CN114072441A - 由脲二酮制备异氰脲酸酯的方法 - Google Patents
由脲二酮制备异氰脲酸酯的方法 Download PDFInfo
- Publication number
- CN114072441A CN114072441A CN202080050417.2A CN202080050417A CN114072441A CN 114072441 A CN114072441 A CN 114072441A CN 202080050417 A CN202080050417 A CN 202080050417A CN 114072441 A CN114072441 A CN 114072441A
- Authority
- CN
- China
- Prior art keywords
- component
- uretdione
- isocyanate
- methylimidazolium
- bis
- 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.)
- Pending
Links
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- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims abstract description 84
- -1 carboxylate anion Chemical class 0.000 claims abstract description 77
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
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Images
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Abstract
本发明涉及用于制备含异氰脲酸酯基团的化合物的方法,包括在组分B)的存在下组分A)的反应:A)至少一种基本上不含异氰酸酯基团的具有至少一个脲二酮基团的组分,B)至少一种催化剂,其含有通式(I)和/或(II)的结构要素其中R1,R2,R3,R4,R5和R6彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,脂族、脂环族、芳脂族或芳族的具有1至18个碳原子的有机基团,所述有机基团是取代或未取代的和/或在链中具有杂原子,其中所述基团还能够彼此任选地与另外的杂原子一起组合形成具有3至8个碳原子的环,该环能够任选地被进一步取代,其中R3,R4,R5和R6也可以彼此独立地代表氢,和R7代表氢或羧酸根阴离子(COO‑)。
Description
本发明涉及一种制备含异氰脲酸酯基团的化合物的方法、含有这种化合物的组合物以及这些组合物在制备聚氨酯塑料或涂层剂中的用途。本发明还涉及包含该组合物的涂层剂和涂覆有该涂层剂的基材。本发明还涉及由所述聚氨酯塑料制成的成型体。
异氰脲酸酯结构在异氰酸酯基团可能的反应产物中具有特殊地位。与其他异氰酸酯后续产物例如缩二脲-、脲二酮-、氨基甲酸酯-或脲基甲酸酯结构相比,其具有例如对水解和温度明显更高的耐受性。异氰脲酸酯的制备通常通过异氰酸酯的催化三聚来实现。过去已经开发了多种方法,它们特别是在所使用的三聚催化剂方面不同。
已知的三聚催化剂是例如叔胺或膦类,羟烷基叔胺(GB 2 221 465),双环叔胺与简单的低分子量脂族醇的混合物(GB 2 222 161),有机金属化合物(DE-A 3 240 613),碱金属和碱土金属羧酸盐 (DE-A 3 219 608,EP-A 0 100 129),碱金属酚盐 (GB-PS 1 391066,GB-PS 1 386 399),碱金属和碱土金属氧化物,-氢氧化物,-碳酸盐,-醇盐和-酚盐(GB809 809),与冠醚或聚醚醇络合的碱性碱金属化合物(EP-A 0 056 158,EP-A 0 056 159),吡咯烷酮钾盐(EP- A 0 033 581),季铵氢氧化物 (DE-A 1 667 309,EP-A 0 013 880,EP-A 0 047 452),羟烷基季铵氢氧化物 (EP-A 37 65,EP-A 10 589),三烷基羟烷基铵羧酸盐(DE-A 2631733,EP-A 0 671 426,EP-A 1 599 526,US 4,789,705),苄基季铵羧酸盐(EP-A1 229 016),四取代的铵-α-羟基羧酸盐(WO 2005/087828),季铵-或鏻氟化物(EP-A 0 339396,EP-A 0 379 914,EP-A 0 443 167),季铵-和鏻多氟化物(EP-A 0 798 299,EP-A 0896 009,EP-A 0 962 455),烷基碳酸四烷基铵 (EP-A 0 668 271),季铵碳酸氢盐 (WO1999/023128),得自叔胺与磷的起烷基化作用的酸酯的季铵盐 (EP 0 102 482)或内酰胺的四取代铵盐(WO 2013/167404)。
同样已经使用具有咪唑鎓盐结构的化合物作为用于异氰酸酯基团的三聚的催化剂。例如,可以在使用含有咪唑鎓-或咪唑啉鎓阳离子的催化剂的情况下,优选将芳族单体二异氰酸酯以及低聚多异氰酸酯(如二聚体或预聚物)三聚成聚异氰脲酸酯-或聚异氰脲酸酯/聚氨酯(WO 2010/054317, WO 2014/160616, WO 2015/006391)。
此外,咪唑鎓-或咪唑啉鎓盐还催化芳族环氧化物与芳族异氰酸酯生成含噁唑烷酮-和异氰脲酸酯基团的塑料的反应(WO 2016/102359)。
根据WO 2005/113626的教导,N-杂环卡宾(NHC),例如具有咪唑鎓-或咪唑啉鎓结构的那些,是出色的用于由任意的单体单异氰酸酯、二异氰酸酯和三异氰酸酯制备脲二酮-和/或异氰脲酸酯多异氰酸酯的催化剂。在此可以使用游离的N-杂环卡宾及其在二氧化碳上的加合物,所谓的咪唑鎓-或咪唑啉鎓羧酸盐。取决于所用异氰酸酯和所用催化剂的类型,该方法在低温下已经提供了脲二酮或异氰脲酸酯,它们也经常以混合物形式获得。
在Eur. J. Inorg. Chem. 2009, 1970-1976中描述了具有咪唑鎓-或咪唑啉鎓结构的N-杂环卡宾在二氧化碳、镁、铝和锌上的加合物作为用于合成聚氨酯以及用于异氰酸酯基团的三聚的催化剂。
在所有已知的用于制备异氰脲酸酯的现有技术方法中,作为起始化合物始终使用具有游离异氰酸酯基团,特别是单体二异氰酸酯的那些。然而,异氰酸酯官能的化合物通常被归类为对健康有害、致敏或甚至有毒的工作物质,在某些情况下其还具有高的蒸气压。因此,出于职业卫生的原因,具有游离异氰酸酯基团的化合物,特别是单体二异氰酸酯的加工需要大的安全技术耗费。
现已令人惊奇地发现,存在于不含异氰酸酯基团的化合物中的脲二酮基团可在具有咪唑鎓-或二氢咪唑鎓阳离子的催化剂的存在下直接转化为异氰脲酸酯结构,而在此不会在中间出现游离的异氰酸酯基团。
这种由脲二酮结构直接生成异氰脲酸酯结构的反应是迄今为止未知的。它首次开启了从基本上不含异氰酸酯基团的生理上不令人担心的聚脲二酮体系出发合成通过异氰脲酸酯基团交联的聚氨酯的可能性。
本发明提供了一种制备含异氰脲酸酯基团的化合物的方法,其包括在组分B)的存在下组分A)的反应:
A) 至少一种基本上不含异氰酸酯基团的具有至少一个脲二酮基团的组分,
B) 至少一种催化剂,其含有通式(I)和/或(II)的结构要素
其中
R1、R2、R3、R4、R5 和R6 彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,脂族、脂环族、芳脂族或芳族的具有1至18个碳原子的有机基团,该有机基团是取代或未取代的和/或在链中具有杂原子,其中所述基团还能够彼此任选地与另外的杂原子一起组合形成具有3至8个碳原子的环,该环能够任选地被进一步取代,其中
R3、R4、R5 和R6 也可以彼此独立地代表氢,和
R7 代表氢或羧酸根阴离子(COO-)。
根据本发明,对“包括”、“含有”等的提及优选表示“基本上由……组成”并且非常特别优选表示“由……组成”。在权利要求中和说明书中提及的其他实施方式可以任意组合,只要上下文中没有明确指示相反的情况。
具有脲二酮基团的组分A)是任意的基本上不含异氰酸酯基团的含脲二酮基团的化合物,如其可通过本身已知的方法获得。在第一优选实施方式中,组分A)是可通过单体异氰酸酯的低聚和/或通过异氰酸酯官能的含脲二酮基团的化合物与醇和/或胺的反应获得的加聚化合物。
用于制备具有脲二酮基团的组分 A) 的起始化合物是任意的、可供使用的具有脂族、脂环族、芳脂族和/或芳族键合的异氰酸酯基团的单-、二-和三异氰酸酯,其可通过各种方式获得,例如通过在液相或气相中的光气化或通过无光气途径,例如通过氨基甲酸酯热裂解。
优选的单异氰酸酯是分子量范围为 99 至 300 的那些,例如异氰酸正丁酯、异氰酸正戊酯、异氰酸正己酯、异氰酸正庚酯、异氰酸正辛酯、异氰酸十一烷基酯、异氰酸十二烷基酯、异氰酸十四烷基酯、异氰酸鲸蜡酯、异氰酸硬脂酯、异氰酸环戊酯、异氰酸环己酯、异氰酸3-和4-甲基环己酯、异氰酸苄酯、异氰酸苯酯或异氰酸萘酯。
优选的二异氰酸酯是分子量范围为 140 至 400 的那些,例如 1,4-二异氰酸根合丁烷、1,5-二异氰酸根合戊烷(五亚甲基二异氰酸酯,PDI)、1,6-二异氰酸根合己烷(六亚甲基二异氰酸酯,HDI)、2-甲基-1,5-二异氰酸根合戊烷、1,5-二异氰酸根合-2,2-二甲基戊烷、2,2,4-和2,4,4-三甲基-1,6-二异氰酸根合己烷、1,10-二异氰酸根合癸烷、1,3-和1,4-二异氰酸根合环己烷、1,3-和1,4-双(异氰酸根合甲基)环己烷、1,3-二异氰酸根合-2(4)-甲基环己烷、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,IPDI)、2,4'-和 4,4'-二异氰酸根合二环己基甲烷 (H12 -MDI)、4,4'-二异氰酸根合-3,3'-二甲基二环己基甲烷、4,4'-二异氰酸根合-3,3',5,5'-四甲基二环己基甲烷、4,4'-二异氰酸根合-1,1'-联(环己基)、4,4'-二异氰酸根合-3,3'-二甲基-1,1'-联(环己基)、4,4'-二异氰酸根合-2,2',5,5'-四甲基-1,1'-联(环己基)、1,8-二异氰酸根合-p-薄荷烷、1,3-二异氰酸根合金刚烷、1,3-二甲基-5,7-二异氰酸根合金刚烷、1-异氰酸根合-1-甲基-4(3)-异氰酸根合-甲基环己烷、双(异氰酸根合甲基)降冰片烷 (NBDI)、1,3- 和 1,4-双(异氰酸根合甲基)苯(苯二亚甲基二异氰酸酯,XDI)、1,3 - 和 1,4-双(2-异氰酸根合丙-2-基)苯(四甲基苯二亚甲基二异氰酸酯,TMXDI)、1,3-双(异氰酸根合甲基)-4-甲基苯、1,3-双(异氰酸根合甲基)-4-乙基苯, 1,3-双(异氰酸根合甲基)-5-甲基苯、1,3-双(异氰酸根合甲基)-4,5-二甲基苯、1,4-双(异氰酸根合甲基)-2,5-二甲基苯、1,4-双(异氰酸根合甲基)-2,3,5,6-四甲基苯、1,3-双(异氰酸根合甲基)-5-叔丁基苯、1,3-双(异氰酸根合甲基)-4-氯苯、1,3-双(异氰酸根合甲基)-4,5-二氯苯、1,3-双(异氰酸根合甲基)-2,4,5,6-四氯苯、1,4-双(异氰酸根合甲基)-2,3,5,6-四氯苯、1,4-双(异氰酸根合甲基)-2,3,5,6-四溴苯、1,4-双(2-异氰酸根合乙基)苯和1,4-双(异氰酸根合甲基)萘、1,2-、1,3-和1,4-二异氰酸根合苯(苯二异氰酸酯)、2,4- 和 2,6 -二异氰酸根合甲苯(甲苯二异氰酸酯,TDI)、2,3,5,6-四甲基-1,4-二异氰酸根合苯、异构的二乙基亚苯基二异氰酸酯、二异丙基亚苯基二异氰酸酯、二异十二烷基亚苯基二异氰酸酯和联苯二异氰酸酯、3,3'-二甲氧基联苯-4,4'-二异氰酸酯、2,2'-, 2,4'- 和 4,4'-二异氰酸根合二苯基甲烷 (MDI)、3,3'-二甲基二苯基甲烷-4,4'-二异氰酸酯、4,4'-二异氰酸根合二苯基乙烷、1,5-二异氰酸根合萘(萘二异氰酸酯,NDI)、二苯基醚二异氰酸酯、乙二醇二苯基醚二异氰酸酯、二乙二醇二苯基醚二异氰酸酯、1,3-丙二醇二苯基醚二异氰酸酯、二苯甲酮二异氰酸酯、三异氰酸根合苯、2,4,6-三异氰酸根合甲苯、三甲基苯三异氰酸酯、二苯基甲烷-2,4,4'-三异氰酸酯、3-甲基二苯基甲烷-4,6,4'-三异氰酸酯、异构的萘三异氰酸酯和甲基萘二异氰酸酯、三苯基甲烷三异氰酸酯或2,4-二异氰酸根合-1-[(5-异氰酸根合-2-甲基苯基)甲基]苯。
此外,其他同样合适的二异氰酸酯可以在例如 Justus Liebigs Annalen derChemie,第 562 卷 (1949)第75-136页中找到。
作为特别合适的三异氰酸酯可以示例性地提及4-异氰酸根合甲基-1,8-辛烷二异氰酸酯(三异氰酸根合壬烷;TIN)。
作为用于制备具有脲二酮基团的组分A)的起始化合物也可以使用至少两种这样的单-、二-和/或三异氰酸酯的混合物。
优选使用单体二异氰酸酯作为用于制备具有脲二酮基团的组分A)的起始化合物。
特别优选使用PDI、HDI、IPDI、NBDI、XDI和/或H12-MDI,非常特别优选使用PDI和/或HDI。因此,在进一步优选的实施方式中,组分A)是基于PDI、HDI、IPDI、NBDI、XDI和/或H12-MDI的含脲二酮基团的化合物。
具有脲二酮基团的组分A)或用于其制备的起始化合物的制备可以通过各种方法进行,这些方法通常基于文献已知的用于简单二异氰酸酯低聚的常规方法,其例如记载在J. Prakt. Chem. 336 (1994) 185 - 200, DE-A 16 70 666, DE-A 19 54 093, DE-A 2414 413, DE-A 24 52 532, DE-A 26 41 380, DE-A 37 00 209, DE-A 39 00 053, DE-A39 28 503, EP-A 336 205, EP-A 339 396 和EP-A 798 299中。
在仅使用或按比例共同使用单异氰酸酯基团的情况下,具有脲二酮基团的组分A)可以在低聚反应后立即以不含异氰酸酯基团的形式存在。然而,在低聚反应中优选至少另外以这样的量使用二-和/或三异氰酸酯,以至于首先得到异氰酸酯官能的含脲二酮基团的化合物,其平均NCO官能度为至少1.6,优选1.8至3.5,特别优选1.9至3.2,非常特别优选2.0至2.7。
在平均NCO官能度> 2.0的情况下,在这些异氰酸酯官能的含脲二酮基团的化合物中,除了线性双官能脲二酮结构以外还存在至少三官能的其它多异氰酸酯分子。所述含脲二酮基团的化合物的这些更高官能的成分特别是具有异氰脲酸酯-、脲基甲酸酯-、缩二脲-、氨基甲酸酯-和/或亚氨基噁二嗪二酮结构的二异氰酸酯已知后续产物。
所述通过低聚获得的含脲二酮基团的化合物通常在其上述的由简单的单体单-、二-和/或三异氰酸酯进行制备后根据已知方法例如通过薄膜蒸馏或萃取立即除去未反应的过量单体。因此,在一个优选的实施方式中,其具有小于5重量%,优选小于2重量%,特别优选小于1重量%的单体二异氰酸酯的残余含量。
对于低聚反应之后并非已经存在不含异氰酸酯基团的具有脲二酮基团的组分A)而是存在异氰酸酯官能的含脲二酮基团的化合物的情况,后者与醇和/或胺反应生成基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A)。
用于制备加聚化合物A)的合适的醇是例如简单的脂族或脂环族一元醇,如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇,异构的戊醇、己醇、辛醇和壬醇,正癸醇、正十二醇、正十四醇、正十六醇、正十八醇、环己醇,异构的甲基环己醇和羟甲基环己烷,醚醇如2-甲氧基乙醇、2-乙氧基乙醇、2-丙氧基乙醇、2-丁氧基乙醇、二乙二醇单甲醚、二乙二醇单乙醚、二乙二醇单丁醚、3-甲氧基-1-丁醇和甘油-1,3-二乙醚,酯醇,如乙酸羟乙酯、乙醇酸丁酯、乳酸乙酯、二乙酸甘油酯或可以通过所提及的一元醇与内酯的反应获得的那些,或醚醇,如其可以通过所提及的一元醇与环氧烷,特别是环氧乙烷和/或环氧丙烷的反应获得。
同样适用于制备基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A)的醇是分子量范围为62至22000的至少双官能的多元醇,优选平均官能度为2至6且数均分子量为62至18 000的那些,特别优选平均官能度为 2 至 4且数均分子量为 90 至 12 000的那些。
适用于制备基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物 A)的多元醇是例如具有2至14个,优选4至10个碳原子的简单的多元醇,例如1,2-乙二醇、1,2-和-1,3-丙二醇,异构的丁二醇、戊二醇、己二醇、庚二醇和辛二醇,1,10-癸二醇、1,12-十二烷二醇、1,2-和-1,4-环己烷二醇、1,4-环己烷二甲醇、1,4-双(2-羟基乙氧基)苯、2,2-双(4-羟基苯基)丙烷(双酚A)、2,2-双-(4-羟基环己基)丙烷(全氢双酚)、1,2,3-丙三醇、1,2,4-丁三醇、1,1,1-三羟甲基乙烷、1,2,6-己三醇、1,1,1-三羟甲基丙烷 (TMP)、双-(2-羟基乙基)氢醌、1,2,4-和1,3,5-三羟基环己烷、1,3,5-三(2-羟基乙基)异氰脲酸酯、3(4),8(9)-双-(羟基甲基)-三环-[5.2.1.02,6]癸烷、二-三羟甲基丙烷、2,2-双(羟基甲基)-1,3-丙二醇(季戊四醇)、2,2,6,6-四(羟基甲基)-4-氧杂-庚烷- 1,7-二醇(二季戊四醇)、甘露醇或山梨醇、低分子量醚醇,例如二甘醇、三甘醇、四甘醇、二丙二醇或二丁二醇,或低分子量酯醇,例如羟基新戊酸新戊二醇酯。
适用于制备基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A)的多元醇也是由聚氨酯化学已知的常见聚合聚醚多元醇、聚酯多元醇、聚碳酸酯多元醇和/或聚丙烯酸酯多元醇,其数均分子量通常为200至22 000,优选250至18 000,特别优选250至12 000。用于制备加聚化合物A2)的合适聚合多元醇的广泛概述可参见例如N.Adam等人Polyurethanes. In: Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCHVerlag GmbH & Co. KgaA; 2005. URL: https://doi.org/10.1002/14356007.a21_665.pub2。
合适的聚醚多元醇例如在 DE 26 22 951 B,第 6 栏第 65 行至第 7 栏第 26行、EP-A 0 978 523 第 4 页第 45 行至第 5 页第 14 行或WO 2011/069966,第 4 页第20 行至第 5 页第 23 行提及的类型中找到,只要它们在官能度和分子量方面相应于前述已给出的说明。特别优选的聚醚多元醇是环氧乙烷和/或环氧丙烷在1,2-丙二醇、1,3-丙二醇、甘油、三羟甲基丙烷、乙二胺和/或季戊四醇上的加成产物或例如根据Angew. Chem.72, 927 (1960) (https://doi.org/10.1002/ange.19600722402)可通过四氢呋喃的聚合获得的数均分子量为400g/mol至4000g/mol的聚四亚甲基醚二醇。
合适的聚酯多元醇例如是在 EP-A 0 978 523,第 5 页,第 17 至 47 行,或 EP-A 0 659 792,第 6 页,第 32 至 45 行中提及类型的那些,只要它们在官能度和分子量方面相应于前述已给出的说明。特别优选的聚酯多元醇是多元醇与不足量的多元羧酸或羧酸酐的缩合产物,所述多元醇例如是1,2-乙二醇、1,2-丙二醇、二甘醇、1,4-丁二醇、1,6-己二醇、新戊二醇、1,4-环己烷二甲醇、1,4-环己烷二醇、全氢双酚、1,1,1-三羟甲基丙烷、1,2,3-丙三醇、季戊四醇和/或山梨醇,所述多元羧酸或羧酸酐例如是琥珀酸、己二酸、癸二酸、十二烷二酸、戊二酸酐、马来酸酐、邻苯二甲酸酐、间苯二甲酸、对苯二甲酸、偏苯三酸、六氢邻苯二甲酸酐和/或四氢邻苯二甲酸酐,或是如可以以本身已知的方式由内酯,例如ε-己内酯,和简单的多元醇,例如上面示例性提到的那些,作为起始剂分子开环获得的那些。
合适的聚碳酸酯多元醇特别是二元醇与碳酸二芳基酯的本身已知的反应产物,所述二元醇例如是上面在多元醇列表中作为示例性提及的那些,所述碳酸二芳基酯例如是碳酸二苯酯、碳酸二甲酯或光气。同样合适的聚碳酸酯多元醇是除了碳酸酯结构而外还包含酯基团的那些。这些尤其是本身已知的聚酯碳酸酯二醇,其例如可根据DE-AS 1 770 245的教导通过二元醇与内酯如特别是ε-己内酯的反应,和由此所得聚酯二醇与碳酸二苯酯或碳酸二甲酯的后续反应获得。
合适的聚丙烯酸酯多元醇例如是WO 2011/124710第10页第32行至第13页第18行中提及类型的那些,只要它们在官能度和分子量方面相应于前述已给出的说明。特别优选的聚丙烯酸酯多元醇是丙烯酸或甲基丙烯酸的羟烷基酯的聚合物或共聚物,所述丙烯酸或甲基丙烯酸的羟烷基酯例如是(甲基)丙烯酸羟乙酯、(甲基)丙烯酸羟丙酯或(甲基)丙烯酸羟丁酯,任选地与丙烯酸烷基酯和/或甲基丙烯酸烷基酯,例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸 2-乙基己酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸月桂酯、苯乙烯或其他可共聚的烯属不饱和单体,例如丙烯酸、甲基丙烯酸或马来酸二甲酯一起。
合适的多元醇例如还是可通过简单二醇例如二甘醇、三甘醇、4,4'-二氧乙氧基-二苯基-二甲基甲烷(2mol环氧乙烷在双酚A上的加合物)或己二醇与甲醛的反应获得的聚缩醛多元醇或通过环状缩醛例如三噁烷的缩聚制备的聚缩醛。
用于制备基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A)的另外的合适的多元醇例如也是在EP-A 0 689 556和EP-A 0 937 110中描述的,例如可通过环氧化脂肪酸酯与脂族或芳族多元醇的反应在环氧化物开环的情况下得到的特殊的多元醇以及含羟基的聚丁二烯。
用于制备基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A)的合适的胺例如是简单的脂族或脂环族单胺,例如甲胺、乙胺、正丙胺、异丙胺、异构的丁胺、戊胺、己胺和辛胺、正十二胺、正十四胺、正十六胺、正十八胺、环己胺、异构的甲基环己胺以及氨基甲基环己烷,仲单胺,如二甲胺、二乙胺、二丙胺、二异丙胺、二丁胺、二异丁胺、双(2-乙基己基)胺、N-甲基-和N-乙基环己胺以及二环己胺。
合适的胺也是具有至少两个伯和/或仲键合氨基的任意的脂族和脂环族胺,例如1,2-二氨基乙烷、1,2-二氨基丙烷、1,3-二氨基丙烷、1,4-二氨基丁烷、1,2-二氨基-2-甲基丙烷、1,5-二氨基戊烷、1,3-二氨基-2,2-二甲基丙烷、1,6-二氨基己烷、1,5-二氨基-2-甲基戊烷、1,6-二氨基-2,2,4-三甲基己烷、1,6-二氨基-2,4,4-三甲基己烷、1,7-二氨基庚烷、1,8-二氨基辛烷、2,5-二氨基-2,5-二甲基己烷、1,9-二氨基壬烷、 2-甲基-1,8-二氨基辛烷、1,10-二氨基癸烷、1,11-二氨基十一烷、1,12-二氨基十二烷、1,2-二氨基环戊烷、1,2-二氨基环己烷、1-氨基-3,3,5-三甲基-5-氨基甲基环己烷(异佛尔酮二胺,IPDA)、3(4)-氨基甲基-1-甲基环己胺、1,3-二氨基-2-和/或-4-甲基环己烷、异丙基-2,4-和/或2,6-二氨基环己烷、1,3-双(氨基甲基)环己烷、1,8-对二氨基薄荷烷、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-3,5-二甲基环己基)甲烷、双(4-氨基-2,3,5-三甲基环己基)甲烷、1,1-双(4-氨基环己基)丙烷、2,2-双(4-氨基环己基)丙烷, 1,1-双(4-氨基环己基)乙烷、1,1-双(4-氨基环己基)丁烷、2,2-双(4-氨基环己基)丁烷、1,1-双(4-氨基-3-甲基环己基)乙烷、2,2-双(4-氨基-3-甲基环己基)丙烷、1,1-双(4-氨基-3,5-二甲基环己基)乙烷、2,2-双(4-氨基-3,5-二甲基环己基)丙烷、2,2-双(4-氨基-3,5-二甲基环己基)丁烷、2,4-二氨基二环己基甲烷、4-氨基环己基-4-氨基-3-甲基环己基甲烷、4-氨基-3,5-二甲基环己基-4-氨基-3-甲基环己基-甲烷和2-(4-氨基环己基)-2-(4-氨基-3-甲基环己基)甲烷,间苯二甲胺,甲基亚氨基双丙胺,亚氨基双丙胺,双(6-氨基己基)胺,N,N-双(3-氨基丙基)-乙二胺、4-氨基甲基-1,8-辛二胺、双(氨基丙基)哌嗪、氨基乙基哌嗪、二亚乙基三胺、二亚丙基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺,七亚乙基辛胺。
合适的胺也是氨基官能的聚亚烷基二醇,例如1,2-双(氨基乙氧基)-乙烷、1,11-二氨基-3,6,9-三氧杂十一烷、1,13-二氨基-4,7,10-三氧杂十三烷和特别是在商品名Jeffamine®下由Huntsman Corp.公司商业销售的数均分子量至多5000,优选至多2000,特别优选至多1000的胺官能化的聚亚烷基二醇。
任选地也可使用具有两个仲键合氨基的位阻脂族二胺用于制备基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A),例如由EP-A 0 403 921已知的脂族和/或脂环族二胺与马来酸酯或富马酸酯的反应产物,根据EP-A 1 767 559的教导可获得的丙烯腈在异佛尔酮二胺上的双加合物,或例如描述于DE-A 19 701 835中的可从脂族和/或脂环族二胺和酮例如二异丙基酮获得的席夫碱的氢化产物。
合适的其它多胺此外也是作为环氧树脂的交联剂组分已知的聚酰胺基胺、聚亚胺和/或聚乙烯胺。
最后也适合用于制备基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A)的是氨基醇,例如2-氨基乙醇、异构的氨基丙醇和氨基丁醇、3-氨基-1,2-丙二醇和1,3-二氨基-2-丙醇。
在由前述类型的异氰酸酯官能的含脲二酮基团的化合物制备基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A)时使用所提及的醇和/或胺,单独地或作为至少两种这样的醇和/或胺的混合物。
基本上不含异氰酸酯基团的、含脲二酮基团的加聚化合物A)的制备可以通过各种方法进行,例如文献已知的用于制备聚脲二酮组合物的方法,其例如描述在WO 99/11690和WO 2011/115669中。
在此,除了通过低聚获得的异氰酸酯官能的含脲二酮基团的化合物之外,任选还可以共同使用另外的上述类型的单体异氰酸酯和/或低聚多异氰酸酯,优选具有异氰脲酸酯-、缩二脲-、亚氨基噁二嗪二酮-、脲基甲酸酯-和/或氨基甲酸酯-结构的那些,以至多30重量%的量,基于所有反应参与物(包括异氰酸酯官能的含脲二酮基团的化合物、醇和/或胺)的总重量计。
该反应优选在遵循异氰酸酯基团与异氰脲酸酯反应性基团的当量比为 1: 0.9至0.5: 1,优选1: 0.95至0.7: 1,特别优选1: 1至0.9: 1的情况下进行。
在另一优选的实施方式中,组分A)是通过异氰酸酯官能的、含脲二酮基团的化合物与分子量范围为62至22000的至少双官能的多元醇和任选的一元醇在遵循异氰酸酯基团与异氰脲酸酯反应性基团的当量比为1.0: 0.9至0.5: 1的情况下反应获得的加聚化合物。
该反应可以无溶剂地或在对异氰酸酯基团呈惰性的合适溶剂中进行。
用于制备加聚化合物A2)的合适溶剂尤其是对化合物A1)的异氰酸酯基团呈惰性的那些,例如已知的常用非质子涂料溶剂,例如乙酸乙酯、乙酸异丙酯、乙酸丁酯、乙酸异丁酯、乙酸戊酯,乙酸2-乙基己酯、乙二醇单甲基醚乙酸酯、乙二醇单乙基醚乙酸酯、乙二醇单丁基醚乙酸酯、1-甲氧基丙基-2-乙酸酯、3-甲氧基-正丁基乙酸酯、丙酮、二乙酮、2-丁酮、4-甲基-2-戊酮,二异丁基酮,环己酮,环己烷,甲苯,二甲苯,氯苯,二氯苯,石油溶剂油,较高取代的芳烃,例如其在名称Solventnaphtha, Solvesso®, Isopar®, Nappar®(Deutsche EXXON CHEMICAL GmbH, Cologne, DE)和Shellsol® (Deutsche Shell ChemieGmbH, Eschborn, DE)下商购,还有溶剂如丙二醇二乙酸酯、二乙二醇二甲醚、二丙二醇二甲醚、二乙二醇乙基-和-丁基醚乙酸酯、乙基乙氧基丙酸酯、碳酸亚丙酯、N-甲基吡咯烷酮和N-甲基己内酰胺、二噁烷、四氢呋喃或此类溶剂的任意混合物。
用以产生含脲二酮基团的加聚化合物A)的异氰酸酯官能的含脲二酮基团的化合物与醇和/或胺的反应可以在无催化的情况下进行。然而,为了加速反应,也可以使用由聚氨酯化学已知的常规催化剂。此处示例性可提及的是叔胺,例如三乙胺、三丁胺、二甲基苄胺、二乙基苄胺、吡啶、甲基吡啶、二环己基甲胺、二甲基环己胺、N,N,N',N'-四甲基二氨基二乙醚、双-(二甲基氨基丙基)脲、 N-甲基-或N-乙基吗啉,N-椰纤维烷基吗啉(N-Cocomorpholin)、N-环己基吗啉,N,N,N',N'-四甲基乙二胺,N,N,N',N'-四甲基-1,3-丁二胺,N,N,N',N'-四甲基-1,6-己二胺、五甲基二亚乙基三胺、N-甲基哌啶、N-二甲基氨基乙基哌啶、N,N'-二甲基哌嗪、N-甲基-N'-二甲基氨基哌嗪、1,8-二氮杂双环(5.4.0)十一碳-7-烯、1,2-二甲基咪唑、2-甲基咪唑、N,N-二甲基咪唑-β-苯乙胺、1,4-二氮杂双环-(2,2,2)-辛烷、双-(N,N-二甲基氨基乙基)己二酸酯;烷醇胺化合物,例如三乙醇胺、三异丙醇胺、N-甲基-和N-乙基二乙醇胺、二甲基氨基乙醇、2-(N,N-二甲基氨基乙氧基)乙醇、N,N',N''-三-(二烷基氨基烷基)六氢三嗪,例如N,N',N''-三-(二甲基氨基丙基)-s-六氢三嗪和/或双(二甲基氨基乙基)醚;金属盐,例如呈金属的常见氧化态的铁、铅、铋、锌和/或锡的无机和/或有机化合物,例如氯化铁(II)、氯化铁(III)、乙酸铋(III)、2-乙基己酸铋(III)、辛酸铋(III)、新癸酸铋(III)、氯化锌、2-乙基己酸锌、辛酸锡(II)、乙基己酸锡(II)、棕榈酸锡(II)、二月桂酸二丁基锡(IV) (DBTL)、二丁基二月桂基锡硫醇盐或辛酸铅;脒类,例如 2,3-二甲基-3,4,5,6-四氢嘧啶;氢氧化四烷基铵,例如氢氧化四甲基铵;碱金属氢氧化物,例如氢氧化钠,和碱金属醇盐,例如甲醇钠和异丙醇钾,以及具有 10 至 20 个碳原子和任选的侧链 OH 基团的长链脂肪酸的碱金属盐。
优选的催化剂是所提及类型的叔胺、铋-和锡化合物。
具有脲二酮基团的组分A)优选是可通过异氰酸酯官能的含脲二酮基团的化合物与醇和/或胺的反应获得的所述类型的基本上不含异氰酸酯基团的加聚化合物。
本发明方法中使用的具有脲二酮基团的组分A)非常特别优选完全不含异氰酸酯基团。然而,在本公开的范围内,术语“基本上不含异氰酸酯基团”应理解为是指在其制备之后组分A)由此仍允许具有少许残留量的异氰酸酯基团。“基本上不含异氰酸酯基团”优选应涉及含脲二酮基团的加聚化合物A),其在无溶剂形式中具有小于2重量%、优选小于1重量%和特别优选小于0.5重量%的游离异氰酸酯基团含量。
本发明优选提供一种用于制备含异氰脲酸酯基团的化合物的方法,包括在B)存在下A)的反应
A) 至少一种组分,其具有至少一个脲二酮基团且在无溶剂形式中游离异氰酸酯基团的含量小于2重量%,优选小于1重量%,特别优选小于0.5重量%,
B) 至少一种催化剂,其含有通式(I)和/或(II)的结构要素
其中
R1,R2,R3,R4,R5 和R6 彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,脂族、脂环族、芳脂族或芳族的具有1至18个碳原子的有机基团,其是取代或未取代的和/或在链中具有杂原子,其中所述基团还能够彼此任选地与另外的杂原子一起组合形成具有3至8个碳原子的环,该环能够任选地被进一步取代,其中
R3,R4,R5 和R6 也可以彼此独立地代表氢,和
R7 代表氢或羧酸根阴离子(COO-)。
补充地或替代地优选, A)至少一种基本上不含异氰酸酯基团的具有至少一个脲二酮基团的组分的反应在B)至少一种含有通式(I) 和/或 (II)的结构要素的催化剂存在下,在不存在羟基-或巯基官能化合物的情况下进行。
在根据本发明的方法中,使所述基本上不含异氰酸酯基团的、具有脲二酮基团的组分A)与具有咪唑鎓阳离子和/或咪唑啉鎓阳离子的至少一种盐型催化剂B)反应。
适合作为催化剂B)的化合物也已知为咪唑鎓-和咪唑啉鎓型离子液体并且例如用作化学合成中的溶剂。它们的制备方法记载在例如Chem. Rev. 99, 8, 2071-2084和WO2005/070896中。
催化剂B)是含有通式(I)或(II)的结构要素的盐型化合物
其中
R1、R2、R3、R4、R5 和R6 彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,脂族、脂环族、芳脂族或芳族的具有1至18个碳原子的有机基团,其是取代或未取代的和/或在链中具有杂原子,其中所述基团还能够彼此任选地与另外的杂原子一起组合形成具有3至8个碳原子的环,该环能够任选地被进一步取代,、
R3、R4、R5和R6 也可以彼此独立地代表氢,和
R7 代表氢或羧酸根阴离子(COO-)。
优选的催化剂B)是含有通式(I)或(II)的结构要素的盐型化合物, 其中
R1 和R2 彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,脂族、脂环族、芳脂族或芳族的具有1至12个碳原子的有机基团,其是取代或未取代的和/或在链中具有杂原子,
R3、R4、R5 和R6 代表氢,和其中
R7 代表氢或羧酸根阴离子(COO-)。
特别优选的催化剂B)是含有通式(I)或(II)的结构要素的盐型化合物,其中
R1 和R2 彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,具有1至12个碳原子的脂族有机基团,
R3、R4、R5 和R6 代表氢,和
R7 代表氢或羧酸根阴离子(COO-)。
作为通式 (I) 的合适催化剂可以示例性地提及含有下述的那些:1,3-二甲基咪唑鎓-、1-甲基-3-乙基咪唑鎓-、1-甲基-3-丙基咪唑鎓-、1-甲基-3-丁基咪唑鎓-、1-甲基-3-戊基咪唑鎓-、1-甲基-3-己基咪唑鎓-、1-甲基-3-辛基咪唑鎓-、1-甲基-3-壬基咪唑鎓-、1-甲基-3-癸基咪唑鎓-、1-癸基-3-甲基咪唑鎓-、1-甲基-3-苄基咪唑鎓-、1-甲基-3-(3-苯基丙基)咪唑鎓-、1-乙基-3-甲基咪唑鎓 (EMIM)-、1-异丙基-3-甲基咪唑鎓-、1-丁基-3-甲基咪唑鎓 (BMIM)-、1-己基-3-甲基咪唑鎓-、1-庚基-3-甲基咪唑鎓-、1-(2-乙基)己基-3-甲基咪唑鎓 (OMIM)-、1,3-双(叔丁基)咪唑鎓-、1,3-双(2,4,6-三甲基苯基)咪唑鎓-或1,3-二甲基苯并咪唑鎓阳离子。
作为通式(II)的合适催化剂可以示例性地提及含有下述的那些:1,3-二甲基咪唑啉鎓,1-乙基-3-甲基咪唑啉鎓-、1-丁基-3-甲基咪唑鎓-1,3-双-(2,6-二异丙基苯基)咪唑啉鎓-或1,3-双(2,4,6-三甲基苯基)咪唑啉鎓-1-(1-金刚烷基)-3-(2,4,6-三甲基苯基)咪唑啉鎓-、1,3-二苯基-4,4,5,5-四甲基咪唑啉鎓-、1,3-二-邻甲苯基-4,4,5,5-四甲基咪唑啉鎓阳离子。
作为咪唑鎓和咪唑啉鎓阳离子的抗衡离子,在根据本发明的方法中使用的催化剂B)包含任意的无机和/或有机阴离子,例如卤离子、硫酸根、羟基硫酸根、亚硫酸根、硝酸根、碳酸根、碳酸氢根、芳基磺酸根、烷基磺酸根、三氟甲基磺酸根、烷基硫酸根、磷酸根、二烷基磷酸根、六氟磷酸根、三氟甲基硼酸根、四氟硼酸根、双(三氟甲基磺酰基)亚氨离子、双氰氨离子和/或羧酸根阴离子。
此外,咪唑鎓和咪唑啉鎓阳离子的抗衡离子还可以是作为通式(I)的R7直接键合到咪唑鎓阳离子上的羧酸根(COO - ),其中催化剂B)在这种情况下具有两性离子结构的形式。
适合于根据本发明的方法的催化剂B)例如是1,3-二甲基咪唑鎓氯化物、1,3-二甲基咪唑鎓-2-甲酸盐、1,3-二甲基咪唑鎓二甲基磷酸盐、1-乙基-3-甲基咪唑鎓氯化物、1-乙基-3-甲基咪唑鎓溴化物、1-乙基-3-甲基咪唑鎓碘化物、1-乙基-3-甲基咪唑鎓硝酸盐、1-乙基-3-甲基咪唑鎓碳酸氢盐、1-乙基-3-甲基咪唑鎓甲磺酸盐、1-乙基-3-甲基咪唑鎓三氟甲磺酸盐、 1-乙基-3-甲基咪唑鎓三氟(三氟甲基)硼酸盐,1-乙基-3-甲基咪唑鎓硫酸氢盐,1-乙基-3-甲基咪唑鎓乙基硫酸盐,1-乙基-3-甲基咪唑鎓二氰氨化物,1-乙基-3-甲基咪唑鎓四氟硼酸盐,1-乙基-3-甲基咪唑鎓二乙基磷酸盐、1-乙基-3-甲基咪唑鎓六氟磷酸盐、1-乙基-3-甲基咪唑鎓-双(三氟甲磺酰基)亚氨化物、1-乙基-3-甲基咪唑鎓-2-甲酸盐、1-乙基-3-甲基咪唑鎓乙酸盐、 1-乙基-3-甲基咪唑鎓-(L)-(+)-乳酸盐,1-甲基-3-丙基咪唑鎓碘化物,1,3-二异丙基-4,5-二甲基咪唑鎓-2-甲酸盐,1-丁基-3-甲基咪唑鎓氯化物,1-丁基-3-甲基咪唑鎓溴化物、1-丁基-3-甲基咪唑鎓碘化物、1-丁基-3-甲基咪唑鎓三氟甲磺酸盐、1-丁基-3-甲基咪唑鎓甲基硫酸盐、1-丁基-3-甲基咪唑鎓正辛基硫酸盐、1-丁基-3-甲基咪唑鎓二氰氨化物、 1-丁基-3-甲基咪唑鎓三氟(三氟甲基)硼酸盐、1-丁基-3-甲基咪唑鎓四氟硼酸盐、1-丁基-3-甲基咪唑鎓二丁基磷酸盐、1-丁基-3-甲基咪唑鎓六氟磷酸盐、1-丁基-3-甲基咪唑鎓-2-甲酸盐、1-丁基-3-甲基咪唑鎓乙酸盐、1-丁基-3-甲基咪唑鎓-双(三氟甲磺酰基)亚氨化物、双(叔丁基)咪唑鎓-2-甲酸盐、1-己基-3-甲基咪唑鎓氯化物、1-己基-3-甲基咪唑鎓溴化物、1-己基-3-甲基咪唑鎓四氟硼酸盐、1-己基-3-甲基咪唑鎓双(三氟甲磺酰基)亚氨化物、1-己基-3-甲基咪唑鎓六氟磷酸盐、1-甲基-3-正辛基咪唑鎓溴化物、1-甲基-3-正辛基咪唑鎓氯化物、1-甲基-3-正辛基咪唑鎓六氟磷酸盐、1-癸基-3-甲基咪唑鎓-双(三氟甲磺酰基)亚氨化物、1,3-二甲基咪唑啉鎓氯化物、1,3-二甲基咪唑啉鎓-2-甲酸盐、1,3-二甲基咪唑啉鎓乙酸盐、1-乙基-3-甲基咪唑啉氯化物、1-乙基-3-甲基咪唑啉鎓-2-甲酸盐、1-乙基-3-甲基咪唑啉鎓乙酸盐、1-丁基-3-甲基咪唑啉鎓-2-甲酸盐、1,3-双(2,6-二异丙基苯基)咪唑啉鎓氯化物或 1,3-双(2,4,6-三甲基苯基)咪唑啉鎓-1-(1-金刚烷基)-3-(2,4,6-三甲基苯基)咪唑啉鎓氯化物和/或1,3-二苯基-4,4,5,5-四甲基咪唑啉鎓氯化物。
特别优选的催化剂B)是具有羧酸根阴离子的所述类型的咪唑鎓盐,非常特别优选1,3-二甲基咪唑鎓-2-甲酸盐, 1-乙基-3-甲基咪唑鎓-2-甲酸盐, 1-乙基-3-甲基咪唑鎓乙酸盐, 1-丁基-3-甲基咪唑鎓-2-甲酸盐和/或1-丁基-3-甲基咪唑鎓乙酸盐。
在另一优选的实施方式中,催化剂B)单独地或作为至少两种这样的催化剂的混合物以0.001至15重量%,优选0.005至12重量%,特别优选0.01至10重量%的量用于根据本发明的方法中,不包括任选存在于这些组分中的溶剂、助剂或添加剂,基于组分A)和B)的总重量计。
根据本发明的方法突出地适用于由基本上不含异氰酸酯基团的具有脲二酮基团的起始组分制备通过异氰脲酸酯结构交联的聚氨酯塑料并用于此。
因此,本发明同样提供组合物,优选涂层剂,其含有至少一种所述类型的可通过异氰酸酯官能的含脲二酮基团的化合物与醇和/或胺的反应获得的基本上不含异氰酸酯基团的加聚化合物A)、至少一种包含根据权利要求1、5至8中任一项所述的通式(I)和/或(II)的结构要素的具有咪唑鎓-或咪唑啉鎓结构的催化剂B)以及任选的其他助剂和添加剂。优选含有至少一种可通过异氰酸酯官能的含脲二酮基团的化合物与醇和/或胺的反应获得的加聚化合物A) 和至少一种包含根据权利要求1、5至8中任一项所述的通式(I)和/或(II)的结构要素的具有咪唑鎓-或咪唑啉鎓结构的催化剂B)以及任选的其他助剂和添加剂的组合物,其中加聚化合物A)在无溶剂形式中的游离异氰酸酯基团的含量小于2重量%,优选小于1重量%,特别优选小于0.5重量%。
根据本发明的方法优选用于制备涂层剂。
在另一优选的实施方式中,本发明方法的实施和本发明组合物的固化在0至230℃,优选40至200℃,特别优选70至180℃,非常特别优选80至160℃的温度范围内,进行优选1分钟至至多12小的时间。
在这些条件下,最初含于组分 A) 中的脲二酮基团通常完全反应生成异氰脲酸酯基团。如红外光谱研究所表明的那样,在此,在整个反应时间内没有形成游离异氰酸酯基团。涉及脲二酮基团直接反应生成异氰脲酸酯基团。
本发明进一步提供了至少一种根据本发明的组合物用于制备聚氨酯塑料的用途。此外,本发明还提供了至少一种根据本发明的组合物用于制备涂层剂的用途。
作为用于借助于根据本发明的组合物配制的涂料的基底可以考虑任意的基材,例如金属、木材、玻璃、石材、陶瓷材料、混凝土、硬质和软质塑料、织物、皮革和纸,它们在涂覆之前也可以任选地具有常规打底。
本发明进一步提供包含至少一种根据本发明的组合物的涂层剂和涂覆有任选在热作用下固化的根据本发明的涂层剂的基材。
用根据本发明的组合物配制的涂层剂可以任选地获取由涂料技术领域的技术人员已知的常规助剂和添加剂,例如溶剂、UV稳定剂、抗氧化剂、流平剂、流变添加剂、滑爽添加剂、染料、消光剂、阻燃剂、水解保护剂、杀微生物剂、杀藻剂、水清除剂、触变剂、润湿剂、脱气剂、增粘剂、填料和/或颜料,在所提及的固化条件下得出具有良好涂料技术性能的薄膜。
本发明同样提供通过异氰脲酸酯基团交联的聚氨酯塑料,优选成型体,其可从任选在热作用下固化的根据本发明的组合物或可通过使用上述涂层剂获得的涂料获得或从任选在热作用下固化的根据本发明的组合物或通过使用上述涂层剂获得的涂料获得。
实施例
除非另有说明,否则所有百分比均基于重量计。
NCO 含量根据 DIN EN ISO 11909:2007-05 滴定来测定。
所有粘度测量用 Anton Paar Germany GmbH (DE) 的 Physica MCR 51 流变仪,根据 DIN EN ISO 3219:1994-10,以 250 s-1 的剪切速率来进行。
残留单体含量根据 DIN EN ISO 10283:2007-11 通过具有内标的气相色谱法测量。
脲二酮模型化合物的组成通过凝胶渗透色谱法根据 DIN 55672-1:2016-03(凝胶渗透色谱法 (GPC) - 第 1 部分:四氢呋喃 (THF) 作为洗脱液)来确定,改变为:流速为0.6 ml/min而不是 1.0 ml/min。用软件辅助确定的由色谱图中提取的不同低聚物的面积%比例在每种情况下都近似等于重量%的比例。根据 DIN EN ISO 1522:2007-04 在玻璃板上测定 König 摆锤阻尼。
在根据本发明的组合物固化时形成的脲二酮后续产物使用质子解耦的13C-NMR光谱(使用CDCl3作为溶剂在仪器Bruker DPX-400上记录)进行测定。与本发明相关的结构要素具有以下化学位移(ppm):脲二酮:157.1;聚氨酯:156.3;异氰脲酸酯:148.4。
使用 Bruker公司的FT-IR 光谱仪Alpha-P IR记录 IR 光谱。使用Bruker公司的矩阵 FM 以 3mm 金刚石头部探头进行原位 IR 测量。借助于Bruker的光谱软件OPUS 7.0分析光谱。
用二甲苯作为典型的涂料溶剂测定耐溶剂性。为此,将少量溶剂加入试管中并在开口处提供棉球,从而在试管内形成被二甲苯饱和的气氛。随后将试管以棉球放在涂料表面上并在那里保持 5 分钟。擦去溶剂后,检查膜的损坏/软化/粘附力损失。(0 = 无变化,5= 膜损坏)。
起始化合物
制备 HDI 脲二酮模型化合物 (HDI-UD1)
1,3-双(6-异氰酸根合己基)-1,3-二氮杂环丁烷-2,4-二酮的制备
根据EP-A 0 789 017的实施例1中描述的方法,通过三丁基膦催化的 1,6-二异氰酸根合己烷 (HDI) 的低聚和随后的蒸馏后处理制备了1,3-双(6-异氰酸根合己基)-1,3-二氮杂环丁烷-2,4-二酮(理想的双(6-异氰酸根合己基)脲二酮)。
NCO含量: 25.0%
单体HDI: <0.03%
粘度(23℃): 28 mPas。
根据凝胶渗透色谱研究 (GPC),存在以下组成:
HDI 脲二酮 (n = 2): 99.2% (根据GPC)
HDI异氰脲酸酯(n = 3): 0.4% (根据GPC)
更高级的低聚物: 0.4% (根据GPC)。
双(6-异氰酸根合己基)脲二酮的二甲基氨基甲酸酯的制备
将 10 g (0.0595 val)的上述 HDI 脲二酮溶于 30 ml二氯甲烷中,与2 g(0.0625 mol)甲醇混合,并在 40℃ 下在干燥氮气下搅拌,直到8 小时后 IR 光谱不再检测到异氰酸酯。然后借助于旋转蒸发器除去二氯甲烷和过量的甲醇。存在双(6-异氰酸根合己基)脲二酮(HDI-UD1)的二甲基氨基甲酸酯,为无色固体。IR 光谱不再存在游离异氰酸酯基团(在 2270 cm-1处没有异氰酸酯吸收带)。
脲二酮基团含量: 21.0% (作为C2N2O2计算,分子量84)。
制备HDI聚脲二酮(HDI-UD2)
将 1000 g (5.95 val)上述理想的双(6-异氰酸根合己基)脲二酮 (NCO含量:25.0%)溶解在 800 g乙酸丁酯中,与4.6 g (0.2重量%) 二月桂酸二丁基锡(DBTL)在乙酸丁酯中的10%的溶液混合,并在干燥氮气和搅拌下加热至60℃。在2小时内将347.5 g (4.76val)的2,2,4-三甲基戊烷-1,3-二醇和154.7 g (1.19 val)的2-乙基-1-己醇的混合物滴加到该溶液中。在 60℃下48小时的搅拌时间后,NCO 含量 < 0.1%。获得了几乎无色的 HDI聚脲二酮交联剂 (HDI-UD2)的溶液。
NCO含量: < 0.1%
脲二酮基团含量: 10.8% (作为C2N2O2计算, 分子量84)
脲二酮官能度: 5 (计算的)
固体含量: 约65%
粘度(23℃): 1400 mPas。
制备PDI 脲二酮模型化合物(PDI-UD1)
1,3-双(5-异氰酸根合戊基)-1,3-二氮杂环丁烷-2,4-二酮的制备
根据EP-A 0 789 017的实施例1中描述的方法,通过三丁基膦催化的 1,5-二异氰酸根合戊烷 (PDI) 而不是 1,6-二异氰酸根合己烷 (HDI) 的低聚和随后的蒸馏后处理制备了1,3-双(5-异氰酸根合戊基)-1,3-二氮杂环丁烷-2,4-二酮(理想的双(5-异氰酸根合戊基)脲二酮)。
NCO含量: 27.3%
单体PDI: 0.03%
粘度(23℃): 22 mPas。
根据凝胶渗透色谱研究 (GPC),存在以下组成:
HDI 脲二酮 (n = 2): 98.7% (根据GPC)
HDI异氰脲酸酯(n = 3): 0.7% (根据GPC)
更高级的低聚物: 0.6% (根据GPC)。
制备双(5-异氰酸根合戊基)脲二酮(PDI-UD1)的二甲基氨基甲酸酯
将10 g (0.065 val)上述 PDI 脲二酮溶于30 ml二氯甲烷中,与2 g (0.068mol)甲醇混合,并在 40℃下在干燥氮气下搅拌,直到8 小时后 IR 光谱不再检测到异氰酸酯。然后借助于旋转蒸发器除去二氯甲烷和过量的甲醇。存在双(5-异氰酸根合戊基)脲二酮(PDI-UD1)的二甲基氨基甲酸酯,为无色固体。IR 光谱表明不再存在游离异氰酸酯基团(在 2270 cm-1处没有异氰酸酯吸收带)。
脲二酮基团含量: 22.3% (作为C2N2O2计算, 分子量84)。
催化剂
1-乙基-3-甲基咪唑鎓乙酸盐 (97%), Sigma-Aldrich Chemie GmbH, 慕尼黑,DE
1-乙基-3-甲基咪唑鎓-(L)-(+)乳酸盐 (≥95%), Sigma-Aldrich Chemie GmbH,慕尼黑, DE
1-乙基-3-甲基咪唑鎓-2-甲酸盐, 根据Chem. Eur. J. 2016, 22, 16292 –16303中记载的方法来制备
1-乙基-3-甲基咪唑鎓碳酸氢盐 (96%), Alfa Chemistry, New York, USA。
实施例1:
在经烘箱干燥且耐压的反应小瓶中,将 70 mg (0.40 mmol) 1-乙基-3-甲基咪唑鎓乙酸盐与 800.0 mg (2.00 mmol) HDI 脲二酮模型化合物 (HDI-UD1) 一起溶解在10.0 ml无水四氢呋喃 (THF)中。关闭反应容器,然后在80℃搅拌1小时。在高真空中除去溶剂后,将残余物在30mL水和50mL乙酸乙酯之间振摇。分离出水相并在每种情况下用50ml乙酸乙酯再萃取3次。合并的有机相用100ml饱和NaCl溶液洗涤,经MgSO4干燥,过滤并在真空下除去溶剂。以定量收率(800mg)获得白色固体作为产物,根据13C NMR,其为三(6-异氰酸根合己基)异氰脲酸酯的三甲基氨基甲酸酯。不再能检测到脲二酮信号。原位IR 测量表明在反应的任何时间点都不存在游离异氰酸酯基团。
实施例2:
在经烘箱干燥且耐压的反应小瓶中,将 8.4 mg (0.04 mmol) 1-乙基-3-甲基咪唑鎓-(L)-(+) 乳酸盐与80.0 mg (0.20 mmol) HDI 脲二酮模型化合物 (HDI-UD1) 一起溶解在 1.0 ml 无水四氢呋喃 (THF) 中。关闭反应容器,然后在80℃搅拌1小时。在高真空下除去溶剂后获得淡黄色油作为产物,根据13C NMR,其为三(6-异氰酸根合己基)异氰脲酸酯的三甲基氨基甲酸酯。不再检测到脲二酮信号。原位IR 测量表明在反应的任何时间点都不存在游离异氰酸酯基团。
实施例3:
在经烘箱干燥且耐压的反应小瓶中,将6.16 mg (0.04 mmol)的1-乙基-3-甲基咪唑鎓-2-甲酸盐与80.0 mg (0.20 mmol)的HDI脲二酮模型化合物(HDI-UD1)一起溶解在1.0ml 无水四氢呋喃 (THF)中。 关闭反应容器,然后在80℃搅拌1小时。在高真空下除去溶剂后获得淡黄色油作为产物,根据13C NMR,其为三(6-异氰酸根合己基)异氰脲酸酯的三甲基氨基甲酸酯。不再能检测到脲二酮信号。原位IR 测量表明在反应的任何时间点都不存在游离异氰酸酯基团。
实施例4:
在经烘箱干燥且耐压的反应小瓶中,将71.7 mg (0.40 mmol)的1-乙基-3-甲基咪唑鎓碳酸氢盐与800 mg (2.00 mmol)的HDI脲二酮模型化合物(HDI-UD1)一起溶解在10 ml无水四氢呋喃 (THF)中。关闭反应容器,然后在80℃搅拌1小时。然后在高真空下除去溶剂,将得到的粗产物根据实施例1中描述的方法进行后处理。以定量收率(800mg)获得白色固体作为产物,根据13C NMR,其为三(6-异氰酸根合己基)异氰脲酸酯的三甲基氨基甲酸酯。不再能检测到脲二酮信号。原位IR 测量表明在反应的任何时间点都不存在游离异氰酸酯基团。
实施例5:
在经烘箱干燥且耐压的反应小瓶中,将6.16 mg (0.04 mmol)的1-乙基-3-甲基咪唑鎓-2-甲酸盐与80.0 mg (0.20 mmol)的HDI脲二酮模型化合物(HDI-UD1)一起溶解在1.0ml 无水四氢呋喃 (THF)中。关闭反应容器,然后在80℃搅拌1小时。在高真空下除去溶剂后获得淡黄色油作为产物,根据13C NMR,其为三(6-异氰酸根合己基)异氰脲酸酯的三甲基氨基甲酸酯。不再能检测到脲二酮信号。原位IR 测量表明在反应的任何时间点都不存在游离异氰酸酯基团。
实施例6:
在经烘箱干燥且耐压的反应小瓶中,将0.05 g (0.3 mmol)的1-乙基-3-甲基咪唑鎓乙酸盐与0.53 g (1.4 mmol) 的PDI脲二酮模型化合物(PDI-UD1)一起溶解在10.6 ml无水四氢呋喃 (THF)中。关闭反应容器,然后在80℃搅拌1小时。在高真空下除去溶剂后获得浅黄色油作为产物,根据13C NMR,其为三(5-异氰酸根合戊基)异氰脲酸酯的三甲基氨基甲酸酯。不再能检测到脲二酮信号。原位IR 测量表明在反应的任何时间点都不存在游离异氰酸酯基团。
实施例7 (根据本发明的和对比):
将 100 g (0.128 val)HDI 聚脲二酮交联剂 (HDI-UD2) 在乙酸丁酯中的 65%的溶液与作为催化剂的 3 g (0.018 mol) 1-乙基-3-甲基咪唑鎓乙酸盐混合成涂层剂,借助于涂膜器(Lackhantel)以150μm的施加-层厚度施加到脱脂玻璃板上。
在室温下蒸发干燥15分钟后,将漆在100℃下固化40分钟。得到硬质的、弹性的和完全透明的涂层,其摆锤硬度为 135 秒,二甲苯耐受性为 1-2。
图 1示出了涂层剂在固化之前 (a)和之后 (b)的 IR 光谱(AU:吸收单位,WN:波数)。可以看到,除了氨基甲酸酯基团(c)之外初始存在的脲二酮基团(d)(在约1780cm-1处的带) 在固化的漆膜中完全消失。替代于此,在约1670 cm-1处出现异氰脲酸酯带(e)。没有检测到异氰酸酯基团(在约2270 cm-1处的带)。
Claims (15)
1.用于制备含异氰脲酸酯基团的化合物的方法,包括在组分B)的存在下组分A)的反应
A) 至少一种基本上不含异氰酸酯基团的具有至少一个脲二酮基团的组分,
B) 至少一种催化剂,其含有通式(I)和/或(II)的结构要素
其中
R1, R2, R3, R4, R5 和R6 彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,脂族、脂环族、芳脂族或芳族的具有1至18个碳原子的有机基团,其是取代或未取代的和/或在链中具有杂原子,其中所述基团还能够彼此任选地与另外的杂原子一起组合形成具有3至8个碳原子的环,该环能够任选地被进一步取代,其中
R3, R4, R5 和R6 也可以彼此独立地代表氢,和
R7 代表氢或羧酸根阴离子(COO-)。
2.根据权利要求1所述的方法,其特征在于,组分A)是能够通过单体异氰酸酯的低聚和/或通过异氰酸酯官能的含脲二酮基团的化合物与醇和/或胺的反应获得的加聚化合物。
3.根据权利要求2所述的方法,其特征在于,组分A)是基于PDI、HDI、IPDI、NBDI、XDI和/或H12-MDI的含脲二酮基团的化合物。
4.根据权利要求2所述的方法,其特征在于,组分A)是通过异氰酸酯官能的、含脲二酮基团的化合物与分子量范围为62至22000的至少双官能的多元醇和任选的一元醇在遵循异氰酸酯基团与异氰脲酸酯反应性基团的当量比为1.0: 0.9至0.5: 1的情况下反应获得的加聚化合物。
5.根据权利要求1至4中任一项所述的方法,其特征在于,组分B)是通式(I)和/或(II)的化合物,其中
R1 和R2 彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,脂族、脂环族、芳脂族或芳族的具有1至12个碳原子的有机基团,所述有机基团是取代或未取代的和/或在链中具有杂原子,
R3, R4, R5 和R6 代表氢,和其中
R7 代表氢或羧酸根阴离子(COO-)。
6.根据权利要求1至5中任一项所述的方法,其特征在于,组分B)是通式(I)和/或(II)的化合物,其中
R1和R2 彼此独立地代表相同或不同的基团,其表示饱和或不饱和的,直链或支链的,具有1至12个碳原子的脂族有机基团,
R3, R4, R5 和R6 代表氢,和
R7 代表氢或羧酸根阴离子(COO-)。
7.根据权利要求1至6中任一项所述的方法,其特征在于,催化剂B)是通式(I)的咪唑鎓盐,其中R7代表羧酸根阴离子。
8.根据权利要求1至6中任一项所述的方法,其特征在于,催化剂B)是1,3-二甲基咪唑鎓-2-甲酸盐、1-乙基-3-甲基咪唑鎓-2-甲酸盐、1-乙基-3-甲基咪唑鎓乙酸盐、1-丁基-3-甲基咪唑鎓-2-甲酸盐和/或1-丁基-3-甲基咪唑鎓乙酸盐。
9.根据权利要求1至8中任一项所述的方法,其特征在于,基于组分A)和B)的总重量计,组分B)以0.001至15重量%的量存在,不包括任选存在于这些组分中的溶剂、助剂或添加剂。
10.组合物,其包含至少一种能通过异氰酸酯官能的含脲二酮基团的化合物与醇和/或胺的反应获得的基本上不含异氰酸酯基团的加聚化合物A)和至少一种包含根据权利要求1、5至8中任一项所述的通式(I)和/或(II)的结构要素的具有咪唑鎓-或咪唑啉鎓结构的催化剂B)以及任选的其他助剂和添加剂。
11.根据权利要求10所述的组合物用于制备聚氨酯塑料或涂层剂的用途。
12.聚氨酯塑料,其能够由任选在热作用下固化的根据权利要求10所述的组合物获得或由任选在热作用下固化的根据权利要求10所述的组合物获得。
13.成型体,其由根据权利要求12所述的聚氨酯塑料制成。
14.包含根据权利要求10所述的组合物的涂层剂。
15.涂覆有在热作用下固化的根据权利要求14所述的涂层剂的基材。
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US (1) | US20220348708A1 (zh) |
EP (2) | EP3763792A1 (zh) |
CN (1) | CN114072441A (zh) |
WO (1) | WO2021004978A1 (zh) |
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- 2020-07-06 US US17/624,883 patent/US20220348708A1/en not_active Abandoned
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Also Published As
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WO2021004978A1 (de) | 2021-01-14 |
EP3763792A1 (de) | 2021-01-13 |
EP3997183A1 (de) | 2022-05-18 |
US20220348708A1 (en) | 2022-11-03 |
EP3997183B1 (de) | 2023-10-04 |
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