CN105939992A - 用于低排放环氧树脂产物的胺 - Google Patents
用于低排放环氧树脂产物的胺 Download PDFInfo
- Publication number
- CN105939992A CN105939992A CN201580005977.5A CN201580005977A CN105939992A CN 105939992 A CN105939992 A CN 105939992A CN 201580005977 A CN201580005977 A CN 201580005977A CN 105939992 A CN105939992 A CN 105939992A
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- Prior art keywords
- amine
- double
- epoxy resin
- monoalkylation
- amino methyl
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 91
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 74
- -1 aryl monoglycidyl ether Chemical compound 0.000 claims abstract description 69
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 10
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims description 73
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
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- 239000003085 diluting agent Substances 0.000 claims description 26
- 150000004985 diamines Chemical class 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 16
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 14
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- 238000006243 chemical reaction Methods 0.000 claims description 12
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- 229910052799 carbon Inorganic materials 0.000 claims description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
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- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 7
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- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 6
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- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
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Abstract
本发明涉及式(I)的胺,所述胺为1,2‑丙二胺与芳基单缩水甘油醚的加成物,本发明还涉及所述胺作为环氧树脂的固化剂的成分的用途和因此获得的环氧树脂组合物。式(I)的胺可以在简单的方法中以高纯度制得,其粘度极低并且特别适合用于固化环氧树脂。其能够实现可容易加工的低排放环氧树脂组合物,所述环氧树脂组合物即使在湿冷条件下仍然迅速固化成具有高硬度和表面品质的产品而无雾浊效应,所述产品在光影响下几乎不变黄。
Description
技术领域
本发明涉及的领域是胺、用于环氧树脂的固化剂、环氧树脂产品及其用途,特别是作为涂料、覆层和刷抹料的用途。
背景技术
适用于涂料目的的环氧树脂产品应当具有尽可能低的粘度,使得其在环境温度下可容易加工并且自流平。此外,其应当即使在湿冷条件下也尽可能迅速和无干扰地固化,从而形成平坦表面而无浑浊、斑点或凹穴。最后,已固化涂料应当具有高硬度和低脆性,从而尽可能好地承受机械负荷。对于视觉要求苛刻的应用(例如地板覆层)来说,涂层还应当具有高的光泽度和在光的影响下尽可能低的变黄倾向。
现有技术中已知的用于环氧树脂涂料的固化剂通常包含多胺与二环氧化物(特别是与双酚液体树脂)的加成物。所述加成物能够实现迅速固化,但是其粘度极高,因此在固化剂中通常加入稀释剂。稀释剂改进可加工性,降低涂料的脆性并且通过避免雾浊效应的出现而改进表面品质。“雾浊效应”表示在固化时出现的通过胺与空气中的二氧化碳(CO2)形成盐(“雾浊”)而造成的且特别是在高空气湿度和低温下出现的表面缺陷,例如浑浊、斑点、粗糙和发粘。通常使用的稀释剂(特别是苯甲醇以及乙二醇和烷基酚)在室温下对环氧树脂不具反应性,并且因此在固化时不结合入树脂基质中。然而目前越来越期望在固化之后具有低含量的通过蒸发过程或扩散过程释放的物质的低排放产物。因此,对于低排放的环氧树脂产品,可以仅以极少的量使用或完全不使用不可结合性稀释剂。
稀释固化剂组分的另一种可能性是在固化剂组分中加入提高量的小分子胺。但是所述胺(例如二甲基氨基丙胺或二亚乙基三胺)具有强烈气味,强烈刺激皮肤和眼睛和是致敏的,并且强烈造成雾浊效应。
此外,还可以使用单环氧化物(特别是单缩水甘油醚)的胺加成物,其相比于二环氧化物的胺加成物具有明显减小的粘度并且因此更少的稀释剂就足够。已知的低粘度加成物由脂族胺1,5-二氨基-2-甲基戊烷(MPMD)和甲苯基缩水甘油醚获得。其能够实现低稀释剂含量至不含稀释剂的环氧树脂涂料,所述涂料可以固化而基本上无雾浊效应。然而所述涂料的固化速度或强度的建立、最终硬度和粘度仍有待改进。
发明内容
因此,本发明的目的是提供低粘度和低气味的胺,所述胺能够配制低排放的环氧树脂,其即使在相对低的温度下也能迅速固化并且形成高品质薄膜或具有高表面品质和强度的物体,并且在光的影响下几乎不变黄。
出人意料地发现,式(I)的胺极好地实现所述目的。其具有低熔点,出人意料地低粘度和低气味,并且可以通过简单方法由可市售购得且廉价的物质以高纯度制得。
对于作为固化剂的用途,式(I)的胺即使在低温下也能够实现具有低粘度因此具有良好的可加工性、迅速建立的强度和高表面品质的环氧树脂产品。不仅在标准气候中而且在湿冷条件(例如8℃和80%的相对空气湿度)下,在平面应用时形成具有高光泽度的透明薄膜,所述薄膜在光的影响下几乎不变黄并且没有斑点、不平、结构或花纹。式(I)的胺具有一个空间位阻的伯氨基和一个通过相邻的羟基活化的仲氨基,并且与市售的基于双酚-A和/或双酚-F的液体环氧树脂出色地相容。相比于使用例如DETA、MPMD、TMD、1,3-BAC或IPDA的相似的加成物,用式(I)的胺可获得具有更低粘度和/或更好表面品质的环氧树脂产品。用式(I)的胺可获得环氧树脂组合物,所述环氧树脂组合物即使在没有稀释剂而且没有具有强烈气味的小分子胺的情况下仍然是低粘度的,并且即使在低温下和较早暴露于喷射水的情况下仍然固化成具有高光泽度的无缺陷的高品质薄膜,所述薄膜在光的影响下几乎不变黄。
本发明的其它方面为其它独立权利要求的主题。本发明的特别优选的实施方式为从属权利要求的主题。
具体实施方式
本发明的主题是式(I)的胺,
其中
R表示任选地包含不饱和部分的具有1至22个碳原子的烷基、环烷基、芳烷基或烷氧基;并且n表示0或1或2或3。
以“聚/多”为首的物质名称,如多胺、多元醇或聚环氧化物,表示形式上每分子包含两个或更多个在其名称中出现的官能团的物质。
“伯氨基”表示键合至一个有机基团的NH2-基团,“仲氨基”表示键合至两个有机基团(其也可以是环的共同部分)的NH-基团。
“胺氢”表示伯氨基和仲氨基的氢原子。
“胺氢当量”表示相对于固化剂或胺中存在的每个胺氢的固化剂或胺的重量份额。
“不可结合性稀释剂”表示可溶于环氧树脂并且使其粘度降低的物质,所述物质在环氧树脂固化时不共价结合入树脂基质。
在本文献中术语“粘度”表示通过剪切应力和剪切率(速度梯度)之间的比例定义并且如DIN EN ISO 3219中所述确定的动态粘度或剪切粘度。
当n表示2或3时,式(I)中的基团R可以彼此相同或不同。
优选地,n表示0或1或2,特别是1。此种式(I)的胺具有特别低的粘度。
优选地,R表示任选地包含不饱和部分的具有1至18个碳原子的烷基或烷氧基,特别优选表示甲基,叔丁基,具有12至18、特别是15个C原子的不饱和脂肪烷基或甲氧基。
特别地,R表示甲基,优选表示2-甲基。
最优选地,n表示1并且R表示甲基,特别是2-甲基。此种式(I)的胺特别容易获得,并且特征在于特别低的粘度和特别好的作为环氧树脂产品的成分的性能,特别是迅速的固化和高的最终硬度。
此外还优选地,n表示1并且R表示叔丁基,特别是4-叔丁基。此种式(I)的胺能够实现非常特别漂亮的表面。此外还优选地,n表示1并且R表示具有15个C原子并且特别在3-位上具有不饱和部分的脂肪烷基。此种式(I)的胺具有特别低的粘度并且能够实现具有相当软的性能的环氧树脂产品。
式(I)的胺优选可通过1,2-丙二胺与芳基单缩水甘油醚的反应获得。其也可以被称为1,2-丙二胺与芳基单缩水甘油醚的加成物。
优选作为芳基单缩水甘油醚的是苯酚、甲酚、邻甲氧基苯酚、4-甲氧基酚、叔丁基酚或腰果酚的缩水甘油醚。在此,腰果酚表示来自腰果壳油的包含8,11,14-十五烷三烯基酚作为主要成分的蒸馏物。
特别优选的芳基单缩水甘油醚是所有异构的甲苯基缩水甘油醚及其任意混合物,特别是2-甲苯基缩水甘油醚。优选使用可市售获得的甲苯基缩水甘油醚,特别是DY-K(来自Huntsman)、PolypoxTM R6(来自Dow)、HeloxyTM KR(来自Moment ive)或GE-10(来自CVC Spec.Chem.)。
在一个优选的制备方法中,1,2-丙二胺与芳基缩水甘油醚如此反应,使得每摩尔芳基缩水甘油醚存在至少一摩尔1,2-丙二胺。
在一个特别优选的制备方法中,每摩尔芳基缩水甘油醚存在多于一摩尔1,2-丙二胺,并且在反应之后优选通过薄膜蒸馏或特别是薄层蒸馏将未反应的1,2-丙二胺蒸馏出。
优选地,所述制备方法采用在1.1至5、特别优选1.5至4范围内的1,2-丙二胺/芳基缩水甘油醚的摩尔比例,并且之后蒸馏除去未反应的1,2-丙二胺。通过这种方式制备的式(I)的胺的特征在于特别高的纯度和特别低的粘度,并且能够实现具有特别好的可加工性和特别漂亮的表面的环氧树脂产品。
优选通过在预置的1,2-丙二胺中缓慢地计量加入芳基单缩水甘油醚进行反应,其中反应物的温度优选保持在40至120℃、特别是50至110℃的范围内。
通过此种制备获得的反应产物除了式(I)的胺之外可能还包含其它胺加成物的成分,特别是式(II)的胺和/或式(III)的胺。然而由于1,2-丙二胺的两个氨基的不同的反应性以及在反应中相对于芳基单缩水甘油醚优选使用的过量的1,2-丙二胺,在蒸馏除去过量的1,2-丙二胺之后通常获得极纯的式(I)的胺。
在式(II)和(III)中,R和n具有已经提及的含义。
式(I)的胺具有非常有利的性能。其为低粘度的并且仅具有弱的胺气味。其熔点足够低,使得即使在冬季温度下也可以以液体状态处理和运输,而不存在结晶风险。其具有一个空间位阻的伯氨基和一个β-羟基取代的仲氨基。因此其特别适合作为环氧树脂的固化剂,其能够实现具有非常漂亮的表面的低粘度组合物,所述组合物即使在湿冷条件下也可以迅速固化形成高的最终硬度而无由雾浊造成的缺陷。
本发明的其他主题是至少一种式(I)的胺在环氧树脂的固化剂中的用途。
式(I)的胺在此具有的优点在于,其仅具有极低挥发性,足够低气味和低粘度,使得即使不使用溶剂或稀释剂也可以实现容易加工的环氧树脂产品。使用式(I)的胺获得具有非常漂亮的表面的低粘度的环氧树脂组合物,所述环氧树脂组合物即使在湿冷条件下也可以迅速和完全地固化而无由雾浊造成的缺陷,并且在光的影响下几乎不变黄。
式(I)的胺可以单独地或与其它胺和/或促进剂和任选地其它物质共同地用作环氧树脂的固化剂。
优选地,固化剂包含如此量的式(I)的胺,使得固化剂中的5至100%,优选10至90%,特别优选15至80%,特别是15至70%的对环氧基团有反应性的胺氢源自式(I)的胺。此种固化剂具有低粘度和迅速固化之间的良好平衡并且能够实现具有漂亮表面和高强度的环氧树脂产品。
固化剂除了式(I)的胺之外优选还包含至少一种具有至少两个对环氧基团有反应性的胺氢的另外的多胺。
为此合适的特别是如下多胺:
-脂族、环脂族或芳脂族伯二胺,特别是2,2-二甲基-1,3-丙二胺、1,3-戊二胺(DAMP)、1,5-戊二胺、1,5-二氨基-2-甲基戊烷(MPMD)、2-丁基-2-乙基-1,5-戊二胺(C11-新二胺)、1,6-己二胺、2,5-二甲基-1,6-己二胺、2,2,4-和2,4,4-三甲基六亚甲基二胺(TMD)、1,7-庚二胺、1,8-辛二胺、1,9-壬二胺、1,10-癸二胺、1,11-十一烷二胺、1,12-十二烷二胺、1,2-、1,3-和1,4-二氨基环己烷、双(4-氨基环己基)甲烷、双(4-氨基-3-甲基环己基)甲烷、双(4-氨基-3-乙基环己基)甲烷、双(4-氨基-3,5-二甲基环己基)甲烷、双(4-氨基-3-乙基-5-甲基环己基)甲烷、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷(=异佛尔酮二胺或IPDA)、2-和4-甲基-1,3-二氨基环己烷及其混合物、1,3-双(氨基甲基)环己烷(1,3-BAC)、1,4-双(氨基甲基)环己烷、2,5(2,6)-双(氨基甲基)双环[2.2.1]庚烷(NBDA)、3(4),8(9)-双(氨基甲基)三环-[5.2.1.02,6]癸烷(TCD-二胺)、1,4-二氨基-2,2,6-三甲基环己烷(TMCDA)、1,8-薄荷烷二胺、3,9-双(3-氨基丙基)-2,4,8,10-四氧杂螺[5.5]十一烷或1,3-双(氨基甲基)苯(MXDA);
-具有两个或三个脂族伯氨基并具有叔氨基的多胺,特别是N,N'-双(氨基丙基)哌嗪、N,N-双(3-氨基丙基)甲胺、N,N-双(3-氨基丙基)乙胺、N,N-双(3-氨基丙基)丙胺、N,N-双(3-氨基丙基)环己胺、N,N-双(3-氨基丙基)-2-乙基-己胺、三(2-氨基乙基)胺、三(2-氨基丙基)胺、三(3-氨基丙基)胺,或通过脂肪胺的双重氰乙基化和随后的还原获得的产物,所述脂肪胺源自天然脂肪酸,如可以Y12D和YT(来自Akzo Nobel)获得的N,N-双(3-氨基丙基)十二烷胺或N,N-双(3-氨基丙基)牛脂烷基胺;
-含醚基团的脂族伯多胺,特别是双(2-氨基乙基)醚、3,6-二氧杂辛烷-1,8-二胺、4,7-二氧杂癸烷-1,10-二胺、4,7-二氧杂癸烷-2,9-二胺、4,9-二氧杂十二烷-1,12-二胺、5,8-二氧杂十二烷-3,10-二胺、4,7,10-三氧杂十三烷-1,13-二胺和这些二胺的更高级的低聚物、双(3-氨基丙基)聚四氢呋喃和其它聚四氢呋喃二胺,来自1,4-二羟甲基环己烷的丙氧基化和之后的胺化的含醚基团的环脂族二胺,特别可以RFD-270(来自Huntsman)获得,或通常为聚氧化亚烷基二元醇和聚氧化亚烷基三元醇的胺化产物的聚氧化亚烷基二胺或聚氧化亚烷基三胺,例如可以名称(来自Huntsman)、以名称Polyetheramine(来自BASF)或以名称PC(来自Nitroil),特别是D-230、D-400、D-2000、D-4000、T-403、T-3000、T-5000、EDR-104、EDR-148和EDR-176获得,以及来自BASF或Nitroil的相应的胺;
-具有仲氨基的伯二胺,如特别是3-(2-氨基乙基)氨基丙胺、双(六亚甲基)三胺(BHMT)、二亚乙基三胺(DETA)、三亚乙基四胺(TETA)、四亚乙基五胺(TEPA)、五亚乙基六胺(PEHA)和线性聚亚乙基胺的更高级的同系物,如具有5至7个亚乙基胺单元的聚亚乙基多胺(所谓的“更高级的亚乙基多胺”,HEPA),通过具有至少两个伯氨基的伯二胺和伯多胺的多重氰乙基化或氰丁基化和随后的氢化而获得的产物,如二亚丙基三胺(DPTA)、N-(2-氨基乙基)-1,3-丙二胺(N3-胺)、N,N'-双(3-氨基丙基)亚乙基二胺(N4-胺)、N,N'-双(3-氨基丙基)-1,4-二氨基丁烷、N5-(3-氨基丙基)-2-甲基-1,5-戊二胺、N3-(3-氨基戊基)-1,3-戊二胺、N5-(3-氨基-1-乙基丙基)-2-甲基-1,5-戊二胺或N,N'-双(3-氨基-1-乙基丙基)-2-甲基-1,5-戊二胺;
-具有一个伯氨基和至少一个仲氨基的多胺,如特别是N-丁基-1,2-乙二胺、N-己基-1,2-乙二胺、N-(2-乙基己基)-1,2-乙二胺、N-环己基-1,2-乙二胺、4-氨基甲基哌啶、N-(2-氨基乙基)哌嗪、N-甲基-1,3-丙二胺、N-丁基-1,3-丙二胺、N-(2-乙基己基)-1,3-丙二胺、N-环己基-1,3-丙二胺、3-甲基氨基-1-戊胺、3-乙基氨基-1-戊胺、3-环己基氨基-1-戊胺、脂肪二胺如N-椰油烷基-1,3-丙二胺,脂族伯二胺与丙烯腈、马来酸二酯或富马酸二酯、柠康酸二酯、丙烯酸酯和甲基丙烯酸酯、丙烯酰胺和甲基丙烯酰胺和衣康酸二酯以1:1摩尔比反应的迈克尔型加成反应的产物,以及还有来自伯多胺与醛或酮的部分还原烷基化的产物,特别是具有两个伯氨基的上述多胺(特别是1,6-己二胺、MPMD、1,3-BAC、1,4-双(氨基甲基)环己烷、MXDA、BHMT、DETA、TETA、TEPA、DPTA、N3-胺或N4-胺)的N-单烷基化产物,其中烷基优选为苄基、异丁基、己基和2-乙基己基,以及还有部分苯乙烯化的多胺,特别是可市售获得的240(来自Mitsubishi GasChemical);
-仲二胺,如特别是具有两个伯氨基的上述多胺的N,N'-二烷基化产物,特别是1,6-己二胺、MPMD、1,3-BAC、1,4-双(氨基甲基)环己烷、MXDA、BHMT、DETA、TETA、TEPA、DPTA、N3-胺或N4-胺的N,N'-二烷基化产物,其中优选作为烷基的是2-苯基乙基、苄基、异丁基、己基或2-乙基己基。
作为具有至少两个对环氧基团有反应性的胺氢的多胺,优选的是具有至少一个仲氨基的伯二胺和/或伯多胺。
具有至少一种伯二胺的固化剂能够实现具有特别低的粘度和/或特别迅速建立的强度的环氧树脂产品。
在一个优选的实施方式中,固化剂除了式(I)的胺之外还包含至少一种伯二胺,所述伯二胺选自2,2,4-和2,4,4-三甲基六亚甲基二胺(TMD)、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷(IPDA)、1,3-双(氨基甲基)苯(MXDA)、1,3-双(氨基甲基)环己烷(1,3-BAC)、1,4-双(氨基甲基)-环己烷、双(4-氨基环己基)甲烷、双(4-氨基-3-甲基环己基)甲烷、2,5(2,6)-双(氨基甲基)双环[2.2.1]庚烷(NBDA)、3(4),8(9)-双(氨基甲基)三环[5.2.1.02,6]癸烷(TCD-二胺)和含醚基团的具有至多500g/mol的平均分子量的多胺。
此种多胺可市售获得并且能够实现不含特别容易挥发的胺的固化剂。
其中特别优选的是含醚基团的多胺,特别是聚氧化亚丙基二胺如特别是D-230(来自Huntsman)或BASF或Nitroil的相应的胺,以及来自1,4-二羟甲基环己烷的丙氧基化和之后的胺化的含醚基团的环脂族二胺,特别是RFD-270(来自Huntsman)。含醚基团的多胺能够实现具有特别低的粘度、迅速的固化和高的抗冲击性的环氧树脂涂料。
其中特别优选的还有IPDA。此种环脂族胺能够实现具有非常漂亮的表面的环氧树脂产品,所述环氧树脂产品具有特别的耐候性和耐化学品性。
其中特别优选的还有1,3-BAC。此种环脂族胺能够实现具有特别迅速建立的强度和高耐候性和耐化学品性的环氧树脂产品。
其中特别优选的还有MXDA。此种芳脂族胺能够实现具有特别迅速建立的强度和特别漂亮的表面的环氧树脂产品。
除了式(I)的胺之外还包含至少一种具有至少一个仲氨基的另外的多胺的固化剂能够实现具有非常特别低的粘度和特别高的冲击韧性的环氧树脂产品。
优选作为具有至少一个仲氨基的多胺的是N-单烷基化和N,N'-二烷基化的伯多胺及其混合物,例如特别通过伯多胺与醛或酮和氢的还原烷基化获得的那些。在此,醛比酮优选。优选的是其中50至100%、优选50至80%、特别是50至65%的原始伯氨基以仲氨基形式存在的那些多胺。其它优选的具有至少一个仲氨基的多胺为来自伯二胺的部分苯乙烯化的产物,特别是240(来自Mitsubishi GasChemical)。
在一个优选的实施方式中,固化剂除了式(I)的胺之外还包含至少一种具有至少一个仲氨基的多胺,所述多胺选自N-单烷基化1,6-己二胺、N,N'-二烷基化1,6-己二胺、N-单烷基化1,5-二氨基-2-甲基戊烷、N,N'-二烷基化1,5-二氨基-2-甲基戊烷、N-单烷基化1,3-双(氨基甲基)环己烷、N,N'-二烷基化1,3-双(氨基甲基)环己烷、N-单烷基化1,4-双(氨基甲基)环己烷、N,N'-二烷基化1,4-双(氨基甲基)环己烷、N-单烷基化1,3-双(氨基甲基)苯、N,N'-二烷基化1,3-双(氨基甲基)苯、N-单烷基化BHMT、N,N'-二烷基化BHMT、N-单烷基化DETA、N,N'-二烷基化DETA、N-单烷基化TETA、N,N'-二烷基化TETA、N-单烷基化TEPA、N,N'-二烷基化TEPA、N-单烷基化DPTA、N,N'-二烷基化DPTA、N-单烷基化N3-胺、N,N'-二烷基化N3-胺、N-单烷基化N4-胺和N,N'-二烷基化N4-胺,其中烷基分别选自苄基、2-苯基乙基、异丁基、己基和2-乙基己基。在此,所述胺和所述烷基之间的任何组合都是可能的。
此种多胺能够实现具有特别低的粘度、高的表面品质和特别高的冲击韧性的环氧树脂产品。其中优选的是单苄基和/或二苄基化的1,3-双(氨基甲基)-苯,单和/或二-2-乙基己基化的1,3-双(氨基甲基)苯和部分苯乙烯化的1,3-双(氨基甲基)-苯,如特别是240(来自Mitsubishi Gas Chemical)。此种芳脂族多胺与市售环氧树脂特别良好地相容并且能够实现具有迅速建立的强度和极高表面品质的环氧树脂产品。
可能有利的是,固化剂中除了式(I)的胺之外还存在至少一种伯二胺以及至少一种具有至少一个仲氨基的多胺。此种固化剂能够实现具有特别低的粘度、迅速建立的强度、高硬度和高冲击韧性的环氧树脂产品。特别优选的是含醚基团的多胺与N-单烷基化和/或N,N'-二烷基化的伯二胺的组合。
非常特别优选的固化剂除了式(I)的胺之外还包含至少一种具有醚基团的二胺和任选地其他伯二胺。优选作为具有醚基团的二胺的是来自Huntsman的D-230或来自BASF或Nitroil的相应的胺,和来自Huntsman的Jeffamine RFD-270,特别是来自Huntsman的D-230或来自BASF或Nitroil的相应的胺。
在此优选的是
固化剂中的10至90%、特别优选15至80%、特别是15至70%的对环氧基团有反应性的胺氢源自式(I)的胺,和
固化剂中的10至60%、优选10至50%、特别是20至50%的对环氧基团有反应性的胺氢源自具有醚基团的二胺。
此种固化剂优选具有至少5重量%,优选至少10重量%,特别是至少20重量%的式(I)的胺的含量。
此种固化剂优选具有小于90重量%,优选小于85重量%,特别是小于80重量%的式(I)的胺的含量。
另一个非常特别优选的固化剂除了式(I)的胺之外还包含至少一种具有醚基团的二胺和至少一种具有至少一个仲氨基的多胺。
在此优选的是
固化剂中的15至80、特别是15至70%的对环氧基团有反应性的胺氢源自式(I)的胺,
固化剂中的15至60%的对环氧基团有反应性的胺氢源自具有醚基团的二胺,和
固化剂中的10至35%、优选10至20%的对环氧基团有反应性的胺氢源自具有至少一个仲氨基的多胺。
此外,固化剂优选还包含至少一种促进剂。适合作为促进剂的是这样的物质,所述物质促进氨基和环氧基团之间的反应,特别为酸或可水解成酸的化合物,特别是有机羧酸例如乙酸、苯甲酸、水杨酸、2-硝基苯甲酸、乳酸,有机磺酸如甲磺酸、对甲苯磺酸或4-十二烷基苯磺酸,磺酸酯,其它有机或无机酸如特别是磷酸,或上述酸和酸酯的混合物;还有叔胺如特别是1,4-二氮杂双环[2.2.2]辛烷、苄基二甲胺、α-甲基苄基二甲胺、三乙醇胺、二甲基-氨基丙胺,咪唑如特别是N-甲基咪唑、N-乙烯基咪唑或1,2-二甲基咪唑,此种叔胺的盐,季铵盐,如特别是苄基三甲基氯化铵,脒例如特别是1,8-二氮杂双环[5.4.0]十一碳-7-烯,胍如特别是1,1,3,3-四甲基胍,酚如特别是双酚,酚树脂,和曼尼希碱如特别是2-(二甲基氨基甲基)酚、2,4,6-三-(二甲基氨基甲基)酚和由苯酚、甲醛和N,N-二甲基-1,3-丙二胺形成的聚合物,亚磷酸酯如特别是二-和三苯基亚磷酸酯,以及具有巯基的化合物。
优选的促进剂为酸、叔胺或曼尼希碱。特别优选的是水杨酸和/或2,4,6-三(二甲基氨基甲基)酚。
固化剂优选不包含具有高挥发性的胺。优选地,固化剂不包含1,2-丙二胺或仅包含痕量(特别是小于0.1重量%)的1,2-丙二胺。此外还优选地,固化剂不包含二甲基氨基丙胺和其它具有相当的高挥发性的胺。
在一个优选的实施方式中,固化剂基本上不包含分子量低于120g/mol、特别是低于150g/mol、特别优选低于180g/mol的胺。优选地,固化剂包含小于2重量%、特别是小于1重量%的分子量低于120g/mol、特别是低于150g/mol、特别优选低于180g/mol的胺。此种固化剂在毒理学方面是特别有利的并且在平面应用时能够实现特别漂亮的表面。
此外,固化剂还可以包含至少一种不可结合性稀释剂。适合作为不可结合性稀释剂的特别是二甲苯、2-甲氧基乙醇、二甲氧基乙醇、2-乙氧基乙醇、2-丙氧基乙醇、2-异丙氧基乙醇、2-丁氧基乙醇、2-苯氧基乙醇、2-苄氧基乙醇、苯甲醇、乙二醇、乙二醇二甲醚、乙二醇二***、乙二醇二丁醚、乙二醇二苯醚、二乙二醇、二乙二醇-单甲醚、二乙二醇-单***、二乙二醇-单-正丁醚、二乙二醇二甲醚、二乙二醇二***、二乙二醇二-正丁醚、丙二醇丁醚、丙二醇苯醚、二丙二醇、二丙二醇单甲醚、二丙二醇二甲醚、二丙二醇二-正丁醚、N-甲基吡咯烷酮、二苯甲烷、二异丙基萘、石油馏分例如-型(来自Exxon)、烷基酚如叔丁基酚、壬基酚、十二烷基酚和8,11,14-十五碳三烯基酚(来自腰果壳油的腰果酚,例如可以Cardolite NC-700获自Cardolite Corp.,USA)、苯乙烯化的酚、双酚,芳族烃树脂,特别是含酚基型,烷氧基化酚,特别是乙氧基化或丙氧基化的酚,特别是2-苯氧基乙醇,己二酸酯、癸二酸酯、邻苯二甲酸酯、苯甲酸酯、有机磷酸酯或磺酸酯或磺酰胺。优选的不可结合性稀释剂是苯甲醇、十二烷基酚、叔丁基酚、苯乙烯化的酚、乙氧基化的酚或含酚基的芳族烃树脂,特别是-型LS 500、LX 200、LA 300和LA 700(来自Rütgers)。
固化剂优选不包含或仅包含少量的,特别优选小于25重量%、特别是小于10重量%和最优选小于5重量%的不可结合性稀释剂。特别地,在固化剂中不加入不可结合性稀释剂。
此外,固化剂还可以包含芳族多胺,特别是间-和对-苯二胺、4,4'-、2,4'-和2,2'-二氨基二苯甲烷、3,3'-二氯-4,4'-二氨基二苯甲烷(MOCA)、2,4-和2,6-甲苯二胺、3,5-二甲基硫代-2,4-和-2,6-甲苯二胺的混合物(可作为300获自Albermarle)、3,5-二乙基-2,4-和-2,6-甲苯二胺的混合物(DETDA)、3,3',5,5'-四乙基-4,4'-二氨基二苯甲烷(M-DEA)、3,3',5,5'-四乙基-2,2'-二氯-4,4'-二氨基二苯甲烷(M-CDEA)、3,3'-二异丙基-5,5'-二甲基-4,4'-二氨基二苯甲烷(M-MIPA)、3,3',5,5'-四异丙基-4,4'-二氨基二苯甲烷(M-DIPA)、4,4'-二氨基二苯砜(DDS)、4-氨基-N-(4-氨基苯基)苯磺酰胺、5,5'-亚甲基二氨茴酸、二甲基-(5,5'-亚甲基二氨茴酸酯)、1,3-亚丙基-双-(4-氨基苯甲酸酯)、1,4-亚丁基-双-(4-氨基苯甲酸酯)、聚四亚甲基氧-双-(4-氨基苯甲酸酯)(可作为获自Air Products)、1,2-双-(2-氨基苯基硫代)乙烷、2-甲基丙基-(4-氯-3,5-二氨基苯甲酸酯)或叔丁基-(4-氯-3,5-二氨基苯甲酸酯)。
此外,固化剂还可以包含额外的加成物,特别是1,2-丙二胺与脂族单环氧化物或与二环氧化物的加成物,或其它伯二胺与单环氧化物或二环氧化物的加成物,以及胺和表氯醇的反应产物,特别是1,3-双(氨基甲基)苯的反应产物,可以328市售获得(来自Mitsubishi Gas Chemical)。
此外,固化剂还可以包含聚酰胺基胺,所述聚酰胺基胺是一价或多价羧酸或其酯或酸酐,特别是二聚脂肪酸,和化学计量比过量使用的脂族、环脂族或芳族多胺,特别是聚亚烷基胺例如DETA或TETA的反应产物,特别是可市售获得的聚酰胺基胺100、125、140和150(来自Cognis),223、250和848(来自Huntsman),3607和530(来自Huntsman)和EH 651、EH 654、EH 655、EH 661和EH 663(来自Cytec)。
此外,固化剂还可以包含曼尼希碱,其为酚与醛(特别是甲醛)和多胺的曼尼希反应的反应产物。特别合适的是也被称为非那明的腰果酚的曼尼希碱,例如可市售获得的非那明NC-541、NC-557、NC-558、NC-566、Lite 2001和Lite 2002(来自Cardolite)、3440、3441、3442和3460(来自Huntsman)和EH614、EH 621、EH 624、EH 628和EH 629(来自Cytec)。
此外,固化剂还可以包含单胺,如己胺和苯甲胺。
此外,固化剂还可以包含具有巯基的化合物,特别是如下化合物:
-硫醇封端的液体聚硫化物聚合物,其以商标名(来自Morton Thiokol;例如可获自SPI Supplies,或来自Toray FineChemicals)已知,特别是LP-3、LP-33、LP-980、LP-23、LP-55、LP-56、LP-12、LP-31、LP-32和LP-2型;以及还以商标名(来自Akzo Nobel)已知,特别是G 10、G 112、G 131、G 1、G 12、G 21、G 22、G 44和G 4型;
-硫醇封端的聚氧化亚烷基醚,其例如可通过聚氧化亚烷基二醇和聚氧化亚烷基三醇与表氯醇或与环氧烷,然后与硫氢化钠反应获得;
-聚氧化亚烷基衍生物形式的硫醇封端的化合物,其以商标名(来自Cognis)已知,特别是WR-8、LOF和3-800型;
-硫代羧酸的聚酯,例如季戊四醇四巯基乙酸酯、三羟甲基丙烷三巯基乙酸酯、乙二醇二巯基乙酸酯、季戊四醇四-(3-巯基丙酸酯)、三羟甲基丙烷三-(3-巯基丙酸酯)和乙二醇二-(3-巯基丙酸酯),以及聚氧化亚烷基二醇和聚氧化亚烷基三醇、乙氧基化三羟甲基丙烷和聚酯-二醇与硫代羧酸如巯基乙酸和2-或3-巯基丙酸的酯化产物;和
-其它具有巯基的化合物,如特别是2,4,6-三巯基-1,3,5-三嗪、2,2'-(亚乙基二氧)-二乙烷硫醇(三乙二醇-二硫醇)和乙二硫醇。
本发明的另一个主题是包含至少一种环氧树脂和上述固化剂的环氧树脂组合物。
常见的工业环氧树脂适合作为环氧树脂。其以已知的方法和方式获得,例如通过相应烯烃的氧化或者通过表氯醇与相应多元醇、多酚或胺的反应获得。
特别适合作为环氧树脂的是所谓的聚环氧化物液体树脂,下文中称为“液体树脂”。其具有低于25℃的玻璃化转变温度。
同样有可能作为环氧树脂的是具有高于25℃的玻璃化转变温度并且在25℃下可以粉碎成可倾倒的粉末的所谓的固体树脂。
合适的环氧树脂特别是芳族环氧树脂,特别是如下物质的缩水甘油基化产物:
-双酚-A、双酚-F或双酚-A/F,其中A表示丙酮并且F表示甲醛,其充当用于制备此种双酚的反应物。在双酚-F的情况下也可以存在特别是源自2,4'-和2,2'-羟基苯基甲烷的位置异构体。
-二羟基苯衍生物如间苯二酚、对苯二酚或邻苯二酚;
-其它双酚或多酚如双(4-羟基-3-甲基苯基)甲烷、2,2-双(4-羟基-3-甲基苯基)丙烷(双酚-C)、双(3,5-二甲基-4-羟基苯基)甲烷、2,2-双(3,5-二甲基-4-羟基苯基)丙烷、2,2-双(3,5-二溴-4-羟基苯基)丙烷、2,2-双(4-羟基-3-叔丁基苯基)丙烷、2,2-双(4-羟基苯基)丁烷(双酚-B)、3,3-双(4-羟基苯基)戊烷、3,4-双(4-羟基苯基)己烷、4,4-双(4-羟基苯基)庚烷、2,4-双(4-羟基苯基)-2-甲基丁烷、2,4-双(3,5-二甲基-4-羟基苯基)-2-甲基丁烷、1,1-双(4-羟基苯基)-环己烷(双酚-Z)、1,1-双-(4-羟基苯基)-3,3,5-三甲基环己烷(双酚-TMC)、1,1-双-(4-羟基苯基)-1-苯基乙烷、1,4-双[2-(4-羟基苯基)-2-丙基]苯(双酚-P)、1,3-双[2-(4-羟基苯基)-2-丙基]苯(双酚-M)、4,4'-二羟基联苯(DOD)、4,4'-二羟基苯甲酮、双(2-羟基萘-1-基)甲烷、双(4-羟基萘-1-基)甲烷、1,5-二羟基萘、三(4-羟基苯基)甲烷、1,1,2,2-四(4-羟基苯基)乙烷、双(4-羟基苯基)醚或双(4-羟基苯基)砜;
-酚与甲醛在酸性条件下获得的缩合产物,如酚-线性酚醛清漆或甲酚-线性酚醛清漆,也被称为双酚-F-线性酚醛清漆;
-芳族胺,如苯胺、对甲苯胺、4-氨基酚、4,4'-亚甲基二苯基二胺、4,4'-亚甲基二苯基二-(N-甲基)-胺、4,4'-[1,4-亚苯基-双(1-甲基亚乙基)]二苯胺(二苯胺-P)或4,4'-[1,3-亚苯基-双(1-甲基亚乙基)]二苯胺(二苯胺-M)。
其它合适的环氧树脂为脂族或环脂族聚环氧化物,特别是
-饱和或不饱和、支化或非支化、环状或开链的二官能、三官能或四官能的C2-至C30-醇的缩水甘油醚,特别是乙二醇、丙二醇、丁二醇、己二醇、辛二醇、聚丙二醇、二羟甲基环己烷、新戊二醇、二溴新戊二醇、蓖麻油、三羟甲基丙烷、三羟甲基乙烷、季戊四醇、山梨醇或甘油,以及烷氧基化甘油或烷氧基化三羟甲基丙烷;
-氢化的双酚-A、双酚-F或双酚-A/F液体树脂,或氢化的双酚-A、双酚-F或双酚-A/F的缩水甘油基化产物;
-酰胺或杂环氮碱的N-缩水甘油基衍生物,如三缩水甘油基氰脲酸酯或三缩水甘油基异氰脲酸酯,以及表氯醇和乙内酰脲的反应产物。
-得自烯烃(例如特别是乙烯基环己烯、二环戊二烯、环己二烯、环十二碳二烯、环十二碳三烯、异戊二烯、1,5-己二烯、丁二烯、聚丁二烯或二乙烯基苯)的氧化的环氧树脂。
环氧树脂优选是如从Dow、Huntsman和Momentive市售获得的那些的基于双酚的液体树脂,特别是双酚-A、双酚-F-或双酚-A/F的二缩水甘油醚。这些液体树脂具有对于环氧树脂来说低的粘度并且在已固化状态下具有作为涂料的良好性质。其可以任选地与双酚A-固体树脂或双酚-F-线性酚醛清漆-环氧树脂组合存在。
环氧树脂可以包含反应性稀释剂,特别是具有至少一个环氧基团的反应性稀释剂。适合作为反应性稀释剂的是例如一价或多价酚或脂族或环脂族醇的缩水甘油醚,如特别是已经提及的二醇或多元醇的聚缩水甘油醚,以及特别还有苯基缩水甘油醚、甲苯基缩水甘油醚、苄基缩水甘油醚、对-正丁基-苯基缩水甘油醚、对-叔丁基-苯基缩水甘油醚、壬基苯基缩水甘油醚、烯丙基缩水甘油醚、丁基缩水甘油醚、己基缩水甘油醚、2-乙基己基缩水甘油醚,以及天然醇的缩水甘油醚,例如C8-至C10-烷基缩水甘油醚或C12-至C14-烷基缩水甘油醚。向环氧树脂中加入反应性稀释剂造成粘度降低,以及玻璃化转变温度和机械值的降低。
环氧树脂组合物任选地包含其它成分,特别是在环氧树脂组合物中常规使用的助剂和添加剂,例如如下物质:
-溶剂、稀释剂、成膜助剂或增量剂,如特别是已经提及的不可结合性稀释剂;
-反应性稀释剂,特别是具有环氧基团的反应性稀释剂,如上文提到的那些,环氧化大豆油或亚麻籽油,具有乙酰乙酸酯基团的化合物,特别是乙酰乙酸酯化的多元醇,丁内酯,碳酸酯,醛,以及还有异氰酸酯和具有反应性基团的硅酮;
-聚合物,特别是聚酰胺、聚硫化物、聚乙烯醇缩甲醛(PVF)、聚乙烯醇缩丁醛(PVB)、聚氨酯(PUR)、具有羧基的聚合物、聚酰胺、丁二烯-丙烯腈-共聚物、苯乙烯-丙烯腈-共聚物、丁二烯-苯乙烯-共聚物、不饱和单体(特别选自乙烯、丙烯、丁烯、异丁烯、异戊二烯、乙酸乙烯酯和(甲基)丙烯酸烷基酯)的均聚物或共聚物,特别是氯磺化的聚乙烯和含氟聚合物、磺酰胺改性的三聚氰胺和纯化的褐煤蜡;
-无机和有机填料,例如任选地涂布有脂肪酸、特别是硬脂酸酯的研磨碳酸钙或沉淀碳酸钙,重晶石(沉晶石),滑石,石英粉,石英砂,云母铁矿,白云石,硅灰石,高岭土,云母(钾-铝-硅酸盐),分子筛,氧化铝,氢氧化铝,氢氧化镁,二氧化硅,水泥,石膏,飞灰,炭黑,石墨,金属粉末如铝、铜、铁、锌、银或钢,PVC-粉末或空心球;
-纤维,特别是玻璃纤维、碳纤维、金属纤维、陶瓷纤维或塑料纤维,如聚酰胺纤维或聚乙烯纤维;
-颜料,特别是二氧化钛和/或氧化铁;
-上述促进剂;
-流变改性剂,特别是增稠剂或抗沉降剂;
-助粘剂,特别是有机烷氧基硅烷;
-抗氧化、热、光和紫外线的稳定剂;
-阻燃物质,特别是氢氧化铝(ATH)、氢氧化镁(MDH)、三氧化锑、五氧化锑、硼酸(B(OH)3)、硼酸锌、磷酸锌、硼酸三聚氰胺、氰脲酸三聚氰胺、多磷酸铵、磷酸三聚氰胺、焦磷酸三聚氰胺、多溴化二苯基氧或二苯醚、磷酸酯如特别是二苯基甲苯基磷酸酯、间苯二酚-双(磷酸二苯酯)、间苯二酚-二磷酸酯低聚物、四苯基间苯二酚二亚磷酸酯、乙二胺二磷酸酯或双酚-A-双(磷酸二苯酯)、三(氯乙基)磷酸酯、三(氯丙基)磷酸酯和三(二氯异丙基)磷酸酯,三[3-溴-2,2-双(溴甲基)丙基]磷酸酯、四溴-双酚-A、双酚A的双(2,3-二溴丙基醚)、溴化环氧树脂、亚乙基-双(四溴邻苯二甲酰亚胺)、亚乙基-双(二溴降莰烷二甲酰亚胺)、1,2-双-(三溴苯氧基)乙烷、三(2,3-二溴丙基)异氰脲酸酯、三溴酚、六溴环十二烷、双(六氯环戊二烯基)环辛烷或氯化石蜡;
-表面活性物质,特别是润湿剂、流平剂、脱气剂和/或消泡剂;
-杀生物剂,例如杀藻剂、杀真菌剂或菌类生长抑制物质。
环氧树脂组合物优选包含其它助剂和添加剂,特别是润湿剂、流平剂、消泡剂、稳定剂、颜料和/或促进剂,特别是水杨酸和/或2,4,6-三(二甲基氨基甲基)酚。
环氧树脂组合物优选不包含或仅包含少量的,特别优选小于10重量%、特别是小于5重量%和最优选小于2重量%的不可结合性稀释剂。
在环氧树脂组合物中,对环氧基团有反应性的基团的数量与环氧基团的数量的比例优选在0.5至1.5,特别是0.7至1.2的范围内。
环氧树脂组合物中存在的胺氢和任选存在的其它对环氧基团有反应性的基团通过其开环(加成反应)与环氧基团反应。此反应的结果是所述组合物聚合并且最终固化。本领域技术人员已知,伯氨基对于环氧基团来说是双官能的,因此一个伯氨基被认为是两个对环氧基团有反应性的基团。
特别地,环氧树脂组合物为由如下物质组成的双组份组合物:
(i)包含至少一种环氧树脂的树脂组分和
(ii)包含所述固化剂的固化剂组分。
双组分组合物的组分分别储存在各自的容器中。双组分环氧树脂组合物的其它成分可以作为树脂组分或固化剂组分的成分存在,其中对环氧基团有反应性的其它成分优选为固化剂组分的成分。用于储存树脂组分或固化剂组分的合适的容器特别是桶、筒、袋、斗、罐、料盒或管。组分是可储存的,亦即其在使用之前可以保存数月至一年和更久,而不会在与其使用相关的程度上改变其各自性质。为了使用双组份环氧树脂组合物,在紧接着施用之前或施用过程中使树脂组分和固化剂组分彼此混合。两种组分之间的混合比例优选如此选择,使得固化剂组分的对环氧基团有反应性的基团以与树脂组分的环氧基团以合适的比例存在,如上文所述。以重量份计,树脂组分和固化剂组分之间的混合比例通常在1:10至10:1的范围内。
两种组分的混合通过合适方法进行;其可以连续或间歇式进行。在施用之前进行混合的情况下,必须注意在组分的混合和施用之间不能停留过多的时间,因为这样可能会造成干扰,例如延缓地或不完全地构建起对基材的粘附力。混合特别在环境温度下进行,所述环境温度通常为约5至50℃,优选约10至30℃。
通过两种组分的混合开始通过化学反应而固化,如上文所述。固化特别在环境温度下进行。固化通常持续数天至数周,直至其在给定条件下基本结束。持续时间主要取决于温度、成分的反应性及其化学计量比以及促进剂的存在。
因此,本发明的另一个主题是通过如本申请中描述的环氧树脂组合物的固化获得的已固化的组合物。
环氧树脂组合物的施用在至少一种基材上进行,其中如下物质是特别合适的:
-玻璃、玻璃陶瓷、混凝土、砂浆、砖、瓦、石膏和天然石材如花岗石或大理石;
-金属和合金,如铝、铁、钢或有色金属,包括经表面处理的金属或合金,如镀锌或镀铬的金属;
-皮革、织物、纸、木材、与树脂(例如酚醛树脂、三聚氰胺树脂或环氧树脂)结合的木质材料、树脂-织物-复合材料或其它所谓的聚合物复合物;
-塑料,特别是硬质和软质PVC、ABS、聚碳酸酯(PC)、聚酰胺(PA)、聚酯、PMMA、环氧树脂、PUR、POM、PO、PE、PP、EPM或EPDM,其中塑料任选地通过等离子体、电晕或火焰进行表面处理;
-纤维增强的塑料,如碳纤维增强的塑料(CFK)、玻璃纤维增强的塑料(GFK)和片状模塑复合物(SMC);
-经涂布的基材,如经粉末涂布的金属或合金;
-颜料或漆。
基材可以在需要的情况下在施用环氧树脂组合物之前预处理。这种预处理包括特别是物理和/或化学清洁方法,例如打磨、喷砂、喷丸、梳洗和/或吹扫,以及用清洁剂或溶剂进行其它处理,或施用增粘剂、增粘剂溶液或底漆。
所述环氧树脂组合物可以有利地用作纤维复合材料(复合物)的成分、浇铸材料、密封剂、粘合剂、覆层、涂料、刷抹料、漆、密封料、底涂剂或底漆。
其特别可用作浇铸材料、密封剂和粘合剂,例如用作电浇铸料(Elektrovergussmasse)、密封料、车身粘合剂、夹心元件粘合剂、轴瓦粘合剂(例如用于风力发电站的转子叶片)、桥接元件粘合剂或锚固粘合剂;以及还作为用于建筑应用和工业应用的覆层、涂料、刷抹料、漆、密封料、底涂剂和底漆,例如特别是作为用于室内(如办公室、工业车间、体育馆或冷藏室)或室外区域(用于阳台、露台、停车场顶(Parkdecks)、桥梁或屋顶)的地面覆层和地面涂料,作为用于混凝土、水泥、金属、塑料或木材的保护涂料,例如用于木材结构、车辆、装料区、水槽、筒仓、竖井、管道、管线、机器或钢制结构,例如船舶、码头、海上平台、水闸、水力发电机、水利工程、游泳池、风力发电站、桥梁、烟囱、起吊设备或板桩墙的表面密封;以及还用作预涂剂、粘附刷涂剂、防腐蚀底漆或用于使表面疏水化。特别地,当其用作涂料、覆层或刷抹料时,可以在完全或部分固化的环氧树脂组合物上施用另一涂料、另一覆层或另一刷抹料,其中所述另一层同样可以是环氧树脂组合物,但是也可以是其它材料,特别是聚氨酯涂料或聚脲涂料。
特别有利地,所述环氧树脂组合物可用作涂料。在此,涂料被理解为任何种类的平面施涂的覆层,特别是如上文所述的刷抹料、漆、密封料、底涂剂和底漆。特别有利地,所述环氧树脂组合物可用于具有环境认证标准(例如Emicode(EC1Plus)、AgBB、DIBt、Der BlaueEngel、AFSSET、RTS(M1)和美国绿色建筑协会(LEED))的低排放产品。
作为涂料,环氧树脂组合物有利地用于涂布方法中,其中所述环氧树脂组合物具有低粘度的液体稠度和良好的流平性能,并且特别可以作为自流平涂料在基本平坦的表面上施用或者作为刷抹料施用。紧接着混合树脂组分和固化剂组分之后,环氧树脂组合物在施用中优选具有在20℃下测得的在300至3000mPa·s范围内、优选在300至2000mPa·s范围内、特别优选在300至1500mPa·s范围内的粘度。通常在环境温度下,在操作时间内将经混合的组合物以层厚度通常为约50μm至约5mm的薄膜的形式平面地施用至基材。特别通过浇注至待涂布的基材上然后例如借助于刮刀或抹刀均匀分布从而进行施用。但是施用也可以通过刷子或辊子进行或者以喷涂形式进行,例如作为钢材上的防锈涂层。
在固化中通常形成具有高硬度的基本透明、有光泽且无粘性的薄膜,所述薄膜对于不同基材具有良好粘附性。
本发明的另一个主题是包含通过固化所述环氧树脂组合物获得的已固化组合物的制品。已固化的组合物在此特别以涂层的形式存在。
所述环氧树脂组合物的特征在于有利的性质。其为极低粘度和低气味的,并且即使在湿冷条件下甚至使用少量不可结合性稀释剂或完全不使用不可结合性稀释剂仍然迅速和充分固化而无雾浊效应,并且特别地也不使用容易挥发的具有强烈气味的胺。在平面应用时产生具有高硬度和高表面品质的非粘性透明薄膜,所述薄膜在光的影响下几乎不变黄。使用所述环氧树脂组合物获得特别低排放的环氧树脂产品,所述环氧树脂产品符合许多环境认证标准的条件并且同时满足工作安全、加工性能和使用性能方面的高要求。
实施例
下文描述实施例,所述实施例更详细地解释本发明。本发明当然不限于所描述的实施例。
“AHEW”表示胺氢当量。
“EEW”表示环氧化物当量。
1.测量方法说明
在Perkin-Elmer的配备有具有ZnSe-晶体的水平ATR-测量单元的FT-IR设备1600上以未稀释薄膜的形式测量红外光谱(FT-IR);吸收谱带以波数(cm-1)表示(测量窗口:4000-650cm-1)。
在恒温锥板式粘度计Rheotec RC30(锥直径50mm,锥角1°,锥间至板的距离0.05mm,剪切速度10s-1)上测量粘度。
通过滴定确定胺值(使用0.1N HClO4乙酸溶液,以结晶紫为指示剂)。
通过DMTA测量在-50℃至25℃的温度范围内以5K/min和10Hz确定熔点。
2.使用的市售物质:
DY-K:(来自Huntsman),2-甲苯基缩水甘油醚,EEW约183g/当量
DY-P:(来自Huntsman),对叔丁基苯基缩水甘油醚,EEW约225g/当量
LITE(来自Cardolite),腰果酚的缩水甘油醚,EEW2513HP:约415g/当量
GY 250:(来自Huntsman),双酚-A-二缩水甘油醚,EEW约187.5g/当量
DY-E:(来自Huntsman),C12至C14醇的单缩水甘油醚,EEW约290g/当量
K 54:(来自Air Products),2,4,6-三(二甲基氨基甲基)酚
A:(来自Invista),1,5-二氨基-2-甲基戊烷,AHEW 29.0g/当量
MXDA:(来自Mitsubishi Gas Chemical),1,3-双(氨基甲基)苯
240:(来自Mitsubishi Gas Chemical),苯乙烯化1,3-双(氨基甲基)苯,AHEW约103g/当量
D-230:(来自Huntsman),聚氧化亚丙基二胺,平均分子量约240g/mol,AHEW 60g/当量
(来自Huntsman),来自1,4-二羟甲基环己烷
RFD-270:的丙氧基化和之后胺化的含醚基团的环脂族二胺,平均分子量约270g/mol,AHEW 67g/当量TMD:(来自Evonik),2,2,4-和2,4,4-三甲基六亚甲基二胺,AHEW 39.6g/当量
1,3-BAC:(来自Mitsubishi Gas Chemical),1,3-双(氨
基甲基)环己烷,AHEW 35.5g/当量
3.胺的制备:
胺A-1:1-((2-氨基丙基)氨基)-3-(2-甲基苯氧基)丙-2-醇
在氮气氛下预置4.15kg(56mol)1,2-丙二胺,加热至70℃并且伴随良好搅拌缓慢地与2.93kg(16mol)DY-K混合,其中通过冷却将反应混合物的温度保持在70和80℃之间。将反应混合物置于80℃下1小时,然后冷却并且通过薄层蒸发器(0.5-1mbar,夹套温度115℃)除去挥发性成分。获得透明的浅黄色液体,所述液体具有20℃下3.3Pa·s的粘度,478.7mg KOH/g的胺值,91.5%的纯度(通过气相色谱确定,8.5%为来自DY-K的1,3-双(2-甲基苯氧基)丙-2-醇),-25℃的熔点和约85.7g/Eq的理论AHEW。
FT-IR:3025,2955,2918,1601,1590,1494,1456,1377,1307,1288,1242,1191,1120,1050,1035,926,837,748,713。
胺A-2:1-((2-氨基丙基)氨基)-3-(4-叔丁基苯氧基)丙-2-醇
在氮气氛下预置77.4g(1.04mol)1,2-丙二胺,加热至70℃并且伴随良好搅拌缓慢地与67.5g(0.3mol)DY-P混合。将反应混合物置于80℃下2小时。然后在旋转蒸发器上在65℃和1mbar下在3小时内除去挥发性成分。获得透明的浅黄色液体,所述液体具有105Pa·s的粘度,374.9mg KOH/g的胺值和约99.7g/Eq的理论AHEW。
胺A-3:
如针对胺A-2所述使51.9g(0.7mol)1,2-丙二胺与83.0g(0.2mol)LITE 2513HP反应。获得透明的浅黄色液体,所述液体具有1.93Pa·s的粘度,204.3mg KOH/g的胺值和约163.0g/Eq的理论AHEW。
胺A-4:(对比)
如针对胺A-1所述使4.65kg(40mol)A与1.83kg(10mol)DY-K反应,其中薄层蒸发器的夹套温度为160℃。获得透明的浅黄色液体,所述液体具有20℃下6.5Pa·s的粘度,367.1mg KOH/g的胺值和约99.7g/Eq的理论AHEW。
胺A-5:(对比)
如针对胺A-2所述使96.2g(1.6mol)乙二胺与73.2g(0.4mol)DY-K反应。获得透明的浅黄色液体,所述液体具有8.26Pa·s的粘度,484.9mg KOH/g的胺值和约81.0g/Eq的理论AHEW。
胺A-1至A-3为式(I)的胺,胺A-4和A-5用于对比。
4.烷基化胺的制备
苄基化MXDA:
在圆底烧瓶中在氮气氛下将17.0g(0.16mol)苯甲醛和13.6g(0.10mol)MXDA溶解在足量异丙醇中。将溶液在23℃下搅拌30分钟,然后在80bar的氢压、80℃的温度和3ml/min的流速下在具有Pd/C-固体床催化剂的连续操作的氢化装置上进行氢化。为了控制反应,通过红外光谱检测亚胺谱带是否在约1665cm-1处消失。之后在真空中在80℃下浓缩所述溶液。获得透明的浅黄色油,所述油具有20℃下0.1Pa·s的粘度,416.8mg KOH/g的胺值和约115.5g/Eq的理论AHEW。
乙基己基化MXDA:
以与针对苄基化MXDA所述的相同方式使25.6g(0.20mol)2-乙基己醛和13.6g(0.10mol)MXDA反应。获得透明的浅黄色液体,所述液体具有20℃下140mPa·s的粘度,308.6mg KOH/g的胺值和约180.3g/Eq的理论AHEW。
5.固化剂和环氧树脂组合物的制备
对于每个实施例,通过离心混合器(SpeedMixerTM DAC 150,FlackTek Inc.)以给出的固化剂组分的量(重量份)混合表1至4中给出的成分,并且在隔绝水分的情况下保存。
同样地,加工表1至4中给出的树脂组份的成分并且保存。
然后通过离心混合器将每种组合物的两种组分加工成均匀液体并且立即以如下方式检测:
混合之后10分钟确定20℃下的粘度(“粘度(10')”)。
以500μm的层厚度在玻璃板上施涂第一层膜,并且在23±1℃和50±5%相对湿度(=标准气候,下文缩写为“NK”)下保存或固化。在此膜上在2天之后(“硬度(NK)(2d)”)、4天之后(“硬度(NK)(4d)”)、7天之后(“硬度(NK)(7d)”)和14天之后(“硬度(NK)(14d)”)确定硬度(摆撞硬度,根据DIN EN ISO 1522测量)。14天之后评估膜的外观(表中用“外观(NK)”表示)。“漂亮”表示透明并且具有光泽和非粘性表面而无结构的膜。“结构”在此表示表面上任何种类的标记或图案。
以500μm的层厚度在玻璃板上施涂第二层膜,并且紧接着施用之后在8℃和80%相对湿度下放置或固化7天,然后在NK下放置或固化3周。施用24小时之后在膜上放置聚丙烯瓶盖,在所述瓶盖下方放置潮湿海绵。再过24小时之后除去海绵和盖并且将其放置在膜的新位置处,在该新位置处24小时之后再度除去并且重新放置,总共4次。然后以与针对外观(NK)所述的相同方式评估膜的外观(在表中用“外观(8°/80%)”表示)。表中也分别给出由于潮湿海绵和/或放置的盖而在膜中可见的标记的数量。再次地,分别在8℃和80%相对湿度下在7天之后(“(7d 8°/80%)”),然后在NK下再过2天之后(“(+2d NK)”)、在NK下再过7天之后(“(+7d NK)”)并且在NK下再过14天之后(“(+14d NK)”)确定已固化的膜的硬度。
结果列于表1至4。
环氧树脂组合物EZ-1至EZ-16为根据本发明的实施例。环氧树脂组合物Ref-1至Ref-9为对比实施例。
表1:EZ-1至EZ-4和Ref-1至Ref-3的组成和性质。“n.m.”表示“不可测”。“n.d.“表示“未确定”。
表2:EZ-5至EZ-11的组成和性质。
“l.”表示“轻微”。
表3:Ref-4至Ref-9的组成和性质。
“l.表示“轻微”。
表4:EZ-12至EZ-16的组成和性质。
1溶解在预混合的胺中
Claims (15)
1.式(I)的胺
其中
R表示任选地包含不饱和部分的具有1至22个碳原子的烷基、环烷基、芳烷基或烷氧基;并且
n表示0或1或2或3。
2.根据权利要求1所述的胺,其特征在于,n表示1。
3.根据权利要求1或2任一项所述的胺,其特征在于,R表示甲基。
4.用于制备根据权利要求1至3任一项所述的胺的方法,所述方法使1,2-丙二胺与芳基缩水甘油醚以范围在1.1至5的1,2-丙二胺/芳基缩水甘油醚的摩尔比例反应,然后蒸馏除去未反应的1,2-丙二胺。
5.至少一种根据权利要求1至3任一项所述的胺在用于环氧树脂的固化剂中的用途。
6.根据权利要求5所述的用途,其特征在于,所述固化剂包含如此量的式(I)的胺,使得固化剂中的5至100%的对环氧基团有反应性的胺氢源自式(I)的胺。
7.根据权利要求5或6任一项所述的用途,其特征在于,所述固化剂除了式(I)的胺之外还包含至少一种具有至少两个对环氧基团有反应性的胺氢的另外的多胺。
8.根据权利要求7所述的用途,其特征在于,所述另外的多胺为伯二胺,所述伯二胺选自2,2,4-和2,4,4-三甲基六亚甲基二胺、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷、1,3-双(氨基甲基)苯、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、双(4-氨基环己基)甲烷、双(4-氨基-3-甲基环己基)甲烷、2,5(2,6)-双(氨基甲基)双环[2.2.1]庚烷、3(4),8(9)-双(氨基甲基)三环[5.2.1.02,6]癸烷,和包含醚基团的具有至多500g/mol的平均分子量的多胺。
9.根据权利要求7所述的用途,其特征在于,所述另外的多胺为选自如下的具有至少一个仲氨基的多胺:N-单烷基化1,6-己二胺、N,N'-二烷基化1,6-己二胺、N-单烷基化1,5-二氨基-2-甲基戊烷、N,N'-二烷基化1,5-二氨基-2-甲基戊烷、N-单烷基化1,3-双(氨基甲基)环己烷、N,N'-二烷基化1,3-双(氨基甲基)环己烷、N-单烷基化1,4-双(氨基甲基)环己烷、N,N'-二烷基化1,4-双(氨基甲基)环己烷、N-单烷基化1,3-双(氨基甲基)苯、N,N'-二烷基化1,3-双(氨基甲基)苯、N-单烷基化BHMT、N,N'-二烷基化BHMT、N-单烷基化DETA、N,N'-二烷基化DETA、N-单烷基化TETA、N,N'-二烷基化TETA、N-单烷基化TEPA、N,N'-二烷基化TEPA、N-单烷基化DPTA、N,N'-二烷基化DPTA、N-单烷基化N3-胺、N,N'-二烷基化N3-胺、N-单烷基化N4-胺和N,N'-二烷基化N4-胺,其中烷基分别选自苄基、2-苯基乙基、异丁基、己基和2-乙基己基。
10.根据权利要求7至9任一项所述的用途,其特征在于,所述另外的多胺为具有醚基团的二胺。
11.根据权利要求5至10任一项所述的用途,其特征在于,所述固化剂具有小于25重量%的不可结合性稀释剂含量。
12.环氧树脂组合物,所述环氧树脂组合物包含至少一种环氧树脂和如权利要求5至11任一项所述的固化剂。
13.根据权利要求12所述的环氧树脂组合物,其特征在于,其为由如下组成的双组份组合物
(i)包含至少一种环氧树脂的树脂组分和
(ii)包含固化剂的固化剂组分。
14.通过根据权利要求12或13任一项所述的环氧树脂组合物的固化获得的经固化的组合物。
15.包含根据权利要求14所述的经固化的组合物的制品。
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CN110312748A (zh) * | 2017-03-14 | 2019-10-08 | Sika技术股份公司 | 用于低排放环氧树脂组合物的固化剂 |
CN112789308A (zh) * | 2018-10-01 | 2021-05-11 | Sika技术股份公司 | 用于环氧树脂的固化剂 |
CN114746471A (zh) * | 2019-09-25 | 2022-07-12 | Sika技术股份公司 | 用于环氧铸塑树脂的硬化剂 |
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EP3375802A1 (de) | 2017-03-14 | 2018-09-19 | Sika Technology Ag | Verfahren zur herstellung eines härters für emissionsarme epoxidharz-zusammensetzungen |
PL425788A1 (pl) * | 2018-05-30 | 2019-12-02 | Ciech R & D Spolka Z Ograniczona Odpowiedzialnoscia | Utwardzacz do żywic epoksydowych, zawierające go kompozycje oraz jego zastosowanie |
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AU2015215175B2 (en) | 2019-05-30 |
JP6535335B2 (ja) | 2019-06-26 |
JP2017506225A (ja) | 2017-03-02 |
CN105939992B (zh) | 2019-04-09 |
EP3102561A1 (de) | 2016-12-14 |
WO2015117846A1 (de) | 2015-08-13 |
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