing glycidyl groups
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/205—Compounds containing groups, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/066—Copolymers with monomers not covered by C08L33/06 containing -OH groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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Abstract
含有具有约150~约1500的环氧当量的丙烯酸类聚合物,具有酸基和氨基甲酸酯基的化合物,以及氨基塑料交联剂的可固化涂料组合物,可被施加到基材上,并且在所述化合物的酸基与氨基甲酸酯基都能发生反应的温度下固化。所述组合物可进一步含有封闭的多异氰酸酯交联剂,以与聚合物上的羟基和/或由环氧基与羧酸基反应形成的羟基反应。
Description
技术领域
本发明涉及热固性涂料组合物,其材料,制备和使用所述涂料组合物的方法。
背景技术
可固化的或可热固化的涂料组合物被广泛应用于涂料领域中,特别是用于汽车和工业涂料工业中的面漆中。颜色加透明复合涂料赋予面漆以优异的光泽、色深度、图象清晰度以及特殊的金属效果。在汽车工业中,将这些涂料广泛应用于汽车车身覆盖件(automobile bodypanel)。面漆涂料应当持久保持其外观,并在被涂覆的制品的使用期限内,在使用条件下提供防护。用于汽车的面漆涂料,例如,典型地暴露于各种气候、来自太阳的紫外射线、在驾驶过程中抛起的砾石或者当停车时放置在车上的物品所造成的磨损、以及能造成涂料降解的其他条件。有一段时间,研究者致力于提供具有更高的耐环境侵蚀性的涂料。“环境侵蚀”是用于描述一种暴露降解的术语,其特征在于,在涂层的面饰上或涂层的面饰中经常无法擦去的斑点或印记。
采用氨基甲酸酯官能的树脂的可固化的涂料组合物已描述在,例如,美国专利5,693,724、5,693,723、5,639,828、5,512,639、5,508,379、5,451,656、5,356,669、5,336,566和5,532,061中,它们中的每一个都以引用的方式并入本发明。这些涂料组合物可提供比其他涂料组合物,如羟基官能的丙烯酸类/密胺涂料组合物在耐环境侵蚀性方面的显著改进。另一方面,氨基甲酸酯官能的树脂倾向于需要更多的有机溶剂,以获得对于施用可接受的粘度以及所施加的漆膜的流平性,从而获得所期望的光滑度。具有更高的有机溶剂含量的涂料,在使用过程中能产生更多的受管制的挥发物。具有用封闭的多异氰酸酯固化的羟基官能的丙烯酸类聚合物的涂料,也能在固化的涂层中,提供优异的耐环境侵蚀性;但是,这些涂料不具备所期望的耐划伤性和耐擦伤性。具有用氨基塑料固化的羟基官能的丙烯酸类聚合物的涂料,相对于所提及的其他组合物,能以更高的固含量配制并且能在更低的温度下固化;但是不能提供所述其他涂料的耐环境侵蚀性,或者耐划伤性和耐擦伤性。也采用了其他涂料化学品,但是这些也具有缺点,如耐老化性差或者具有高挥发性有机物(VOC)含量。采用环氧/酸交联反应的涂料能提供优良的性质,但是在较长时间的老化中,会产生粉化和剥落。
美国专利5,693,724、5,693,723、5,639,828、5,512,639、5,508,379、5,451,656、5,356,669、5,336,566、5,532,061和6531560描述了通过对羟基官能的丙烯酸类树脂进行“转氨基甲酸酯化”,引入氨基甲酸酯官能度。但是,该反应步骤是一个耗时的过程,并且能产生副产物如甲醇,所述副产物必须与用于反应介质的其他溶剂一起,以某种方式除去。同样,由于存在氨基甲酸酯基团,得到的树脂是一种较高粘度的溶液,导致油漆固含量较低且VOC较高。美国专利6,391,970描述了一种涂料,所述涂料通过环氧基与羧基之间的第一个反应(该反应产生羟基),以及所产生的羟基与多异氰酸酯交联剂之间的第二个反应而固化。
有利的是提供一种能提供所期望的耐环境侵蚀性、以及改善的耐划伤性和耐擦伤性,而不会使所述涂料组合物的粘度显著增大的涂料组合物。
发明简述
本发明提供一种可固化的涂料组合物,其含有具有约150~约1500的环氧当量的丙烯酸类聚合物,具有酸基和氨基甲酸酯基的化合物,以及氨基塑料交联剂。这种涂料组合物可被施加到基材上,并且在所述化合物的酸基与氨基甲酸酯基都能反应的温度下固化。所述具有酸基和氨基甲酸酯基的化合物可平均具有一个酸基每0.5~1.5个氨基甲酸酯基,但是优选地,所述化合物具有基本上大致相同的酸基当量和氨基甲酸酯基当量。特别地,所述具有酸基和氨基甲酸酯基的化合物可为环状羧酸酐化合物与羟烷基氨基甲酸酯的反应产物。
用于本发明目的的氨基塑料是一种通过如下反应获得的物质:使活性氮与低分子量的醛反应,形成烷醇基团,任选进一步与醇(优选具有1~4个碳原子的一元醇)反应,从而形成醚基。
氨基甲酸酯基具有如下结构:
其中R为H或烷基。优选地,R是H或1~约4个碳原子的烷基,更优选地R为H。
本发明还提供一个具体实施方案,其中所述丙烯酸类聚合物还具有约300~约700的羟基当量。
本发明还提供一个具体实施方案,其中所述涂料组合物进一步含有第二种丙烯酸类聚合物,所述第二种丙烯酸类聚合物具有约300~约700的羟基当量。
本发明还提供一种具体实施方案,其中所述涂料组合物进一步含有封闭的多异氰酸酯固化剂。
本发明还提供一个具体实施方案,其中所述涂料组合物含有具有羧酸基、氨基甲酸酯基、环氧基或羟基的另一种物质。
本发明还提供一种涂覆基材的方法,包括如下步骤:施加本发明的涂料组合物,固化所施加的涂料组合物的层。特别地,固化温度可加以选择,以使得所述具有酸基和氨基甲酸酯基的化合物的酸基和氨基甲酸酯基都能进行反应。
本发明所用的“一”表示存在“至少一个”物品;当可能时,可存在多个所述物品。当“约”被用于数值时,表示计算或测量值允许存在某种程度的微小的不精确度(与所述值的精确值在某种程度上接近;近似地或合理地接近所述值;几乎是)。如果出于某种原因,由“约”所提供的不精确度在本领域中,与这种通常的意思不存在其他理解的话,那么本发明所用的“约”是指在所述值中存在最多为5%的可能的变化。
优选的具体实施方案的详细描述
对优选的具体实施方案的下文的描述,本质上仅仅是示例性的,并且绝不意于限制本发明,其应用或用途。
所述可固化的涂料组合物包括具有约150~约1500环氧当量的丙烯酸类聚合物,具有酸基和氨基甲酸酯基的化合物,以及氨基塑料交联剂。本发明还提供一个具体实施方案,其中所述丙烯酸类聚合物还具有约300~约700的羟基当量。所述可固化的涂料组合物在具有环氧官能度的相同的丙烯酸类聚合物上,或者在第二种丙烯酸类聚合物上还可具有羟基官能度。所述可固化的涂料组合物可进一步包括封闭的多异氰酸酯固化剂、其他树脂、聚合物或具有羧基、环氧基、氨基甲酸酯基或羟基的化合物,以及其他有用的涂料物质,如颜料、溶剂、催化剂和其他添加剂。
具有约150~约1500的环氧当量的丙烯酸类聚合物可通过将适量的缩水甘油基单体共聚,例如通过将丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯、或者烯丙基缩水甘油基醚单体中的一种或多种共聚而制备。
所述具有约150~约1500的环氧当量的丙烯酸类聚合物还可具有羟基。羟基可通过在聚合物合成中,将羟基官能单体共聚而方便地引入,所述羟基官能单体如丙烯酸羟乙酯、甲基丙烯酸羟乙酯、丙烯酸羟丙酯、甲基丙烯酸羟丙酯、丙烯酸羟丁酯、甲基丙烯酸羟丁酯等,或者这些单体的组合。
除了在所述具有约150~约1500的环氧当量的丙烯酸类聚合物上引入羟基官能度之外,或者作为在所述丙烯酸类聚合物上引入羟基官能度的代替,清漆组合物还可任选地进一步包括具有羟基官能度的第二种丙烯酸类聚合物。所述具有羟基的第二种丙烯酸类聚合物可通过将上文已提及的羟基官能的单体中的一种进行聚合,方便地获得。
所述具有环氧基的丙烯酸类聚合物(如果采用羟基单体制备的话)或所述第二种丙烯酸类聚合物(如果含有的话)的羟基当量,优选为约300~约700。
所述丙烯酸类聚合物可采用一种或多种其他共聚单体进行聚合。所述共聚单体的例子包括,但不限于,含有3~5个碳原子的α,β-烯属不饱和单羧酸,如丙烯酸、甲基丙烯酸和巴豆酸的酯,以及含有4~6个碳原子的α,β-烯属不饱和二元羧酸的酯;乙烯基酯,乙烯基醚,乙烯基酮和芳族或杂脂环族乙烯基化合物。丙烯酸、甲基丙烯酸和巴豆酸的适当的酯的代表性例子包括,但不限于,由与含1~20个碳原子的饱和的脂族和环脂族醇反应所获得的那些酯,如丙烯酸、甲基丙烯酸和巴豆酸的甲酯、乙酯、丙酯、异丙酯、正丁酯、异丁酯、叔丁酯、2-乙基己酯、月桂酯、硬脂基酯、环己酯、三甲基环己酯、四氢糠基酯、硬脂基酯、磺乙基酯和异冰片基酯。其他烯属不饱和可聚合单体的代表性例子包括,但不限于,如二烷基富马酸酯、马来酸酯和衣康酸酯这样的化合物,它们是通过与醇的反应制备的,所述醇如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、和叔丁醇。聚合乙烯基化合物单体的代表性例子包括,但不限于,如醋酸乙烯酯,丙酸乙烯酯,乙烯基醚如乙烯基乙基醚,卤乙烯和偏卤乙烯,以及乙烯基乙基酮这样的化合物。芳族或杂脂环族乙烯基化合物的代表性例子包括,但不限于,如苯乙烯、α-甲基苯乙烯、乙烯基甲苯、叔丁基苯乙烯和2-乙烯基吡咯烷酮这样的化合物。所述共聚单体可以任意组合地使用。
所述丙烯酸类聚合物可采用常规的技术制备,如在聚合引发剂和任选地链转移剂的存在下,将所述单体加热。聚合优选在溶液中进行,尽管也能在本体中聚合所述丙烯酸类聚合物。适当的聚合溶剂包括,但不限于,酯、酮、乙二醇单烷基醚和丙二醇单烷基醚、醇和芳烃。
典型的引发剂为有机过氧化物,如二烷基过氧化物如二叔丁基过氧化物,过氧化酯如过氧辛酸叔丁酯和过氧乙酸叔丁酯,过氧化二羧酸,二酰基过氧化物,氢过氧化物如叔丁基过氧化氢,以及过氧化酮缩醇;偶氮化合物如2,2’-偶氮基双(2-甲基丁腈)和1,1’-偶氮基双(环己腈);以及这些的组合。典型的链转移剂是硫醇,如辛硫醇、正-或叔-十二烷硫醇;氢化的化合物,硫代水杨酸,巯基乙酸,巯基乙醇和二聚α-甲基苯乙烯。
所述溶剂或溶剂混合物通常被加热至反应温度,并且以受控的速率在一段时间内,典型地为约2~约6小时,加入单体和引发剂,以及任选地链转移剂。所述聚合反应通常是在约20℃~约200℃的温度下进行的。所述反应可在所述溶剂或溶剂混合物回流的温度下方便地进行,尽管采用适度控制可保持温度低于所述回流温度。所述引发剂应加以选择,使得其与进行反应的温度匹配,从而使所述引发剂在该温度下的半衰期应当优选为不超过约30分钟,更优选地为不超过约5分钟。可同时再加入溶剂。在添加完成之后,可将混合物保持在反应温度下一段时间,以完成聚合。任选地,可加入额外的引发剂,以确保单体完全转化为聚合物。
所述丙烯酸类聚合物应当具有至少约2400,优选至少约3000,更优选至少约3500,特别优选为至少约4000的重均分子量。重均分子量可通过采用聚苯乙烯作为标准的凝胶渗透色谱法测定。此外,所述重均分子量优选最高为约7000,更优选地最高为约5000,还更优选地最高为约4500。
所述清漆涂料组合物优选含有约50wt%~约85wt%,更优选约60wt%~约75wt%的具有环氧官能度的第一种乙烯基聚合物,基于漆料重量计。所述“漆料重量”是所述涂料组合物中的热固性成膜组分的总重。所述清漆涂料组合物优选含有约5wt%~约40wt%,更优选约15wt%~约30wt%的具有羟基官能度的第二种乙烯基聚合物,基于漆料重量计。
所述涂料组合物还含有具有酸基和氨基甲酸酯基的化合物。所述具有酸基和氨基甲酸酯基的化合物可平均含有一个酸基每0.5~1.5个氨基甲酸酯基,但是优选地,所述化合物具有基本上大致相同的酸基当量和氨基甲酸酯当量。所述化合物优选为单体型,并且具有约191~约471的分子量。所述化合物可选优具有约6~约25个碳原子,至少一个羧基和至少一个氨基甲酸酯基。
特别地,所述具有酸基和氨基甲酸酯基的化合物可为环状羧酸酐化合物与羟烷基氨基甲酸酯的反应产物。适当的酸酐化合物的例子包括,但不限于,邻苯二甲酸酐、四氢邻苯二甲酸酐、琥珀酸酐、戊二酸酐、马来酸酐、偏苯三酸酐、苯均四酸酐、六氢邻苯二甲酸酐和甲基六氢邻苯二甲酸酐。适当的羟烷基氨基甲酸酯化合物的例子包括,但不限于,羟甲基氨基甲酸酯,羟乙基氨基甲酸酯,羟丙基氨基甲酸酯,羟丁基氨基甲酸酯,C-36二聚醇单氨基甲酸酯,二乙基辛二醇单氨基甲酸酯(DEOD单氨基甲酸酯),以及新癸酸缩水甘油酯的氨基甲酸酯的反应产物。酸酐可与羟基氨基甲酸酯反应,直至所有的酸酐基团已经发生反应。所述反应通常是在100~140℃的温度下进行的,反应的终点可通过如下方法进行监控:红外光谱法或者在将任何剩余的酸酐羟基化之后,对酸基进行滴定。
所述涂料组合物还含有作为交联剂的氨基塑料。用于本发明目的的氨基塑料是一种通过如下反应获得的物质:使活性氮与低分子量的醛反应,任选进一步与醇(优选为具有1~4个碳原子的一元醇)反应,以形成醚基。活性氮的优选的例子为活性胺如密胺、苯基胍胺、环己基碳化胍胺(cyclohexylcarboguanamine)和乙酰基胍胺;脲,包括脲本身、硫脲、乙烯脲、二羟基乙烯脲和脒基脲;甘脲;酰胺,如双氰胺;以及具有至少一个伯氨基甲酸酯基或者至少两个仲氨基甲酸酯基的氨基甲酸酯官能化合物。
所述活性氮与低分子量醛反应。所述醛可选自甲醛、乙醛、巴豆醛、苯甲醛、或者用于制备氨基塑料树脂的其他醛,尽管甲醛和乙醛,特别是甲醛,是优选的。采用所述醛,将所述活性氮基至少部分烷醇化(alkylolated),并且可完全烷醇化;优选地,所述活性氮基被全部烷醇化。所述反应可采用酸进行催化,如美国专利3,082,180所教导的那样,其内容以引用方式并入本发明。
通过所述活性氮与醛的反应形成的烷羟基,可采用一种或多种单官能醇部分或完全醚化。所述单官能醇的适当的例子包括,但不限于,甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、叔丁醇、苄醇等。具有1~4个碳原子的单官能醇及其混合物是优选的。所述醚化可,例如,通过美国专利4,105,708和4,293,692所公开的方法实施,其公开内容以引用方式并入本发明。
所述氨基塑料优选为至少部分醚化的,所述氨基塑料特别优选为完全醚化的。所述优选的化合物具有多个羟甲基和/或醚化的羟甲基,其可以以任意组合,并且与未取代的氮氢一起存在。完全醚化的密胺-甲醛树脂是特别优选的,例如(但不限于)六甲氧基甲基密胺。
所述可固化的涂料组合物还可含有封闭的多异氰酸酯固化剂。封闭的多异氰酸酯交联剂包括,但不限于,封闭的异氰脲酸酯、封闭的缩二脲、封闭的脲基甲酸酯、脲二酮化合物、以及封闭的异氰酸酯官能的预聚物如一摩尔三元醇与三摩尔二异氰酸酯的反应产物。
异氰酸酯的用量优选进行选择,以使得其与所有的羟基,来自羟基丙烯酸类树脂的羟基以及由于羧酸与环氧化物的反应而形成的羟基反应。异氰酸酯的用量也可更低,从而使得在固化结束时存在一些游离的羟基,从而有助于在存在漆膜缺陷的情况下修复粘附性。美国专利6,391,970教导了对于所期望的漆膜性质而言,环氧化物与酸与异氰酸酯的比例。
所述涂料组合物可含有一种或多种其他具有羧酸基、氨基甲酸酯基、环氧基或羟基的组分。所述其他组分的例子包括,但不限于,新癸酸、新癸酸的缩水甘油酯、羟基硬脂酸、具有8~18个碳原子的脂肪酸、二聚脂肪酸、三聚脂肪酸、具有8~18个碳原子的脂肪醇、二聚脂肪醇、三聚脂肪酸、以及这些的组合,如果期望的话,其可被加入以赋予所述涂料以柔性。
颜料和填料可以以典型的最高为约40wt%的用量使用,基于所述涂料组合物的总重计。所用的颜料可为无机颜料,包括金属氧化物、铬酸盐、钼酸盐、磷酸盐和硅酸盐。可采用的无机颜料和填料的例子为二氧化钛、硫酸钡、炭黑、赭石、富铁黄土、棕土、赤铁矿、褐铁矿、氧化铁红、透明氧化铁红、氧化铁黑、氧化铁褐、氧化铬绿、铬酸锶、磷酸锌、二氧化硅如煅烧二氧化硅、碳酸钙、滑石、重晶石、亚铁氰化铁铵(普鲁士蓝)、群青、铬酸铅、钼酸铅和云母薄片颜料。也可采用有机颜料。可用的有机颜料的例子为金属化的非金属化的偶氮红、喹吖啶酮红和紫、芘红、铜酞菁蓝和绿、咔唑紫、单苯胺和联苯胺黄、苯并咪唑酮黄、甲苯基橙(tolyl orange)、萘酚橙等。
所述涂料组合物可含有催化剂,以促进固化反应。这样的催化剂是本领域技术人员所公知的,并且包括,但不限于,锌盐、锡盐、封闭的对甲苯磺酸、封闭的二壬基萘磺酸、或者苯基酸磷酸盐(phenylacid phosphate)。同样,可加入锡化合物如二月桂酸二丁基锡、二丁基氧化锡,以促进羟基-异氰酸酯反应。
一种溶剂或多种溶剂也可包括在所述涂料组合物中。一般地,所述溶剂可为任何有机溶剂和/或水。在一个优选的具体实施方案中,所述溶剂包括极性有机溶剂。更优选地,所述溶剂包括一种或多种选自极性脂肪族溶剂或极性芳族溶剂的有机溶剂。还更优选地,所述溶剂包括酮、酯、醋酸酯或者这些物质中的任何物质的组合。可用的溶剂的例子包括,但不限于,甲基乙基酮、甲基异丁基酮、醋酸m-戊酯、乙二醇丁醚醋酸酯、丙二醇单甲醚醋酸酯、二甲苯、N-甲基吡咯烷酮、芳烃的混合物、以及这些物质的混合物。在另一个优选的具体实施方案中,所述溶剂是水或水与少量共溶剂的混合物。一般地,当所述涂料组合物含有任选的多异氰酸酯交联剂时,应当避免质子溶剂如醇和二醇醚,尽管可采用少量的质子溶剂,即使可以预期在所述涂料的固化期间,可能会发生与异氰酸酯基的某种反应。
其他试剂,例如位阻胺光稳定剂、紫外光吸收剂、抗氧化剂、表面活性剂、稳定剂、润湿剂、流变调节剂、分散剂、增粘剂等,也可加入到所述涂料组合物中。这些添加剂是公知的,并且可以以典型地用于涂料组合物的用量被包含。
所述涂料组合物可通过喷涂,涂覆在基材上。静电喷涂是一种优选的方法。所述涂料组合物可通过一个或多个通路施加,以获得固化后典型地为约20~约100微米的漆膜厚度。
所述涂料组合物可被施加到不同种类的基材上,包括金属基材如裸钢、磷酸盐护层钢、镀锌钢或铝;以及非金属基材,如塑料和复合材料。所述基材也可为其上已具有另一种涂料的层的这些材料中的任意一种,如电沉积底漆、中涂漆和/或头道底漆的层,其可为固化的或未固化的。
在将所述涂料组合物施加到所述基材上之后,将所述涂料固化,优选通过在一定温度下加热一段足以导致反应物形成不溶的聚合物网络的时间。固化温度通常为约105℃~约175℃,固化时间通常为约15分钟~约60分钟。优选地,所述涂料在约120℃~约150℃下固化约20~约30分钟。加热可在红外和/或对流加热烘箱中进行。
在一个具体实施方案中,所述涂料组合物被用作汽车复合颜色加透明涂装的清漆。在其上进行施加的着色的底漆组合物可为本领域技术人员所公知的许多种类中的任意一种,此处不需进行详细地说明。本领域技术人员所公知的可用于底漆组合物中的聚合物包括丙烯酸类树脂、乙烯基化合物的聚合物、聚氨酯、聚碳酸酯、聚酯、醇酸树脂和聚硅氧烷。优选的聚合物包括丙烯酸类树脂和聚氨酯。在本发明的一个优选的具体实施方案中,所述底漆组合物也采用了氨基甲酸酯官能的丙烯酸类聚合物。头道底漆聚合物可为热塑性的,但是优选为可交联的,并且含有一种或多种可交联的官能团。这样的基团包括,例如,羟基、异氰酸酯基、胺基、环氧基、丙烯酸酯基、乙烯基、硅烷基和乙酰乙酸酯基。这些基团可以以如下方式掩蔽或封闭,使得它们在所期望的固化条件下,通常是在升高的温度下,能够解封闭并且能用于交联反应。有用的可交联的官能团包括羟基、环氧基、酸基、酸酐基、硅烷基和乙酰乙酸酯基。优选的可交联的官能团包括羟基官能团和氨基官能团。
底漆聚合物可以为可自交联的,或者可能需要能与所述聚合物的官能团反应的独立的交联剂。例如,当所述聚合物含有羟基官能团时,所述交联剂可为氨基塑料树脂、异氰酸酯和封闭的异氰酸酯(包括异氰脲酸酯)、以及酸或酸酐官能的交联剂。
本发明的清漆涂料组合物通常以湿碰湿的方式,施加在头道底漆涂料组合物上,正如工业中广泛进行的那样。如上所述,本发明所述的涂料组合物优选处于特定的条件下,以固化涂层。
在下文的实施例中,将进一步描述本发明。所述实施例仅仅是示意性的,绝对不是为了限制本发明所描述和请求保护的范围。所有的份数都是重量份,除非另有说明。
制备1:环氧官能的丙烯酸树脂的合成
将400g芳烃100在圆底烧瓶中加热至150℃,在3小时内,以均匀的速率,加入1600g甲基丙烯酸缩水甘油酯、40g甘氨酰基甲基丙烯酸酯碳酸酯、160g丙烯酸正丁酯、200g甲基丙烯酸甲酯和100g芳烃100的混合物,同时加入200g叔丁基-过氧化-2-乙基己酸酯和100g芳烃100的混合物。在加入所有的混合物之后,在30分钟内,以均匀的速率,向反应混合物中再加入20gTBPO和30g芳烃100,以转化任何未反应的单体。将烧瓶的内容物在反应温度下再保持1小时,然后冷却。丙烯酸类聚合物产物具有70%的非挥发份含量,滴定重量每环氧基(WPE)为180g/环氧基。所述聚合物的分子量Mn为2120,Mw为3670,多分散性为1.7,采用聚苯乙烯标准,并且计算的Tg(采用Fox方程)为64℃。
制备2:环氧官能的丙烯酸类树脂的合成
将60g芳烃100在反应釜中加热至140℃,在4小时内,以均匀的速率,加入99.4g甲基丙烯酸缩水甘油酯、40.6g丙烯酸正丁酯、60g甲基丙烯酸丁酯和10g芳烃100的混合物,同时加入处于10g芳烃100中的20g叔丁基-过氧化-2-乙基己酸酯。在加入所有的混合物之后,在30分钟内,以均匀的速率,向反应混合物中加入处于10g芳烃100中的2g叔丁基-过氧化-2-乙基己酸酯,以转化任何未反应的单体。将烧瓶的内容物在140℃下再保持1小时,然后冷却。丙烯酸类聚合物产物具有70%的非挥发份含量,滴定重量每环氧基(WPE)为300g/环氧基。所述聚合物的分子量Mn为745,Mw为1400,多分散性为1.9,由GPC测定,采用聚苯乙烯标准。该树脂具有23℃的计算的Tg(采用Fox方程)。
制备3:合成酸基、氨基甲酸酯基化合物
将308g六氢邻苯二甲酸酐、238g羟丙基氨基甲酸酯和103g醋酸正丁酯加热至并在100-110℃下保持约12小时,直至IR显示完全不存在酸酐峰1850和1780cm-1,并且用氢氧化钠水溶液进行的滴定表明酸当量为260~273g/COOH。发现最终产物具有77.6wt%的非挥发份,并且是具有274.9g/COOH酸当量的蜡状固体。
制备4:酸基、氨基甲酸酯基化合物的合成
将200g琥珀酸酐、119g羟丙基氨基甲酸酯和100g甲苯,在反应釜中,保持在100-110℃。反应之后,进行红外光谱分析(IR)(在1850和1780cm-1处的酸酐峰消失),并用氢氧化钠水溶液滴定。当IR显示1850和1780cm-1处没有出现峰,并且滴定显示酸当量为210-230g/COOH时,停止反应。最终产物具有81wt%的非挥发份,并且具有213g/COOH的当量。
制备5:含羟基的丙烯酸类聚合物的合成
向含有处于150℃下的25g丙二醇单丙醚的反应釜中,在4小时内,均匀加入12.4g丙烯酸、48.2g甲基丙烯酸2-羟乙酯、16.6g丙烯酸2-乙基己酯、8g苯乙烯、42g甲基丙烯酸正丁酯和7.4g甲基丙烯酸甲酯的混合物,同时加入处于2g丙二醇单丙醚中的12.4g的叔丁基过氧2-乙基己酸酯和6g叔丁基过氧醋酸酯的溶液。加入之后,将产物在140℃下再保持1小时,以完成转化。加入30g甲基丙基酮,使树脂成为65%的非挥发性溶液。计算理论Tg为23.4℃,测量的当量为330g/羟基,采用聚苯乙烯标准的GPC分析显示分子量Mn为3300,Mw为5850,多分散性为1.8。
实施例1-7的涂料组合物
1.Resimene BM-9539获自UCB Surface Specialties
2.HDI:DMP=二甲基吡唑封闭的六亚甲基二异氰酸酯
3.CYMEL 327获自Cytec Industries
4.所述添加剂包括光稳定剂、流变调节剂、强酸催化剂、流平剂和溶剂。
所述涂料组合物采用了下述组成:
配方 | 羟基丙烯酸树脂+交联剂% | 环氧树脂+酸-氨基甲酸酯+交联剂% |
1 | 100 | |
2 | 90 | 10 |
3 | 75 | 25 |
4 | 50 | 50 |
配方 | 羟基丙烯酸树脂+交联剂% | 环氧树脂+酸-氨基甲酸酯+交联剂% |
5,6和7 | 100 |
对实施例1~7的涂料组合物按照如下方式测试。测定了非挥发份含量。所述涂料组合物实施例被喷涂在钢板上,所述钢板涂覆有电沉积底漆,1mi(25.4mm)的喷涂底漆(由BASF提供的U28底漆),和0.6mil的水基黑色底漆E54KW225(由BASF提供),并在285°F(140℃)下烘烤20分钟。固化的涂膜约1.8密耳(45.7mm)厚。固化程度按照ASTM方法D5402,通过甲基乙基酮双摩擦法测定。固化涂层的硬度根据DIN50359,作为Fisher硬度测定,采用Fisherscope硬度测试仪,型号为HM100V,设置最大力为100mN,在50,1第二步骤系列中进行斜面分析(ramped)。硬度值以N/mm记录。Tukon硬度按照ASTM方法D1474测定,并且以Knoop单位记录。采用Crockmeter测试固化涂层在10次测试循环前后的耐划伤性和耐擦伤性,采用HunterPro光泽度测定仪,按照ASTM方法D523测定光泽度。测试结果列在下表中。
实施例 | %NV(喷涂) | MEK双摩擦 | Fisher硬度 | Tucon硬度 | Crockmeter光泽保持度 |
1 | 60 | 100 | 86 | 10.2 | 81.2% |
2 | 60.5 | >200 | 92.6 | 10.3 | 86.5% |
3 | 60.2 | >200 | 102.6 | 10.8 | 85.8% |
4 | 60.4 | >200 | 127.5 | 16.1 | 86.3% |
5 | 61 | >200 | 140.3 | 14.2 | 43.5% |
6 | 62.2 | >200 | 131.7 | 12.2 | 94% |
7 | 62.0 | >200 | 194 | 11.2 | 未测试 |
结果表明,含有能经受“级联交联”的材料的油漆配方在通过MEK双摩擦,Fisher和Tukon硬度以及非挥发份(因此VOC数值较低)测量方面,表现出相同的或者更好的漆膜性质。
本发明的描述在本质上仅仅是示例性的,因而,不偏离本发明的主旨的改变也处于本发明的范围之内。这种改变不能被认为是偏离了本发明的主旨和范围。
Claims (19)
1.可固化的涂料组合物,含有:
(a)具有约150~约1500的环氧当量的丙烯酸类聚合物;
(b)环状羧酸酐化合物与羟烷基氨基甲酸酯化合物的反应产物,以及
(c)氨基塑料交联剂。
2.如权利要求1所述的可固化涂料组合物,其中所述酸酐化合物是单官能酸酐化合物。
3.如权利要求1所述的可固化涂料组合物,其中所述酸酐化合物是多官能酸酐化合物。
4.如权利要求1所述的可固化涂料组合物,其中所述酸酐化合物选自如下组:邻苯二甲酸酐、四氢邻苯二甲酸酐、琥珀酸酐、马来酸酐、偏苯三酸酐、苯均四酸酐、六氢邻苯二甲酸酐、十二烯基琥珀酸酐和己二酸酐。
5.如权利要求1所述的可固化涂料组合物,其中所述羟烷基氨基甲酸酯选自如下组:羟乙基氨基甲酸酯、羟丙基氨基甲酸酯和羟丁基氨基甲酸酯。
6.如权利要求1所述的可固化涂料组合物,进一步含有封闭的多异氰酸酯交联剂。
7.如权利要求1所述的可固化涂料组合物,其中所述丙烯酸类聚合物进一步具有羟基官能度。
8.如权利要求7所述的可固化涂料组合物,其中所述丙烯酸类聚合物具有约300~约700的羟基当量。
9.如权利要求1所述的可固化涂料组合物,进一步含有具有约300~约700的羟基当量的第二种丙烯酸类聚合物。
10.如权利要求1所述的可固化涂料组合物,进一步含有封闭的多异氰酸酯固化剂。
11.如权利要求1所述的可固化涂料组合物,进一步含有选自如下组中的一种:新癸酸、新癸酸的缩水甘油酯、羟基硬脂酸、具有8~18个碳原子的脂肪酸、二聚脂肪酸、三聚脂肪酸、具有8~18个碳原子的脂肪醇、二聚脂肪醇、三聚脂肪醇、以及它们的组合。
12.涂覆基材的方法,包括如下步骤:
(a)将可固化涂料组合物的层施加到所述基材上,所述组合物含有具有约150~约1500的环氧当量的丙烯酸类聚合物,具有酸基和氨基甲酸酯基的化合物,以及氨基塑料交联剂;
(b)在所述化合物的酸基与氨基甲酸酯基都能发生反应的温度下,固化所施加的涂料组合物层。
13.如权利要求12所述的涂覆基材的方法,其中所述可固化涂料组合物进一步含有封闭的多异氰酸酯交联剂。
14.如权利要求12所述的涂覆基材的方法,其中所述丙烯酸类聚合物进一步含有羟基官能度。
15.如权利要求14所述的涂覆基材的方法,其中所述丙烯酸类聚合物具有约300~约700的羟基当量。
16.如权利要求12所述的涂覆基材的方法,其中所述可固化涂料组合物进一步含有具有约300~约700的羟基当量的第二种丙烯酸类聚合物。
17.如权利要求12所述的涂覆基材的方法,其中所述具有酸基和氨基甲酸酯基的化合物平均具有一个酸基每0.5~1.5个氨基甲酸酯基。
18.如权利要求12所述的涂覆基材的方法,其中所述具有酸基和氨基甲酸酯基的化合物是酸酐化合物与羟烷基氨基甲酸酯的反应产物。
19.如权利要求18所述的涂覆基材的方法,其中所述酸酐化合物选自如下组:邻苯二甲酸酐、四氢邻苯二甲酸酐、琥珀酸酐、马来酸酐、偏苯三酸酐、苯均四酸酐和六氢邻苯二甲酸酐;并且进一步地,其中所述羟烷基氨基甲酸酯选自如下组:羟乙基氨基甲酸酯、羟丙基氨基甲酸酯和羟丁基氨基甲酸酯。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/841,034 US20090053420A1 (en) | 2007-08-20 | 2007-08-20 | Thermosetting coating compositions with multiple cure mechanisms |
US11/841,034 | 2007-08-20 | ||
PCT/US2008/008853 WO2009025708A1 (en) | 2007-08-20 | 2008-07-21 | Thermosetting coating compositions with multiple cure mechanisms |
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CN101778914A true CN101778914A (zh) | 2010-07-14 |
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CN200880100112A Pending CN101778914A (zh) | 2007-08-20 | 2008-07-21 | 具有多重固化机理的热固性涂料组合物 |
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US (1) | US20090053420A1 (zh) |
EP (1) | EP2181165A1 (zh) |
JP (1) | JP2010536990A (zh) |
CN (1) | CN101778914A (zh) |
WO (1) | WO2009025708A1 (zh) |
Cited By (3)
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CN102391743A (zh) * | 2011-09-01 | 2012-03-28 | 中国海洋石油总公司 | 一种自行车用水性底漆 |
CN102850863A (zh) * | 2012-08-31 | 2013-01-02 | 芜湖县双宝建材有限公司 | 一种五合一墙面漆及其生产工艺 |
CN104231799A (zh) * | 2013-06-24 | 2014-12-24 | 郎溪县鑫泽涂料有限公司 | 高固体分高光泽阳极电泳涂料及涂装方法 |
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JP6762209B2 (ja) * | 2016-11-29 | 2020-09-30 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングBASF Coatings GmbH | アクリル樹脂及びメラミン樹脂を主体樹脂とするトップコート用塗料組成物 |
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US3082180A (en) * | 1960-10-04 | 1963-03-19 | American Cyanamid Co | Modified melamine-formaldehyde resin for decorative laminating and process for preparing same |
US4105708A (en) * | 1976-09-07 | 1978-08-08 | American Cyanamid Company | Dimethoxymethyl diethoxymethyl glycoluril and coating compositions containing the same as a cross-linking agent |
US4293692A (en) * | 1977-11-17 | 1981-10-06 | American Cyanamid Company | Continuous process for manufacturing substantially fully methylated substantially fully methylolated melamine compositions |
US5356669A (en) * | 1992-10-23 | 1994-10-18 | Basf Corporation | Composite color-plus-clear coating utilizing carbamate-functional polymer composition in the clearcoat |
US5384367A (en) * | 1993-04-19 | 1995-01-24 | Ppg Industries, Inc. | Carbamate urea or urethane-functional epoxy acrylic with polyacid |
US5336566A (en) * | 1993-04-30 | 1994-08-09 | Basf Corporation | Tri-carbamate-functional crosslinking agents |
US5512639A (en) * | 1993-07-28 | 1996-04-30 | Basf Corporation | Curable compositions containing carbamate-modified polyisocyanates |
EP0653468A3 (de) * | 1993-11-12 | 1995-12-13 | Herberts & Co Gmbh | Überzugsmittel für transparente Decklackschichten und deren Verwendung bei Verfahren zur Herstellung von Mehrschichtüberzügen. |
US5532061A (en) * | 1994-12-21 | 1996-07-02 | Basf Corporation | Carbamate-functional polyester polymer or oligomer having pendant carbomate groups |
US5508379A (en) * | 1994-12-21 | 1996-04-16 | Basf Corporation | Carbamate-functional polyester polymer or oligomer and coating composition |
US5451656A (en) * | 1994-12-21 | 1995-09-19 | Basf Corporation | Carbamate-functional polyester polymer or oligomer and coating composition |
DE69629145T2 (de) * | 1995-04-21 | 2004-05-27 | Basf Corp. | Vernetzbare Beschichtungszusammensetzung |
US5693724A (en) * | 1996-07-01 | 1997-12-02 | Basf Corporation | Low VOC curable coating composition utilizing carbamate-functional compound |
US5693723A (en) * | 1996-07-01 | 1997-12-02 | Basf Corporation | Low voc curable coating composition utilizing carbamate-functional compound |
CA2230612A1 (en) * | 1997-04-24 | 1998-10-24 | Basf Corporation | Acid epoxy-isocyanate clear coat systems |
ES2218230T3 (es) * | 1999-09-30 | 2004-11-16 | Basf Corporation | Resinas con funcionalidad carbamato de adhesion mejorada, procedimiento para su preparacion y metodo para mejorar la adhesion entre capas. |
US7250480B2 (en) * | 2004-03-04 | 2007-07-31 | Basf Corporation | Acrylic composition and a curable coating composition including the same |
US7858190B2 (en) * | 2005-09-15 | 2010-12-28 | Basf Coatings Gmbh | Thermosetting coating compositions with multiple cure mechanisms |
US20070083014A1 (en) * | 2005-10-07 | 2007-04-12 | Basf Corporation | Clearcoat coating composition |
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- 2007-08-20 US US11/841,034 patent/US20090053420A1/en not_active Abandoned
-
2008
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- 2008-07-21 JP JP2010521844A patent/JP2010536990A/ja not_active Withdrawn
- 2008-07-21 CN CN200880100112A patent/CN101778914A/zh active Pending
- 2008-07-21 WO PCT/US2008/008853 patent/WO2009025708A1/en active Application Filing
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102391743A (zh) * | 2011-09-01 | 2012-03-28 | 中国海洋石油总公司 | 一种自行车用水性底漆 |
CN102391743B (zh) * | 2011-09-01 | 2013-09-25 | 中国海洋石油总公司 | 一种自行车用水性底漆 |
CN102850863A (zh) * | 2012-08-31 | 2013-01-02 | 芜湖县双宝建材有限公司 | 一种五合一墙面漆及其生产工艺 |
CN102850863B (zh) * | 2012-08-31 | 2016-08-24 | 芜湖县双宝建材有限公司 | 一种五合一墙面漆及其生产工艺 |
CN104231799A (zh) * | 2013-06-24 | 2014-12-24 | 郎溪县鑫泽涂料有限公司 | 高固体分高光泽阳极电泳涂料及涂装方法 |
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EP2181165A1 (en) | 2010-05-05 |
WO2009025708A1 (en) | 2009-02-26 |
JP2010536990A (ja) | 2010-12-02 |
US20090053420A1 (en) | 2009-02-26 |
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