CN105849114A - 甲硅烷基化的多异氰酸酯 - Google Patents
甲硅烷基化的多异氰酸酯 Download PDFInfo
- Publication number
- CN105849114A CN105849114A CN201480051738.9A CN201480051738A CN105849114A CN 105849114 A CN105849114 A CN 105849114A CN 201480051738 A CN201480051738 A CN 201480051738A CN 105849114 A CN105849114 A CN 105849114A
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- CN
- China
- Prior art keywords
- acid
- polyisocyanates
- group
- alcohol
- diisocyanate
- 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.)
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- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 96
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000000576 coating method Methods 0.000 claims abstract description 21
- 239000011248 coating agent Substances 0.000 claims abstract description 20
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- 238000006243 chemical reaction Methods 0.000 claims description 33
- 125000005442 diisocyanate group Chemical group 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 28
- 239000012948 isocyanate Substances 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 27
- 239000000049 pigment Substances 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 150000002513 isocyanates Chemical class 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 16
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 16
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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Abstract
本发明涉及甲硅烷基化的多异氰酸酯、其制备方法、其用途以及包含其涂料组合物。
Description
本发明涉及甲硅烷基化的多异氰酸酯、其制备方法、其用途以及包含它们的涂料组合物。
含有聚氨酯或基于聚氨酯的有色涂料和透明清漆已经为人所知了几十年。
近来,已发现,含有被烷氧基甲硅烷基基团部分取代的异氰酸酯基团的多异氰酸酯,不仅使所得产物的游离的异氰酸酯基团固化,还通过硅氧烷的形成而赋予所得产物其他的固化机理。对于此类多异氰酸酯结构,通常使用容易市售可得的3-(三烷氧基甲硅烷基)丙胺或其N-烷基化的衍生物——参见例如WO2008/074489。
此反应方法的一个缺点是:所述的异氰酸酯基团与3-(三烷氧基甲硅烷基)丙胺的反应产生脲基团,该脲基团降低了所得产物的溶解性。
期望的是,例如,通过氨基甲酸酯基团连接烷氧基甲硅烷基。然而,要做到这一点,需要使用不仅具有烷氧基甲硅烷基而且具有用于连接至异氰酸酯基团的游离羟基的化合物。但是,这样的情形是相互排斥的,原因在于游离羟基会立即与烷氧基甲硅烷基反应。
本发明的目的是开发一种可将烷氧基甲硅烷基连接至多异氰酸酯且不会使产物表现出含有脲基团的多异氰酸酯的差的溶解性的方法。
所述目的通过一种制备带有甲硅烷基的多异氰酸酯的方法达到,所述方法包括:
-在第一步骤中使至少一种二异氰酸酯或多异氰酸酯(A)与至少一种带有至少一个C=C双键和至少一个羟基的不饱和的醇(B)反应,以及
-随后,使至少一种带有至少一个Si-H键的硅烷化合物(C)通过氢化硅烷化加成至至少一部分C=C双键上,所述C=C双键因此键合至所得的含有氨基甲酸酯基团的多异氰酸酯上。
由于化合物的特殊的两步合成,因此根据本发明获得的甲硅烷基化的多异氰酸酯不包含上述破坏性的脲基团。相比于类似的含有脲基团的多异氰酸酯,所获得的多异氰酸酯表现出在常规溶剂中的更好的溶解性和/或更低的熔点。
二异氰酸酯或多异氰酸酯(A)为具有至少2个游离异氰酸酯基团的化合物。所述化合物可为单体型(monomeric)二异氰酸酯或多异氰酸酯,或可通过至少一种二异氰酸酯的反应获得的多异氰酸酯——优选后者。
用于制备多异氰酸酯的二异氰酸酯和单体型异氰酸酯可为芳族、脂族或脂环族的二异氰酸酯,优选脂族或脂环族的二异氰酸酯,其在本文中简称为(环)脂族的二异氰酸酯;特别优选脂族异氰酸酯。
芳族异氰酸酯为包含至少一个芳环体系的那些,换言之,其不仅为芳族化合物而且为芳脂族化合物。芳族异氰酸酯天然地表现出更大的反应性,其可通过使用催化剂而更进一步的提高。
脂环族异氰酸酯为包含至少一个脂环族环体系的那些。
脂族异氰酸酯为仅包含直链或支链的那些,即,无环化合物。
单体型异氰酸酯优选为仅带有两个异氰酸酯基团的二异氰酸酯。
原则上,平均具有大于2个异氰酸酯基团的更高级的异氰酸酯也是可能的。适合于此的是例如三异氰酸酯,如三异氰酸根合壬烷、2,6-二异氰酸根合己酸2’-异氰酸根合乙酯、2,4,6-三异氰酸根合甲苯、三苯基甲烷三异氰酸酯或2,4,4’-三异氰酸根合二苯基醚;或二异氰酸酯、三异氰酸酯和更高级的多异氰酸酯的混合物,所述更高级的多异氰酸酯例如通过相应的苯胺/甲醛缩合物的光气化作用获得并代表亚甲基-桥连的多苯基多异氰酸酯。
这些单体型异氰酸酯基本上不包含任何异氰酸酯基团与自身的反应产物。
单体型异氰酸酯优选为具有4至20个碳原子的异氰酸酯。典型的二异氰酸酯的实例为:脂族二异氰酸酯,如四亚甲基二异氰酸酯、五亚甲基1,5-二异氰酸酯、六亚甲基二异氰酸酯(1,6-二异氰酸根合己烷)、八亚甲基二异氰酸酯、十亚甲基二异氰酸酯、十二亚甲基二异氰酸酯、十四亚甲基二异氰酸酯、赖氨酸二异氰酸酯的衍生物(例如,2,6-二异氰酸根合己酸甲酯或2,6-二异氰酸根合己酸乙酯)、三甲基己烷二异氰酸酯或四甲基己烷二异氰酸酯;脂环族二异氰酸酯,如1,4-、1,3-或1,2-二异氰酸根合环己烷、4,4’-或2,4’-二(异氰酸根合环己基)甲烷、1-异氰酸根合-3,3,5-三甲基-5-(异氰酸根合甲基)环己烷(异佛尔酮二异氰酸酯)、1,3-或1,4-双(异氰酸根合甲基)环己烷、或2,4-或2,6-二异氰酸根合-1-甲基环己烷,以及3(或4),8(或9)-双(异氰酸根合甲基)三环[5.2.1.02,6]癸烷异构体混合物;以及芳族二异氰酸酯,如甲苯2,4-二异氰酸酯或甲苯2,6-二异氰酸酯及其异构体混合物、间亚二甲苯基二异氰酸酯或对亚二甲苯基二异氰酸酯,2,4’-或4,4’-二异氰酸根合二苯基甲烷及其异构体混合物、亚苯基1,3-二异氰酸酯或亚苯基1,4-二异氰酸酯、1-氯亚苯基2,4-二异氰酸酯、亚萘基1,5-二异氰酸酯、二亚苯基4,4’-二异氰酸酯、4,4’-二异氰酸根合-3,3’-二甲基联苯、3-甲基二苯基甲烷4,4’-二异氰酸酯、四甲基亚二甲苯基二异氰酸酯、1,4-二异氰酸根合苯或二苯醚4,4’-二异氰酸酯。
特别优选六亚甲基1,6-二异氰酸酯、1,3-双(异氰酸根合甲基)环己烷、异佛尔酮二异氰酸酯和4,4’-或2,4’-二(异氰酸根合环己基)甲烷,非常特别优选异佛尔酮二异氰酸酯和六亚甲基1,6-二异氰酸酯,且尤其优选六亚甲基1,6-二异氰酸酯。
还可存在所述异氰酸酯的混合物。
异佛尔酮二异氰酸酯通常为混合物形式,具体为比例通常为约60:40至90:10(w/w)、优选70:30-90:10的顺式异构体和反式异构体的混合物。
二环己基甲烷4,4’-二异氰酸酯同样可为不同的顺式异构体和反式异构体的混合物形式。
对于本发明,不仅可以使用通过使相应的胺光气化而获得的那些二异氰酸酯,而且可以使用不使用光气(即通过无光气方法)制备的那些二异氰酸酯。根据EP-A-0 126 299(US 4 596 678)、EP-A-126 300(US 4 596 679)和EP-A-355 443(US 5 087 739),例如,(环)脂族二异氰酸酯如六亚甲基1,6-二异氰酸酯(HDI)、在亚烷基基团中具有6个碳原子的异构的脂族二异氰酸酯、4,4’-或2,4’-二(异氰酸根合环己基)甲烷以及1-异氰酸根合-3-异氰酸根合甲基-3,5,5-三甲基环己烷(异佛尔酮二异氰酸酯或IPDI)可通过如下方法制备:使(环)脂族二胺与例如脲和醇反应得到(环)脂族二氨基甲酸酯,并使所述酯热裂解成相应的二异氰酸酯和醇。合成通常在循环过程中并且如果需要,在N-未取代的氨基甲酸酯、碳酸二烷基酯以及从反应过程中再循环的其他副产物的存在下连续进行。以此方式获得的二异氰酸酯通常包含非常低的或甚至不可测量的份数的氯化化合物,其例如在电子工业中的应用中是有利的。
在本发明的一个实施方案中,所使用的异氰酸酯的总的可水解的氯的含量小于100ppm、非常优选小于30ppm,特别是小于20ppm,且尤其是小于10ppm。这可通过例如ASTM标准D4663-98测定。总氯量为例如1000ppm以下,优选800ppm以下,且更优选500ppm以下(水解后通过银量滴定法测定)。
应理解,还可以使用通过使(环)脂族二胺与例如脲和醇反应并使所得的(环)脂族二氨基甲酸酯裂解而获得的那些单体型异氰酸酯与通过使相应的胺光气化而获得的那些二异氰酸酯的混合物。
可由单体型异氰酸酯低聚化得到的多异氰酸酯(A)通常具有如下特征:
此类化合物的平均NCO官能度通常为至少1.8且可为最高达8,优选2至5,且更优选2.4至4。
除非另外说明,低聚反应后的异氰酸酯基团——以NCO=42g/mol计——的含量通常为5重量%至25重量%。
多异氰酸酯(A)优选为下列化合物:
1)含有异氰脲酸酯基团且衍生自芳族、脂族和/或脂环族的二异氰酸酯的多异氰酸酯。在本文中特别优选的是相应的脂族和/或脂环族的异氰酸根合异氰脲酸酯,且特别是基于六亚甲基二异氰酸酯和异佛尔酮二异氰酸酯的异氰脲酸酯。所存在的异氰脲酸酯具体为三异氰酸根合烷基异氰脲酸酯和/或三异氰酸根合环烷基异氰脲酸酯——其构成二异氰酸酯的环状三聚体;或为与含有多于一个异氰脲酸酯环的更高级同系物的混合物。所述异氰酸根合异氰脲酸酯通常具有的NCO含量为10重量%至30重量%,特别为15重量%至25重量%,且平均NCO官能度为2.6至8。含有异氰脲酸酯基团的多异氰酸酯还可在较小程度上包含氨基甲酸酯基团和/或脲基甲酸酯基团,优选的结合醇的含量小于2%,基于多异氰酸酯计。
2)含有脲二酮基团且含有以芳族、脂族和/或脂环族方式连接的异氰酸酯基团、优选以脂族和/或脂环族方式连接的异氰酸酯基团的多异氰酸酯,且特别为衍生自六亚甲基二异氰酸酯或异佛尔酮二异氰酸酯的多异氰酸酯。脲二酮二异氰酸酯为二异氰酸酯的环状二聚产物。在本发明的上下文中,含有脲二酮基团的多异氰酸酯作为与其他多异氰酸酯、更特别为1)项下所指定的多异氰酸酯的混合物而得到。含有脲二酮基团的多异氰酸酯通常具有的官能度为2至3。
为此目的,可使二异氰酸酯在不仅形成脲二酮基团而且形成其他多异氰酸酯的反应条件下反应;或首先形成脲二酮基团且随后反应得到其他多异氰酸酯;或二异氰酸酯首先反应得到其他多异氰酸酯,随后反应得到含有脲二酮基团的产物。
3)含有缩二脲基团且含有以芳族、脂环族或脂族方式连接的、优选以脂环族或脂族方式连接的异氰酸酯基团的多异氰酸酯,尤其为三(6-异氰酸根合己基)缩二脲或其与它的更高级同系物的混合物。这些含有缩二脲基团的多异氰酸酯通常具有的NCO含量为18重量%至24重量%且平均NCO官能度为2.8至6。
4)含有氨基甲酸酯和/或脲基甲酸酯基团且含有以芳族、脂族或脂环族方式连接的、优选以脂族或脂环族方式连接的异氰酸酯基团的多异氰酸酯,其可通过例如使过量的二异氰酸酯(如过量的六亚甲基二异氰酸酯或异佛尔酮二异氰酸酯)与一元醇或多元醇(优选烷醇)反应而得到。这些含有氨基甲酸酯和/或脲基甲酸酯基团的多异氰酸酯通常具有的NCO含量为12重量%至24重量%且平均NCO官能度为2.0至4.5。此类含有氨基甲酸酯和/或脲基甲酸酯基团的多异氰酸酯可在无催化剂存在下或优选在催化剂的存在下制备,所述催化剂为例如羧酸铵催化剂或氢氧化铵催化剂或脲基甲酸酯化催化剂,如铋、钴、铯、Zn(II)或Zr(IV)化合物,在每种情况下均在一元醇、二元醇或多元醇、优选一元醇的存在下进行。
这些含有氨基甲酸酯和/或脲基甲酸酯基团的多异氰酸酯通常以与1)项下所指定的多异氰酸酯的混合形式存在。
5)包含噁二嗪三酮基团的多异氰酸酯,优选衍生自六亚甲基二异氰酸酯或异佛尔酮二异氰酸酯。此类包含噁二嗪三酮基团的多异氰酸酯可由二异氰酸酯和二氧化碳得到。
6)包含亚氨基噁二嗪二酮基团的多异氰酸酯,优选衍生自六亚甲基二异氰酸酯或异佛尔酮二异氰酸酯。此类包含亚氨基噁二嗪二酮基团的多异氰酸酯可由二异氰酸酯借助于特定的催化剂制备。
7)脲酮亚胺改性的多异氰酸酯。
8)碳二亚胺改性的多异氰酸酯。
9)超支化的多异氰酸酯,此类多异氰酸酯已知于例如DE-A1 10013186或DE-A1 10013187中。
10)聚氨酯-多异氰酸酯预聚物,来自二异氰酸酯和/或多异氰酸酯与醇。
11)聚脲-多异氰酸酯预聚物。
12)多异氰酸酯1)-11)、优选多异氰酸酯1)、3)、4)和6)可在它们的制备之后被转化为含有缩二脲基团或氨基甲酸酯/脲基甲酸酯基团且具有以芳族、脂环族或脂族方式连接的、优选以(环)脂族方式连接的异氰酸酯基团的多异氰酸酯。缩二脲基团的形成例如通过添加水或通过与胺反应实现。氨基甲酸酯和/或脲基甲酸酯基团的形成通过与一元醇、二元醇或多元醇、优选一元醇如果需要在合适的催化剂的存在下反应实现。这些含有缩二脲或氨基甲酸酯/脲基甲酸酯基团的多异氰酸酯通常具有的NCO含量为10重量%至25重量%且平均NCO官能度为3至8。
13)亲水性改性的多异氰酸酯,即,这样的多异氰酸酯:其除了包含在上述1-12项下描述的基团外还包含形式上通过将含有NCO-反应性基团和亲水性基团的分子加入到以上分子的异氰酸酯基团中而产生的基团。亲水性基团为非离子基团如烷基聚环氧乙烷和/或源自磷酸、膦酸、硫酸或磺酸和/或其盐的离子基团。
14)用于双重固化(dual cure)应用的改性多异氰酸酯,即,这样的多异氰酸酯:其除了包含在上述1-13项下描述的基团外还包含形式上通过将含有NCO-反应性基团和UV-可交联基团或光化辐射可交联基团的分子加入到以上分子的异氰酸酯基团中而产生的基团。这些分子为,例如,(甲基)丙烯酸酯羟烷基酯和其他的羟基乙烯基化合物。
在本发明的一个优选的实施方案中,多异氰酸酯(A)选自异氰脲酸酯、缩二脲、氨基甲酸酯和脲基甲酸酯,优选选自异氰脲酸酯、氨基甲酸酯和脲基甲酸酯;更优选其为含有异氰脲酸酯基团的多异氰酸酯。
在一个特别优选的实施方案中,多异氰酸酯(A)包括含有异氰脲酸酯基团且由1,6-六亚甲基二异氰酸酯获得的多异氰酸酯。
在另一个特别优选的实施方案中,多异氰酸酯(A)包括含有异氰脲酸酯基团且非常优选由异佛尔酮二异氰酸酯和由1,6-六亚甲基二异氰酸酯获得的多异氰酸酯的混合物。
在一个特别优选的实施方案中,多异氰酸酯(A)为包含下列物质的混合物:粘度为200-1500mPa*s、优选400-1300mPa*s的低粘度多异氰酸酯,优选包含异氰脲酸酯基团的多异氰酸酯;粘度为200-1600mPa*s、更特别是600-1500mPa*s的低粘度氨基甲酸酯和/或脲基甲酸酯;和/或包含亚氨基噁二嗪二酮基团的多异氰酸酯。
在本说明书中,除非另有说明,粘度在23℃下根据DIN EN ISO3219/A.3在剪切速率为1000s-1的锥/板(cone/plate)系统中记录。
本发明的甲硅烷基化的多异氰酸酯例如可通过相应的二异氰酸酯或多异氰酸酯的两步反应获得,优选通过相应的二异氰酸酯或多异氰酸酯的两步反应获得。在第一步中,使此化合物与不饱和一元醇(B)、优选烯丙醇反应,在下一步中式(V)的化合物(C)通过过渡态金属催化的、优选铂催化的氢化硅烷化而连接至所述醇的双键,
在该式中,R9-R11彼此独立地为
-烷基基团或
-基团–O–R12,
其中
R12可为烷基或芳基。
用于本说明书的目的的烷基为具有1至20个碳原子的直链烷基或支链烷基,优选C1-C8烷基,即,例如,甲基、乙基、正丙基、异丙基、正丁基、异丁基、2-丁基、叔丁基、1-戊基、2-戊基、异戊基、正己基、正辛基或2-乙基己基。
在本说明书中C1-C4烷基意指甲基、乙基、正丙基、异丙基、正丁基、异丁基、2-丁基或叔丁基。
R9至R11彼此独立地为烷基、式–O–R12的基团、优选式–OR12的基团、更优选其中R12为烷基、非常优选甲基或乙基、且更特别是乙基。
所述铂催化的氢化硅烷化通常以下述方式进行:在无水惰性溶剂的溶液中,在环境温度下,在装备有用于保持惰性气体覆盖层(blanket)(优选氮气覆盖层或氩气覆盖层)的装置的反应容器中,将所使用的二异氰酸酯或多异氰酸酯(A)与不饱和一元醇(B)的反应产物与硅烷(V)混合,所述混合在惰性气体覆盖层下进行。催化剂在搅拌下加入,所述催化剂为例如过渡金属,例如,优选第VIII族的过渡贵金属,更优选镍、镍盐、铱盐且非常优选氯铂酸或Karstedt催化剂(铂-二乙烯基四甲基二硅氧烷)。温度在惰性气体覆盖层下上升至约60℃。该反应可通过NMR光谱中的烯丙基基团的乙烯次甲基质子(-CH=5.9ppm,在CDCl3中)的多重峰的消失来监测。
所使用的二异氰酸酯或多异氰酸酯可包含至少一种不与异氰酸酯基团反应的溶剂,实例为酯、醚、酮或芳族烃,如甲苯或二甲苯异构体混合物。
化合物(B)包含至少一种、优选仅一种不饱和醇(B),其带有至少一个、优选仅一个C=C双键和至少一个、优选仅一个羟基。
本发明的C=C双键是未活化的双键,这意指它们是不直接连接到(即不直接邻近)除了氢原子和sp3-杂化的碳原子之外的任何基团的C=C双键或共轭双键体系。所述sp3-杂化的碳原子可包括,例如,烷基基团、未取代的亚甲基基团、单取代的亚烷基基团(1,1-亚烷基基团)或二取代的亚烷基基团(n,n-亚烷基基团)。
在共轭双键体系的情况下,C=C双键与一个或多个其他C=C双键和/或与芳族体系共轭,所述的键和/或体系优选为一个至三个、更优选一个至两个且非常优选仅一个其他C=C双键和/或优选仅一个碳环芳环体系。本发明的重要之处在于:在此情况下共轭双键体系不直接与除了氢和sp3-杂化的碳原子之外的任何基团连接。芳环体系为碳环体系,杂芳族体系被本发明排除。
C=C双键优选为孤立的双键;带有共轭双键体系的醇(B)是较不优选的。
另一方面,排除那些电子活化的C=C双键,即,例如,乙烯基醚基团、丙烯酸酯基团或甲基丙烯酸酯基团。
在C=C双键和羟基基团之间存在至少一个sp3-杂化的碳原子,优选一个至十个,更优选一个至五个,非常优选一个至3个,更特别是一个至两个,且尤其是一个。
这些类型的化合物(B)的实例为烯丙醇(2-丙烯-1-醇)、甲基烯丙醇(2-甲基-2-丙烯-1-醇)、高烯丙醇(3-丁烯-1-醇)、1-丁烯-3-醇、3-甲基-2-丁烯-1-醇、2-甲基-3-丁烯-2-醇、1-辛烯-3-醇、2-己烯-1-醇、1-戊烯-3-醇且此外还有叶绿醇、法呢醇和沉香醇。
具有多个C=C双键的化合物(B)的实例为1,4-戊二烯-3-醇、1,4-己二烯-3-醇和5-甲基-1,4-己二烯-3-醇。然而,具有多个C=C双键的化合物较不优选。
带有与碳环芳环体系共轭的C=C双键的化合物(B)的一个实例为肉桂醇。然而,带有与芳族化合物共轭的C=C双键的化合物较不优选。
优选烯丙醇、甲基烯丙醇和高烯丙醇,特别优选烯丙醇。
化合物(C)优选为式(V)的化合物:
其中R9-R11具有上面给出的定义。
在此式中,R9至R11彼此独立地优选为
-C1-C4烷基或
-基团–O–R12,
其中
R12为C1-C4烷基或苯基。
更优选R9至R11选自甲基、乙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、叔丁氧基和苯氧基,非常优选选自甲基、乙基、甲氧基和乙氧基。
所使用的硅烷(C)优选为三(烷氧基)硅烷或烷基双(烷氧基)硅烷,更优选三(C1-C4-烷氧基)硅烷或C1-C4-烷基-双(C1-C4-烷氧基)硅烷。
所使用的硅烷(C)非常优选为三乙基硅烷、三异丙基硅烷、二甲基苯基硅烷、二乙氧基甲基硅烷、二甲氧基甲基硅烷、乙氧基二甲基硅烷、苯氧基二甲基硅烷、三乙氧基硅烷、三甲氧基硅烷、双三甲基甲硅烷氧基甲基硅烷,或其混合物。
不饱和醇(B)与二异氰酸酯或多异氰酸酯(A)中的异氰酸酯基团的化学计量通常为1:0.1至0.1:1,优选1:0.2至0.2:1,更优选1:0.3至0.3:1,非常优选1:0.5至0.5:1,且更特别是1:0.66至0.66:1。
式(V)的硅烷(C)与通过与不饱和醇反应获得的二异氰酸酯或多异氰酸酯中的双键的化学计量通常为0.1:1至1.0:1,优选0.5:1至1.0:1,更优选0.6:1至1.0:1,且非常优选0.8:1至1.0:1。
还可想到的是使用带有多于一个(例如至少两个,优选两个至四个,更优选两个或三个,且非常优选两个)Si-H键的化合物(C)。
其实例为下式的硅氧烷-桥连化合物(C1)
或它们的更高级的同系物,其中n=2至5
其中R9和R10可具有上述定义。
其实例为四甲基硅氧烷、四乙基硅氧烷和四苯基硅氧烷。
得到本发明的甲硅烷基化的多异氰酸酯的反应可在第一阶段中优选在40℃和120℃之间、更优选60℃和110℃之间、且非常优选在80℃和100℃之间进行,以及在第二阶段中优选在40℃和80℃之间、更优选在50℃和70℃之间,且非常优选在60℃下进行。
该反应可在本体中进行,但是优选在惰性的无水溶剂中进行。
所使用的二异氰酸酯或多异氰酸酯与不饱和醇的反应可在使用或不使用催化剂以及加入或不加入共沸生成添加物(例如甲苯)的情况下进行。催化剂的实例在下文中列举。不饱和醇以上文说明的比例使用,取决于所需的取代程度。
在本发明的一个优选的实施方案中,选择醇(B)比二异氰酸酯或多异氰酸酯(A)的比例,以使所得的包含氨基甲酸酯基团的多异氰酸酯具有的醇(B)的优选为至少1,更优选1至3,非常优选1至2,且尤其优选1的平均官能度。如果需要,仅带有少量醇基团(B)的产物可通过加入其他的醇(B)而进一步反应。
硅烷(C)至不饱和醇(B)的双键的连接在过渡金属催化下进行。所考虑的过渡金属优选为第八族的过渡金属,更优选铂、铑、钯、钴和镍,其为金属形式或络合物形式。一种优选的催化剂为例如被称作Karstedt催化剂(铂-二乙烯基四甲基二硅氧烷)的催化剂或六氯铂酸水合物,其例如为Speier催化剂形式(即,在异丙醇中的溶液形式),以及活性炭上的铂的形式。
第一阶段中的反应通常通过下列方式进行:引入所使用的不饱和醇,任选与催化剂一起引入;使此初始进料处于所需温度;并缓慢加入二异氰酸酯或多异氰酸酯,任选在溶于合适的溶剂中的溶液中。
与不饱和醇的反应可在存在或不存在至少一种催化剂的的情况下进行。优选的催化剂选自锡、铁、钛、铝、锰、镍、锌、钴、锆和铋的化合物,优选为钛、铝、锌、锆或铋的化合物,更优选为钛、锌或铋的化合物,非常优选为钛或铋的化合物,且更特别是铋化合物。
可能的是例如金属络合物,如铁、钛、铝、锆、锰、镍、锌和钴的乙酰丙酮化物。
用作锆、铋、钛和铝化合物的化合物的实例包括下列物质:四乙酰丙酮锆(例如,购自King Industries的4205);二酮锆(例如,购自King Industries的XC-9213;XC-A 209和XC-6212);以及二酮铝(例如,购自King Industries的5218)。
在此上下文中所考虑的锌化合物为其中使用了下列阴离子的那些:F–、Cl–、ClO–、ClO3 –、ClO4 –、Br–、I–、IO3 –、CN–、OCN–、NO2 –、NO3 –、HCO3 –、CO3 2–、S2–、SH–、HSO3 –、SO3 2–、HSO4 –、SO4 2–、S2O2 2–、S2O4 2–、S2O5 2–、S2O6 2–、S2O7 2–、S2O8 2–、H2PO2 –、H2PO4 –、HPO4 2–、PO4 3–、P2O7 4–、(OCnH2n+1)–、(CnH2n–1O2)–、(CnH2n–3O2)–和(Cn+1H2n–2O4)2–,其中n代表1至20的数值。此处优选的是其中阴离子符合式(CnH2n–1O2)–以及(Cn+1H2n-2O4)2–(其中n为1至20)的羧酸盐。特别优选的盐具有通式(CnH2n–1O2)–的一元羧酸根阴离子,其中n代表1至20的数值。在此上下文中尤其值得注意的是甲酸盐、乙酸盐、丙酸盐、己酸盐、新癸酸盐和2-乙基己酸盐。
在锌催化剂中,优选羧酸锌,更优选具有至少六个碳原子、非常优选至少八个碳原子的那些羧酸盐,更特别是二乙酸锌(II)、二辛酸锌(II)或新癸酸锌(II)。市售催化剂的实例包括购自OMG Borchers GmbH,Langenfeld,Germany的Kat 22。
在钛化合物中,优选四醇化钛Ti(OR)4,更优选具有1至8个碳原子的那些醇ROH,实例为甲醇、乙醇、异丙醇、正丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、正己醇、正庚醇和正辛醇,优选甲醇、乙醇、异丙醇、正丙醇、正丁醇或叔丁醇,更优选异丙醇和正丁醇。
作为催化剂(C),优选使用至少一种铋化合物,例如一种至三种、优选一种或两种、且更优选仅一种+3氧化态的铋的化合物。
在此上下文中所考虑的铋化合物(C)为带有下列阴离子的铋的化合物:F–、Cl–、ClO–、ClO3 –、ClO4 –、Br–、I–、IO3 –、CN–、OCN–、NO2 –、NO3 –、HCO3 –、CO3 2–、S2–、SH–、HSO3 –、SO3 2–、HSO4 –、SO4 2–、S2O2 2–、S2O4 2–、S2O5 2–、S2O6 2–、S2O7 2–、S2O8 2–、H2PO2 –、H2PO4 –、HPO4 2–、PO4 3–、P2O7 4–、(OCxH2x+1)–、(CxH2x–1O2)–、(CxH2x–3O2)–和(Cx+1H2x–2O4)2–,其中x代表1至20的数值。此处优选的是其中阴离子符合式(CxH2x–1O2)–以及(Cx+1H2x–2O4)2–(其中x为1至20)的羧酸盐。特别优选的盐具有通式(CxH2x– 1O2)–的一元羧酸根阴离子,其中x代表1至20、优选1至10的数值。在此上下文中尤其值得注意的是甲酸盐、乙酸盐、丙酸盐、己酸盐、新癸酸盐和2-乙基己酸盐。
在铋催化剂中,优选的是羧酸铋,更优选具有至少六个碳原子的那些羧酸盐,更特别是辛酸铋、乙基己酸铋、新癸酸铋或新戊酸铋;实例为购自King Industries的K-KAT 348、XC-B221;XC-C227、XC 8203和XK-601,购自TIB Chemicals的TIB KAT 716、716LA、716XLA、718、720和789,和购自Shepherd Lausanne的那些,以及例如购自OMGBorchers GmbH,Langenfeld,Germany的Kat 24、315和320。
在此上下文中,还可涉及不同金属的混合物,例如,购自OMGBorchers GmbH,Langenfeld,Germany的Kat 0245。
然而,特别优选的是新癸酸铋、2-乙基己酸铋和2-乙基己酸锌。
可额外通过酸的存在提高催化剂的效果,例如通过pKa为<2.5的酸,如记载于EP 2316867A1中,或pKa在2.8和4.5之间的酸,如记载于WO 04/029121A1中。优选使用pKa不大于4.8、更优选不大于2.5的酸。
所获得的反应产物可通过柱色谱法在硅胶上(Silicagel Si 60,40-63μm,Merck)用比例为1:2的乙酸乙酯和戊烷的洗脱剂混合物纯化。然而,通常,粗产物中的杂质水平是最小的,因此可用于随后的合成中而无需进一步的纯化。
第二反应阶段通常通过如下方式进行:优选在惰性气氛下,将第一反应阶段的初级产物与相应的硅烷一起引入到无水的惰性溶剂中,并加入——在剧烈搅拌下——过渡金属催化剂在相同溶剂中的溶液。反应混合物在前述温度下搅拌30分钟至24小时,优选1至20小时,且随后,任选地,在减压下除去溶剂。产物无需进行后处理且因此优选不进行后处理。
所获得的甲硅烷基化的多异氰酸酯在23℃下的根据ISO 3219/B的粘度优选在100和20 000mPas之间,更优选在500和10 000mPas之间。
在此情况下剪切速率应优选为250s-1。
所获得的甲硅烷基化的多异氰酸酯的数均摩尔重量Mn通常为小于3500g/mol,优选小于3000g/mol,且更优选小于2500(通过凝胶渗透色谱法使用四氢呋喃和聚苯乙烯作为标准品测定,DIN 55672,第1部分)。
根据本发明获得的甲硅烷基化的多异氰酸酯随后可与常规溶剂混合。
所述溶剂的实例为芳族烃和/或(环)脂族烃及其混合物、卤代烃、酯、醚和醇。
优选芳族烃、(环)脂族烃、链烷酸烷基酯、烷氧基化的链烷酸烷基酯,及其混合物。
特别优选单烷基化的或多烷基化的苯和萘、链烷酸烷基酯和烷氧基化的链烷酸烷基酯,及其混合物。
优选的芳族烃混合物为主要包含芳族C7至C14烃且沸程为110℃至300℃的那些;特别优选甲苯、邻二甲苯、间二甲苯或对二甲苯、三甲基苯异构体、四甲基苯异构体、乙基苯、异丙基苯、四氢化萘,以及包含它们的混合物。
其实例为购自ExxonMobil Chemical的系列,尤其是100(CAS号64742-95-6,主要为C9和C10芳族化合物,沸程为约154℃至178℃),150(沸程为约182℃至207℃)和200(CAS号64742-94-5),以及购自Shell的系列。链烷烃、环烷烃和芳族化合物的烃混合物还可以下列名称购得:名为Kristalloel的那些(例如,Kristalloel 30,沸程为约158℃至198℃或Kristalloel 60:CAS号64742-82-1),石油溶剂油(例如同样的CAS登记号64742-82-1)或溶剂石脑油(轻质:沸程为约155℃至180℃,重质:沸程为约225℃至300℃)。此类烃混合物的芳族化合物的含量通常大于90重量%,优选大于95重量%,更优选大于98重量%,且非常优选大于99重量%。使用具有特别降低的萘含量的烃混合物是合理的。
根据DIN 51757,在20℃下,烃的密度可为小于1g/cm3,优选小于0.95且更优选小于0.9g/cm3。
脂族烃的含量通常小于5重量%,优选小于2.5重量%,且更优选小于1重量%。
卤代烃为例如氯苯和二氯苯或其异构体混合物。
酯为例如乙酸正丁酯、乙酸乙酯、乙酸1-甲氧基丙-2-基酯和乙酸2-甲氧基乙酯,以及乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇或三丙二醇的单乙酰基酯和二乙酰基酯,例如,乙酸丁二醇酯(butylglycolacetate)。其他的实例还有碳酸酯,例如优选碳酸1,2-亚乙基酯、碳酸1,2-亚丙基酯或碳酸1,3-亚丙基酯。
醚为例如四氢呋喃(THF)、二噁烷以及乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇或三丙二醇的二甲基醚、二乙基醚或二正丁基醚。
(环)脂族烃为例如萘烷、烷基化的萘烷以及直链或支链烷烃和/或环烷烃的异构体混合物。
进一步优选的是乙酸正丁酯、乙酸乙酯、乙酸1-甲氧基丙-2-基酯、乙酸2-甲氧基乙酯,及其混合物,尤其是与上述芳族烃的混合物。
此类混合物可以以10:1至1:10、优选5:1至1:5且更优选1:1的体积比制备。
优选的实例为乙酸丁酯/二甲苯、1:1乙酸甲氧基丙酯/二甲苯、1:1乙酸丁酯/溶剂石脑油100、1:2乙酸丁酯/100和3:1Kristalloel30/A。
醇为例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、异丁醇、戊醇异构体混合物、己醇异构体混合物、2-乙基己醇或辛醇。
本发明的甲硅烷基化的多异氰酸酯的优点在于,在涂料材料中,它们展示出可与那些未甲硅烷基化的多异氰酸酯相比的或甚至改善的硬度和光泽度性质。此外,通过存在的甲硅烷基基团,它们具有其他的交联机理。
固化通常通过以下方式实现:在用包含本发明的多异氰酸酯——其任选地与其他常规涂料添加剂和热固化树脂混合——的涂料组合物或制剂涂覆基底,之后干燥涂层,如果需要,在80℃以下的温度下、优选在室温至60℃的温度下且更优选在室温至40℃的温度下干燥,干燥时间最长达72小时,优选最长达48小时,更优选最长达24小时,非常优选最长达12小时,且特别地最长达6小时;在含氧气氛下(优选空气)或在惰性气体下,在80℃和270℃之间、优选在100℃和240℃之间且更优选在120℃和180℃之间的温度下,对其进行热处理(固化)。根据所施用的涂料的量和所引入的交联能量的量,涂层的固化通过高能辐射、来自加热表面的热传递进行或通过气体介质的对流进行,历时几秒(例如在卷材涂布与NIR干燥结合的情况下)至最长达5小时(例如基于温度敏感材料的厚层体系(high-build system)),通常不小于10分钟,优选不小于15分钟,更优选不小于30分钟,且非常优选不小于45分钟。干燥基本上包括除去存在的溶剂,且此外在此步骤中甚至还存在与粘合剂的反应,而固化基本上包括与粘合剂的反应。
代替热固化或除了热固化之外,固化还可通过IR和NIR辐射进行,其中本文中NIR辐射指的是波长范围为760nm至2.5μm、优选900至1500nm的电磁辐射。
固化在1秒至60分钟、优选1分钟至45分钟的时间内进行。
本发明还提供包含至少一种本发明的甲硅烷基化的多异氰酸酯的涂料组合物。
作为粘合剂,此类涂料组合物包含至少一种含有对异氰酸酯呈反应性的基团的粘合剂。这些粘合剂通常选自含羟基的粘合剂和含氨基的粘合剂。
含羟基的粘合剂优选包括聚醚醇、聚酯醇、聚丙烯酸酯多元醇、聚碳酸酯多元醇、醇酸树脂或环氧树脂。特别优选的是聚酯醇和聚丙烯酸酯多元醇,非常特别优选的是聚丙烯酸酯多元醇。
粘合剂平均每分子具有至少两个、优选两个至十个、更优选三个至十个、且非常优选三个至八个羟基基团。
根据DIN 53240-2测定的羟值通常为10至200mg KOH/g,优选为30至140mg KOH/g。
此外,根据DIN EN ISO 3682,粘合剂还可具有的酸值为0至200mgKOH/g,优选0至100mg KOH/g,且更优选0至10mg KOH/g。
聚丙烯酸酯多元醇为例如(甲基)丙烯酸酯与至少一种具有至少一个、优选仅一个羟基和至少一个、优选仅一个(甲基)丙烯酸酯基团的化合物的共聚物。
至少一种具有至少一个、优选仅一个羟基和至少一个、优选仅一个(甲基)丙烯酸酯基团的化合物可为,例如,α,β-不饱和羧酸与二元醇或多元醇的单酯,所述α,β-不饱和羧酸为例如丙烯酸、甲基丙烯酸(在此文中简称为“(甲基)丙烯酸”),所述二元醇或多元醇优选具有2至20个碳原子和至少两个羟基基团,例如为乙二醇;二乙二醇;三乙二醇;1,2-丙二醇;1,3-丙二醇;1,1-二甲基-1,2-乙二醇;二丙二醇;三乙二醇;四乙二醇;五乙二醇;三丙二醇;1,4-丁二醇;1,5-戊二醇;新戊二醇;羟基新戊酸新戊二醇酯;2-乙基-1,3-丙二醇;2-甲基-1,3-丙二醇;2-丁基-2-乙基-1,3-丙二醇;1,6-己二醇;2-甲基-1,5-戊二醇;2-乙基-1,4-丁二醇;2-乙基-1,3-己二醇;2,4-二乙基-1,3-辛二醇;2,2-双(4-羟基环己基)丙烷;1,1-、1,2-、1,3-和1,4-双(羟甲基)环己烷;1,2-、1,3-或1,4-环己二醇;丙三醇;三羟甲基乙烷;三羟甲基丙烷;三羟甲基丁烷;季戊四醇;双三羟甲基丙烷;二季戊四醇;山梨糖醇;甘露醇;二甘油;苏糖醇;赤藓醇;阿东糖醇(核糖醇);阿拉伯糖醇(arabitol(lyxitol));木糖醇;卫矛醇(半乳糖醇);麦芽糖醇;异麦芽酮糖醇(isomalt);摩尔重量在162和2000之间的聚THF;摩尔重量在134和2000之间的聚-1,3-丙二醇或聚丙二醇;或摩尔重量在238和2000之间的聚乙二醇。
优选丙烯酸2-羟基乙酯、甲基丙烯酸2-羟基乙酯、丙烯酸2-羟基丙酯或丙烯酸3-羟基丙酯、单丙烯酸1,4-丁二醇酯或丙烯酸3-(丙烯酰氧基)-2-羟基丙基酯,且特别优选丙烯酸2-羟基乙酯和/或甲基丙烯酸2-羟基乙酯。
带羟基的单体在共聚反应中以与其他可聚合的、优选可自由基聚合的单体的混合物形式使用,所述可聚合的单体优选为包含大于50重量%的下列物质的那些:(甲基)丙烯酸C1-C20烷基酯、具有最高达20个碳原子的乙烯基芳族化合物、包含最高达20个碳原子的羧酸的乙烯基酯、乙烯基卤化物、具有4至8个碳原子和1或2个双键的非芳族烃、不饱和的腈及其混合物。特别优选包含大于60重量%的(甲基)丙烯酸C1-C10烷基酯、苯乙烯或其混合物的聚合物。
聚合物还可包含与上述羟基含量一致的羟基官能单体,以及——如果需要——其他单体,实例为烯键式不饱和酸,尤其是羧酸、酸酐或酸酰胺。
其他的粘合剂为聚酯醇,例如可通过使多羧酸、尤其是二羧酸与多元醇、尤其是二元醇缩合而获得。
聚酯多元醇可从例如Ullmannsder technischenChemie,第4版,卷19,第62至65页获知。优选使用通过使二元醇与二元羧酸反应获得的聚酯多元醇。为替代游离的多羧酸,还可以使用相应的多羧酸酐或相应的多羧酸低级醇酯或其混合物,以制备聚酯多元醇。多羧酸可为脂族的、脂环族的、芳脂族的、芳族的或杂环的且可任选被例如卤素原子取代,和/或为未饱和的。可提及的实例包括:
草酸、马来酸、富马酸、丁二酸、戊二酸、己二酸、癸二酸、十二烷二酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、壬二酸、1,4-环己烷二羧酸或四氢苯二甲酸、辛二酸、壬二酸、邻苯二甲酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、四氯邻苯二甲酸酐、内亚甲基四氢邻苯二甲酸酐、戊二酸酐、马来酸酐、二聚脂肪酸、其异构体、其氢化产物及其酯化衍生物,例如酸酐或二烷基酯,如C1-C4烷基酯,优选所述酸的甲酯、乙酯或正丁酯。优选通式HOOC-(CH2)y-COOH的二元羧酸,其中y为1至20的数值,优选2至20的偶数;特别优选丁二酸、己二酸、癸二酸和十二烷二羧酸。
用于制备聚酯醇的合适的多元醇包括1,2-丙二醇;乙二醇;2,2-二甲基-1,2-乙二醇;1,3-丙二醇;1,2-丁二醇;1,3-丁二醇;1,4-丁二醇;3-甲基-1,5-戊二醇;2-乙基-1,3-己二醇;2,4-二乙基-1,3-辛二醇;1,6-己二醇;摩尔质量在162和2000之间的聚THF;摩尔质量在134和1178之间的聚-1,3-丙二醇;摩尔质量在134和898之间的聚-1,2-丙二醇;摩尔质量在106和458之间的聚乙二醇;新戊二醇;羟基新戊酸新戊二醇酯;2-乙基-1,3-丙二醇;2-甲基-1,3-丙二醇;2,2-双(4-羟基环己基)丙烷;1,1-、1,2-、1,3-和1,4-环己烷二甲醇;1,2-、1,3-或1,4-环己二醇;三羟甲基丁烷;三羟甲基丙烷;三羟甲基乙烷;新戊二醇;季戊四醇;丙三醇;双三羟甲基丙烷;二季戊四醇;山梨糖醇;甘露醇;二甘油;苏糖醇;赤藓醇;阿东糖醇(核糖醇);阿拉伯糖醇(arabitol(lyxitol));木糖醇;卫矛醇(半乳糖醇);麦芽糖醇或异麦芽酮糖醇(isomalt),其可任选地被烷氧基化,如上所述。
优选通式HO-(CH2)x-OH的醇,其中x为1至20的数值,优选2至20的偶数。优选乙二醇、1,4-丁二醇、1,6-己二醇、1,8-辛二醇和1,12-十二烷二醇。进一步优选新戊二醇。
还合适的是聚碳酸酯二醇,例如可通过例如使光气与过量的所述作为聚酯多元醇的合成组分的低分子量醇反应获得。
还合适的是基于内酯的聚酯二醇,其为内酯的均聚物或共聚物,优选内酯与合适的二官能起始物分子的羟基端基加成产物。合适的内酯优选为衍生自通式HO-(CH2)z-COOH的化合物的那些,其中z为1至20的数值且亚甲基单元的一个氢原子还可被C1至C4烷基基团取代。实例为ε-己内酯、β-丙内酯、γ-丁内酯和/或甲基-ε-己内酯、4-羟基苯甲酸、6-羟基-2-萘甲酸或新戊内酯,及其混合物。合适的起始组分为例如上面描述的作为聚酯多元醇的合成组分的低分子量二元醇。相应的ε-己内酯的聚合物是特别优选的。低级聚酯二醇或聚醚二醇也可用作制备内酯聚合物的起始物。为了代替内酯的聚合物,还可以使用相应的、化学当量的、与内酯对应的羟基羧酸的缩聚物。
其他合适的聚合物为聚醚醇,其通过环氧乙烷、环氧丙烷或环氧丁烷与H-活性组分的加成反应来制备。丁二醇的缩聚物也是合适的。
当然,聚合物还可为具有伯胺基基团或仲胺基基团的化合物。
还合适的是聚碳酸酯多元醇,例如可通过例如使光气与过量的作为聚酯多元醇的合成组分的低分子量醇反应获得。
醇酸树脂为由多元醇、多元羧酸和脂肪油,或天然的和/或合成的游离脂肪酸制备的缩聚树脂;至少一种多元醇必须具有3以上的官能度。
作为多元醇和多元羧酸,可以使用例如上面描述的与聚酯醇有关的组分。
优选的多元醇为丙三醇;季戊四醇;三羟甲基乙烷;三羟甲基丙烷;多种二醇,如乙二醇/丙二醇、二乙二醇、新戊二醇。
优选的多元羧酸为邻苯二甲酸(酐)(PAA)、间苯二甲酸、对苯二甲酸、偏苯三酸酐、己二酸、壬二酸、癸二酸。
合适的油组分和/或脂肪酸的实例包括干性油,如亚麻籽油、奥蒂树油或桐油;半干性油,如大豆油、葵花籽油、红花油、ricinene油或妥尔油;非干性油,如蓖麻油、椰子油或花生油;或上述油的游离脂肪酸,或合成的一元羧酸。
典型的醇酸树脂的摩尔质量在1500和20 000之间,优选在3500和6000之间。酸值优选为2至30mg KOH/g,或在水溶性树脂的情况下为35至65mg KOH/g。OH值通常为最高达300mg KOH/g,优选最高达100mg KOH/g。
此类聚丙烯酸酯多元醇、聚酯醇和/或聚醚醇具有的分子量Mn优选为至少1000g/mol,更优选至少2000g/mol,且非常优选至少5000g/mol。分子量Mn可为例如最高达200 000g/mol,优选最高达100 000g/mol,更优选最高达80 000g/mol,且非常优选最高达50 000g/mol。
此外,本发明的多异氰酸酯还可以与不可交联的粘合剂——即,不含有对异氰酸酯具有反应性的基团的那些——一起使用。在此情况下,本发明的多异氰酸酯通过其硅烷基团的彼此缩合而交联。
交联通常通过加入酸来加速。
用于本文的目的的弱酸为pKa介于1.6和5.2之间、优选介于1.6和3.8之间的一元或多元的、有机或无机的、优选有机的酸。
其实例为碳酸、磷酸、甲酸、乙酸和马来酸、乙醛酸、溴乙酸、氯乙酸、巯基乙酸、甘氨酸、氰基乙酸、丙烯酸、丙二酸、羟基丙二酸、丙酸、乳酸、3-羟基丙酸、甘油酸、丙氨酸、肌氨酸、富马酸、乙酰乙酸、琥珀酸、异丁酸、戊酸、抗坏血酸、柠檬酸、次氮基三乙酸、环戊烷羧酸、3-甲基戊二酸、己二酸、己酸、苯甲酸、环己烷羧酸、庚二酸、庚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、甲苯甲酸(tolylic acid)、苯乙酸、苯氧基乙酸、苦杏仁酸或癸二酸。
优选有机酸,优选一元或多元的羧酸。特别优选甲酸、乙酸、马来酸或富马酸。
用于本文的目的的强酸为pKa小于1.6且更优选小于1的一元或多元的、有机或无机的、优选有机的酸。
其实例为硫酸、焦磷酸、亚硫酸和四氟硼酸、三氯乙酸、二氯乙酸、草酸和硝基乙酸。优选有机酸,优选有机磺酸。特别优选甲磺酸、对甲苯磺酸、苯磺酸、十二烷基苯磺酸、环十二烷磺酸和樟脑磺酸。
酸的用量通常为最高达10重量%,优选0.1重量%至8重量%,更优选0.3重量%至6重量%,非常优选0.5重量%至5重量%,且特别是1重量%至3重量%,基于所使用的聚氨酯计。
所述酸还可作为游离酸或以封端(blocked)的形式使用。
所使用的其他典型的涂料添加剂的实例可为抗氧化剂、稳定剂、活化剂(促进剂)、填料、颜料、染料、抗静电剂、阻燃剂、增稠剂、触变剂、表面活性剂、粘度改进剂、增塑剂或螯合剂。
除了自由基(共)聚合的(共)聚合物之外,合适的增稠剂还包括常规的有机增稠剂和无机增稠剂,如羟甲基纤维素或膨润土。
可使用的螯合剂包括例如乙二胺乙酸及其盐,以及β-二酮。
合适的填料包括硅酸盐,实例为可通过四氯化硅水解获得的硅酸盐,如购自Evonik的硅质土;滑石;硅酸铝;硅酸镁;碳酸钙等。
合适的稳定剂包括典型的UV吸收剂,如草酰替苯胺、三嗪和苯并三唑(苯并三唑可作为系列从BASF SE,Ludwigshafen购得),以及二苯甲酮。它们可单独使用或与合适的自由基清除剂一起使用,实例为空间位阻胺,如2,2,6,6-四甲基哌啶、2,6-二叔丁基哌啶或其衍生物,例如,双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯。稳定剂通常以0.1重量%至5.0重量%的量使用,基于包含在制剂中的固体组分计。
还可包含颜料。根据CDChemie Lexikon–Version 1.0,Stuttgart/New York:Georg Thieme Verlag 1995,参考DIN 55943,颜料为颗粒状的“有机或无机的、有色或无色的着色剂,其基本上不溶于应用介质”。
此处基本上不溶意指在25℃下的溶解度在1g/1000g应用介质以下,优选在0.5g/1000g应用介质以下,更优选在0.25g/1000g应用介质以下,非常优选在0.1g/1000g应用介质以下,且特别是在0.05g/1000g应用介质以下。
颜料的实例包括任何期望的吸收颜料和/或效果颜料体系,优选吸收颜料。对于颜料组分的数目和选择皆不存在限制。它们可按照需要根据特殊要求调节,例如所需的色彩效果(color impression)。
效果颜料意指呈现片状结构并赋予表面涂层特定装饰色彩效果的所有颜料。效果颜料包括例如通常可用于车辆涂装和工业涂料的所有的赋予效果的颜料。此类效果颜料的实例为纯金属颜料,例如铝、铁或铜颜料;干涉颜料,如二氧化钛涂布的云母、氧化铁涂布的云母、混合氧化物涂布的云母(例如,用二氧化钛和Fe2O3或二氧化钛和Cr2O3)、金属氧化物涂布的铝或液晶颜料。
赋予颜色的吸收颜料为例如可用于涂料工业中的常规有机或无机吸收颜料。有机吸收颜料的实例为偶氮颜料、酞菁颜料、喹吖啶酮颜料和吡咯并吡咯颜料。无机吸收颜料的实例为氧化铁颜料、二氧化钛和炭黑。
因此,本发明的涂料组合物组成如下:
-至少一种本发明的甲硅烷基化的多异氰酸酯,
-任选地至少一种能够催化异氰酸酯基团与对异氰酸酯具有反应性的基团的反应的催化剂,
-至少一种含有对异氰酸酯具有反应性的基团的粘合剂,
-任选地至少一种常规的涂料添加剂,
-任选地至少一种溶剂,以及
-任选地至少一种颜料。
按照技术人员已知的常规技术用本发明的涂料组合物涂布基板,所述常规技术包括将至少一种本发明的涂料组合物或制剂以期望的厚度施用于目标基板,并且——如果需要——通过加热(干燥)除去涂料组合物中的挥发性组分。如果需要,可重复此操作一次或多次。施用于基板可以已知方式进行,例如通过喷涂、抹涂、刮涂、刷涂、旋涂(rolling)、辊涂(roller-coating)或浇注进行。涂层的厚度范围通常为约3至约1000g/m2且优选10至200g/m2。
然后可按照上面的描述进行固化。
用于本发明的涂料组合物的合适的基板的实例包括热塑性聚合物,特别是聚甲基丙烯酸甲酯、聚甲基丙烯酸丁酯、聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚偏二氟乙烯、聚氯乙烯、聚酯、聚烯烃、丙烯腈-乙烯-丙烯-二烯-苯乙烯共聚物(A-EPDM)、聚醚酰亚胺、聚醚酮、聚苯硫醚、聚苯醚或其混合物。
还可提及的是聚乙烯、聚丙烯、聚苯乙烯、聚丁二烯、聚酯、聚酰胺、聚醚、聚碳酸酯、聚乙烯醇缩醛(polyvinylacetal)、聚丙烯腈、聚缩醛、聚乙烯醇、聚乙酸乙烯酯、酚醛树脂、脲树脂、三聚氰胺树脂、醇酸树脂、环氧树脂或聚氨酯,其嵌段共聚物或接枝共聚物及其共混物。
可优选提及的是ABS、AES、AMMA、ASA、EP、EPS、EVA、EVAL、HDPE、LDPE、MABS、MBS、MF、PA、PA6、PA66、PAN、PB、PBT、PBTP、PC、PE、PEC、PEEK、PEI、PEK、PEP、PES、PET、PETP、PF、PI、PIB、PMMA、POM、PP、PPS、PS、PSU、PUR、PVAC、PVAL、PVC、PVDC、PVP、SAN、SB、SMS、UF、UP塑料(根据DIN 7728的缩写名)和脂族聚酮。
特别优选的基板为聚烯烃,如PP(聚丙烯),其任选可为等规立构的、间规立构或无规立构的且任选可为未定向的或可通过单轴拉伸或双轴拉伸定向;SAN(苯乙烯-丙烯腈共聚物);PC(聚碳酸酯);PVC(聚氯乙烯);PMMA(聚甲基丙烯酸甲酯);PBT(聚(对苯二甲酸丁二醇酯));PA(聚酰胺);ASA(丙烯腈-苯乙烯-丙烯酸酯共聚物)和ABS(丙烯腈-丁二烯-苯乙烯共聚物),以及它们的物理混合物(共混物)。特别优选PP、SAN、ABS、ASA以及ABS或ASA与PA或PBT或PC的共混物。非常特别优选聚烯烃、PMMA和PVC。
特别是根据DE 196 51 350,尤其优选ASA以及ASA/PC共混物。同样优选聚甲基丙烯酸甲酯(PMMA)或冲击改性的PMMA。
用于使用本发明的涂料组合物涂布的其他优选的基板为金属,其如果需要可用底漆预处理。
关于金属的类型,合适的金属原则上可为任何所需的金属。然而,特别地,它们为常规用作需要防腐蚀保护的建筑的金属材料的金属或合金。
所述表面特别是铁、钢、Zn、Zn合金、Al或Al合金的那些。其为全部由所述金属或合金组成的元件的表面。或者,元件可仅用这些金属涂布,而它们自身可由其他类型的材料组成,如其他金属、合金、聚合物或复合材料。它们可为由镀锌铁或钢制成的铸造物的表面。在本发明的一个优选的实施方案中,表面为钢表面。
Zn合金或Al合金对技术人员来说是已知的。技术人员根据所需的最终用途应用选择合金组分的性质和量。锌合金的典型组分具体包括Al、Pb、Si、Mg、Sn、Cu或Cd。铝合金的典型组分具体包括Mg、Mn、Si、Zn、Cr、Zr、Cu或Ti。合金还可为Al/Zn合金,其中Al和Zn以大约相等的量存在。用这类合金涂布的钢是市售可得的。钢可包括技术人员已知的常规合金组分。
还可想到的是本发明的涂料组合物用于处理镀锡铁/钢(马口铁)的用途。
本发明的涂料组合物和制剂还适用于涂布以下基板:例如木材、纸、织物、皮革、无纺布、塑料表面、玻璃、陶瓷、矿物建筑材料如水泥模制品和纤维水泥板、或经涂布或未经涂布的金属,优选塑料或金属,特别是片材形式的塑料或金属,更优选金属。
本发明的多异氰酸酯、涂料组合物或涂料制剂适合用作或用于:外部涂料,即,其中它们会曝露于日光中的应用,优选建筑物的部件;内部涂料以及车辆和航空器上的涂料。特别地,本发明的多异氰酸酯和涂料组合物被用作或用于汽车清漆和面漆材料。其他优选的应用是用于罐涂料和卷材涂料。
它们特别适合在工业、木材、汽车尤其是OEM、涂料或装饰涂料领域中用作底漆、面漆(surfacer)、着色面漆材料和清漆材料。涂料组合物特别适合用于这样的应用:其中需要特别高的应用可靠性、外部耐候性、光学性质、耐溶剂性和/或耐化学性。
下面的实施例意图说明本发明的性质,但是不限制本发明。
实施例
除非另有说明,本文中的份数为重量份数。
HI 100:HDI异氰脲酸酯,购自BASF SE,Ludwigshafen,Germany,并且NCO含量为22.2%且在23℃下的粘度为2800mPa*s。
IPDI三聚物
发明实施例1
将5g的T 1890E(市售可得的包含异氰脲酸酯基团且基于异佛尔酮二异氰酸酯的多异氰酸酯,购自Evonik)在减压下除去溶剂。在80℃下,在25ml的甲苯中,使剩余的无色固体与3ml的购自Aldrich的烯丙醇反应48小时,得到平均具有2个烯丙基基团的产物2a。将此产物溶解在5ml的无水甲苯中。将溶液加热至65℃并加入2.64ml的购自ABCR的HSi(OEt)3。在剧烈搅拌下,加入100μl的购自ABCR Gelest的Pt-二乙烯基四甲基二硅氧烷(2.1%Pt)的二甲苯溶液。在2小时后,在50℃下在减压下蒸馏掉溶剂。得到6.1g无色树脂2。
比较实施例1
在室温下,在25ml的干燥二氯甲烷中,使5g的购自Evonik的T 1890E与2.2ml的购自Aldrich的3-(三乙氧基甲硅烷基)丙胺反应30分钟,得到平均具有2个脲基团的无色固体形式的产物1。
熔点测定如下:
来自比较实施例1的化合物1:约110-120℃
来自发明实施例1的化合物2:约65-70℃
还测定了在乙酸正丁酯中的溶解度。
将来自比较实施例1的0.5g化合物1与0.2ml乙酸丁酯混合。获得玻璃状固体。
将来自发明实施例1的0.5g化合物2与0.2ml乙酸丁酯混合。获得高粘度溶液。
可以看出,作为本发明改进的结果,来自发明实施例1的带有氨基甲酸酯基团的化合物2具有相比于来自比较实施例1的带有脲基团的类似化合物1更低的熔点和更高的溶解度。
发明实施例2
在80℃下,在50ml甲苯中,使10g的购自BASF SE的HI100与1.2ml的购自Aldrich的烯丙醇反应24小时,得到平均具有1个烯丙基基团的中间体。将2g此中间体溶解于5ml无水THF中。将溶液加热至65℃并加入0.65ml的购自ABCR的HSi(OEt)3。在剧烈搅拌下,加入50μl的购自ABCR Gelest的Pt-二乙烯基四甲基二硅氧烷(2.1%Pt)的二甲苯溶液。在6小时之后,在50℃下在减压下蒸馏掉溶剂。得到2.5g无色油状物。
测定中间体和终产物的表面张力:
中间体:45.96±2.44mN/m
终产物:29.49±0.95mN/m
可以看出,通过连接烷氧基-硅烷降低了表面张力。
比较实施例2
在室温下,在50ml干燥二氯甲烷中,使5g的购自BASF SE的Basonat HI 100与2.3ml的购自Aldrich的3-(三乙氧基甲硅烷基)丙胺反应30分钟,得到平均具有1个脲基团的无色固体形式的产物。
可以看出,所述来自比较实施例2的带有脲基团的产物为固体,而来自发明实施例2的带有氨基甲酸酯基团的终产物代表无色油状物。
产物通过1H-NMR和IR光谱表征。
发明实施例3-4:
产物VF 55和VF 54通过与上述方法类似的方法制备,对于VF 51和VF 55而言,使用2当量的烯丙醇和三乙氧基硅烷,并且对于VF 50和VF 54而言,使用3当量的烯丙醇和三乙氧基硅烷。
产物VF 55和VF 54为高粘度油。
测定表面张力:
VF 51:~44mN/m
VF 55:30.23mN/m
可以看出,通过连接烷氧基-硅烷降低了表面张力。
产物通过1H-NMR和IR光谱表征。
发明实施例5-6:
发明实施例5
将1g的单烯丙基化的HDI三聚物(VF 40;参见图1的1H-NMR和图2的IR光谱)溶解于5ml干燥THF中,加入0.25ml的购自Aldrich的三甲氧基硅烷,将溶液加热至65℃,并且在剧烈搅拌下,加入12μl的购自ABCR Gelest的Pt-二乙烯基四甲基二硅氧烷(2.1%Pt)的二甲苯溶液。反应过程通过1H-NMR光谱监测。在2小时的反应时间后,在40℃下在减压下蒸馏掉溶剂。得到无色油状形式的产物VF 48。
发明实施例6
将2g的单烯丙基化的HDI三聚物溶解于5ml的干燥THF中,加入1.1ml的购自ABCR的HSiMe(OSiMe3)2,将溶液加热至65℃,并且在剧烈搅拌下,加入10μl的购自ABCR Gelest的Pt-二乙烯基四甲基二硅氧烷(2.1%Pt)的二甲苯溶液。反应过程通过1H-NMR光谱监测。在2小时和5小时的反应时间后,加入其他部分——各25μl——的催化剂溶液。在完成反应之后,在50℃下在减压下蒸馏掉溶剂。得到无色油状形式的产物VF 47。
产物通过1H-NMR和IR光谱表征:对于VF 41的1H-NMR,参见图3,以及对于VF 41的IR光谱,参见图4。
Claims (15)
1.一种制备带有甲硅烷基基团的多异氰酸酯的方法,其包括
-在第一步骤中使至少一种二异氰酸酯或多异氰酸酯(A)与至少一种带有至少一个C=C双键和至少一个羟基的不饱和醇(B)反应,以及
-随后,使至少一种带有至少一个Si-H键的硅烷化合物(C)通过氢化硅烷化加成至至少一部分C=C双键上,所述C=C双键因此键合至所得的含有氨基甲酸酯基团的多异氰酸酯上。
2.根据权利要求1所述的方法,其中二异氰酸酯或多异氰酸酯(A)包括脂族或脂环族二异氰酸酯或可通过至少一种脂族或脂环族二异氰酸酯的反应获得的多异氰酸酯。
3.根据权利要求2所述的方法,其中二异氰酸酯选自六亚甲基1,6-二异氰酸酯、1,3-双(异氰酸根合甲基)环己烷、异佛尔酮二异氰酸酯和4,4’-或2,4’-二(异氰酸根合环己基)甲烷。
4.根据前述权利要求中任一项所述的方法,其中化合物(A)为具有异氰脲酸酯基团、缩二脲基团、氨基甲酸酯基团和/或脲基甲酸酯基团的多异氰酸酯。
5.根据前述权利要求中任一项所述的方法,其中化合物(A)选自包含异氰脲酸酯基团并衍生自六亚甲基1,6-二异氰酸酯的多异氰酸酯;和包含异氰脲酸酯基团并衍生自异佛尔酮二异氰酸酯的多异氰酸酯。
6.根据前述权利要求中任一项所述的方法,其中化合物(C)具有式(V)
其中R9-R11彼此独立地为
-烷基基团或
-基团-O-R12,
其中
R12可为烷基或芳基基团。
7.根据前述权利要求中任一项所述的方法,其中化合物(C)选自三乙基硅烷、三异丙基硅烷、二甲基苯基硅烷、二乙氧基甲基硅烷、二甲氧基甲基硅烷、乙氧基二甲基硅烷、苯氧基二甲基硅烷、三乙氧基硅烷、三甲氧基硅烷、双三甲基甲硅烷氧基甲基硅烷,或其混合物。
8.根据前述权利要求中任一项所述的方法,其中化合物(B)仅带有一个C=C双键且仅带有一个羟基。
9.根据权利要求8所述的方法,其中化合物(B)的C=C双键为孤立的双键。
10.根据前述权利要求中任一项所述的方法,其中化合物(B)选自烯丙醇(2-丙烯-1-醇)、甲基烯丙醇(2-甲基-2-丙烯-1-醇)、高烯丙醇(3-丁烯-1-醇)、1-丁烯-3-醇、3-甲基-2-丁烯-1-醇、2-甲基-3-丁烯-2-醇、1-辛烯-3-醇、2-己烯-1-醇、1-戊烯-3-醇、叶绿醇、法呢醇和沉香醇。
11.根据前述权利要求中任一项所述的方法,其中不饱和醇(B)与二异氰酸酯或多异氰酸酯(A)中的异氰酸酯基团的化学计量为1:0.1至0.1:1。
12.根据前述权利要求中任一项所述的方法,其中反应温度在第一阶段中为40℃至120℃且在第二阶段中为40℃至80℃。
13.甲硅烷基化的多异氰酸酯,其可根据前述权利要求中的任一项获得。
14.涂料组合物,其组成如下:
-至少一种根据权利要求13所述的甲硅烷基化的多异氰酸酯,
-任选地至少一种能够催化异氰酸酯基团与对异氰酸酯具有反应性的基团的反应的催化剂,
-至少一种含有对异氰酸酯具有反应性的基团的粘合剂,
-任选地至少一种常规的涂料添加剂,
-任选地至少一种溶剂,以及
-任选地至少一种颜料。
15.根据权利要求14所述的涂料组合物用于涂布基板的用途。
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