CN1705723A - 水性经非离子稳定的环氧树脂 - Google Patents
水性经非离子稳定的环氧树脂 Download PDFInfo
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- CN1705723A CN1705723A CNA2003801017368A CN200380101736A CN1705723A CN 1705723 A CN1705723 A CN 1705723A CN A2003801017368 A CNA2003801017368 A CN A2003801017368A CN 200380101736 A CN200380101736 A CN 200380101736A CN 1705723 A CN1705723 A CN 1705723A
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- Prior art keywords
- epoxy
- resins
- tackiness agent
- ghi
- radiation curable
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- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F299/026—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight
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Abstract
本发明涉及一种包含经非离子稳定的环氧树脂ABC的、水性可辐射固化性粘合剂,其包含经聚乙二醇修饰的环氧树脂A、无聚乙二醇的环氧树脂B和烯属不饱和酸C的结构单元,所有衍生自环氧树脂A和B的反应产物中的至少50%具有至少一个通过末端环氧基与烯属不饱和酸C的反应而形成的酯基。本发明还涉及制备该树脂的方法和其用作涂敷试剂的用途。
Description
本发明涉及水性经非离子稳定的环氧树脂。此外还涉及其制法及其作为特别是用于线圈涂敷漆的可辐射固化性粘合剂的用途。
背景技术
已经知道水性可辐射固化性粘合剂,例如从EP-B 0 694 531得知。由此制得的漆膜虽然是有弹性的,但它们的防腐蚀性不足。
可辐射固化性粘合剂没有溶剂(本体)或溶解于有机溶剂中,在它们的聚合程度(为了所追求的物理性质)足够时,其在施用形式中的粘度显著高于含水体系。只有添加反应性稀释剂才能降低粘度。与之相反,水性分散体的粘度与分散相的聚合程度无关,而是基本上仅与其在分散体中的体积份有关。
已经从例如US-A 5,763,507中得知用于所谓“线圈涂敷”法的水性漆。这些漆基于衍生自经(甲基)丙烯酸酯修饰的水可稀释性环氧树脂的粘合剂,并提供令人满意的防腐蚀性;它们借助于含有羟甲基的树脂(特别是酚醛树脂A)而固化。在连续式加热炉中的固化温度是240℃。
相对于现有技术,本发明的任务是提供以可于低温(特别是借助于高能量辐射作用)固化的水可稀释性环氧树脂为基础的粘合剂。在此,通过涂敷形成的膜应当快速在基材上干燥,应当可固化成弹性膜,且应当非常有效地保护基材不受腐蚀损害。
本发明的任务通过提供包含具有可自由基聚合基团的经非离子稳定的水性环氧树脂的水性粘合剂而实现。
因此,本发明的主题是这样的粘合剂,其包含具有烯属不饱和基团的经非离子稳定的水性环氧树脂ABC,该环氧树脂ABC含有衍生自经聚乙二醇修饰的环氧树脂A、无聚氧乙烯基的环氧树脂B和烯属不饱和酸C的结构单元。
本发明的另一主题是经非离子稳定的水性环氧树脂ABC与不饱和氨基甲酸乙酯DEF的混合物,其中,该氨基甲酸乙酯DEF衍生自多官能异氰酸酯D、多官能脂族醇E和含羟基的烯属不饱和化合物F。
本发明此外还涉及经非离子稳定的水性环氧树脂ABC的制备方法,以及环氧树脂ABC和不饱和氨基甲酸乙酯DEF的混合物的制备方法。
此外,本发明涉及一个优选的实施方案,其中将经非离子稳定的环氧树脂ABC(任选地与不饱和氨基甲酸乙酯DEF混合)和每个分子具有至少两个环氧基的环氧树脂G′与反应产物GHI(GHI为环氧树脂G、脂肪酸H和胺I的反应产物,此描述于欧洲专利申请EP-A 1 233 034中)的反应产物G′GHI混合。
在此,所有衍生自环氧树脂A和B的反应产物中的至少50%具有至少一个通过末端环氧基与烯属不饱和酸C的反应而形成的酯基。
环氧树脂A包含每个分子具有至少两个环氧基的如对B所述的多官能环氧树脂和每个分子具有至少两个羟基的聚乙二醇的结构单元。由DE-A 36 43 751已知这种经修饰的环氧树脂,在此将其中与这种环氧树脂相关的公开内容引入作为参考。也可以使用具有氧亚乙基和氧亚丙基结构单元的共聚醚多元醇代替聚乙二醇,其中这些结构单元可以嵌段或无规方式分布。在此优选的是,这样的共聚醚多元醇含有至少50%,优选至少70%,特别优选至少80%的质量份额的氧亚乙基。也可能通过使聚环氧化物与伯或仲聚乙/丙二醇单醚胺(商品名为Jeffomine)反应,或通过使含OH的聚环氧化物与二异氰酸酯和聚乙/丙二醇单醚反应而制得亲水性环氧树脂,如EP-A0 661 314中所述。优选的是衍生自重均摩尔质量Mw为200克/摩尔至20,000克/摩尔,优选300克/摩尔至10,000克/摩尔的聚乙二醇的环氧树脂A。此外,这样的环氧树脂A是优选的,即在其制备中,聚乙二醇中的羟基数与环氧树脂中的环氧基数的比遵循约1∶0.8至约1∶4,优选1∶1至1∶3.5,还有这样的环氧树脂是优选的,即其环氧基的比含量介于2.5毫摩尔/千克和200毫摩尔/千克之间(5千克/摩尔至400千克/摩尔的“环氧当量”)。
没有聚氧乙烯基的环氧树脂B选自每个分子平均具有多于一个环氧基,优选两个环氧基的化合物。在此,这些环氧化合物(环氧基树脂)可为饱和或不饱和的,以及可为脂族、环脂族、芳族或杂环的,且还可含有羟基。它们也可包含在混合和反应条件下不引起干扰性副反应的取代基,例如烷基或芳基取代基、醚基等。优选地,它是多元酚或多元醇的缩水甘油醚,其环氧基的比含量介于1.1摩尔/千克和6.7摩尔/千克之间(“环氧当量”或“EV值”介于150克/摩尔和900克/摩尔之间),但特别优选介于1.5摩尔/千克和6.7摩尔/千克之间(150克/摩尔和650克/摩尔之间),羟基数是0毫克/克至200毫克/克,优选5毫克/克至100毫克/克。
根据DIN EN ISO 4629(DIN 53 240)的定义,羟基数是具有与待检测的样品一样多的羟基的氢氧化钾的质量mKOH比样品质量mB(就溶液和分散体而言,为样品中的固体质量)的商:常用单位是“毫克/克”。
至于多元酚,例如为间苯二酚、氢醌、2,2-双(4′-羟基苯基)-丙烷(双酚A)、二羟基二苯基甲烷(双酚F)的异构体混合物、4,4′-二羟基二苯基环己烷、4,4′-二羟基-3,3′-二甲基二苯基丙烷、4,4′-二羟基联苯、4,4′-二羟基二苯甲酮、双(4′-羟基苯基)-1,1-乙烷、双(4′-羟基苯基)-1,1-异丁烷、双(4′-羟基-叔丁基苯基)-2,2-丙烷、双(2-羟基萘基)-甲烷、1,5-二羟基萘、三(4-羟基苯基)-甲烷、双(4-羟基苯基)乙醚、双(4-羟基苯基)砜及前述化合物的氯化和溴化产物。
也可以使用多羟基醇的多缩水甘油醚,如乙二醇-1,2-二缩水甘油醚,丙二醇-1,2-二缩水甘油醚,丙二醇-1,3-二缩水甘油醚,丁二醇二缩水甘油醚,戊二醇二缩水甘油醚,新戊二醇二缩水甘油醚,己二醇二缩水甘油醚,二甘醇二缩水甘油醚,二丙二醇二缩水甘油醚,高碳聚亚氧烷基乙二醇二缩水甘油醚(如:高碳聚氧乙烯二醇二缩水甘油醚和聚氧丙烯二醇二缩水甘油醚、混合型聚氧乙烯-丙烯二醇二缩水甘油醚),聚氧丁烯二醇二缩水甘油醚,甘油、三羟甲基丙烷、三羟甲基乙烷、季戊四醇、山梨糖醇的多缩水甘油醚,烷氧基化的多元醇如甘油、三羟甲基丙烷、季戊四醇的多缩水甘油醚,环己烷二甲醇、双(4-羟基环己基)甲烷和2,2-双(4′-羟基环己基)丙烷的二缩水甘油醚,蓖麻油或三缩水甘油基三(2-羟基乙基)异氰脲酸酯的多缩水甘油醚。优选的是环氧基的比含量为1.25摩尔/千克至6.7摩尔/千克(环氧当量为150克/摩尔至800克/摩尔),特别是2.5至3.4摩尔/千克(300克/摩尔至400克/摩尔)的多缩水甘油醚。此外,还可以使用多元羧酸的多缩水甘油酯,其通过表氯醇或类似的环氧化合物与脂族、环脂族或芳族多元羧酸,如草酸、琥珀酸、己二酸、戊二酸、邻苯二甲酸、对苯二甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸、2,6-萘二羧酸和高碳二羧酸二缩水甘油酯,如二聚或三聚的亚麻酸,的反应而制得。例子包括己二酸、邻苯二甲酸和六氢邻苯二甲酸的二缩水甘油酯。此处优选相同范围的环氧基的比含量。
烯属不饱羧酸C具有至少一个酸基,优选为羧基,和具有至少一个烯属双键。优选的是,酸具有一个位于相对于酸基的α位置的双键,特别优选的是在α-碳原子上具有氢原子或甲基的这样的化合物。合适的酸C特别是丙烯酸和异丁烯酸、巴豆酸、异巴豆酸、马来酸、富马酸、柠康酸、中康酸和所述二元羧酸的半酯。
多官能异氰酸酯D是至少二官能的,和可以选自芳族和脂族直链、环状或支化异氰酸酯,特别是二异氰酸酯。优选的是其中其质量的至多5%可由三官能或更高官能异氰酸酯替代的二异氰酸酯。
此异氰酸酯优选地具有式Q(NCO)2,其中,Q代表具有4至40个碳原子,特别是4至20个碳原子的烃基,优选表示具有4至12个碳原子的脂族烃基、具有6至15个碳原子的环脂族烃基、具有6至15个碳原子的芳族烃基或具有7至15个碳原子的芳脂族烃基。这种优选使用的二异氰酸酯的例子为二异氰酸四亚甲基酯、二异氰酸六亚甲基酯、二异氰酸十二亚甲基酯、1,4-二异氰酸根合环己烷、3-异氰酸根合甲基-3,5,5-三甲基环己基异氰酸酯(异佛合尔酮二异氰酸酯,IPDI)、4,4′-二异氰酸根合二环己基甲烷、4,4′-二异氰酸根合二环己基丙烷-(2,2)、1,4-二异氰酸根合苯、2,4-或2,6-二异氰酸根合甲苯或其异构体的混合物,4,4′-或2,4′-二异氰酸根合二苯基甲烷、4,4′-二异氰酸根合二苯基丙烷-(2,2)、亚对二甲苯基二异氰酸酯和α,α,α′,α′-四甲基-亚间或对二甲苯基二异氰酸酯及这些化合物的混合物。
除了这样简单的多异氰酸酯以外,也适合的是连接异氰酸基的基团中含杂原子的多异氰酸酯。对此的例子为具有碳二亚胺基、脲基甲酸酯基、异氰脲酸酯基、氨基甲酸乙酯基、酰化的脲基或缩二脲基团的多异氰酸酯。其他适当的多异氰酸酯例如参考DE-A 29 28 552。
多官能脂族醇E的每个分子具有至少两个羟基和2至150个碳原子,优选3至40个碳原子,特别优选4至20个碳原子。它们可以是直链、支化或环状的,并且分子中也可含有非碳碳连接,如醚键、酯键或者仲或叔胺键。这样的化合物是醚醇或聚醚醇如聚乙二醇、聚丙二醇、它们的混合物和共聚物,和聚氧化亚丁基二醇(“聚-THF”),以及聚酯醇和氨基醇。优选的是乙二醇、1,2-和1,3-丙二醇、1,2-和1,4-丁二醇、新戊二醇、1,6-己二醇、三羟甲基乙烷、甘油、三羟甲基丙烷、赤藓醇、季戊四醇、山梨糖醇、甘露糖醇、二(三羟甲基)乙烷、双甘油、二(三羟甲基)丙烷、二甘醇、三甘醇、二和三丙二醇、二乙醇胺、N-甲基二乙醇胺、三乙醇胺、乙氧基化的三羟甲基丙烷和乙氧基化的甘油。
特别优选的是1,4-丁二醇和1,6-己二醇。
含羟基的烯属不饱和化合物F是具有3至20个碳原子和至少一个羟基的脂族单或多不饱和化合物。特别优选的是烯丙醇、丙烯酸羟乙基酯、异丁烯酸羟乙基酯、2-和3-羟基丙基-(甲基)-丙烯酸酯、1-羟基-2-丙基-(甲基)-丙烯酸酯、4-羟基丁基-(甲基)-丙烯酸酯和6-羟基己基-(甲基)-丙烯酸酯,以及通过(甲基)丙烯酸与1,2-环氧基化合物,特别是缩水甘油基醇与优选具有叔或季碳原子的一元脂族醇或酸的酯或醚,的反应而形成的丙烯酸酯和异丁烯酸酯。这样的化合物例如为缩水甘油基醇与称为Versatic酸、在α位置支化且具有5至12个碳原子的脂族一元羧酸的酯。
本发明进一步涉及经非离子稳定的水性环氧树脂ABC的混合物的制备方法,其中,首先,从经聚乙二醇修饰的环氧树脂A开始通过以前进反应(advancement reaction)的模式与基于环氧树脂的羟基化合物和基于环氧树脂的双环氧化合物,例如优选与双酚A和双酚A的二缩水甘油醚反应而制备得到链增长的树脂,将此链增长的环氧树脂和未用聚氧乙烯基修饰的环氧树脂B混合,并在第二步骤中共同与烯属不饱和酸C反应。在此于环氧环的开环情况下,形成加合物混合物ABC,其中分子具有半酯基和羟基,其优选为仲的。在分开的反应(步骤3)中,氨基甲酸乙酯丙烯酸酯DEF由多官能异氰酸酯D、任选地饱和多官能脂族羟基化合物E和具有羟基及至少一个烯属双键的烯属不饱和脂族化合物F制得。随后在第四步骤中,将加合物混合物ABC与不饱和氨基甲酸乙酯DEF混合,从而形成本发明的混合物。
在该混合物中,环氧树脂ABC的质量与氨基甲酸乙酯DEF的质量的比(每次只考虑固体树脂的质量,也就是不考虑分散剂或溶剂的份额)为(90至30)∶(10至70),优选(80至35)∶(20至65),特别是(60至40)∶(40至60)。
优选地,首先,从平均每个分子具有大约两个环氧基的环氧树脂和聚乙二醇开始于环氧基开环下制备水可分散的环氧树脂,然后,通过与一种在组分B的描述中所述的多元酚和一种在组分B的描述中所述的缩水甘油醚或酯以前进反应进行反应而形成亲水性环氧树脂A,直至优选的约1.2摩尔/千克至约1.5摩尔/千克(约670克/摩尔至约830克/摩尔的“EV值”)的环氧基含量。在添加催化剂之前,于减压下通过蒸馏而从环氧树脂与聚乙二醇的反应产物中去除作为分散剂的水。然后,混合入环氧树脂B,并将酸C加至该混合物中。向环氧树脂混合物中添加酸C于优选90℃至130℃的温度进行约6至10小时,在该过程中混合物的酸值降低至小于10毫克/克。
根据DIN EN ISO 3682(DIN 53 402)的定义,酸值是中和待检测的样品所需的氢氧化钾质量mKOH比样品质量mB(就溶液和分散体而言,为样品中的固体质量)的商;常用单位是“毫克/克”。
优选地如此制备不饱和丙烯酸酯,即先加入含羟基的不饱和化合物F,其任选地与多官能脂族醇E混合,和优选与促进氨基甲酸乙酯形成的催化剂一起加入,将预置物加热至60℃至90℃,并以使得温度保持于所述范围内的方式添加异氰酸酯D。在异氰酸酯的含量达到低于0.1cg/g(低于1%的质量份额)之后,冷却此反应混合物,和将获得的氨基甲酸乙酯DEF与环氧化物组分ABC混合。
也可以在ABC和DEF的混合物中再添加根据组分A的环氧树脂和聚乙二醇的加合物,以改善混合物的可分散性。这一添加数量可以优选为ABC和DEF质量总和的2%至10%,特别是4%至8%。该比例分别与固体的质量有关。
本发明进一步涉及一优选的实施方案,其中,将经非离子稳定的环氧树脂ABC或其与不饱和丙烯酸酯DEF的混合物与G′GHI混合,G′GHI是每个分子具有至少两个环氧基的环氧树脂G′与环氧树脂G、脂肪酸H和胺I的反应产物GHI(此描述于欧洲专利申请EP-A 1 233034)的反应产物。在本申请中引入该申请中针对这些反应产物的描述和其制备方法作为参考。导致本发明的实验显示:这样的混合能够进一步改善由根据本发明水性的经非离子稳定的环氧树脂配制得到的涂层的已经优异的防腐蚀性。
在此,环氧树脂ABC的质量或环氧树脂ABC和氨基甲酸乙酯DEF的质量总和与反应产物G′GHI的质量的比为(90到30)∶(10至70),优选(80至40)∶(20至60),特别优选(70至45)∶(30至55)。
此外,环氧树脂G和G′符合关于组分B的描述,它们的环氧基比含量各自独立地优选为0.4摩尔/千克至7摩尔/千克,特别是0.6摩尔/千克至6摩尔/千克。在一个优选的实施方案中,对于G和G′各使用双环氧化合物,其中G的环氧基比含量是0.5摩尔/千克至4摩尔/千克,G′是2摩尔/千克至5.9摩尔/千克。
特别优选的是对于G和G′在每种情况下使用基于双酚A和双酚F及其混合物的环氧树脂。
脂肪酸H具有至少一个烯属双键,和具有6至30个,优选8至26个,特别是16至22个碳原子。优选的是棕榈油酸、油酸、芥酸、亚油酸、亚麻酸、桐酸、花生四烯酸和鰶鱼酸,以及从天然存在的油作为混合物得到的脂肪酸如亚麻油脂肪酸、大豆油脂肪酸、Conjuvandol-脂肪酸、妥尔油脂肪酸、棉籽油脂肪酸、油菜籽油脂肪酸、鱼油脂肪酸和从脱水蓖麻油中获得的脂肪酸混合物。
胺I优选为具有至少一个伯或仲氨基的脂族直链、环状或支化的胺。它们优选具有2至12个碳原子,还可含有叔氨基和/或羟基作为官能团。特别适用的是具有6至12个碳原子的伯一元胺(如己胺、环己胺、2-乙基己胺和硬脂胺)、伯二胺(如乙二胺、1,4-二氨基丁烷和1,6-二胺基己烷)、伯-叔二胺(如二甲氨基丙胺、二乙氨基丙胺)、二伯-仲胺(如二亚乙基三胺、1,9-二氨基-5-氮杂壬烷、1,13-二氨基-7-氮杂十三烷、三亚乙基四胺和四亚乙基五胺以及以商品名Polymin而市售得到的低聚合的二氨基聚乙烯亚胺的混合物)、仲胺和仲二胺(如哌啶、哌嗪、二正丁基胺、吗啉)和具有羟基官能团的胺(如乙醇胺、二乙醇胺和二异丙醇胺)。也可以使用所述胺的混合物。
产物GHI可由顺序的反应而制得,其中,首先将环氧化合物G与胺I反应形成产物GI,然后将该加合物在第二个步骤中与脂肪酸H反应成中间产物GHI。但也可以首先使环氧化合物G与脂肪酸H反应生成产物GH,然后使GH中剩余的环氧基与胺I反应。同样也可以同时进行反应,即在一个步骤中得到中间产物GHI。选择原料G、H和I的量,以使得基本上所有的环氧基,即至少90%,优选至少95%,特别优选至少98%的原来存在于G中的环氧基被反应。该反应还优选地以这样的方式来进行,以致于中间产物GHI不再具有反应性胺氢原子,但是胺氢原子的含量最大可以为10毫摩尔/千克。
为了制备本发明的反应产物G′GHI,各组分优选以下列摩尔份额进行反应:
将1摩尔环氧化合物G、0.1摩尔至1.0摩尔(优选0.2摩尔至0.9摩尔,特别优选0.25摩尔至0.8摩尔)脂肪酸H、0.5至1.9摩尔(优选0.6摩尔至1.75摩尔,特别优选0.65摩尔至1.5摩尔)胺I在第一个阶段中进行反应,然后在第二个阶段中,将0.2摩尔至1.0摩尔(优选0.25至0.9,特别优选0.3摩尔至0.8摩尔)环氧化合物G′与阶段1的加合物反应。
根据本发明水性的经非离子稳定的环氧化物树脂及包含其的混合物可以配制成涂层剂,这种涂层剂迅速地于基材如金属、塑胶、木材、纺织品或纸板上形成干膜,此干膜通过用高能量光或其他光化辐射照射而固化成粘弹性的膜,这种膜展现了与基材极佳的粘合性,而且即使受到撞击也不会撕破或剥落,并提供了极佳的防腐蚀性,特别是抗酸性和含盐水溶液的防腐蚀性。
本发明的涂层剂特别适用于金属的涂覆,其中漆膜极为有效地保护基材免受腐蚀损害,并形成具有优异弹性的涂层。
为了配制涂漆,优选添加光引发剂,任选地添加其他常用添加剂如消泡剂、均化剂,或者在着色漆的情况下还可添加抗沉降剂。在根据常用方法如辊压、浸涂、刷涂、刮涂或喷涂进行涂敷之后,将漆层于20℃至90℃,优选约60℃至约70℃风干,然后借助于高能量辐射特别是紫外线通过交联而固化。
用下列实施例更详细地说明本发明。若未另外规定,则在实施例中,所有带有单位“%”的数据与前述内容一样都是指质量比例(有关的物质的质量与混合物的质量的商)。以“%”表示的浓度数据是指溶解的物质在溶液中的质量份额(溶解的物质的质量除以溶液的质量)。
实施例1 亲水性环氧树脂
将1000g聚乙二醇PEG4000(平均摩尔质量为约4000克/摩尔)加热至120℃,并于减压和通氮气的情况下除去溶解的水。然后添加110g双酚A-二缩水甘油醚,随后添加1.7g50%的四氟硼酸水溶液。在达到恒定的约0.1至0.2摩尔/千克的环氧基比含量之后,添加1100g水以稀释至约50%的固体质量份额。
实施例2 环氧树脂-酸加合物
将534g双酚A-二缩水甘油醚与165g双酚A和600g实施例1中的水溶液混合,加热至125℃。于减压下从混合物中蒸馏出约300g水,向除去水的混合物中于此温度下添加0.2g三苯基膦。因为放热反应,混合物的温度升高至约140℃。混合物维持于此温度下约4小时,直到环氧基比含量降至1.3摩尔/千克至1.4摩尔/千克。随后另外添加700g双酚A-二缩水甘油醚,并将此混合物冷却至105℃。在空气中,在2小时内滴加365g丙烯酸(经4g氢醌一甲基醚稳定)和2g苄基二甲胺。再搅拌反应混合物8小时,至酸值降至低于10mg/g。
实施例3 氨基甲酸乙酯丙烯酸酯
将1334g等物质数量的丙烯酸与Versatic-10-酸(具有10个碳原子的在α位置上支化的饱和脂族单羧酸(其中α位置上的至少一个烷基是甲基)的混合物)的缩水甘油酯的加合物、180g 1,4-丁二醇、3g氢醌一甲基醚和0.6克二月桂酸二丁基锡混合,并加热至70至80℃。在空气中,以能够维持温度的方式添加696g 2,4-和2,6-亚甲苯基二异氰酸酯的工业级混合物。约两小时之后,未反应的异氰酸基的质量份额比率降低至0.1%以下。
实施例4 氨基甲酸乙酯丙烯酸酯与环氧树脂-酸加合物的混合物
将1845g实施例2的环氧树脂-酸加合物与1760g实施例3的氨基甲酸乙酯丙烯酸酯充分地搅拌混合。分三次每次添加609g软化水,并用高速搅拌器进行充分混合。再添加502g软化水,以使得固体质量份额达到约60%。
实施例5 实施例4的粘合剂的测试
在100g实施例4的水性分散体中添加3g光引发剂(Irgacure184)于3g丁基乙二醇中的溶液。如此制备的透明涂漆的粘度在23℃和25S-1的剪切梯度下是1014mPa·s。
使用此透明涂漆涂敷防锈磷化板(来自ST 1405的钢板,未经处理,一面磨光,实施例5.1)和钢板26S/60/OC(来自ST 1405,经喷磷酸盐处理,实施例5.2),并于60℃干燥10分钟。干膜的厚度各是50微米。膜的摆锤硬度(于50微米的干膜层厚度的情况下在玻璃平板上测得)在干燥之后24小时是174s。
作为比较(实施例5V.1和5V.2),将相同材料的钢板用溶解于反应性稀释剂(三羟甲基丙烷-缩甲醛-单丙烯酸酯)的市售氨基甲酸乙酯丙烯酸酯涂漆以同样的干膜厚度进行测试。对比实施例V3和V4用水性透明涂漆来进行,这种水性透明涂漆描述于EP-B 0 694 531、使用实施例4的聚氨酯树脂的实施例6之中。
在此,用刮刀涂敷该水性透明涂漆,于室温风干10至15分钟,然后通过用UV灯(80瓦)以10cm距离进行照射而硬化,以5至10m/分钟的速率推进。
除了机械测试以外,经涂敷的钢板还就涂层的耐水性和耐溶剂性进行测试,和在喷盐试验(在漆层中有和没有裂缝)中就防腐蚀性进行测试。在测试耐溶剂(丙酮)和耐水性的情况下,指出了未看到漆层的表面变化的时间。在测试防腐蚀性的情况下,指出了多少比例的经涂敷的表面生了锈。
结果总结于表1和2中。
实施例6 实施例4的粘合剂和环氧化物-胺-脂肪酸加合物的混合物
根据EP-A 1 233 034制备加合物:
将1900g基于双酚A的环氧树脂,其环氧基比含量为2.1摩尔/千克(“环氧当量”EEW=475克/摩尔),和420g妥尔油脂肪酸(1.5摩尔)、102g二甲氨基丙胺(1摩尔)和53g(0.5摩尔)二乙醇胺溶解于作为溶剂的甲氧基丙醇中,形成70%的溶液(70g固体于100g溶液中),于110℃反应直到环氧基完全耗尽。
然后,在每100g固态树脂中添加60毫摩尔醋酸。然后用软化水稀释至40%的固体质量份额(非挥发性物质的质量份额)。
在此水溶液中,于90℃在1小时内添加250g双酚A-二缩水甘油醚,将此混合物于此温度下搅拌,直到不再测得有环氧基。此溶液通过进一步添加水而稀释至38%固体质量份额。
将60g此水性粘合剂与60g实施例4的粘合剂混合,再添加30g水以及3gIrgacure 184于3g丁基乙二醇中的溶液。如此制备的透明涂漆的粘度是122mPa·s。在干燥之后24小时测得的膜的摆锤硬度(于50微米的干膜层厚度的情况下在玻璃平板上测得)是111s。
实施例7 实施例6的树脂的测试
由与实施例5相同的材料制得的钢板用实施例6(实施例6.1和6.2)的透明涂漆进行涂敷,同样至干膜厚度为50微米。涂漆的涂布和通过辐射的交联与实施例5一样进行。机械测试、耐抗性测试和防腐蚀性测试的结果总结于表1和2中。
表1 机械测试结果
实施例的透明涂漆 | 5 | 对比 | 6 | |||||
钢板 | 5.1防锈磷化 | 5.2经磷酸盐化处理 | V.1防锈磷化 | V.2经磷酸盐化处理 | V.3防锈磷化 | V.4经磷酸盐化处理 | 6.1防锈磷化 | 6.2经磷酸盐化处理 |
Erichsen深冲值(毫米) | 8.5 | 6.5 | 9 | 9 | 8 | 7 | 9 | 9 |
球撞击试验(焦耳(英寸·磅)) | 7.9/3.4(70/30) | 3.4/1.1(30/10) | 9.0/9.0(80/80) | 9.0/9.0(80/80) | 9.0/7.9(80/70) | 7.9/5.7(70/50) | 7.9/5.7(70/50) | 5.7/4.5(50/40) |
格切 | 3/4 | 0/0 | 0/0 | 0/0 | 3/4 | 1/2 | 0/0 | 0/0 |
Erichsen深冲值根据标准DIN EN ISO 1520,格切(grid cut)根据标准DIN EN ISO 2409进行测定和评价。撞击试验根据ASTM-标准D2794施行。
可以清楚看出,根据实施例5和7的透明涂料得到这样的膜,即其机械值与已知的溶解于反应性稀释剂中的体系的机械值相当。
表2 耐抗性和防腐蚀性
实施例的透明涂漆 | 5 | 对比 | 6 | |||||
钢板 | 5.1防锈磷化 | 5.2经磷酸盐化处理 | V.1防锈磷化 | V.2经磷酸盐化处理 | V.3防锈磷化 | V.4经磷酸盐化处理 | 6.1防锈磷化 | 6.2经磷酸盐化处理 |
耐水性(小时) | >24 | >24 | >24 | >24 | >24 | >24 | >24 | >24 |
耐丙酮性(小时) | >24 | >24 | >4 | >4 | 16 | 16 | 1 | 1 |
喷盐试验24小时之后有裂缝无裂缝 | 10mm | i.0. | 20mm | i.0. | 20mm | 10mm | i.0. | i.0 |
30%B | i.0. | 80%R | i.0. | 40%B | 20%B | i.0. | i.0 | |
喷盐试验72小时之后有裂缝无裂缝 | 20mm | i.0. | i.0. | 100%B | 90%B | 2mm | i.0 | |
80%B | i.0. | 5%R | 100%B | 90%B | i.0. | i.0 | ||
喷盐试验96小时之后有裂缝无裂缝 | i.0. | i.0. | 2mm | i.0 | ||||
i.0. | 10%R | i.0. | i.0 | |||||
喷盐试验360小时之后有裂缝无裂缝 | 7mm | 5mm,10%R | 20mm,10%R | 2mm | ||||
2%R | 30%R | 40%R,w | W |
在此,“耐抗性”是指膜与有关试剂(水或丙酮)接触之后不显出可见变化的时间。在喷盐试验中,长度数据(mm)是指自裂缝的锈蚀路径的长度,符号“R”是生锈的面积份额(%),小“w”是指“白锈”。在该试验中,钢板的边缘粘贴上胶粘带,直至距离边缘大约1cm,以防止漆膜从边缘翘起。
由这些数据可以清楚看出,根据本发明的水性透明涂漆的防腐蚀性比已知的基于反应性稀释剂的体系(V1、V2)以及已知的基于经阴离子稳定的氨基甲酸乙酯丙烯酯的含水体系(V3和V4,根据EP-B 0 694531)要明显地好得多。
Claims (13)
1.一种包含经非离子稳定的环氧树脂ABC的、水性可辐射固化性粘合剂,其特征在于其包含经聚乙二醇修饰的环氧树脂A、无聚乙二醇的环氧树脂B和烯属不饱和酸C的结构单元,和在于所有衍生自环氧树脂A和B的反应产物中的至少50%具有至少一个通过末端环氧基与烯属不饱和酸C的反应而形成的酯基。
2.根据权利要求1的水性可辐射固化性粘合剂,其特征在于,其含有不饱和的氨基甲酸乙酯DEF,该氨基甲酸乙酯DEF衍生自多官能异氰酸酯D、多官能脂族醇E和含羟基的烯属不饱和化合物F。
3.根据权利要求2的水性可辐射固化性粘合剂,其特征在于,环氧树脂ABC的质量与氨基甲酸乙酯DEF的质量的比是90-30∶10-70。
4.根据权利要求1的水性可辐射固化性粘合剂,其特征在于,其另外包含每个分子具有至少两个环氧基的环氧树脂G′与环氧树脂G、脂肪酸H和胺I的反应产物GHI的反应产物G′GHI。
5.根据权利要求4的水性可辐射固化性粘合剂,其特征在于,环氧树脂ABC的质量与反应产物G′GHI的质量的比是90-30∶10-70。
6.根据权利要求2的水性可辐射固化性粘合剂,其特征在于,其另外包含每个分子具有至少两个环氧基的环氧树脂G′与环氧树脂G、脂肪酸H和胺I的反应产物GHI的反应产物G′GHI。
7.根据权利要求6的水性可辐射固化性粘合剂,其特征在于,环氧树脂ABC和氨基甲酸乙酯DEF的质量总和与反应产物G′GHI的质量的比是90-30∶10-70。
8.一种制备根据权利要求1的水性可辐射固化性粘合剂的方法,其特征在于,首先,通过基于环氧树脂的羟基化合物与基于环氧树脂的双环氧化合物以前进反应的模式进行反应而制得经聚乙二醇修饰的环氧树脂A,并将此环氧树脂与未经聚氧乙烯基修饰的环氧树脂B混合,和在第二步骤中,将此混合物与烯属不饱和酸C反应,其中通过环氧环的开环而形成加合物混合物ABC。
9.一种制备根据权利要求2的水性可辐射固化性粘合剂的方法,其特征在于,由多官能异氰酸酯D、任选地饱和的多官能脂族羟基化合物E和具有羟基与至少一个烯属双键的烯属不饱和脂族化合物F制得氨基甲酸乙酯丙烯酸酯DEF,并将该氨基甲酸乙酯丙烯酸酯DEF与根据权利要求8制备的加合物ABC混合。
10.一种制备根据权利要求4的水性可辐射固化性粘合剂的方法,其特征在于,通过环氧化合物G与胺I和脂肪酸H的反应制得中间产物,该中间产物随后与每个分子具有至少两个环氧基的环氧树脂G′反应形成加合物G′GHI,该加合物G′GHI随后与根据权利要求8制备的加合物ABC混合。
11.一种制备根据权利要求6的水性可辐射固化性粘合剂的方法,其特征在于,通过环氧化合物G与胺I和脂肪酸H的反应制得中间产物,该中间产物随后与每个分子具有至少两个环氧基的环氧树脂G′反应形成加合物G′GHI,该加合物G′GHI随后与根据权利要求9制备的混合物混合。
12.根据权利要求1、2、4或6的水性可辐射固化性粘合剂用于制备基材上的防腐蚀涂层的用途,其包括步骤:混合粘合剂与光引发剂和任选地其他添加剂,根据辊压、浸涂、喷涂、刮涂或刷涂的方法之一将含水漆涂敷在基材上,将涂层于20℃至90℃风干,并通过借助于高能量辐射的照射而交联。
13.根据权利要求12的用途,用于在金属上制备防腐蚀涂层。
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-
2002
- 2002-10-21 AT AT0159802A patent/AT504465A1/de unknown
-
2003
- 2003-10-17 KR KR1020057006808A patent/KR101037044B1/ko not_active IP Right Cessation
- 2003-10-17 WO PCT/EP2003/011561 patent/WO2004037935A1/de active Application Filing
- 2003-10-17 AU AU2003276119A patent/AU2003276119A1/en not_active Abandoned
- 2003-10-17 JP JP2004545885A patent/JP4652811B2/ja not_active Expired - Fee Related
- 2003-10-17 MX MXPA05004190A patent/MXPA05004190A/es active IP Right Grant
- 2003-10-17 EP EP03809292.0A patent/EP1556450B1/de not_active Expired - Lifetime
- 2003-10-17 BR BRPI0306519-7A patent/BR0306519B1/pt not_active IP Right Cessation
- 2003-10-17 CA CA2502961A patent/CA2502961C/en not_active Expired - Fee Related
- 2003-10-17 US US10/531,090 patent/US7560143B2/en not_active Expired - Fee Related
- 2003-10-17 CN CNB2003801017368A patent/CN1322079C/zh not_active Expired - Fee Related
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CN102648228A (zh) * | 2009-09-21 | 2012-08-22 | Igm集团公司 | 可辐射固化的环氧丙烯酸酯的水分散体 |
Also Published As
Publication number | Publication date |
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US7560143B2 (en) | 2009-07-14 |
KR101037044B1 (ko) | 2011-05-26 |
EP1556450A1 (de) | 2005-07-27 |
CN1322079C (zh) | 2007-06-20 |
AT504465A1 (de) | 2008-05-15 |
CA2502961A1 (en) | 2004-05-06 |
BR0306519B1 (pt) | 2014-05-20 |
MXPA05004190A (es) | 2005-06-08 |
AU2003276119A1 (en) | 2004-05-13 |
BR0306519A (pt) | 2004-11-30 |
JP2011017015A (ja) | 2011-01-27 |
TW200420596A (en) | 2004-10-16 |
CA2502961C (en) | 2011-05-17 |
WO2004037935A1 (de) | 2004-05-06 |
JP2006503944A (ja) | 2006-02-02 |
JP4652811B2 (ja) | 2011-03-16 |
EP1556450B1 (de) | 2013-09-18 |
US20050287302A1 (en) | 2005-12-29 |
TWI322160B (en) | 2010-03-21 |
KR20050083790A (ko) | 2005-08-26 |
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