CN104662061A - 贮藏稳定的亲水性多异氰酸酯 - Google Patents
贮藏稳定的亲水性多异氰酸酯 Download PDFInfo
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- CN104662061A CN104662061A CN201380051230.4A CN201380051230A CN104662061A CN 104662061 A CN104662061 A CN 104662061A CN 201380051230 A CN201380051230 A CN 201380051230A CN 104662061 A CN104662061 A CN 104662061A
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- Prior art keywords
- agent
- polyisocyanates
- water
- composition
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- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 76
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 76
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- 239000011230 binding agent Substances 0.000 claims abstract description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 8
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- 239000002253 acid Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 11
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 10
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- 239000002585 base Substances 0.000 description 5
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
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- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
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Abstract
本发明涉及新型的在水中可分散的亲水性多异氰酸酯和多异氰酸酯混合物、其制备方法、包含本发明亲水性多异氰酸酯的组合物及其作为制备聚氨酯-塑料时的起始组分的用途,特别是作为用于水溶性或者可水分散的具有相对于异氰酸酯基团的可反应基团的漆料-、胶粘剂-、密封剂粘合剂或者粘合剂组分的交联剂的用途。
Description
本发明涉及新型的在水中可分散的亲水性多异氰酸酯和多异氰酸酯混合物、其制备方法、包含本发明的亲水性多异氰酸酯的组合物及其作为制备聚氨酯-塑料时的起始组分的用途,特别是作为用于水溶性或者可水分散的具有相对于异氰酸酯基团的可反应基团的漆料-、胶粘剂-、密封剂粘合剂或者粘合剂组分的交联剂的用途。
基于日益更严格的环境立法的背景,可水分散的多异氰酸酯近年来对于多种应用领域变得重要。其如今尤其用作高质量的可水稀释的二组分-聚氨酯-漆料(2K-PUR-漆料)的交联剂组分或者用作水性的分散体胶粘剂的添加剂。其用于纺织设备或皮革设备、或者不含甲醛的纺织印刷油墨中的水性分散体的交联,并且此外还适合例如用作纸张的湿增强助剂,例如公开于EP 0 959 087中。
对于制备可水分散的亲水性多异氰酸酯,多种不同方法是已知的,在此尤其实现离子改性。EP-A 0 443 138、E-A 0 510 438和EP-A 0 548 669例如描述了含有化学相连的羧基的多异氰酸酯混合物。
这样的多异氰酸酯虽然可以在中和羧基之后非常细分地搅拌到水性体系中,而不需要高的剪切力,但是其尤其以中和的形式具有完全不够的贮藏稳定性。
EP 0 703 255 B2描述了离子亲水化的可水乳化的多异氰酸酯,其具有来自与2-羟基乙磺酸或者3-羟基丙磺酸的反应的反应产物作为乳化剂。然而,这些亲水剂同样具有一系列缺点。例如,羟基丙磺酸处于与其酸酐的平衡中,其是归为致癌的1,3-丙磺内酯。因此尤其在工业大规模生产中,其仅能够以水溶液的形式使用,并且因此原则上不适合作为制备改性的多异氰酸酯的合成组分。此外,EP 0 703 255 B2未作出关于由该亲水性多异氰酸酯制备的乳状液的稳定性和加工窗口(“贮存期”)的陈述。
EP 1 287 052 B1公开了改性的多异氰酸酯,其可以通过在合适的中和剂的存在下使多异氰酸酯与 2-(环己基氨基)乙磺酸和/或3-(环己基氨基)-丙磺酸反应来获得,其中获得贮藏稳定、浅色的产物。然而对于贮藏稳定性仅公开了,可以由所述亲水性改性的多异氰酸酯获得的水性乳状液在5小时的放置时间之后仍是完全稳定的。其既不显示可见的CO2-产生,也不显示沉淀或者沉淀物。然而,未作出关于该体系在5小时之后的实际的NCO-含量和反应性的陈述。
事实上如今为了主要多数的应用,仅使用非离子的借助聚醚亲水性改性的多异氰酸酯。这样的可水分散的多异氰酸酯的制备例如详细讨论于EP 0 959 087、EP 0 206 059和EP
0 540 985中。尽管其广泛用于最不同的应用,但是用非离子的聚醚改性的多异氰酸酯具有一系列原则上的缺点。其通常在分散期间仅能够通过使用巨大的剪切力来均匀地加入到水性介质中。尤其在用作水性2K-PUR-漆料中的交联剂的情况下,为了足够的可分散性而所需的高的聚醚含量还赋予所获得的涂料持久的亲水性。此外,这样改性的多异氰酸酯具有在水性乳状液中的过小的稳定性(“贮存期”),虽然在此期间它维持其完全的NCO-活性和反应性。因此,能够在其中加工所述亲水性多异氰酸酯的时间段也是受限的。
因此希望的是,既可以容易地加入到水中的,也具有高的贮存期的亲水性多异氰酸酯。
上述的符合现有技术的基于外部封端的多异氰酸酯的1K-焙烤体系的缺点是,在焙烤时消去各个封端剂。
因此本发明的目的是,提供新的可水分散的多异氰酸酯,其在不使用外部乳化剂或者不使用高的剪切力的情况下能够使用,并且不含有外部封端剂。该新的多异氰酸酯尤其应产生具有长的放置时间(“贮存期”)和加工时间的水性乳状液或者分散体,并且同时在整个放置时间内维持异氰酸酯基团的完全的反应性。不含有催化剂的分散体或者乳状液的放置时间在50℃下应为至少8周,优选至少12周,在此不允许潜在的NCO-含量下降多于30%,基于起始值计。
令人惊奇地发现了,所述目的可以通过具有特别的内部乳化剂的含脲二酮的改性多异氰酸酯实现。
本发明的主题是在水中可分散的亲水性的含脲二酮的多异氰酸酯和多异氰酸酯混合物、其制备方法、包含本发明的亲水性多异氰酸酯的组合物及其作为制备聚氨酯-塑料时的起始组分的用途,特别是作为用于水溶性或者可水分散的具有相对于异氰酸酯基团的可反应基团的漆料粘合剂或者漆料粘合剂组分的交联剂的用途。
为了简化本发明的描述,以下的术语“多异氰酸酯”也同义地表示不同的多异氰酸酯的混合物。
在本发明的意义上,“可水分散”是指,该亲水性的可水分散的多异氰酸酯与水接触,在24小时内形成流体,其在无视觉辅助器的情况下不能够用肉眼辨认出固体颗粒。为了检验聚合物是否是可水分散的,将100 mg的聚合物以100
µm厚的薄膜的形式放入100
ml水(20℃)中,并且在商业常见的振荡台上振荡24小时。如果振荡之后不能再辨认出固体颗粒,但是该流体是混浊的,那么该聚合物是可水分散的,在无混浊的情况下称为“水溶性的”。
制备亲水性多异氰酸酯C的本发明方法包括使带有脲二酮基团的预聚物A与至少一种乳化剂B反应,其中乳化剂B包含至少一个离子基团,其在酸性离子基团的情况中在水中在室温下具有>8,优选>10,和非常特别优选>12的pKa值,或者在碱性离子基团的情况中在室温下具有>8,优选>10,和非常特别优选>12的pKb值。
含有脲二酮基团的多异氰酸酯是众所周知的,并且例如描述于US 4,476,054、US
4,912,210、US 4,929,724以及EP 417 603中。J. Prakt. Chem. 336 (1994)
185–200提供了关于工业上重要的异氰酸酯二聚为脲二酮的方法的全面概述。
以下经验通常是占优势的,即引入到水中的具有脲二酮基团的物质在数天之后就已经在NCO-含量方面明显分解了。例如,最简单形式的亲水化,接合聚醚基团导致在水中是不稳定的产物。
例如在DE-A
25 38 484中描述了单组分-分散体,其中首先由羟基-官能的聚酯和多异氰酸酯制备预聚物,其与30至70当量%的二胺或者二元醇反应,随后亲水化,并且然后分散。作为多异氰酸酯,使用异佛尔酮二异氰酸酯的脲二酮,任选地以与异佛尔酮二异氰酸酯与其三聚体的混合物的形式,其中在该1K-体系中,在两个嵌入(verkappen)脲二酮中的异氰酸酯-基团上各出现一个羟基,其中该羟基在分散期间或者之后添入。亲水化的多异氰酸酯的特点在于在水中非常受限的稳定性。
在DE
10 2005 036654中要求保护聚氨酯-分散体,其在相同分子中具有脲二酮-基团和相对于异氰酸酯基团的反应性基团。由此除了聚氨酯分子之间的交联以外,称为“内穿网络”的聚合物中的交联也是可能的。该无消去的水性的聚氨酯固化剂在水中也仅是非常受限地贮藏稳定的。
根据本发明,异氰酸酯至脲二酮的反应优选地在可溶的二聚催化剂,例如二烷基氨基吡啶、三烷基膦、膦酸三酰胺或者咪唑的存在下进行。该反应任选地在溶剂中,但是优选地在不存在溶剂的情况下实施。其可以在达到所希望的转化率时通过加入催化剂毒物来停止,但是这不是强制必须的。过量的单体异氰酸酯随后通过短程蒸发来分离。如果该催化剂是足够挥发性的,能够使反应混合物在单体分离的期间不含催化剂。在该情况下,可以放弃加入催化剂毒物。
根据本发明,多种异氰酸酯是对于制备含有脲二酮的多异氰酸酯而言合适的。合适的异氰酸酯优选地选自异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)、2,2'-二环己基甲烷二异氰酸酯(2,2'-H12MDI)、2,4'-二环己基甲烷二异氰酸酯(2,4'-H12MDI)、4,4'-二环己基甲烷二异氰酸酯(4,4'-H12MDI)、2-甲基戊烷二异氰酸酯(MPDI)、2,2,4-三甲基六亚甲基二异氰酸酯(2,2,4-TMDI)、2,4,4-三甲基六亚甲基二异氰酸酯(2,4,4-TMDI)、降冰片烷二异氰酸酯(NBDI)、亚甲基二苯基二异氰酸酯(MDI)、甲苯胺二异氰酸酯(TDI)、四甲基亚二甲苯基二异氰酸酯(TMXDI)及其混合物。在一个优选的实施方案中,该异氰酸酯是IPDI和/或4,4'-H12MDI和/或HDI。
带有脲二酮基团的多异氰酸酯至具有脲二酮基团的预聚物A的反应,包括使游离的NCO-基团与含羟基的单体、低聚和/或聚合的化合物反应。该含羟基的化合物优选地选自聚酯、聚硫醚、聚醚、聚己内酰胺、聚环氧化物、聚酯酰胺、聚氨酯、低分子量的二元醇、低分子量的三元醇、低分子量的四元醇和一元醇。低分子量的二元醇、三元醇和/或四元醇是适合作为增链剂的。作为链终止剂,可以使用例如描述于EP 669353、EP 669354、DE 3030572、EP 639598或者EP 803524中的一元胺和/或一元醇。
优选地使用具有30至250 mg KOH/g的OH-值和300至6000 g/mol的平均分子量的聚酯;或者单体二元醇,例如乙二醇、丙烷-(1,2)-二醇和丙烷-(1,3)-二醇、2,2-二甲基丙烷-(1,3)-二醇、丁烷-(1,4)-二醇、己烷-(1,6)-二醇、2-甲基戊烷-1,5-二醇、2,2,4-三甲基己烷-(1,6)-二醇、2,4,4-三甲基己烷-(1,6)-二醇、庚烷-(1,7)-二醇、十二烷-(1,12)-二醇、十八-9,10-烯-(1,12)-二醇、硫二甘醇、十八烷-(1,18)-二醇、2,4-二甲基-2-丙基庚烷-(1,3)-二醇、二乙二醇、三乙二醇、四乙二醇、反式-和顺式-1,4-环己烷二甲醇。
优选的具有脲二酮的预聚物A具有至少0.2,但是不多于20重量%的游离的NCO-含量,基于该预聚物的总重量计,并且具有0.5至25重量%,优选2至20重量%的脲二酮基团含量(计算为C2N2O2,分子量84),基于该预聚物的总重量计。NCO-含量优选为1.5至14重量%,基于该预聚物的总重量计。
除了脲二酮基团以外,预聚物A还具有异氰脲酸酯-、缩二脲-、脲基甲酸酯-、氨基甲酸酯-和/或脲-结构。
乳化剂B包含一个或者多个离子基团,优选地包含一个离子基团。离子基团优选地选自磺酸盐和磷酸盐。
在一个优选的实施方案中,乳化剂B的离子基团是在水中主要中性反应的残基。在酸性离子基团的情况中,其在水中在室温下具有>8的pKa-值,或者在碱性离子基团的情况中,在室温下具有>8的pKb-值。
乳化剂B可以具有一个或者多个OH-、NH-或者NH2-基团、或者其它的相对于异氰酸酯的反应性基团。数均分子量(Mn)优选为<1000和非常特别优选为<500。
乳化剂B优选为至少一种选自羟基烷基磺酸、羟基聚醚磺酸、氨基烷基磺酸和氨基聚醚磺酸的磺酸。优选的羟基烷基磺酸是2-羟基乙磺酸和3-羟基丙磺酸。优选的氨基烷基磺酸是2-(环己基氨基)乙磺酸和3-(环己基氨基)丙磺酸。特别优选的乳化剂B是含有氨基的磺酸盐。
在另一个实施方案中,乳化剂B为至少一种磷酸盐。
用于乳化剂B的含酸基团的离子基团的合适中和剂,选自碱金属氢氧化物和碱土金属氢氧化物。
将含脲二酮的预聚物A和乳化剂B在有或者无溶剂的情况下混合,并且然后在合适的温度下使其反应。该溶剂优选地选自水、丙酮、二甲基甲酰胺、N-甲基吡咯烷酮、乙酸乙酯、四氢呋喃和二氧杂环己烷。该溶剂优选为水。
制备亲水性多异氰酸酯的本发明方法可以任选地在合适的相对于异氰酸酯基团的惰性溶剂中实施。合适的溶剂例如为本身已知的常见漆料溶剂,例如乙酸甲氧基丙酯、乙酸丁酯、含烃类的芳族混合物(来自ExxonMobil的SolvessoR)和二甲苯。
含氨基的乳化剂在室温下就反应并产生热,而对于含羟基的乳化剂,任选地在使用文献已知的催化剂,例如二月桂酸二丁基锡(DBTL)的情况下,建议设定40至100 ℃的反应温度。
A中游离NCO-基团与B中NCO-反应性基团的比例,在其反应之前优选为2:1至1:2,特别优选为1.1:1至1:1.1。在反应之后,亲水性多异氰酸酯C的游离NCO-含量优选为< 2%,特别优选为< 1%。
本发明的主题为包含来自A与B的反应的产物C的反应性组合物。
产物C为亲水性多异氰酸酯,其以下也称为固化剂C。优选地,本发明的反应性组合物为水性组合物。
可以将亲水性多异氰酸酯C在有或者无助溶剂的情况下,根据已知方法引入到水中,以在此处形成分散体、悬浮体、乳状液或者溶液。本发明的组合物在50℃下至少8周、优选至少12周是稳定的,即亲水性多异氰酸酯C在50℃下8周或者12周之后,还显示相对于起始混合物的可比的反应性。
任选地,可以在乳化之前向根据本发明方法制备的多异氰酸酯中还加入其它的非亲水化的多异氰酸酯,特别是漆料多异氰酸酯,例如IPDI、HDI、TMDI、H12MDI,及其衍生物,例如三聚体、脲基甲酸酯和缩二脲等。
本发明的组合物可以优选地进一步包含以下物质:
D)在水中可溶、可乳化或者可分散的含羟基的用于亲水性多异氰酸酯C(固化剂)的反应物,和
E)任选的助剂和附加剂,
F)任选的催化剂F。
水溶性、在水中可乳化或者在水中可分散的含羟基的组分D在文献中是已知的。对于组分D,其可以为单体、低聚和/或聚合的化合物。聚合的化合物优选地选自聚醚、聚酯、聚碳酸酯、聚醇酸树脂、聚丙烯酸酯、聚氨酯和聚己内酯。该聚合的化合物可以借助外部或者内部的乳化剂改性,以使其变得水溶性、可乳化或者可分散。单体和低聚的化合物优选地选自单体的二元醇、三元醇、四元醇、二胺、三胺和四胺。
作为用于组分D的内部乳化剂,优选地考虑离子或者非离子的结构单元。离子结构单元由酸或者碱组成,其还可以含有反应性基团,和借助单体的碱(例如三乙胺)或者酸(例如乙酸)来中和。非离子的乳化剂通常含有较长或者较短的聚醚单元。这样的产物D是文献已知和市场可购的,并且例如描述于DE-A 25 38 484、DE 102005036654中、或者Stoye,Freitag,“Lackharze”,Carl Hanser Verlag,München Wien,1996、或者Meyer-Westhues,“Polyurethane",Vincentz Network Verlag,Hannover,2007中。
制备具有内部乳化剂的树脂D的可能性是,使合适的醇组分与由二羟甲基丙酸和二异氰酸酯或者多异氰酸酯构成的混合物在40至100℃下,优选地在有机溶剂中,例如丙酮、乙酸乙酯、二甲基甲酰胺或者N-甲基吡咯烷酮中反应。任选地去除该有机溶剂。在分离该溶剂之前或者之后加入中和剂,例如三乙胺,并且将反应产物引入水中。
作为任选的组分E,可以加入0.05至5重量%的总量的常见添加剂,例如流平剂,例如聚硅酮或者丙烯酸酯;光稳定剂,例如立***阻的胺;或者例如描述于EP 0 669 353中的其它助剂,例如稳定剂、脱气剂、乳化助剂和分散添加剂,基于所述组合物的总重量计。填料和颜料,例如二氧化钛可以以最高50重量%的量加入到整个组合物中。优选为在漆料领域中常见的助剂和添加剂,例如流平剂、着色颜料、填料、消光剂和外部乳化剂。
有机溶剂是适合作为助剂E的。不与其它内容物反应的液体物质,可以加入到本发明的水性组合物中,例如乙酸乙酯、乙酸丁酯、乙二醇单甲醚乙酸酯、乙二醇单***乙酸酯、1-甲氧基丙基-2-乙酸酯、乙酸-3-甲氧基-正丁酯、丙酮、2-丁酮、4-甲基-2-戊酮、环己酮、甲苯、二甲苯、氯苯、溶剂油,例如以名称溶剂石脑油、Solvesso®、Isopar®、Nappar®(Deutsche EXXON CHEMICAL
GmbH)和Shellsol®(Deutsche Shell Chemie GmbH)购得的更高程度取代的芳族化合物,例如碳酸二甲酯、碳酸二乙酯、1,2-碳酸亚乙酯和1,2-碳酸亚丙酯的碳酸酯,例如丙内酯、丁内酯、己内酯和甲基己内酯的内酯,但是还例如丙二醇二乙酸酯、二乙二醇二甲醚、二丙二醇二甲醚、二乙二醇***乙酸酯、二乙二醇丁醚乙酸酯、N-甲基吡咯烷酮和N-甲基己内酰胺或者这些溶剂的任意的混合物。
这些溶剂优选地仅用作助溶剂,并且相比于主溶剂水而言仅占较小的比例。水:助溶剂的体积比优选为大于2:1,并且优选为100:1至10:1。
在一个优选的实施方案中为了制备本发明的组合物,将含脲二酮的水性固化剂C与水性树脂D混合,并且任选地加入其它助剂组分和附加组分E。在另一个实施方案中为了制备本发明的组合物,将非水性的组分C和/或D和任选的E中的一种或者多种,加入到水性组分C和/或D和任选的E之一中。在另一个实施方案中为了制备本发明的组合物,将所有的非水性的组分C、D和任选的E相继或者同时地加入到水中。
本发明的组合物在50℃下至少8周,优选在12周之后是稳定的,即其在50℃下8周或者12周之后还显示与起始混合物基本上相同的反应性。本发明的水性组合物的潜在的NCO-损失,在50℃下8周,优选在50℃下12周的贮藏之后为最高30%,基于起始值计。这些值适用于不具有用于提高反应性的催化剂F的组合物。
除了C、D和任选的E以外,本发明的组合物还包含催化剂或者催化剂混合物F(以下为催化剂F)。
将催化剂F加入到所述组合物中,以提高脲二酮-基团的反应性,并且其特别地对于粉末漆料而言是已知的。
合适的催化剂F优选为F1和/或F2,
其中F1选自金属乙酰丙酮化物和捕获酸的组分,其中金属乙酰丙酮化物优选为乙酰丙酮锌,任选地以与四烷基铵-卤化物或者四烷基鏻-卤化物的组合的形式,并且捕获酸的组分例如为环氧化物、碳二亚胺、氮杂环丙烷、噁唑啉或者羟基烷基酰胺,和
其中F2选自四烷基铵氢氧化物、四烷基鏻氢氧化物和羧酸盐,任选地以与环氧化物的组合的形式。F2优选为羧酸四烷基铵,特别优选为苯甲酸四烷基铵。
为了调节F的反应性,可以将一元酸、二元酸或者多元酸,优选羧酸,例如草酸加入到反应混合物中。
也可以使用常见的从聚氨酯化学中已知的催化剂,例如叔胺,例如三乙胺、吡啶、甲基吡啶、苄基二甲胺、N,N-桥亚乙基哌嗪、N-甲基哌啶、五甲基二亚乙基三胺、N,N-二甲基氨基环己烷、N,N'-二甲基哌嗪,或者金属盐,例如氯化铁(II)、三-(乙基乙酰乙酸)铝、氯化锌、正辛酸锌(II)、2-乙基-1-己酸锌(II)、2-乙基己酸锌(II)、硬脂酸锌(II)、环烷酸锌(II)、乙酰丙酮锌(II)、正辛酸锡(II)、2-乙基-1-己酸锡(II)、乙基己酸锡(II)、月桂酸锡(II)、软脂酸锡(II)、***(IV)、二氯化二丁基锡(IV)、二乙酸二丁基锡(IV)、二马来酸二丁基锡(IV)、二月桂酸二丁基锡(IV)、二乙酸二辛基锡(IV)、甘醇酸钼或者这些催化剂的任意的混合物。
可以在本发明的方法中以0.001至2重量%,优选0.005至0.5重量%的浓度使用催化剂F,基于反应物的总重量计。
相比于无F的变型而言,C、D和F以及任选的E的组合具有提高的反应性。但是,反应性以及贮藏稳定性取决于组分F的组成和浓度。但是,贮藏稳定性在室温(20℃)下为至少8周,优选为至少12周。相比于不含催化剂的组合物而言的较低的贮藏稳定性,由于催化剂提高反应性和因此减小贮藏稳定性而发生。尽管如此,具有催化剂的本发明组合物的贮藏稳定性始终仍高于同样含有催化剂的现有技术的比较产品。
本发明的另一主题是本发明的多异氰酸酯作为制备聚氨酯-塑料时的起始组分的用途,特别是作为用于水溶性或者可分散的漆料粘合剂或者漆料粘合剂组分的交联剂,在通过使用基于这种粘合剂或者粘合剂组分的水性涂敷剂来制造涂层时的用途。
最后,本发明的主题还是所述多异氰酸酯作为在制备可水分散或者在水中分散地存在的经封端的多异氰酸酯时的起始组分的用途。
本发明的多异氰酸酯为用于根据异氰酸酯-加聚方法制备聚氨酯-塑料的有价值的起始材料。
因此,本发明的主题还是涂层、胶合剂和密封剂,其通过使用包含至少一种本发明的多异氰酸酯的组合物来制备,及其制备方法。优选地,所述的至少一种多异氰酸酯借助本发明的方法制备。特别优选的是通过使用本发明的组合物制备的本发明的涂层、胶合剂和密封剂。
制备涂层、胶合剂或密封剂的方法包括,将包含至少一种本发明的多异氰酸酯和/或至少一种根据本发明制备的多异氰酸酯的组合物施加到基材上。施加的组合物可以包含如上所述的其它组分。
施加的组合物的固化和干燥,优选地在80℃至240℃的温度下实施30秒至一周的时间。特别优选地,该固化和干燥在120至200℃下实施5分钟至1小时的时间。
在一个实施方案中,本发明的涂层、胶合剂和密封剂在100至240℃,优选120至200℃,特别优选140至180℃的合适的干燥之后具有良好的漆料技术性能。
作为在其上施加本发明组合物的基材,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、硬性和柔韧的塑料、纺织品、皮革和纸张,其在施加之前任选地还可以配有常见的底层。
除了作为用于水性1K-PUR-漆料的交联剂组分的有利用途以外,本发明的组合物极其适合作为用于水性的分散体胶粘剂、皮革涂层、纺织品涂层或者纺织品印刷糊料的交联剂,作为不含有机键合的卤素(不含AOX)的纸张助剂,或者还作为用于矿物质的建筑材料,例如混凝土物料或者灰浆物料的添加剂。
以下示例性地描述本发明的反应性的固化剂C和组合物、其制备方法及其用途,而不应将本发明限制于这些示例性的实施方案。
如果以下说明范围、通式或者化合物种类,那么这些应不仅包括明确提及的对应的范围或者化合物的组,也还包括所有的子范围和化合物的子组,其可以通过取出单个值(范围)或者化合物来获得。如果在本说明书的范围内引用文件,那么其内容应完全附属于本发明的公开内容中。
以下的实施例应进一步阐述本发明。示例性地描述本发明,而不应将从整个说明书和权利要求中得出其应用范围的本发明限制于在实施例中提及的实施方案。
实施例
实施例a
制备中性的非离子稳定化的脲二酮(不根据本发明)
将223.9 g IPDI-脲二酮(参见实施例c1)与300.9 g
Polyglycol M350(聚乙二醇单甲醚,Clariant)和0.3 g二月桂酸二丁基锡(Aldrich)溶于250 ml丙酮中。在15小时的回流之后冷却。向250 g的该产物中在Dispermat的剧烈搅拌(3000转/分钟)下加入262.5 g去矿物质水。在60℃ 和40 mbar下在旋转蒸发器上去除丙酮,并且此后将产物用50 µm的滤器过滤。潜在的NCO-含量为4.59%,固体约为46%,并且粘度为200 mPas。
该水性的分散体在20℃下8周之后具有3.0%的潜在的NCO-含量,并且在50℃下8周之后具有1.26%的潜在的NCO-含量。因此,含脲二酮的固化剂用聚醚的亲水化得不到贮藏稳定的水性分散体。
实施例b
制备非中性的离子稳定化的脲二酮(不根据本发明)
将307.6 g IPDI-脲二酮(参见实施例c1)溶于180 ml丙酮中,并且加入0.3 g二月桂酸二丁基锡(Aldrich)。小心地滴加112.4 g二甲基氨基丙胺(DMAPA,Aldrich),并且通过冷却将温度维持在低于 30℃。在1小时的二次反应时间之后,将200 g的该产物首先用23.8 g乙酸中和,并且此后在Dispermat的剧烈搅拌(3000转/分钟)下加入163.8 g去矿物质水。在60℃ 和40 mbar下在旋转蒸发器上去除丙酮,并且此后将产物用50 µm的滤器过滤。潜在的NCO-含量为0.55%(理论值4.17%),固体约为46%,并且粘度为200 mPas。该产物一开始就不具有期望的NCO-含量。因此,含脲二酮的固化剂用氨基烷基叔胺的亲水化得不到贮藏稳定的水性分散体。
实施例c
制备含脲二酮的固化剂C
c1) 由IPDI制备脲二酮-预聚物(不根据本发明)
根据DE 10 2005 036654的指示制备基于IPDI的脲二酮。向10 000 g(45.0 mol)异佛尔酮二异氰酸酯(Vestanat IPDI,Evonik)在室温下在干燥的氮气和搅拌下加入200 g(2%)4-二甲基氨基吡啶(DMAP)作为催化剂。在24小时之后,使具有对应于26.5%低聚度的27.2%NCO-含量的反应混合物不通过之前加入催化剂毒物,借助薄层蒸发器在160℃的温度和0.3 mbar的压力下而去除挥发性组分。得到了高粘性的黑黄色的脲二酮多异氰酸酯,其具有16.8%的游离的NCO-含量和0.3%的IPDI单体含量。在13C-NMR-光谱中不能确定异氰脲酸酯结构。
c2) 制备固化剂C(根据本发明)
将1050.6 g IPDI-脲二酮(来自制备指示c1)与95.5 g三羟甲基丙烷(Aldrich)和0.23 g DBTL(二月桂酸二丁基锡,Aldrich)溶于1.4 l丙酮中。在回流下搅拌一小时(游离的NCO-含量:3.64%)之后加入103 g 丁醇,并且在回流下再加热1.5小时,之后游离的NCO-含量为1.49%。在冷却之后,还逐滴地加入151 g Vestamin A95(经氢氧化钠中和的含胺的烷基磺酸盐,在水中50%,Evonik)作为内部乳化剂。在加入结束之后,再次加热至回流1.5小时,并且之后冷却产物。游离的NCO-含量为0.1%,游离的胺值为0.2%。
向650 g的该产物中在Dispermat的剧烈搅拌(3000转/分钟)下加入604 g去矿物质水。在60℃ 和40 mbar下在旋转蒸发器上去除丙酮,并且此后将产物用50 µm的滤器过滤。潜在的NCO-含量为4.5%,固体约为27%,并且粘度为163 mPas。
实施例d
制备基于水的树脂D(不根据本发明)
将829.5 g Vestanat H12MDI(二环己基亚甲基二异氰酸酯,Evonik)和169.4 g 二羟甲基丙酸(Aldrich)与0.5 g DBTL(二月桂酸二丁基锡,Aldrich)溶于1.1 l丙酮中。在回流下12小时之后冷却,并且加入57 g 1,4-丁二醇(Aldrich)、1363 g 氧基酯T1136(具有112的OH-值的液体羟基-聚酯,Evonik)、169 g三羟甲基丙烷(Aldrich)和0.8 g DBTL(二月桂酸二丁基锡,Aldrich)。在回流下继续搅拌18小时之后,NCO-含量降至0.1%。酸值为27,OH值为82,各自基于固体计。
将250 g的该产物用7.6 g二甲基氨基乙醇中和,并且加入8.2 g的10%的己二酸酰肼(Aldrich)在水中的溶液。之后在Dispermat的剧烈搅拌(3000转/分钟)下加入345 g去矿物质水。最后还加入一滴三乙胺。接着在60℃ 和40 mbar下在旋转蒸发器上去除丙酮,并且此后将产物用50 µm的滤器过滤。固体约为35%,并且粘度为190 mPas。
实施例e
贮藏稳定性和反应性
e1) 贮藏固化剂
将固化剂C(潜在的NCO-含量4.9%)在50℃下贮藏8周。经贮藏的变型此后简称为C(g)。固化剂C(g)显示了4.6%的潜在的NCO-含量。
e2) 贮藏混合物:70.4 g C + 29.6 g D
起始值
50℃下8周
NCO-含量
1.2%
0.9%
在180℃下固化30 min
Erichsen深冲[mm]
>
10
> 10
网格切割[0-5]
0
0
MEK-强度[DR]
>100
>100。
e3) 具有经贮藏的固化剂的混合物70.4 g C(g)+ 29.6 g D
在经贮藏的固化剂C与D混合之后,不再贮藏该混合物。因此,在此仅测量起始值。
具有经贮藏的固化剂C的值
NCO-含量
1.1%
在180℃下固化30 min
Erichsen深冲[mm]
> 10
网格切割[0-5]
0
MEK-强度[DR]
>100。
不取决于是否仅贮藏含脲二酮的固化剂(e3)或者整个混合物(e2),反应性在50℃下8周之后仍是足够的。
实施例f
经催化的体系
由于催化剂,经催化的体系具有相比于未催化的体系而言的较高的反应性,其在以上所述的实施例中测量。因此,其仍不是如此贮藏稳定的,但是在明显较低的温度下就固化,这对于某些应用而言是较有利的。因此,在130℃下固化30分钟之后,测量贮藏稳定性。
f1) 比较例
将163.2 g来自实施例c2)的固化剂C在搅拌下与15 g Voranol CP 450(含羟基的聚醚,Dow)、3.75 g Poly G 55-37 (含羟基的聚醚,Arch Chemicals)、5 g去矿物质水和2 g Byk 011(添加剂,Byk-Chemie)混合。此后,还加入0.4 g Byk 348和0.1 g Byk 333 (添加剂,Byk-Chemie)。
f2) 根据本发明的实施例
向混合物f1)中加入3.62 g 50%的苯甲酸四乙基铵-溶液(催化剂,Sachem)和4.8 g Polypox IE700 8W(活化剂,经亲水化的双酚A二环氧化物,UPPC,Dow)。
固化(130℃下30 min)
f1*
f2
摆撞硬度[s]
53
193
MEK-强度[DR]
1-2
> 100
* f1为比较例
f2的贮藏
起始值
室温下8周
摆撞硬度[s]
193
204
MEK-强度[DR]
>100
>100。
在室温下8周之后,在f2情况下的反应性仍未改变。
测量值如下确定:
Erichsen深冲根据DIN 53 156
球冲击根据ASTM
D 2794-93
摆撞硬度根据DIN
53 157
网格切割根据DIN
53 151
MEK强度:
甲基乙基酮-耐受性测试通过用在甲基乙基酮中浸渍的棉球在1 kg施重下的摩擦来进行,直至层溶解。在此计数双冲程(DR)。因此,>100的值意味着,在大于100个双冲程下,仍未观察到该层溶解。
Claims (15)
1.制备亲水性多异氰酸酯的方法,其包括使带有脲二酮基团的预聚物A与至少一种乳化剂B反应,其中乳化剂B包含至少一个离子基团,其在酸性离子基团的情况中在水中在室温下具有>8的pKa,或者在碱性离子基团的情况中在室温下具有>8的pKb值。
2.根据权利要求1的方法,其中乳化剂B是至少一种选自磺酸盐和磷酸盐的化合物。
3.根据权利要求1或者2的方法,其中乳化剂B是至少一种选自羟基烷基磺酸盐、羟基聚醚磺酸盐、氨基烷基磺酸盐和氨基聚醚磺酸盐的磺酸盐。
4.根据权利要求1至3任一项的方法,其进一步包括使带有脲二酮基团的多异氰酸酯与含羟基的单体、低聚和/或聚合的化合物反应,其中获得预聚物A,并且其中所述的含羟基的化合物优选地选自聚酯、聚硫醚、聚醚、聚己内酰胺、聚环氧化物、聚酯酰胺、聚氨酯、低分子量的二元醇、低分子量的三元醇、低分子量的四元醇和一元醇。
5.根据权利要求1至4任一项的方法,其中预聚物A具有0.2重量%至20重量%的游离的NCO-含量,基于预聚物A的总重量计,并且优选地具有0.5至25重量%的脲二酮基团含量,基于预聚物A的总重量计。
6.具有至少一个脲二酮基团的亲水性多异氰酸酯,其中所述多异氰酸酯包含至少一种内部乳化剂。
7.根据权利要求6的亲水性多异氰酸酯,其可以根据权利要求1至5任一项的方法制备。
8.组合物,其包含
C 至少一种根据权利要求6和7任一项的亲水性多异氰酸酯和/或至少一种根据权利要求1至5任一项的方法制备的亲水性多异氰酸酯和任选的水。
9.根据权利要求8的组合物,其进一步包含
D 在水中可溶、可乳化或者可分散的含羟基的用于所述亲水性多异氰酸酯C的反应物,和任选的
E 助剂和/或附加剂,和任选的
F 催化剂。
10.根据权利要求9的组合物,其中反应物D选自聚醚、聚酯、聚碳酸酯、聚醇酸树脂、聚丙烯酸酯、聚氨酯和聚己内酯。
11.根据权利要求6和7任一项的多异氰酸酯和/或根据权利要求1至5任一项的方法制备的多异氰酸酯用于制备聚氨酯-塑料的用途。
12.根据权利要求6和7任一项的多异氰酸酯和/或根据权利要求1至5任一项的方法制备的多异氰酸酯作为用于水溶性或者可水分散的具有相对于异氰酸酯基团的可反应基团的漆料粘合剂、胶粘剂粘合剂、密封剂粘合剂或者粘合剂组分的交联剂的用途。
13.根据权利要求8至10任一项的组合物用于制备聚氨酯-塑料的用途,特别是用于制备水溶性或者可水分散的具有相对于异氰酸酯基团的可反应基团的漆料粘合剂、胶粘剂粘合剂、密封剂粘合剂或者粘合剂组分的用途。
14.涂层、胶合剂或者密封剂,其通过使用包含根据权利要求6和7任一项的多异氰酸酯和/或根据权利要求1至5任一项的方法制备的多异氰酸酯的组合物来制备,优选地通过使用根据权利要求8至10任一项的组合物来制备。
15.制备涂层、胶合剂或者密封剂的方法,其包括施加包含根据权利要求6和7任一项的多异氰酸酯和/或根据权利要求1至5任一项的方法制备的多异氰酸酯的组合物,优选地通过使用根据权利要求8至10任一项的组合物。
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Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102014209183A1 (de) | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Reaktive Zusammensetzung aus einer Uretdiongruppen haltigen Dispersion und Polyaminen |
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EP4029892A1 (de) | 2021-01-13 | 2022-07-20 | Covestro Deutschland AG | Uretdiongruppen enthaltende zusammensetzungen |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006321839A (ja) * | 2005-05-17 | 2006-11-30 | Toyo Seikan Kaisha Ltd | 缶端シーリング材 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2538484C2 (de) | 1975-08-29 | 1985-02-07 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von lösungsmittelfreien, ausschließlich wäßrigen, thermisch vernetzbaren lagerstabilen Dispersionen von lichtstabilen Polyurethanen |
DE3030572A1 (de) | 1980-08-13 | 1982-03-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von uretdiongruppenhaltigen polyadditionsprodukten sowie die danach hergestellten produkte |
DE3030513A1 (de) | 1980-08-13 | 1982-03-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung eines isocyanuratfreien uretdions aus isophorondiisocyanat sowie das danach hergestellte uretdion |
DE3437635A1 (de) | 1984-10-13 | 1986-04-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von uretdiongruppen aufweisenden verbindungen, die nach diesem verfahren erhaeltlichen verbindungen und ihre verwendung bei der herstellung von polyurethankunststoffen |
DE3521618A1 (de) | 1985-06-15 | 1986-12-18 | Bayer Ag, 5090 Leverkusen | In wasser dispergierbare polyisocyanat-zubereitung und ihre verwendung als zusatzmittel fuer waessrige klebstoffe |
DE3739549C2 (de) | 1987-11-21 | 1994-10-27 | Huels Chemische Werke Ag | Verfahren zur Herstellung (cyclo)aliphatischer Uretdione |
DE3930669A1 (de) | 1989-09-14 | 1991-03-28 | Basf Ag | Verfahren zur herstellung von uretdiongruppen aufweisenden polyisocyanaten |
DE4001783A1 (de) | 1990-01-23 | 1991-07-25 | Bayer Ag | Polyisocyanatgemische, ein verfahren zu ihrer herstellung und ihre verwendung als bindemittel fuer ueberzugsmittel oder als reaktionspartner fuer gegenueber isocyanatgruppen oder carboxylgruppen reaktionsfaehige verbindungen |
DE4113160A1 (de) | 1991-04-23 | 1992-10-29 | Bayer Ag | Polyisocyanatgemische, ein verfahren zu ihrer herstellung und ihre verwendung |
DE4136618A1 (de) | 1991-11-07 | 1993-05-13 | Bayer Ag | Wasserdispergierbare polyisocyanatgemische |
DE4142275A1 (de) | 1991-12-20 | 1993-06-24 | Bayer Ag | Isocyanatocarbonsaeuren, ein verfahren zu ihrer herstellung und ihrer verwendung |
DE4327573A1 (de) | 1993-08-17 | 1995-02-23 | Bayer Ag | Uretdion-Pulverlackvernetzer mit niedriger Schmelzviskosität |
DE4406444A1 (de) | 1994-02-28 | 1995-08-31 | Huels Chemische Werke Ag | Hydroxyl- und uretdiongruppenhaltige Polyadditionsprodukte und Verfahren zu ihrer Herstellung sowie deren Verwendung zur Herstellung abspaltfreier Polyurethan-Pulverlacke hoher Reaktivität und die danach hergestellten Polyurethan-Pulverlacke |
DE4406445C2 (de) | 1994-02-28 | 2002-10-31 | Degussa | Verfahren zur Herstellung von uretdiongruppenhaltigen Polyadditionsprodukten und deren Verwendung in Polyurethan-Lacksystemen |
JP2959399B2 (ja) * | 1994-06-13 | 1999-10-06 | 日本ポリウレタン工業株式会社 | 自己乳化型ポリイソシアネート混合物、並びにこれを用いた水性塗料組成物および水性接着剤組成物 |
DE4433929A1 (de) | 1994-09-23 | 1996-03-28 | Basf Ag | Wasseremulgierbare Polyisocyanate |
DE19616496A1 (de) | 1996-04-25 | 1997-10-30 | Bayer Ag | Abspaltfreier Polyurethan-Pulverlack mit niedriger Einbrenntemperatur |
EP0959087B1 (de) | 1998-05-22 | 2003-10-15 | Bayer Aktiengesellschaft | Wasserdispergierbare Polyether-modifizierte Polyisocyanatgemische |
DE10024624A1 (de) | 2000-05-18 | 2001-11-22 | Bayer Ag | Modifizierte Polyisocyanate |
DE10140206A1 (de) * | 2001-08-16 | 2003-03-06 | Bayer Ag | Einkomponentige isocyanatvernetzende Zweiphasen-Systeme |
DE102004017005A1 (de) * | 2004-04-02 | 2005-10-20 | Bayer Materialscience Ag | Abspalterfreier Polyurethan-Pulverlack mit niedriger Einbrenntemperatur |
DE102005036654A1 (de) | 2005-08-04 | 2007-02-15 | Bayer Materialscience Ag | Selbstvernetzende PUR-Dispersionen mit Uretdionstruktur |
DE102010029235A1 (de) * | 2010-05-21 | 2011-11-24 | Evonik Degussa Gmbh | Hydrophile Polyisocyanate |
-
2012
- 2012-10-04 DE DE102012218081.8A patent/DE102012218081A1/de not_active Withdrawn
-
2013
- 2013-08-20 WO PCT/EP2013/067330 patent/WO2014053269A1/de active Application Filing
- 2013-08-20 US US14/431,085 patent/US20150232609A1/en not_active Abandoned
- 2013-08-20 CN CN201380051230.4A patent/CN104662061A/zh active Pending
- 2013-08-20 EP EP13752624.0A patent/EP2904028A1/de not_active Withdrawn
- 2013-08-20 JP JP2015534944A patent/JP2015533189A/ja not_active Withdrawn
-
2017
- 2017-08-21 US US15/681,954 patent/US20170349693A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006321839A (ja) * | 2005-05-17 | 2006-11-30 | Toyo Seikan Kaisha Ltd | 缶端シーリング材 |
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CN108350144A (zh) * | 2015-09-07 | 2018-07-31 | 巴斯夫欧洲公司 | 具有改进特性的水可乳化型异氰酸酯 |
CN108350144B (zh) * | 2015-09-07 | 2021-11-05 | 巴斯夫欧洲公司 | 具有改进特性的水可乳化型异氰酸酯 |
CN111868131A (zh) * | 2018-03-23 | 2020-10-30 | 科思创德国股份有限公司 | 包含亲水基团的含脲二酮的聚氨酯分散体 |
CN111886272A (zh) * | 2018-03-23 | 2020-11-03 | 科思创德国股份有限公司 | 含脲二酮基团的水性组合物及其制备方法 |
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CN111886272B (zh) * | 2018-03-23 | 2022-11-15 | 科思创德国股份有限公司 | 含脲二酮基团的水性组合物及其制备方法 |
CN110396165A (zh) * | 2018-04-25 | 2019-11-01 | 科思创德国股份有限公司 | 离子亲水化多异氰酸酯和抗氧化剂 |
CN112041369A (zh) * | 2018-04-25 | 2020-12-04 | 科思创知识产权两合公司 | 离子亲水化多异氰酸酯、水含量 |
CN111978509A (zh) * | 2019-05-24 | 2020-11-24 | 旭化成株式会社 | 多异氰酸酯组合物、涂料组合物和涂膜 |
CN112062935A (zh) * | 2020-09-04 | 2020-12-11 | 广东也乐新材料制造有限公司 | 一种净味水分散聚异氰酸酯的制备方法及其应用 |
CN116063657A (zh) * | 2022-11-18 | 2023-05-05 | 广州秀珀化工涂料有限公司 | 刚性结构聚合物改性水性多异氰酸酯及其制备方法 |
Also Published As
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US20150232609A1 (en) | 2015-08-20 |
US20170349693A1 (en) | 2017-12-07 |
JP2015533189A (ja) | 2015-11-19 |
WO2014053269A1 (de) | 2014-04-10 |
DE102012218081A1 (de) | 2014-04-10 |
EP2904028A1 (de) | 2015-08-12 |
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