CN101033204A - 用于流变性控制的缩二脲化合物 - Google Patents
用于流变性控制的缩二脲化合物 Download PDFInfo
- Publication number
- CN101033204A CN101033204A CNA2007100860760A CN200710086076A CN101033204A CN 101033204 A CN101033204 A CN 101033204A CN A2007100860760 A CNA2007100860760 A CN A2007100860760A CN 200710086076 A CN200710086076 A CN 200710086076A CN 101033204 A CN101033204 A CN 101033204A
- Authority
- CN
- China
- Prior art keywords
- acid
- polyoxyalkylenes
- alkylidene group
- aralkyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000000518 rheometry Methods 0.000 title abstract 2
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- 238000006243 chemical reaction Methods 0.000 claims description 17
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Abstract
本发明涉及用于流变性控制的缩二脲化合物,所述缩二脲化合物具有如上的典型通式(式中,R1~R6、Z和a的定义见说明书)。本发明还涉及制备所述缩二脲化合物的方法,以及所述缩二脲化合物作为防流挂剂和/或防沉降剂而进行流变性控制和赋予涂料体系触变性的应用。
Description
技术领域
本发明涉及缩二脲化合物、制备缩二脲化合物的方法和缩二脲化合物作为涂料体系的流变性控制剂的应用,所述涂料体系为例如含溶剂涂料、无溶剂涂料和水性涂料、PVC增塑溶胶、环氧基涂料和基于不饱和聚酯树脂的涂料等。
背景技术
如美国专利4,208,218、4,410,364和4,412,018等所述,为了控制液体涂料体系的流变性,通常使用二氧化硅、氢化蓖麻油或有机改性的膨润土。此外还广泛使用聚酰胺蜡。具体来说,在聚酰胺和聚酰胺酯的领域已经有许多专利,例如DE 69523221、EP 0528363、EP 0239419、US5,510,452和US 5,349,011等。
如EP 0509202和DE 69704691所述,也可以使用改性膨润土与聚酰胺的组合。
这些物质的缺点是,它们一般为干燥固体或膏体,必须使用溶剂和剪切力将其解离为半成品,然后通过控制目标温度将该半成品加入到液体涂料体系中。如果这些温度不能维持,在最终的涂料体系中将发生结晶,从而在涂布时产生缺陷。这些体系的普遍缺点是,它们使清晰透明的涂料变得混浊和模糊。此外,干燥产品在处理过程中会产生灰尘,采用这种干燥产品进行操作是不理想的。
聚酰胺酯通常是液体,因此效果比本身为固体的物质更差。
在EP 0198519中提出了用于流变性控制的其它方案。在粘合剂的存在下异氰酸酯与胺反应形成脲,这些脲以非常细的分散形式形成针状晶体。由此而改性的这些粘合剂被用作流变性控制和防流挂粘合剂(称为流挂控制剂)。
这些产品的缺点在于,它们因在粘合剂中制备而总是附着于这些粘合剂,因此随后不能对最终涂料进行通用的修正(universal correction)。
EP 0006252描述了一种克服上述部分缺点的制备触变剂的方法,该文献描述了脲氨基甲酸酯(urea urethane),该脲氨基甲酸酯是在非质子溶剂中,在LiCl的存在下,通过多胺的异氰酸酯加成物的反应而制备的。如此制备的产品的缺点是,由于该制备方法的原因,这些脲氨基甲酸酯的结构不确定。在该方法中,1摩尔二异氰酸酯首先与1摩尔一元醇反应。这不仅生成所需要的含NCO官能团的一元加成物,而且生成不含NCO官能团的二元加成物。并且,一部分单体二异氰酸酯未发生反应。随着NCO基团的反应性和例如温度和时间等反应条件的不同,这些不同化合物的含量将发生波动。但是,以这种方式制备的所有加成物都含有相当大量的未反应的二异氰酸酯,未反应的二异氰酸酯与多胺进一步反应,导致分子的链增长无法控制。于是这些产品表现出产生沉淀现象或早期胶凝的趋势,从而在粘合剂中形成所谓的“种子”。在DE 19919482中,通过除去过量的异氰酸酯而避免了这些缺点。但是,这些产品的缺点是,它们仅在例如NMP等高极性溶剂中并在碱性金属盐的辅助下才能得到稳定的溶液。
发明内容
本发明的目的是寻找一种方法,该方法能够制备结构更加确定的触变剂,从而确保触变的效果特性和再现性得到改善。
本发明人惊讶地发现,利用以下缩二脲化合物可以达到该目的,这种缩二脲化合物可以由脲二酮(uretdione)(组分A)和含一元胺官能团的化合物(组分B)制备并具有结构通式A-B。
因此,本发明提供具有如下典型通式的缩二脲化合物:
式中,R1为(C1-C22)亚烷基、(C3-C22)亚烯基、(C5-C15)环亚烷基、亚芳基、(C7-C12)亚芳烷基、聚氧化烯基或聚酯基,
R2为(C1-C22)烷基、羟基-(C1-C22)烷基、(C3-C18)烯基、芳基、(C7-C12)芳烷基、(C5-C12)环烷基、羟基聚氧化烯基、(C1-C22)烷氧基聚氧化烯基、(C5-C12)环烷氧基聚氧化烯基或(C7-C12)芳烷氧基聚氧化烯基,或由(C1-C22)烷醇、(C5-C12)环烷醇或(C7-C12)芳烷醇或由(C1-C22)烷氧基聚氧化烯、(C6-C12)环烷氧基聚氧化烯或(C7-C12)芳烷氧基聚氧化烯起始制备的聚酯基,
Y代表相同或不同的O、NH、CO-NH-NH或NH-NH-CO基团,
R3、R4和R5相互独立地为(C2-C40)亚烷基、(C3-C40)亚烯基、(C5-C40)环亚烷基、亚芳基、(C7-C40)亚芳烷基或聚氧化烯基,或为聚酯基,
R6为(C1-C30)烷基、(C3-C22)烯基、羟烷基、羟烯基、(C4-C13)环烷基、芳基或(C7-C12)芳烷基,
Z代表下列基团COO、OCO、NHCO、CONH、NHCOO、OOCNH和NHCONH中的一个或多个基团,以及
a为1~19的数字。
在本发明中,不管它们所表征的化合物如何,基团R1、R2、R3、R4、R5、R6、Y和Z以及下标a的定义都对应着上述定义。可以在各个分段中找到这些基团的优选方案。
当基团R1、R2、R3、R4和/或R5中的一个或多个含有聚氧化烯部分时,不管它们表征的化合物如何,这些基团都优选由氧化乙烯、氧化丙烯和/或氧化丁烯单元以无规或嵌段排列构成,适当时,这些单元中的一个或多个可以被苯乙烯单元取代。特别优选氧化乙烯基和氧化丙烯基。
当基团R1、R2、R3、R4和/或R5中的一个或多个包含聚酯基时,不管它们表征的化合物如何,这些基团都优选以一种或多种(C1-C18)羟基羧酸或一种或多种内酯为基础构成,所述内酯为例如β-丙内酯、δ-戊内酯、ε-己内酯和具有(C1-C6)烷基取代基的ε-己内酯等。
R1更优选为六亚甲基。
R2优选为(C1-C22)烷基或(C1-C22)烷氧基聚氧化烯基。
基团R3和R5相互独立地优选为(C2-C18)亚烷基、(C7-C15)亚芳烷基,更优选为(C2-C12)亚烷基、(C7-C12)亚芳烷基,非常优选为(C2-C8)亚烷基、(C7-C9)亚芳烷基,例如六亚甲基、八亚甲基或间亚二甲苯基。基团R3和R5优选相同。
R4为(C2-C40)亚烷基、(C3-C40)亚烯基、(C5-C40)环亚烷基、亚芳基或(C7-C40)亚芳烷基,优选为(C30-C40)亚烷基、(C30-C40)亚烯基、(C30-C40)环亚烷基、亚芳基或(C30-C40)亚芳烷基,例如二聚酸的两个羧酸基之间的基团。R4更优选为C34基团。
R6优选为(C1-C30)烷基或(C3-C22)烯基,适当时它们可以被羟基取代,R6更优选为(C12-C30)烷基或(C12-C22)烯基,非常优选为(C12-C20)烷基或(C12-C20)烯基,例如C17烷基或C17烯基。
Z更优选为NHCO和CONH。
下标a为1~19的数字,更优选为2~7。
本发明还提供一种制备具有结构通式A-B的可产生触变和防止流挂的缩二脲化合物的方法,该化合物可以通过使具有典型结构通式(A)的脲二酮与具有典型结构通式(B)的含一元胺官能团化合物反应得到。
式中,R1为(C1-C22)亚烷基、(C3-C22)亚烯基、(C5-C15)环亚烷基、亚芳基、(C7-C12)亚芳烷基、聚氧化烯基或聚酯基,
R2为(C1-C22)烷基、羟基-(C1-C22)烷基、(C3-C18)烯基、芳基、(C7-C12)芳烷基、(C5-C12)环烷基、羟基聚氧化烯基、(C1-C22)烷氧基聚氧化烯基、(C5-C12)环烷氧基聚氧化烯基或(C7-C12)芳烷氧基聚氧化烯基,或为由(C1-C22)烷醇、(C5-C12)环烷醇或(C7-C12)芳烷醇或由(C1-C22)烷氧基聚氧化烯、(C6-C12)环烷氧基聚氧化烯或(C7-C12)芳烷氧基聚氧化烯起始制备的聚酯基,
Y代表相同的或不同的O、NH、CO-NH-NH或NH-NH-CO基团;
(B)H2N-R3-[Z-R4-Z-R5]a-Z-R6
式中,R3、R4和R5相互独立地为(C2-C40)亚烷基、(C3-C40)亚烯基、(C5-C40)环亚烷基、亚芳基、(C7-C40)亚芳烷基或聚氧化烯基,或为聚酯基,
R6为(C1-C30)烷基、(C3-C22)烯基、羟烷基、羟烯基、(C4-C13)环烷基、芳基或(C7-C12)芳烷基,
Z代表下列基团COO、OCO、NHCO、CONH、NHCOO、OOCNH和NHCONH中的一个或多个基团,以及
a为1~19的数字。
在具有结构通式A-B的本发明的缩二脲化合物的制备中,含脲二酮的多异氰酸酯首先与一元醇反应,脲二酮部分被保留,从而形成含氨基甲酸酯的聚合物,或者多异氰酸酯与一元胺和/或烷醇胺和/或一元酰肼反应形成含脲和/或氨基脲的聚合物,并且在另一步骤中,在打开脲二酮环的同时与胺官能性化合物反应,由此制得本发明的缩二脲化合物。
本领域的技术人员知道,可以使用特定的催化剂由单体二异氰酸酯的加成反应制备脲二酮(Laas,H.J.;Halpaap,R.;Pedain,J.;J.prakt.Chemie336(1994),185-200)。除了例如购自Rhein-Chemie的名为DesmodurTT/G的TDI脲二酮外,优选使用购自BAYER的名为Desmodur N 3400的HDI脲二酮。这些化合物都是市售产品,通常不是纯净形式,而是具有类似结构的化合物的混合物。
用于化合物A的一元醇为脂肪族、脂环族和芳脂族醇。就脂肪醇而言,可以使用链长为C1-C22的直链、支链或环状醇,例如甲醇、乙醇、正丙醇、2-丙醇、正丁醇、异丁醇、叔丁醇、己醇、辛醇、癸醇、十二烷醇、油醇和硬脂醇。还包括二元醇单醚,例如乙二醇单丙醚、乙二醇单丁醚、乙二醇单(2-乙基己醚)或乙二醇单苯醚。脂环醇包括例如环戊醇和环己醇。也可以使用例如苄醇等芳脂醇。环状醇的代表例子包括例如1-(2-羟基乙基)咪唑烷-2-酮。本发明还包括例如聚烯烃一元醇、聚丙烯酸酯一元醇、聚碳酸酯一元醇、聚己内酯一元醇、聚噁唑啉一元醇或聚硅氧烷一元醇等聚合物醇,这些聚合物醇是烷氧化程度不同的脂肪醇烷氧化物,属于本领域技术人员所知道的BASF的商品名为Lutensol的种类。优选使用以下聚氧化烯一元醇,该聚氧化烯一元醇含有氧化乙烯和/或氧化丙烯和/或氧化丁烯基团,且适当时被氧化苯乙烯改性。特别优选使用例如MPEG 350、MPEG 500和MPEG 750等聚氧化烯一元醇,它们是由甲醇起始制备的含有端羟基的聚氧化乙烯。也可以以混合物使用一元醇。
用来制备含脲二酮的化合物A的一元胺为脂肪族、脂环族和芳脂族胺。就脂肪族胺而言,可以使用链长为C2-C22的直链、支链或环状胺,例如乙胺、丙胺、异丙胺、丁胺、仲丁胺、叔丁胺、3-甲基-1-丁胺、己胺、2-乙基己胺、辛胺、环戊胺、环己胺、十三烷胺、油胺、十八烷胺和来自Akzo Nobel的商品名为Armeen的C12-C22胺的混合物。依据本发明的胺不仅为例如聚异丁烯胺等聚烯烃胺,而且优选为含氧化乙烯和/或氧化丙烯基团的来自Huntsman的商品名为Jeffamine M 600、M 1000、M2005和M 2070的聚氧化烯一元胺。芳脂族胺为例如苄胺和糠胺等产品。但是,也可以使用例如苯甲酰肼等酰肼。一元胺也可以作为混合物使用,一元胺还可以作为与一元醇和一元酰肼以任意比例的混合物使用。
也可以使用烷醇胺来制备含脲二酮的化合物A。这里可给出的例子包括2-氨基乙醇、3-氨基-1-丙醇、1-氨基-2-丙醇、2-(2-氨基乙氧基)乙醇、二乙醇胺、3-(2-羟基乙氨基)-1-丙醇、二异丙醇胺和它们的羟基被烷氧化的化合物。
含脲二酮的多异氰酸酯与一元醇之间的反应在15℃~90℃,优选20℃~75℃的温度下进行,适当时在例如二月桂酸二丁锡(DBTL)等催化剂的辅助下进行。含脲二酮的多异氰酸酯与一元胺和/或烷醇胺和/或一元酰肼之间的反应在15℃~45℃,优选20℃~30℃的温度下进行。加入共反应物的顺序一般是任意的;首先引入含脲二酮的多异氰酸酯,适当时将其引入惰性溶剂中,然后逐滴加入一元醇、一元胺、烷醇胺或一元酰肼。也可以首先引入一元醇、一元胺、烷醇胺或一元酰肼,而逐滴加入含脲二酮的多异氰酸酯。当组分A不仅含有氨基甲酸酯基团,而且含有脲基团和/或氨基脲基团时,含脲二酮的多异氰酸酯首先与醇反应,然后与胺和/或一元酰肼反应。适当时,该反应也可以在例如乙酸甲氧基丙酯、环己烷、甲苯、二甲苯或例如Shellsol A等较高沸点的芳烃等惰性溶剂中进行。
具有通式(B)的含一元胺官能团的化合物在本领域技术人员已知的条件下制备。
(B)H2N-R3-[Z-R4-Z-R5]a-Z-R6
例如,可以通过使一元羧酸和多元羧酸(优选二元羧酸和/或二元酸酐)的混合物与二元胺反应,反应温度优选为100℃~250℃,更优选140℃~200℃,将水分离出去,由此得到通式(B)的含一元胺官能团的化合物。二元胺∶多元羧酸∶一元羧酸的比例为3∶2∶1~20∶19∶1,更优选3∶2∶1~8∶7∶1。在一个优选方案中,可以由以下方式制备通式(B)的化合物:首先使二元羧酸和/或二元酸酐与二元胺在100℃~250℃,更优选140℃~200℃的温度下反应,将水分离出去,从而得到通式(C)的缩合产物,然后在100℃~250℃,更优选140℃~200℃的温度下使化合物(C)与一元羧酸反应,将水分离出去,从而得到化合物(B),以100%的活性物质为基础,该缩合产物(B)具有优选3~80,更优选8~50的胺数。
(C)H2N-R3-[Z-R4-Z-R5]a-NH2
以100%的活性物质为基础,缩合产物(C)具有优选5~180,更优选15~100的胺数。
二元胺优选为脂肪族、芳香族和芳脂族二元伯胺,例如乙二胺、新戊二胺、1,2-丙二胺、1,3-丙二胺、1,4-丁二胺、1,5-戊二胺、2-丁基-2-乙基-1,5-戊二胺、1,6-六亚甲基二胺(也可以是水溶液)、1,8-八亚甲基二胺、1,12-十二亚甲基二胺、环己二胺、4,4’-二氨基二环己基甲烷、3,3’-二甲基-4,4’-二氨基二环己基甲烷、异佛尔酮二胺、4,7-二氧杂癸烷-1,10-二胺、4,11-二氧杂十四烷-1,14-二胺、4,7,10-三氧杂癸烷-1,13-二胺、聚氧化烯二胺(含有无规或嵌段排列的氧化乙烯和/或氧化丙烯基团,数均分子量为148~4000g/mol,例如来自Huntsman的Jeffamine D 230、D 400、D2000、D 4000以及Jeffamine ED 600、ED 900、ED 2003和EDR 148)、例如双(3-氨基丙基)聚四氢呋喃350、750、1100和2100(数字表示大约的分子量)等聚四氢呋喃二胺、4,4’-二氨基二苯基甲烷、3,3’-二氨基二苯砜及对苯二甲胺和间苯二甲胺。优选使用1,6-六亚甲基二胺、1,8-八亚甲基二胺和间苯二甲胺。也可以使用H2N-R-NR-R-NH2型的胺,R独立地代表(C1-C18)烷基或(C1-C4)烷氧基。它的一个例子为N,N’-双(3-氨基丙基)甲胺。但是,也可以使用例如乙二酰肼、丁二酰肼或己二酰肼等二酰肼。还可以使用二元胺的混合物,其中包括与二酰肼的混合物。二元胺也可以用作碳酸酯化合物,在缩合反应中,碳酸酯化合物与多元羧酸反应,分离出水并排出CO2,从而形成本发明优选的酰胺部分。
多元羧酸优选为脂肪族、脂环族或芳香族的二元羧酸,该二元羧酸为直链或支链的,且为饱和或不饱和的,且具有至少2个、更优选3~40个碳原子。这类多元羧酸的例子为己二酸、草酸、丙二酸、琥珀酸、戊二酸、庚二酸、辛二酸、癸二酸、壬二酸、十一烷二酸、1,11-十一烷二羧酸、十二烷二酸、十六烷二酸、二十二烷二酸、马来酸、富马酸、对苯二甲酸或间苯二甲酸,这些酸可以单独或以混合物使用。本发明也包括酸酐,例如马来酸酐、戊二酸酐、邻苯二酸酐和琥珀酸酐,适当时,这些酸酐用烷基或亚烷基改性,例如十二烯基琥珀酸酐。也可以使用例如聚丁二烯的二元羧酸等聚合的多元羧酸,也可以是例如酒石酸、柠檬酸和羟基邻苯二甲酸等含羟基官能团的多元羧酸。还包括例如3,6,9-三氧杂十一烷二酸和聚乙二醇二酸等氧杂二羧酸。特别优选具有36个碳原子的碳链长度的被本领域技术人员称为二聚酸的二聚脂肪酸。这些二聚酸可具有低的单体含量(通常小于8重量%)和不大于25重量%的三聚酸。
一元羧酸为饱和、单不饱和至多不饱和、直链和支链脂肪族羧酸,例如乙酸、丙酸、丁酸、异丁酸、戊酸、异戊酸、己酸、庚酸、辛酸、壬酸、癸酸、十一烷酸、月桂酸、十三烷酸、十四烷酸、十五烷酸、十六烷酸、十七烷酸、硬脂酸、十九烷酸、二十烷酸、二十二烷酸、二十四烷酸、蜡酸、三十烷酸、月桂烯酸、肉豆寇烯酸、棕榈油酸、岩芹酸、油酸、反油酸、十八碳烯酸、芥酸、亚油酸、亚麻酸、花生四烯酸、二十二碳五烯酸、9,11-十八碳二烯酸、α-桐酸、α-十八碳四烯酸、椰子油脂肪酸、棕榈仁油脂肪酸、椰子/棕榈仁油脂肪酸、棕榈油脂肪酸、棉籽油脂肪酸、花生油脂肪酸、豆油脂肪酸、葵花籽油脂肪酸、菜子油脂肪酸和动物脂肪酸。还可以使用例如十八碳三烯-4-酮酸等酮羧酸和例如苯甲酸等芳香族一元羧酸。作为羟基羧酸的代表,可以提及例如羟基乙酸、5-羟基戊酸、6-羟基己酸、蓖麻醇脂肪酸、12-羟基硬脂酸、12-羟基十二烷酸、5-羟基十二烷酸、5-羟基癸酸或4-羟基癸酸。也可以使用一元羧酸的混合物。
一元羧酸和/或多元羧酸可以被单和/或二异氰酸酯部分地替换,二元胺可以被二元醇部分地替换,在这种情况中,酯、氨基甲酸酯和/或脲基团出现在通式(B)和(C)的化合物的优选酰胺部分的侧旁。
单独的或混合物形式的二元醇优选为聚氧化烯二醇、适当地被(C1-C4)烷基和/或(C1-C4)烷氧基改性的聚氧化烯二醇、聚酯二醇、混合的聚酯-聚氧化烯-二醇、聚内酯二醇、混合的聚氧化烯-聚内酯-二醇、聚碳酸酯二醇、聚烯烃二醇、聚丙烯酸酯二醇、烷氧化的双酚A二醇、α,ω-二羟基亚烷基硅氧烷型的二醇和它们的具有250~5000g/mol的平均分子量Mn的烷氧化化合物。
使用的二异氰酸酯可以优选为脂肪族、脂环族和芳香族二异氰酸酯或它们的混合物。所述二异氰酸酯的例子为1,4-四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、2,2,4-三甲基-1,6-六亚甲基二异氰酸酯、1,10-十亚甲基二异氰酸酯、1,4-环己烷二异氰酸酯、对苯二异氰酸酯、间苯二异氰酸酯、2,6-甲苯二异氰酸酯、2,4-甲苯二异氰酸酯和它们的混合物、对二甲苯二异氰酸酯、间二甲苯二异氰酸酯、1,5-萘二异氰酸酯、异佛尔酮二异氰酸酯、4,4’-二异氰酸根合二环己基甲烷、3,3’-二甲基-4,4’-联苯二异氰酸酯、3,3’-二甲基二异氰酸根合二苯基甲烷、2,4’-异氰酸根合二苯基甲烷与4,4’-二异氰酸根合二苯基甲烷的异构体混合物和C36二聚体二异氰酸酯。
为了制备具有结构通式A-B的本发明的缩二脲化合物,具有通式A的脲二酮和具有通式B的含一元胺官能团的化合物在60℃~120℃,更优选75℃~90℃的反应温度下反应。在这种情况中,对组分A和B的比例进行选择,使得相对于1摩尔化合物A,使用0.8~1.2摩尔,优选0.9~1.1摩尔,更优选1摩尔化合物B。该反应可以在有溶剂或无溶剂下进行。合适的溶剂均为脂肪族、芳香族、质子溶剂和非质子溶剂,例如乙酸甲氧基丙酯、环己烷、甲苯、二甲苯或例如Shellsol A或Exxsol D 40等较高沸点的溶剂。N-甲基吡咯烷酮或N-乙基吡咯烷酮以及例如乙醇、丙醇、异丁醇或丁二醇等醇类也是合适的。该加成反应也可以在作为溶剂的例如聚丙二醇600(数字表示大约的分子量)等聚醚中进行。也可以使用溶剂的混合物。
本发明还提供了具有结构通式A-B的本发明的缩二脲化合物和由本发明的方法得到的具有结构通式A-B的缩二脲化合物作为流变性控制添加剂的应用,所述应用特别是在基于粘合剂的含溶剂和无溶剂涂料中的应用,所述涂料为例如聚氨基甲酸酯(1K和2K-1-组分和2-组分)、聚丙烯酸酯、聚酯树脂、醇酸树脂和环氧树脂、PVC增塑溶胶和PVC有机溶胶、环氧基涂料和不饱和聚酯树脂等。可以理解,涂料还可包括例如美国专利6,156,325中所述种类的指甲油。
以整个配方的重量为基础,具有结构通式A-B的本发明的缩二脲化合物的使用量为0.05重量%~5.0重量%的活性物质,优选0.1重量%~3.0重量%的活性物质,更优选0.2重量%~2.0重量%的活性物质。
另外,本发明还提供了固化和未固化的聚合物组合物,所述聚合物组合物包含一种或多种具有结构通式A-B的本发明的缩二脲化合物或由本发明的方法得到的具有结构通式A-B的缩二脲化合物。
具体实施方式
下面参照实施例进一步解释本发明。
实施例
本发明的组分A的制备:
实施例1:
在配有搅拌器、回流冷凝器和温度计的1升3口烧瓶中,室温下加入195.0g(0.5mol)六亚甲基二异氰酸酯脲二酮(Bayer的DesmodurN3400,NCO含量=21.5%)和138.2g(1.0mol)乙二醇单苯醚,将该最初的加入物加热到70℃。进行该反应直到NCO含量小于0.1%。然后,将反应混合物冷却到50℃。
表1:
组分A:
实施例 | 脲二酮 | 胺/醇组分 |
2 | 六亚甲基二异氰酸酯脲二酮 | 癸醇 |
3 | 六亚甲基二异氰酸酯脲二酮 | 油醇 |
4 | 六亚甲基二异氰酸酯脲二酮 | Polyglycol M 350 |
5 | 六亚甲基二异氰酸酯脲二酮 | 苄胺 |
6 | 六亚甲基二异氰酸酯脲二酮 | 十三烷胺 |
7 | 六亚甲基二异氰酸酯脲二酮 | Jeffamine M 600 |
8 | 六亚甲基二异氰酸酯脲二酮 | Jeffamine M 1000 |
9 | 六亚甲基二异氰酸酯脲二酮 | Polyglycol M 500/十三烷胺(比例1∶1) |
备注1:
Jeffamine M 600:Huntsman的含一元胺官能团的EO/PO聚醚(EO∶PO=1∶9),Mn~600g/mol
Jeffamine M 1000:Huntsman的含一元胺官能团的EO/PO聚醚(EO∶PO=19∶3),Mn~1000g/mol
Polyglycol M 350、500:Clariant的由甲醇起始制备的含单羟基官能团的EO聚醚,Mn~350或500g/mol
本发明的组分B的制备:
实施例10:
在配有搅拌器、水分离器和温度计的1升3口烧瓶中,顺序加入227.8g(0.4mol)二聚酸PripolTM 1009(氢化的二聚脂肪酸,Uniqema,三聚酸最多1%)、69.6g(0.6mol)六亚甲基二胺和152.1g Exxsol D40(脱芳香化的烃,ExxonMobil Chemical),将该最初的加入物慢慢加热到170℃。通过水分离器共沸分离出反应时慢慢释放的水。缩合产物具有51的胺数。然后,加入57.6g(0.2mol)妥尔油脂肪酸(含有高含量的油酸和亚油酸和约2%的树脂酸(松香酸)的一元羧酸混合物,ArizonaChemical GmbH),通过水分离器共沸分离出反应时释放的水。该缩合产物具有22.7的胺数。然后,将反应混合物冷却到50℃。
表2:
组分B:
实施例 | 二元胺a | 二元羧酸b | 一元羧酸c | 摩尔比a∶b∶c |
11 | 六亚甲基二胺 | PripolTM 1006 | 妥尔油脂肪酸 | 6∶5∶1 |
12 | 六亚甲基二胺 | PripolTM 1009 | 庚酸 | 7∶6∶1 |
13 | 六亚甲基二胺 | PripolTM 1013 | 12-羟基硬脂酸 | 5∶4∶1 |
14 | 八亚甲基二胺 | Empol 1062 | 硬脂酸 | 3∶2∶1 |
15 | 间苯二甲胺 | PripolTM 1017 | 妥尔油脂肪酸 | 6∶5∶1 |
16 | Jeffamine ED 600 | 己二酸 | 硬脂酸 | 4∶3∶1 |
17 | Jeffamine D 230 | 己二酸/PripolTM1006,比例1∶2 | 妥尔油脂肪酸 | 5∶4∶1 |
18 | 六亚甲基二胺 | PripolTM 1006 | 乙酸 | 3∶2∶1 |
19 | 六亚甲基二胺/间苯二甲胺(比例2∶3) | Empol 1012 | 油酸 | 4∶3∶1 |
备注2:
PripolTM 1006:氢化的二聚脂肪酸(三聚酸最多4%),来自Uniqema
PripolTM 1009:氢化的二聚脂肪酸(三聚酸最多1%),来自Uniqema
PripolTM 1013:二聚脂肪酸(三聚酸最多4%),来自Uniqema
PripolTM 1017:二聚脂肪酸(三聚酸最多22%),来自Uniqema
Empol 1062:部分氢化的二聚脂肪酸(多元羧酸最多3.5%),来自Cognis
Empol 1012:氢化的二聚脂肪酸(多元羧酸最多5%),来自Cognis
Jeffamine ED 600:含二元胺官能团的EO/PO聚醚(EO∶PO=9∶3.6),Mn~600g/mol,来自Huntsman
Jeffamine D 230:含二元胺官能团的PO聚醚,Mn~230g/mol,来自Huntsman
本发明的缩二脲加成物的制备:
实施例20:
在配有搅拌器、回流冷凝器和温度计的1升3口烧瓶中,室温下顺序加入66.6g(0.1mol)来自实施例1的加成物和247.1g(0.1mol;胺数=22.7)来自实施例10的缩合产物,将该最初的加入物加热到85℃。搅拌该反应混合物直到胺数小于1。然后,该产物用异丁醇稀释至固体含量为30%。
表3:
缩二脲加成物:
实施例 | 组分A | 组分B |
21 | 实施例2 | 实施例19 |
22 | 实施例4 | 实施例11 |
23 | 实施例7 | 实施例15 |
24 | 实施例8 | 实施例13 |
25 | 实施例9 | 实施例14 |
性能结果:
白漆配方:Worléekyd S 365白漆,64%粘合剂,20%TiO2
Worléekyd S 365在K 030中70% 34.4
Disperbyk 110 0.6
RKB-2(TiO2) 20.0
BYK 066 0.3
分散:30分钟,Dispermat,50℃,8500转/分,4cm的特富龙盘(Teflondisc)
Nuodex Combi APB 4.5
Borchi Nox M2 0.2
K 030 10.4
100
备注3:
Worléekyd S 365:长油醇酸树脂,空气干燥,来自Worlée
Disperbyk 110:润湿分散添加剂(含酸性基团的共聚物的溶液),来自BYK-Chemie
RKB-2:白色颜料(二氧化钛),来自BAYER AG
BYK 066:来自BYK-Chemie的硅酮消泡剂
Nuodex Combi APB:来自Sasol Servo BV的组合干燥剂
Borchi Nox M2:来自Borchers的防结皮剂(甲乙酮肟)
K030:C8-C11范围的链烷烃、环烷烃和芳香烃的混合物,来自SolvadisDeutschland
添加剂用量:占整个组合物的重量的1重量%的活性物质
加料:在Dispermat搅拌下加入添加剂,带齿的盘2.5cm,1200转/分,2分钟。
评价:流挂极限形式的流变行为的测定:
为了该目的,使用来自BYK Gardner的自动涂布机(速度:3cm/秒),使用50μm~500μm和550μm~1000μm的阶梯涂布刀将加入添加剂的漆体系涂布到BYK Gardner 2801对照图上。将对照图竖直地悬挂干燥。湿润时以μm读出稳定性。这是流变行为的量度。结果列于表4中。
表4:
添加剂 | 流挂极限[μm] |
对照(没有添加剂) | 150 |
BYK 411 | 450 |
实施例20 | 900 |
实施例21 | 550 |
实施例22 | 800 |
实施例23 | 650 |
实施例24 | 1000 |
实施例25 | 750 |
备注4:
BYK 411:来自BYK-Chemie的液体流变性添加剂。
Claims (11)
1.具有如下典型通式的缩二脲化合物:
式中,R1为(C1-C22)亚烷基、(C3-C22)亚烯基、(C5-C15)环亚烷基、亚芳基、(C7-C12)亚芳烷基、聚氧化烯基或聚酯基,
R2为(C1-C22)烷基、羟基-(C1-C22)烷基、(C3-C18)烯基、芳基、(C7-C12)芳烷基、(C5-C12)环烷基、羟基聚氧化烯基、(C1-C22)烷氧基聚氧化烯基、(C5-C12)环烷氧基聚氧化烯基或(C7-C12)芳烷氧基聚氧化烯基,或由(C1-C22)烷醇、(C5-C12)环烷醇或(C7-C12)芳烷醇或由(C1-C22)烷氧基聚氧化烯、(C6-C12)环烷氧基聚氧化烯或(C7-C12)芳烷氧基聚氧化烯起始制备的聚酯基,
Y代表相同或不同的O、NH、CO-NH-NH或NH-NH-CO基团,
R3、R4和R5相互独立地为(C2-C40)亚烷基、(C3-C40)亚烯基、(C5-C40)环亚烷基、亚芳基、(C7-C40)亚芳烷基或聚氧化烯基,或为聚酯基,
R6为(C1-C30)烷基、(C3-C22)烯基、羟烷基、羟烯基、(C4-C13)环烷基、芳基或(C7-C12)芳烷基,
Z代表下列基团COO、OCO、NHCO、CONH、NHCOO、OOCNH和NHCONH中的一个或多个基团,以及
a为1~19的数字。
2.如权利要求1所述的缩二脲化合物,其特征在于,R1为六亚甲基。
3.如权利要求1或2所述的缩二脲化合物,其特征在于,R2为(C1-C22)烷基或(C1-C22)烷氧基聚氧化烯基。
4.如权利要求1~3任一项所述的缩二脲化合物,其特征在于,基团R3和R5相互独立地为(C2-C18)亚烷基、(C7-C15)亚芳烷基,更优选为(C2-C12)亚烷基、(C7-C12)亚芳烷基,非常优选为(C2-C8)亚烷基、(C7-C9)亚芳烷基,例如六亚甲基、八亚甲基或间亚二甲苯基。
5.如权利要求1~4任一项所述的缩二脲化合物,其特征在于,R4为(C2-C40)亚烷基、(C3-C40)亚烯基、(C5-C40)环亚烷基、亚芳基或(C7-C40)亚芳烷基,优选为(C30-C40)亚烷基、(C30-C40)亚烯基、(C30-C40)环亚烷基、亚芳基或(C30-C40)亚芳烷基。
6.如权利要求1~5任一项所述的缩二脲化合物,其特征在于,R6为(C1-C30)烷基或(C3-C22)烯基。
7.如权利要求1~6任一项所述的缩二脲化合物,其特征在于,Z为NHCO或CONH。
8.如权利要求1~7任一项所述的缩二脲化合物,其特征在于,a为2~7。
9.制备权利要求1~8任一项所述缩二脲化合物的方法,其特征在于,具有典型通式(A)的脲二酮与具有典型结构通式(B)的含一元胺官能团的化合物反应,
式中,R1为(C1-C22)亚烷基、(C3-C22)亚烯基、(C5-C15)环亚烷基、亚芳基、(C7-C12)亚芳烷基、聚氧化烯基或聚酯基,
R2为(C1-C22)烷基、羟基-(C1-C22)烷基、(C3-C18)烯基、芳基、(C7-C12)芳烷基、(C5-C12)环烷基、羟基聚氧化烯基、(C1-C22)烷氧基聚氧化烯基、(C5-C12)环烷氧基聚氧化烯基或(C7-C12)芳烷氧基聚氧化烯基,或为由(C1-C22)烷醇、(C5-C12)环烷醇或(C7-C12)芳烷醇或由(C1-C22)烷氧基聚氧化烯、(C6-C12)环烷氧基聚氧化烯或(C7-C12)芳烷氧基聚氧化烯起始制备的聚酯基,
Y代表相同的或不同的O、NH、CO-NH-NH或NH-NH-CO基团;
(B)H2N-R3-[Z-R4-Z-R5]a-Z-R6
式中,R3、R4和R5相互独立地为(C2-C40)亚烷基、(C3-C40)亚烯基、(C5-C40)环亚烷基、亚芳基、(C7-C40)亚芳烷基或聚氧化烯基,或为聚酯基,
R6为(C1-C30)烷基、(C3-C22)烯基、羟烷基、羟烯基、(C4-C13)环烷基、芳基或(C7-C12)芳烷基,
Z代表下列基团COO、OCO、NHCO、CONH、NHCOO、OOCNH和NHCONH中的一个或多个基团,以及
a为1~19的数字。
10.如权利要求1~8任一项所述的缩二脲化合物作为流变性控制剂的应用。
11.如权利要求1~8任一项所述的缩二脲化合物作为防流挂剂和/或防沉降剂而赋予涂料体系触变性的应用。
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CN107226788A (zh) * | 2017-05-04 | 2017-10-03 | 明光市飞洲新材料有限公司 | 一种铸造涂料专用防流挂剂生产工艺 |
CN108070066A (zh) * | 2017-12-29 | 2018-05-25 | 陈鹏 | 一种涂料油墨防沉剂及其制备方法 |
CN110494462A (zh) * | 2017-01-30 | 2019-11-22 | 毕克化学有限公司 | 作为流变控制剂和在流变控制剂中的含脲基团和/或含氨基甲酸酯基团的酰胺、它们的制备和它们的用途 |
CN111704692A (zh) * | 2020-07-03 | 2020-09-25 | 怀宁大有医药科技有限公司 | 一种防沉降剂的制备方法及其在水性涂料中的应用 |
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DE102004022753B3 (de) * | 2004-05-07 | 2006-02-16 | Byk-Chemie Gmbh | Als Dispergiermittel und Dispersionsstabilisatoren geeignete Additionsverbindungen |
DE102006012999A1 (de) * | 2006-03-22 | 2007-09-27 | Byk-Chemie Gmbh | Additionsverbindungen als Dispergiermittel und Dispersionsstabilisatoren |
EP2199344B1 (de) * | 2008-12-17 | 2018-03-21 | Ems-Patent Ag | Xylylenbasierte Polyamide und deren Verwendung |
WO2013136892A1 (ja) * | 2012-03-13 | 2013-09-19 | Dic株式会社 | ウレタン樹脂組成物、コーティング剤、物品及び皮革様シート |
EP2931771B1 (de) | 2012-12-15 | 2016-09-07 | BYK-Chemie GmbH | Komposition zur rheologiesteuerung |
TR201808677T4 (tr) * | 2014-04-15 | 2018-07-23 | Byk Chemie Gmbh | Reoloji kontrol ajanı olarak kullanıma uygun, saklama-stabiliteli üre preparatları. |
WO2015158407A1 (de) | 2014-04-15 | 2015-10-22 | Byk-Chemie Gmbh | Komposition zur rheologiesteuerung |
WO2019016356A1 (en) | 2017-07-20 | 2019-01-24 | Solvay Sa | FUNCTIONALIZED PARTICULATE BICARBONATE AS EXPANSION AGENT, FOAMABLE POLYMERIC COMPOSITION CONTAINING THE SAME, AND USE THEREOF IN THE PRODUCTION OF A FOAMED THERMOPLASTIC POLYMER |
EP3431536A1 (en) | 2017-07-20 | 2019-01-23 | Solvay Sa | Functionalized particulate bicarbonate as blowing agent, foamable polymer composition containing it, and its use in manufacturing a thermoplastic foamed polymer |
US11655327B2 (en) | 2018-09-20 | 2023-05-23 | 3M Innovative Properties Company | Polymeric material including a uretdione-containing material and an epoxy component, two-part compositions, and methods |
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CN102725365A (zh) * | 2010-01-28 | 2012-10-10 | 比克化学股份有限公司 | 含有脲组分和酰胺组分的漆料配制剂 |
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CN108070066A (zh) * | 2017-12-29 | 2018-05-25 | 陈鹏 | 一种涂料油墨防沉剂及其制备方法 |
CN111704692A (zh) * | 2020-07-03 | 2020-09-25 | 怀宁大有医药科技有限公司 | 一种防沉降剂的制备方法及其在水性涂料中的应用 |
CN111704692B (zh) * | 2020-07-03 | 2021-11-30 | 永康市莱莉雅水性涂料科技有限公司 | 一种防沉降剂的制备方法及其在水性涂料中的应用 |
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KR20070092176A (ko) | 2007-09-12 |
US7655815B2 (en) | 2010-02-02 |
DE102006010721B4 (de) | 2010-04-15 |
KR101423747B1 (ko) | 2014-08-06 |
US20070225451A1 (en) | 2007-09-27 |
JP5324045B2 (ja) | 2013-10-23 |
CA2581016A1 (en) | 2007-09-08 |
DE102006010721A1 (de) | 2007-09-13 |
TW200740869A (en) | 2007-11-01 |
EP1832573B1 (de) | 2011-12-21 |
TWI385190B (zh) | 2013-02-11 |
ES2377944T3 (es) | 2012-04-03 |
JP2007238943A (ja) | 2007-09-20 |
EP1832573A3 (de) | 2007-12-12 |
EP1832573A2 (de) | 2007-09-12 |
CN101033204B (zh) | 2012-06-06 |
DK1832573T3 (da) | 2012-02-13 |
ATE538087T1 (de) | 2012-01-15 |
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