CN1046165A - α-氨基亚甲基膦酸同环氧化合物的反应产物及其在涂料组合物中的应用 - Google Patents
α-氨基亚甲基膦酸同环氧化合物的反应产物及其在涂料组合物中的应用 Download PDFInfo
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- CN1046165A CN1046165A CN90101839A CN90101839A CN1046165A CN 1046165 A CN1046165 A CN 1046165A CN 90101839 A CN90101839 A CN 90101839A CN 90101839 A CN90101839 A CN 90101839A CN 1046165 A CN1046165 A CN 1046165A
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
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- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
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Abstract
本发明涉及一种化合物,它是由含至少一个下式基团的α-氨基亚甲基膦酸的至少一个膦酸基团同含至少一个环氧基的化合物的环氧基反应制得的产物,
本发明还涉及含上述反应产物的水基涂料组合物、有机溶剂基涂料组合物,以及粉末涂料组合物。
Description
本发明涉及由α-氨基亚甲基膦酸同环氧化合物反应制得的化合物及其在涂料组合物中的应用。
美国专利4,621,112述及使用正磷酸的有机酯,它可以避免因金属颜料与水基涂料组合物的水相发生反应而释出气体(本发明又称作“放气”),按照说明,这种酯是由含-O-PO3H2基的化合物同含环氧化物基的化合物反应制得的产物。使用这种正磷酸的有机酯,虽然可以满足水基组合物提供一种阻气添加剂的要求,但应用中已经发现一些缺点。例如,用放入这类化合物的水基涂料组合物制成的干膜抗湿性不足。而且,它们作为阻气剂的效果也不尽人意。
本发明涉及一类新型化合物,它们不仅比上述的正磷酸有机酯抑制或避免含金属颜料的水基涂料组合物生成气体效果更好,而且还具有不损害用它们制得的干膜的抗湿性的优点。另外,本发明也涉及在含有机颜料的有机溶剂基涂料组合物中使用这类新型化合物,以改善这种组合物的色稳定性。此外,本发明还涉及在粉末涂料中使用这类新型化合物,以改善其中颜料的分散性。参看下文,对本发明的这些目的和其它目的会愈加清楚。
本发明提供一种化合物,它是由含至少一个下式基团的α-氨基亚甲基膦酸的至少一个膦酸基团同含至少一个环氧基的化合物的环氧基反应制得的产物,
α-氨基亚甲基膦酸的分子式一般如下所示:
其中a=1,2或3,a+b+c=3,R可以相同或不同,並可以从烷基,芳基,烷芳基,芳烷基,以及多醚化合物的一价残基这类基团中选取。
本发明还提供一种水基涂料组合物,它是由成膜聚合物,金属颜料,以及含水的稀释剂介质所组成,其中的颜料易于同含水的介质发生反应,由于在这种水基涂料组合物中放入有效量的本发明化合物,避免或抑制了释放出气体物质。
本发明也提供一种有机溶剂基涂料组合物,它是由成膜聚合物,金属颜料,有机溶剂介质,以及本发明的化合物所组成,这种有机溶剂基涂料组合物另外还特别含有一种有机颜料。
最后,本发明还提供一种粉末涂料组合物,它是由成膜聚合物和颜料所组成,其中,所述颜料在该组合物中的分散性,因加入有效量的本发明化合物而得到改善。
本发明的化合物是由含至少一个下式基团的α-氨基亚甲基膦酸的至少一个膦酸基团同含至少一个1.2-环氧基的化合物的环氧基反应制得的产物,
不言而喻,上式中N左边的两根短划线代表N上的两个价键,它们当然在各自的α-氨基亚甲基膦酸中被饱和。在本发明的优选实施方案中,这种α-氨基亚甲基膦酸一般如下式所示:
式中a=1,2或3,以a=2为佳,a+b+c=3,Rb,Rc可以相同或不同,並可从下面这些基团中选取,它们是烷基,芳基(诸如苯基之类),烷芳基(诸如甲苯基,二甲苯基之类),芳烷基(诸如苄基、苯乙基之类,以及多醚化合物的一价残基。不言而喻,这里所用的烷基,芳基,烷芳基和芳烷基被认为还包括含有一个或多个杂原子(如N,O或S)的基团,尤其是这些基团中的芳族部分含有这种杂原子。
可用来同环氧化合物反应制备本发明化合物的α-氨基亚甲基膦酸的例子包括(2-羟乙基)氨基双(亚甲基膦酸),即HOCH2CH2N(CH2PO3H2)2;异丙基氨基双(亚甲基膦酸),即异丙基N(CH2PO3H2)2;正丙基氨基双(亚甲基膦酸),即正丙基N(CH2PO3H2)2;正丁基氨基双(亚甲基膦酸),即正丁基N(CH2PO3H2)2;正己基氨基双(亚甲基膦酸),即正己基N(CH2PO3H2)2;(2-乙基己基)氨基双(亚甲基膦酸),即(2-乙基己基)-N(CH2PO3H2)2;正辛基氨基双(亚甲基膦酸),即正辛基N(CH2PO3H2)2;异壬基氨基双(亚甲基膦酸)即异壬基N(CH2PO3H2)2;十二烷基氨基双(亚甲基膦酸),即十二烷基N(CH2PO3H2)2;二乙氨基(亚甲基膦酸),即(CH3CH2)2NCH2PO3H2;二甲氨基(亚甲基膦酸),即(CH3)2NCH2PO3H2;次氮基三(亚甲基膦酸),即N(CH2PO3H2)3;乙二胺四(亚甲基膦酸),即〔CH2N(CH2PO3H2)2〕2;二亚乙基三胺五(亚甲基膦酸),即H2O3PCH2N〔CH2CH2N(CH2PO3H2)2〕2;苄氨基双(亚甲基膦酸;亚磷酸和甲醛同聚乙二醇多胺和聚乙二醇单胺的反应产物(例如,这种多胺和单胺可以购自Texaco公司,牌号为JEFFAMINE
);以及由亚磷酸,可可胺,和甲醛反应制得的产物(例如,可分别以2∶1∶2的摩尔比,按下面实施例1的说明制备可可胺双(亚甲基膦酸)。α-氨基亚甲基膦酸一般是已知化合物,通常可采用已知的方法制备。许多α-氨基亚甲基膦酸可从市场上购到。
正如前面所述,本发明的化合物是由最好符合上面分子式的α-氨基亚甲基膦酸的至少一个膦酸基同含至少一个环氧基的化合物的环氧基(最好采用含至少一个1。2-环氧基的化合物的环氧基)反应制得的产物。在这类环氧化合物中也可以含有並常常是含有羟基。环氧化合物的环氧化物当量一般在44~约4000的范围之内,又以150~500左右为多见。这类环氧化合物可以是饱和或不饱和的,环状或非环状的,脂族的,脂环族的,芳族的或杂环族的化合物。它们可以含有诸如卤素,羟基和醚基之类的取代基。
可以利用的环氧化合物的例子包括如环氧乙烷,环氧丙烷,环氧丁烷,环氧化己烯等那样简单的化合物。
可以利用的环氧化合物的例子还包括:由环氧氯丙烷同多酚在碱存在下反应制得的环氧多醚。合适的多醚包括:2,2-双(4-羟基苯基)丙烷(即双酚A),1,1-双(4-羟基苯基)异丁烷,2,2-双(4-羟基叔丁基苯基)丙烷,4,4-二羟基二苯甲酮,1,1-双(4-羟基苯基)乙烷,双(2-羟基萘基)甲烷,1,5-二羟基萘,1,1-双(4-羟基-3-烯丙基苯基)乙烷,以及这些化合物的氢化衍生物。通过改变环氧氯丙烷同多酚的摩尔比,可按已知方法制得各种分子量的多酚的多缩水甘油醚。
还可以利用的环氧化合物包括如下这些例子:单核多羟基酚的多缩水甘油醚诸如间苯二酚,焦棓酚,对苯二酚,以及邻苯二酚的多缩水甘油醚,以及单羟基酚的单缩水甘油醚诸如苯基缩水甘油醚,α-萘基缩水甘油醚,β-萘基缩水甘油醚,以及对应的在芳环上带有烷基取代基的化合物。
可利用的环氧化合物的例子还有芳香醇的缩水甘油醚诸如苄基缩水甘油醚和苯基缩水甘油醚。
可利用的环氧化合物的例子还有多羟基醇的多缩水甘油醚诸如环氧氯丙烷或二氯丙醇同例如下列脂族醇和环脂族醇的反应产物,它们是乙二醇,二甘醇,三甘醇,一缩二丙二醇,二缩三丙二醇,丙二醇,丁二醇,戊二醇,丙三醇,1,2,6-己三醇,季戊四醇,以及2,2-双(4-羟基环己基)丙烷。
别的可利用的环氧化合物的例子有多羧酸的多缩水甘油醚,诸如一般已知的己二酸,苯二甲酸等的多缩水甘油酯,还有单羧酸的单缩水甘油酯诸如苯甲酸缩水甘油酯,萘甲酸缩水甘油酯,以及取代的苯甲酸和萘甲酸的单缩水甘油酯。
也可以使用含有环氧基团的加成聚合的树脂。这类材料可以从环氧官能单体诸如丙烯酸缩水甘油酯,甲基丙烯酸缩水甘油酯和烯丙基缩水甘油醚,通过加成聚合制得,聚合中一般同时加入烯属不饱和共聚单体,诸如苯乙烯,α-甲基苯乙烯,α-乙基苯乙烯,乙烯基甲苯,叔丁基苯乙烯,丙烯酰胺,甲基丙烯酰胺,丙烯腈,甲基丙烯腈,乙基丙烯腈,甲基丙烯酸乙酯,甲基丙烯酸甲酯,甲基丙烯酸异丙酯,甲基丙烯酸异丁酯,丙烯酸羟乙酯,甲基丙烯酸羟乙酯,丙烯酸2-乙基己酯,甲基丙烯酸2-乙基己酯,甲基丙烯酸异冰片酯等。
在环氧树脂手册(Handbook of Epoxy Resins,Henry Lee & Kris Neville著,McGraw Hill Book Company 1967年出版)中介绍了其它很多环氧化合物的例子。
α-氨基亚甲基膦酸同含至少一个环氧基的化合物一起反应生成本发明的化合物,两者的相对用量可变化很大。但是,一般选择在使环氧基的摩尔数与膦酸基中可取代的氢的摩尔数,两者的比值在1.0∶8.0~1.0∶1.0的范围,常常是选在1.0∶4.0~1.0∶1.0的范围,又以1.0∶4.0为佳。还应明白的是,在反应物是多官能的情况下,反应产物可能是一些不同分子种类的统计混合物。就优选的比值1.0∶4.0而言,已经发现,在某些情况下,环氧用量较少时,加入反应产物的含金属颜料(如铝的片状粉末)的水基组合物,其阻气作用和形成的干膜的抗湿性不完全如上述1.0∶4.0比值时的效果那样好。而在环氧用量较多时,虽然所得干膜的抗湿性有所改善,但多少削弱这种化合物作阻气剂所起的效果。
α-氨基亚甲基膦酸同含至少一个环氧基的化合物的反应,可以在如25℃~约150℃范围某个温度进行,一般选在80~100℃左右,通常选择在85~95℃左右。需要的话,反应中可使用使环氧开环的催化剂如叔胺,不过,在本发明推荐的实施方案中一般不用这种催化剂。为了保持反应混合物的流动性,尤其在环氧化合物熔点较高的固体的场合,反应宜在某种惰性的极性稀释剂或溶剂中进行,例如1-甲氧基-2-丙醇,二噁烷,四氢呋喃等。在采用极性稀释剂或极性溶剂的情况下,反应可以简便地在稀释剂或溶剂的迥流温度进行。
已经发现,在含金属颜料的水基涂料组合物中加入本发明的一种化合物(本发明的某个推荐实施方案),抑制或避免了该涂料组合物生成气体。还发现,在上述组合物中加入的本发明化合物,对由这种组合物形成的干膜(涂层)的抗湿性没有不良影响。而且,这种化合物还可以起到防止颜料沉降的作用。本发明的水基组合物由成膜聚合物,金属颜料,含水的稀释介质,以及本发明化合物所组成。由于在组合物中加入有效量的本发明化合物,避免或抑制颜料去同含水介质反应並释放出气体。对本发明实施方案来说,一般采用的是由相应于上述分子式中a=2的α-氨基亚甲基膦酸同含1。2-环氧基的二环氧化合物反应制得的化合物。
虽然α-氨基亚甲基膦酸同含至少一个环氧基的化合物反应制得的产物可以直接用于本发明的水基涂料组合物作阻气剂,一般来说,已将反应产物用氨或胺(如N.N-二甲基乙醇胺,三乙胺等)中和后才加以使用,例如,这种反应产物的酸度会影响涂料组成物其它组分,尤其是成膜聚合物的稳定性时就是如此。在成膜聚合物是一种含羧酸基的加成聚合物时,用氨或胺中和羧酸基可使聚合物溶于或分散在水中,如果添加未中和的本发明化合物,就可能会造成成膜聚合物沉淀(絮凝)。
用于本发明水基涂料组合物的金属颜料,其例子包括通常已知用于加颜料的水基涂料组合物的任何金属颜料。这些例子包括的金属颜料,尤其是金属片状粉末颜料,它们的成分有铝、铜、锌和/或黄铜,以及其它有展性的金属和含有诸如镍,锡,银,铬,铝-铜合金,铝-锌合金,和铝-镁合金。其中优选使用的是铝片状粉末颜料。不过,本发明的水基涂料组合物还可以含有,一般确实含有,一种或多种许多别的颜料,这些颜料已知常用于涂料组合物,诸如各种白色和带色的颜料。其例子包括公知的金属氧化物颜料;金属氢氧化物;金属硫化物;金属硫酸盐,金属碳酸盐;碳墨;陶土;酞菁兰和酞菁绿,有机红,以及其它有机染料。
可以采用不同的方法将本发明的化合物混入本发明的水基涂料组合物。一种方法是,在把颜料混入水基涂料组合物之前,将本发明的化合物金属颜料先相接触。具体实施起来可把本发明的化合物加入颜料膏(例如通常市售的颜料),或者可在早期如颜料的实际生产过程中便加入本发明的化合物。也可以在配制水基涂料组合物时,例如在将成膜树脂,金属颜料,含水介质与别的常用的和任选的组分(诸如交联剂,助溶剂,增稠剂和填料)一起混合过程中,把本发明的化合物只是作为一种另外的组分直接加入配方。不管采用什么方法,往水基涂料组合物中加入的本发明化合物的用量,要使它能有效地抑制或避免金属颜料在含水介质中生成气体。为此,水基组合物中该化合物的用量,按金属颜料(如铝的片状粉末)的重量计算,一般为0.50%~25.0%(重量),常用量为5.0%~15.0%(重量)。
本发明的水基涂料组合物可以含有任何聚合物或已知常用于水基涂料组合物的聚合物作成膜聚合物。例子中包括可通过用氨或胺中和聚合物所含的羧酸基而使其溶解或分散在含水介质中的聚合物,其中有些例子包括水溶性或水分散的丙烯酸类聚合物,聚氨酯,聚酯,环氧树脂,氨基塑料或它们的混合物。这类成膜聚合物可以与已知常用于水基涂料组合物的各种组分任选结合使用。所述的各种组分的例子包括:填料;增塑剂;抗氧剂;防霉剂和杀菌剂;表面活性剂;各种流动控制剂,包括例如能防止流挂和/或颜料取向的触变剂和添加剂诸如沉淀法二氧化硅,气相二氧化硅,有机改性的二氧化硅,膨润土,有机改性的膨润土,以及基于聚合物微粒(有时称作微凝胶)的添加剂,后者例如在美国专利4,025,474;4,055,607;4,075,141;4,115,472;4,147,688;4,180,489;4,242,384;4,268,547;4,220,679以及4,290,932中作了介绍,本文引入以作参考。
在由成膜聚合物,金属颜料,以及有机溶剂和/或有机稀释剂介质所组成的有机溶剂基涂料组合物中加入本发明化合物,可以抑制因吸潮产生的涂料组合物生成气体,潮气可来自配制前未彻底干燥的各种颜料,或涂料组合物在储存期内大气中的潮气有时能缓慢地进入储罐。同时又发现,在一种另外含有有机颜料的有机溶剂基涂料组合物中(这容易导致涂料组合物储存中色泽变化),加入本发明化合物,可以提高这种溶剂基涂料组合物的色泽稳定性。在本发明现在推荐的实施方案中,采用一种含一个1。2-环氧基的化合物制取供此用途的本发明化合物。並没有打算非要牵强附会,可以认为,在另外含有有机颜料的有机溶剂基涂料组合物中(如采用GAF公司得来的咔唑紫),加入本发明的化合物,有助于避免组合物中金属颜料(如铝的片状粉末)的胶凝和/或金属颜料同别的颜料(如着色颜料)的胶凝。
可用于本发明的有机溶剂基涂料组合物的金属颜料例子包括已知常用于加颜料的有机溶剂基涂料组合物的任何金属颜料。也包括前面所述的本发明水基涂料组合物中所用的金属颜料,尤其是金属片状粉末颜料。在这些例子中,优选使用的是铝的片状粉末颜料。另外,本发明的有机溶剂基涂料组合物还可以含有,一般也确实含有,一种或多种已知常用于涂料组合物的许多别的颜料诸如白色和带色的颜料。其例子包括前面谈到的可用于本发明水基涂料的白色和带色颜料中所述的熟知的颜料。正如水基涂料组合物那样,可以采用不同的方法将本发明的化合物混入本发明的有机溶剂基涂料组合物,例如,在把颜料混入有机溶剂基涂料组合物之前,将本发明的化合物预先加入颜料膏,或者在颜料的实际生产过程中便加入本发明的化合物,或者在配制有机溶剂基涂料组合物时,例如在将成膜树脂,颜料,有机介质与别的常用的和任选的组分(诸如交联剂,助溶剂,增稠剂和填料)一起混合中,把本发明的化合物作为一种另外的组分直接了当地加入配方。不管采用什么方法,往本发明的有机溶剂基涂料组合物中加入本发明的化合物,该化合物的一般用量,要使它能有效地抑制或避免含金属颜料的有机溶剂基涂料组合物生成气体。为此,按所用的金属片状粉末颜料(如铝的片状粉末)重量计算,其用量一般为0.10%~15.0%(重量),常用量为2.0%~8.0%(重量)。在涂料组合物中所使用的带色颜料容易造成组合物色泽随时间变化的场合,要使这种组成物色泽稳定性有效,通常使用适量的本发明化合物。其用量按所用金属片状粉末(如铝的片状粉末)重量计算,一般为0.10%~15.0%(重量),通常为2.0%~8.0%(重量)。
本发明的有机溶剂基涂料组合物可以含有任何聚合物或已知常用于有机溶剂基涂料组合物的聚合物作成膜聚合物。这些聚合物的例子包括丙烯酸类聚合物,聚氨酯,聚酯,环氧树脂,氨基塑料或它们的混合物。这类成膜聚合物可以同已知常用于有机溶剂基涂料组合物(其中含有这类成膜聚合物)的各种组分任选结合使用。所述各种组分的例子包括:填料;增塑剂;抗氧剂;防霉剂和杀菌剂;表面活性剂;各种流动控制剂。包括例如能防止流挂和/或颜料取向的触变剂和添加剂诸如沉淀法二氧化硅,气相二氧化硅,有机改性的二氧化硅,膨润土,有机改性的膨润土,以及例如在下面的美国专利中所介绍的基于聚合物微粒的这类添加剂,其专利号为4,025,474;4,055,607;4,075,141;4,115,472;4,147,688;4,180,489;4,242,384;4,268,547;4,220,679;以及4,290,932,本文引入以作参考。
本发明的有机溶剂基涂料组合物可采用的有机溶剂和/或稀释剂的例子包括以下各类,它们有醇类,诸如含1~8个碳原子的低级链烷醇包括甲醇,乙醇,正-丙醇,异丙醇,丁醇,仲丁醇,叔丁醇,戊醇,己醇,以及2-乙基己醇;醚和醚醇类,诸如乙二醇单乙醚,乙二醇单丁醚,乙二醇二丁醚,丙二醇单甲醚,二甘醇单丁醚,二甘醇二丁醚,二丙二醇单甲醚,以及二丙二醇单丁醚;酮类,诸如甲乙酮(即丁酮),甲基异丁基酮,甲基戊基酮,以及甲基正丁基酮;酯类诸如醋酸丁酯,2-乙氧基乙基醋酸酯,以及2-乙基己基醋酸酯;脂肪族和脂环族烃类,诸如各种石脑油和环己烷;以及芳香族烃类,诸如甲基和二甲苯。本发明的有机溶剂基涂料组合物中所用的有机溶剂和/或稀释剂的量可变化很大。不过,它们的用量一般可在10%~50%左右范围内变化,通常为20%~40%左右(重量,按组合物总重量计算)。
另外还发现,本发明的化合物用于由成膜聚合物和颜料组成的粉末涂料组合物可具有特别的好处。例如,在这种组合物中加入有效量的本发明化合物,改善了颜料在组合物中的分散性。这种改进后的颜料分散体可带来以下的优点,诸如改善了涂层的色泽均匀性,涂料不易结皮,光泽度好,成象清晰(DOI),以及在加热时组合物的流动性和流平性变好。
下面的实施例对本发明作了说明,但不应视作是对本发明的范围所作的限制。除非另外具体表明,所有的百分数和用量均被认作是按重量计算。本文中各处所用的“Pbw”指的是重量份数。
实施例1
本实施例说明可可胺双(亚甲基膦酸)的制备方法,以及用它同双酚A二缩水甘油醚制取本发明化合物的反应。
将含有98.0克亚磷酸(1.19摩尔)和75.0克1-甲氧基-2-丙醇的溶液在氮气氛下加热到85℃。然后,将130.0克可可胺(0.66摩尔,市售牌号为ARMEEN CD
,胺当量为196)和98.0克37%(重量)的甲醛水溶液(1.20摩尔甲醛)从不同的加料口用1.5小时同时加到上述溶液中。所得的反应混合物在迥流温度(98~100℃)保持4小时,接着,用一小时加入含有116.2克双酚A二缩水甘油醚(0.30摩尔,市售的牌号为EPON
828,Shell化学公司产品)和30.0克1-甲氧基-2-丙醇的混合物,随后,使反应混合物保持迥流1.5小时。制得的产物冷却到60℃,再用15分钟加入55.0克N,N-二甲基乙醇胺(0.62克分子)中和,然后使反应产物冷却到室温。制得的含本发明化合物的产物,其Gardner-Holdt气泡管粘度为X,总的固含量为67%(重量),PH为5.35。
实施例2
本实施例说明可可胺双(亚甲基膦酸)的制备方法,以及用它同苯基缩水甘油醚制取本发明化合物的反应。
将含有864.6克亚磷酸(10.54摩尔)和1440.2克1-甲氧基-2-丙醇的溶液在氮气氛下加热到85℃。然后,将1036.0克可可胺(5.28摩尔,牌号为ARMEENCD
)和840.0克37%(重量)的甲醛水溶液(10.35摩尔甲醛)从不同的加料口用1.5小时同时加到上述溶液中。所得的反应混合物在100℃(迥流温度)保持4小时,接着冷却到85℃,然后用一小时逐步往溶液中加入790.0克苯基缩水甘油醚(5.26摩尔)。所得的反应混合物在85℃保持3小时,待冷却到低于60℃,再用30分钟加入467.0克N,N-二甲基乙醇胺(5.24摩尔)中和,将制得的含本发明化合物的产物经真空汽提,所得产物的Gardner-Holdt气泡管粘度为Z-4/Z-5,总的固含量为83.9%(重量),PH为5.05。
实施例3
本实施例说明可可胺双(亚甲基膦酸)的制备方法,以及用它同双酚A二缩水甘油醚制取本发明化合物的反应。
将含有135.0克亚磷酸(1.65摩尔)和225.0克1-甲氧基-2-丙醇的溶液在氮气氛下加热到85℃。然后,将161.9克可可胺(0.83摩尔,牌号为ARMEEN CD
)和131.3克37%(重量)的甲醛水溶液(1.62摩尔甲醛)从不同的加料口用1.5小时同时加到上述溶液中。所得的反应混合物在100℃保持5小时,然后冷却到60℃,接着,用73.3克N,N-二甲基乙醇胺(0.82摩尔)在50.0克1-甲氧基-2-丙醇中的溶液中和。再加入含有155.5克双酚A二缩水甘油醚(0.41摩尔,牌号为EPON828
)和50.0克1-甲氧基-2-丙醇的混合物。将得到的反应混合物加热到100℃,並在该温度保持5小时,然后冷却到室温。制得的含本发明化合物的产物是均匀的液体,其Gardner-Holdt气泡管粘度为0,总的固含量为56.7%(重量)。
实施例4
本实施例说明可可胺双(亚甲基膦酸)的制备方法,以及用它同苯基缩水甘油醚制取本发明化合物的反应。
将含有135.0克亚磷酸(1.65摩尔)和225.0克1-甲氧基-2-丙醇的溶液在氮气氛下加热到85℃。然后,将161.9克可可胺(0.83摩尔,牌号为ARMEEN CD
)和131.3克37%(重量)的甲醛水溶液(1.62摩尔甲醛)从不同的加料口用1.5小时同时加到上述溶液中。所得的反应混合物在100℃保持5小时,待冷却到60℃,再用73.3克N,N-二甲基乙醇胺(0.82摩尔)中和。随后,加入123.5克苯基缩水甘油醚(0.82摩尔);将所得的反应混合物加热到100℃,並在该温度保持5小时;然后冷却。所得的含本发明化合物的产物经真空汽提除去溶剂和水,制得的产物其Gardner-Holdt气泡管粘度为Z-5,总的固含量为82.2%(重量)。
实施例5
本实施例采用一种美国专利4,693,754揭示的称作“硼砂试验”的方法,以评价阻气剂防止水基组合物中的铝的片状粉末与水反应的效果。该试验提供一种加速测试方法,将铝的片状粉末颜料膏加入一种Na2B4O7的摩尔浓度为0.024,NaoH的摩尔浓度为0.002的水溶液(加入NaoH是为了调节溶液的pH至9.26)。在恒温浴中(60℃)加热溶液,並记录氢气的放出速度。将本发明的阻气剂加入含上述铝的片状粉末的水基组合物(下面的组合物A),並从比较它与对照组合物的氢气放出速度,评价阻气剂的相对效果,所用的对照组合物同组合物A的差别仅在于,组合物B用的是一种已知的阻气剂(大致按美国专利4,621,112制得的一种磷酸有机酯),组合物C不含阻气剂。上述的已知的阻气剂是按美国专利4,621,112的例1的方法制备,不同之处在于,合成中用二异丙醇胺代替三乙胺作中和剂,用1-甲氧基-2-丙醇代替四氢呋喃作溶剂。
上述的组合物A,B,C的组分如下面表1所示。
表1
阻气作用
组合物 铝膏1)阻气剂 1-甲氧基-2-丙醇 硼酸盐溶液2)
A 15.38g 1.67g3)20毫升 25毫升
B 15.38g 2.38g4)20毫升 25毫升
C 15.38g 无 20毫升 25毫升
1)在200#溶剂油和油酸中含65.0%(固体量)铝的片状粉末的颜料膏(市售牌号为7575FG铝膏,Silberline Manufacturing公司产品)。
2)含0.024摩尔/升Na2B4O7和0.002摩尔/升NaoH的无离子水溶液。
3)上面实施例3所得的含本发明化合物产物,它在1-甲氧基-2-丙醇和水中的固含量减少到30%。
4)大致按美国专利4,621,112的实施例1制得的已知阻气剂,它在1-甲氧基-2-丙醇和水中的固含量为21%。
将组合物A,B和C分别放入烧瓶里;每个烧瓶均用胶皮塞封口,立即把烧瓶放到已加热到140°F(60℃)恒温浴中。使放出的氢气通过活塞上的一个小孔进入一支充满水的倒置的量管。然后在24小时中不时记录放出的气体的体积(如量管中被气体排出的水的体积所示,並扣除因加热烧瓶和溶液引起的体积膨胀)。在5小时和24小时测得的结果归纳在下面的表2。其中所列的放出的氢气的毫升数是各组合物作三次不同的实验得到的平均值。並检验了结果的重复性。表2中的符号“>”是指“大于”。
表2
放出的氢气的毫升数
组合物 5小时 24小时
A 0 1
B 17.7 >50
C 34.2 >50
正如上面表2归纳的结果所示,含有本发明的阻气剂的金属颜料水基组合物,其放气性要比组合物B(含有大致按美国专利4,621,112的实施例1制得的磷酸有机酯阻气剂)或组合物C(不含阻气剂)远低得多。
实施例6
很早就已经知道,同样含有无机颜料,有机颜料(特别是如咔唑紫那样的颜料),以及铝颜料的丙烯酸类聚合物的有机溶剂溶液易于色泽不稳定和发生颜料胶凝。这种情况会因添加水和热老化而加剧。本实施例采用一种溶剂基丙烯酸类清漆涂料组合物(市售牌号为Duracryl
DBC-3704,PPG工业公司出品),用它来评价本发明化合物(上面例4的产物)在缓和含上述某些颜料和铝粉的涂料的不良作用上的能力。
将含本发明化合物的以上实施例4的产物在配入Duracryl
DBC-3704涂料组合物之前,先把它同铝颜料膏混合浆化(产物重量占铝的固体重量为5%)。下面表3所示的试样1-4是按加入溶液重量0%或2%的水,以及加入0%或5%(重量)的例4产物(按铝粉固体重量计)制得。具体说明归纳在表3。
表3
例4产物占铝粉 水占溶液重量的%
固体重量的%
样品1 0 0
样品2 0 2
样品3 5 0
样品4 5 2
为了同老化后的样品作比较对照,用一根制涂层用的3密耳Bird圆棒,在Leneta纸上制作各样品供试验用的涂层样(湿膜)。将上面的各样品分成两半,一半留在室温下老化,另一半封入隔离的罐中在120°F(48.9℃)热老化。在五周内,定期制作经过老化的各样品的供试验用涂层样,同时与对照涂层样作比较,鉴定色泽变化和颜料的胶凝。后者是通过肉眼观察以出现小块加以确定。下面表4中所用的符号“Sl、Ag、”是指“略有胶凝”,“Sev、Ag、”是指“严重胶凝”,+C.S、”是指样品色泽发生正向变化,而“N.C.”是指同对照样相比,未发现胶凝和色泽变化。
表4
用经过老化的涂料组合物制作的涂膜的外观
从上面表4所归纳的结果可明显看出,由于加入了本发明的实施例4的产物,明显改善了Duracryl
DBC-3704涂料组合物的色泽稳定性和抗颜料胶凝性。
Claims (20)
1、一种由含至少一个下式基团的α-氨基亚甲基膦酸的至少一个膦酸基同含至少一个环氧基的化合物的环氧基反应制得的化合产物,
3、根据权利要求1的化合物,其中所述的环氧基团是1,2-环氧基。
4、根据权利要求2的化合物,其中a=2,而且所述的环氧基团是1,2-环氧基。
7、根据权利要求5的水基涂料组合物,其中所述的金属颜料由铝颜料组成。
8、根据权利要求7的水基涂料组合物,其中所述的金属颜料由铝颜料组成,所述的环氧基是1,2-环氧基。
9、根据权利要求6的水基涂料组合物,其中在所述分子式中的a=2,所述金属颜料由铝颜料组成,而所述环氧基是1,2-环氧基。
10、根据权利要求9的水基涂料组合物,其中所述含至少一个环氧基的化合物是二环氧化物。
13、根据权利要求11的有机溶剂基涂料组合物,其中所述的金属颜料由铝颜料组成。
14、根据权利要求11的有机溶剂基涂料组合物,其中所述的环氧基是1,2-环氧基。
15、根据权利要求11的有机溶剂基涂料组合物含有有机着色颜料,这种类型的有机溶剂基涂料组合物,它的色泽稳定性因其中加入了有效量所述反应产物而提高。
16、根据权利要求12的有机溶剂基涂料组合物,其中所述分子式中的a=2。
17、根据权利要求16的有机溶剂基涂料组合物,其中含至少一个环氧基的所述化合物是单环氧化物。
19、根据权利要求18的粉末涂料组合物,其中所述的α-氨基亚甲基膦酸的分子式为
式中a=1,2或3,a+b+c=3,Rb,Rc可以相同或不同,並可从烷基、芳基,烷芳基,芳烷基,以及多醚化合物的一价残基这类基团中选取。
20、根据权利要求19的粉末涂料组合物,其中所述的环氧基是1,2-环氧基。
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NZ502608A (en) * | 1997-07-30 | 2001-07-27 | Charles T Berge | Coating compositions comprising phosphonic acid reaction products and metallic pigments |
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US6440580B1 (en) | 1998-12-01 | 2002-08-27 | Ppg Industries Ohio, Inc. | Weldable, coated metal substrates and methods for preparing and inhibiting corrosion of the same |
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US6410926B1 (en) | 1999-10-01 | 2002-06-25 | Ppg Industries Ohio, Inc. | Coating with optical taggent |
US6558796B2 (en) | 2000-12-06 | 2003-05-06 | E. I. Du Pont De Nemours And Company | Aqueous coating compositions with phosphonic acid based compounds |
US6750274B2 (en) * | 2001-02-08 | 2004-06-15 | Ppg Industries Ohio. Inc. | Weldable coating of phosphated epoxy polymer, curing agent and electroconductive pigment |
US6863718B2 (en) | 2001-10-31 | 2005-03-08 | Silberline Manufacturing Co., Inc. | Phosphonic acid derivative treatment of metallic flakes |
US6749939B2 (en) | 2002-02-19 | 2004-06-15 | Ppg Industries, Ohio, Inc. | Composition having sealing and sound dampening properties and methods related thereto |
US6841251B2 (en) * | 2002-02-19 | 2005-01-11 | Ppg Industries Ohio, Inc. | Composition having sealing and sound dampening properties and methods related thereto |
US20040086718A1 (en) * | 2002-11-06 | 2004-05-06 | Pawlik Michael J | Corrosion and alkali-resistant compositions and methods for using the same |
US7345101B2 (en) * | 2002-11-06 | 2008-03-18 | Ppg Industries Ohio, Inc. | Aqueous composition of reaction product of epoxy and phosphorus materials with curing agent |
US7462394B2 (en) * | 2004-05-06 | 2008-12-09 | Ppg Industries Ohio, Inc. | Method of stabilizing metal pigments against gassing |
US9139715B2 (en) | 2012-09-14 | 2015-09-22 | Silberline Manufacturing Co., Inc. | Coating of metal pigments using phosphonic acid-based compounds |
JP6445826B2 (ja) * | 2014-10-08 | 2018-12-26 | 共栄社化学株式会社 | ホスホン酸誘導体、不飽和基含有ホスホン酸誘導体及びこれらの製造方法 |
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NL285361A (zh) * | 1961-11-13 | 1900-01-01 | ||
DE2043985A1 (de) * | 1969-09-05 | 1971-03-25 | Monsanto Co , St Louis, Mo (V St A ) | Verfahren zur Herstellung von Organophos phorsauren |
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GB8308003D0 (en) * | 1983-03-23 | 1983-04-27 | Albright & Wilson | Phosphonates |
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AT386000B (de) * | 1985-06-20 | 1988-06-10 | Vianova Kunstharz Ag | Verfahren zur stabilisierung von aluminiumpigmenten |
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US4777091A (en) * | 1987-04-28 | 1988-10-11 | The Dow Chemical Company | Metal substrates treated with aminophosphonic acid compounds and products resulting from coating such substrates |
-
1989
- 1989-04-03 US US07/333,355 patent/US5034556A/en not_active Expired - Lifetime
-
1990
- 1990-03-21 CA CA002012684A patent/CA2012684C/en not_active Expired - Fee Related
- 1990-03-22 AU AU52134/90A patent/AU617245B2/en not_active Ceased
- 1990-03-28 EP EP90105898A patent/EP0391230B1/en not_active Expired - Lifetime
- 1990-03-28 DE DE69027250T patent/DE69027250T2/de not_active Expired - Lifetime
- 1990-03-28 AT AT90105898T patent/ATE138952T1/de not_active IP Right Cessation
- 1990-03-28 ES ES90105898T patent/ES2090055T3/es not_active Expired - Lifetime
- 1990-03-30 MX MX020140A patent/MX169220B/es unknown
- 1990-04-02 AR AR90316529A patent/AR247400A1/es active
- 1990-04-02 BR BR909001501A patent/BR9001501A/pt unknown
- 1990-04-03 CN CN90101839A patent/CN1046165A/zh active Pending
- 1990-04-03 KR KR1019900004575A patent/KR930009042B1/ko not_active IP Right Cessation
- 1990-04-03 JP JP2090082A patent/JP2568728B2/ja not_active Expired - Lifetime
-
1991
- 1991-03-04 US US07/663,354 patent/US5091451A/en not_active Expired - Fee Related
-
1994
- 1994-02-28 JP JP6029680A patent/JP2577529B2/ja not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101809097B (zh) * | 2007-08-15 | 2013-03-20 | Ppg工业俄亥俄公司 | 用螯合剂稳定阴离子树脂水性分散体 |
Also Published As
Publication number | Publication date |
---|---|
AU5213490A (en) | 1990-10-04 |
ATE138952T1 (de) | 1996-06-15 |
EP0391230B1 (en) | 1996-06-05 |
AR247400A1 (es) | 1994-12-29 |
KR900016239A (ko) | 1990-11-13 |
JPH06340825A (ja) | 1994-12-13 |
AU617245B2 (en) | 1991-11-21 |
CA2012684C (en) | 1995-09-19 |
CA2012684A1 (en) | 1990-10-03 |
JP2568728B2 (ja) | 1997-01-08 |
KR930009042B1 (ko) | 1993-09-22 |
JPH02290890A (ja) | 1990-11-30 |
MX169220B (es) | 1993-06-24 |
US5091451A (en) | 1992-02-25 |
BR9001501A (pt) | 1991-04-16 |
ES2090055T3 (es) | 1996-10-16 |
US5034556A (en) | 1991-07-23 |
EP0391230A3 (en) | 1992-02-05 |
JP2577529B2 (ja) | 1997-02-05 |
EP0391230A2 (en) | 1990-10-10 |
DE69027250D1 (de) | 1996-07-11 |
DE69027250T2 (de) | 1997-01-02 |
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