CN107541176A - 烷氧基硅烷官能化的脲基甲酸酯 - Google Patents

烷氧基硅烷官能化的脲基甲酸酯 Download PDF

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CN107541176A
CN107541176A CN201710493119.0A CN201710493119A CN107541176A CN 107541176 A CN107541176 A CN 107541176A CN 201710493119 A CN201710493119 A CN 201710493119A CN 107541176 A CN107541176 A CN 107541176A
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alkoxysilane
allophanate
functionalized
diisocyanate
reaction
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W.施塔赫
T.昂克尔霍伊泽
E.斯皮劳
A.利利恩塔尔
I.布吕克纳
J.普芬斯滕
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Evonik Operations GmbH
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Evonik Degussa GmbH
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Abstract

本发明涉及烷氧基硅烷官能化的脲基甲酸酯。本发明还涉及烷氧基硅烷官能化的脲基甲酸酯的制备方法及其用途。

Description

烷氧基硅烷官能化的脲基甲酸酯
技术领域
本发明涉及烷氧基硅烷官能化的脲基甲酸酯、其制备方法及其用途。
背景技术
数十年来，聚氨酯被证明是漆料、胶粘剂、密封剂和塑料体系的高品质组分。在此，额外的烷氧基硅烷基团可以起到重要作用，例如在网络密度、耐化学品性和耐刮擦性方面，这里主要是通过形成硅氧烷和聚硅氧烷的结构。
既具有烷氧基硅烷基团又具有异氰酸酯基团的分子实现了通过一种组分引入作为反应产物得到的官能度、硅氧烷和聚氨酯基团。长期以来一直使用这样的物质，例如以异氰酸根合烷基三烷氧基硅烷的形式。
由异氰酸根合烷基三烷氧基硅烷和醇制得的烷氧基硅烷封端的聚氨酯同样是已知的并且例如用于制备高度交联的、硬质涂覆剂 (例如WO 2013/189882 A2)。然而，如果这样的烷氧基硅烷封端的聚氨酯在室温固化的体系中用作单一的粘合剂，则获得仅具有中等硬度的涂层。
因此，需要能够克服现有技术的缺点的新型粘合剂。
含有脲基甲酸酯的粘合剂是长久已知的。烷氧基硅烷官能化的脲基甲酸酯也是已知的。这里区分为下面描述的不同类型，但是它们在结构和应用方面都不对应于本发明的烷氧基硅烷官能化的脲基甲酸酯。
例如，在WO 2008/043722 A1中描述的脲基甲酸酯 III (1) 通过NCO封端的含有脲基甲酸酯的聚氨酯 I (1) 与对异氰酸酯呈反应性的烷氧基硅烷 II (1) (例如氨基烷基三烷氧基硅烷) 的反应而获得。由此，脲基甲酸酯基团位于聚氨酯链的中心和烷氧基硅烷官能团通过末端的异氰酸酯基团连接到脲官能团的结构中 (结构 III (1)，反应式1)。
DE102005041953 A1 描述了平均分子量为3000-20000 g/mol 的多元醇 I (2)与过量的异氰酸根合丙基三甲氧基硅烷II (2) 的反应，从而在形成聚氨酯 III (2) 之后形成每个脲基甲酸酯单元具有两个烷氧基硅烷官能团的脲基甲酸酯 IV (2)。
在DE102005041954 A1中，将聚氨酯 I (3) 与异氰酸根合丙基三甲氧基硅烷II(3) 混合并且加热直至形成脲基甲酸酯结构。在这种情况下，将烷氧基硅烷基团结合到脲基甲酸酯基团 III (3) 的末端氮上 (反应式3)。
J. Kozakiewicz等人在Progress in Organic Coatings 72 (2011) 120–130中公开了异氰酸根合丙基三甲氧基硅烷I (4) 与甲醇反应得到相应的氨基甲酸酯 II (4)和随后与六亚甲基二异氰酸酯三聚体 III (4)反应。在由此获得的高粘度脲基甲酸酯 IV(4) 中，烷氧基硅烷官能团挂接到脲基甲酸酯基团的中心叔胺上 (反应式4)。
在所述的应用中，脲基甲酸酯官能团用作六亚甲基二异氰酸酯三聚体的阻隔剂，而六亚甲基二异氰酸酯三聚体用作羟基官能化的聚酯多元醇的交联剂。
即使如今仍然需要新型的、具有特定性质的、含硅烷的粘合剂。
发明内容
本发明的目的在于，提供新型的含硅烷的化合物，其适用于研发高度交联的硬质涂层。
该目的通过本发明的烷氧基硅烷官能化的脲基甲酸酯而实现。
令人惊讶地发现，本发明的烷氧基硅烷官能化的脲基甲酸酯适用作漆料、胶粘剂或密封剂。特别地，本发明的烷氧基硅烷官能化的脲基甲酸酯可以用于研发高度交联的、特别是硬质的涂层。在此，本发明的烷氧基硅烷官能化的脲基甲酸酯可以作为单一的粘合剂用在冷固化和热固化中，甚至在需要无溶剂的情况下使用。
本发明涉及烷氧基硅烷官能化的脲基甲酸酯，其包含A)与B)的反应产物：
A) 至少一种，优选一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 A)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
B) 至少一种二异氰酸酯 B)，
其中A)与B)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1。
在本文中，包含所述反应产物的烷氧基硅烷官能化的脲基甲酸酯特别是指这样的脲基甲酸酯，其由单氨基甲酸酯和二异氰酸酯的反应产物本身组成或者基于可能在反应产物中未反应的异氰酸酯基团衍生化或者进一步反应。优选地，所述反应产物是这样的脲基甲酸酯，其由单氨基甲酸酯和二异氰酸酯的反应产物本身组成或者基于可能在反应产物中未反应的异氰酸酯基团衍生化，即反应或封端得到（verkappt）。特别优选地，所述反应产物是这样的脲基甲酸酯，其由单氨基甲酸酯和二异氰酸酯的反应产物本身组成或者基于可能在反应产物中未反应的异氰酸酯基团与至少一种醇反应。
如由至少一种单氨基甲酸酯与至少一种二异氰酸酯的反应可以看出的，本发明的脲基甲酸酯是指平均具有一个或两个脲基甲酸酯单元的加合物，因为二异氰酸酯可以部分或完全地与一个或两个单氨基甲酸酯反应。然而优选地，本发明的脲基甲酸酯具有两个脲基甲酸酯单元。
所述反应产物通过至少一种单氨基甲酸酯与至少一种二异氰酸酯以所述化学计量反应获得。优选地，所述反应产物通过一种单氨基甲酸酯与至少一种二异氰酸酯以所述化学计量反应获得。更优选地，所述反应产物通过一种单氨基甲酸酯与一种二异氰酸酯以所述化学计量反应获得。
在此，“一种”单氨基甲酸酯或“一种”二异氰酸酯分别特别是指一个结构式中的各个单氨基甲酸酯或各个二异氰酸酯。
优选地，本发明涉及如上所定义的由A)与B)的反应产物组成的烷氧基硅烷官能化的脲基甲酸酯，其中A)与B)的反应的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选2:1。
本发明还涉及烷氧基硅烷官能化的脲基甲酸酯，其通过下列物质的反应获得：
A) 至少一种，优选一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 A)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
B) 至少一种二异氰酸酯 B)，
其中A)与B)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1；
C)任选地在至少一种催化剂 C) 的存在下，
和
D) 任选地，源自B)的残余量的NCO基团与醇D)反应。
优选 R、R1、R2和R3同时或彼此独立地表示甲基、乙基、正丙基、异丙基、正丁基、仲丁基或叔丁基。
优选n = 0。
R1和R3 优选同时或彼此独立地表示甲基或乙基。
R2 优选甲基或丙基。
优选的是这样的化合物，其中n等于0，R1 和R3 同时或彼此独立地表示甲基或乙基，和R2 同时或彼此独立地表示甲基或丙基。
优选R3 = R1。
优选的是这样的化合物，其中n等于0和R2表示甲基或丙基，和R1表示甲基或乙基和R3 = R1。
非常特别优选的是这样的化合物，其中n等于0，R1和R3表示甲基和R2表示丙基，N-三甲氧基甲硅烷基丙基甲基氨基甲酸酯。
在含有烷氧基硅烷基团的单氨基甲酸酯 A) 与二异氰酸酯 B) 的根据本发明的反应之后，在终产物中的NCO含量优选为 <3重量%，特别优选 <1重量%，非常特别优选 <0.2重量%。
根据本发明使用的二异氰酸酯 B) 可以是任意的脂族的、环脂族的和/或(环)脂族的二异氰酸酯。在一个优选的实施方案中，本文中使用的术语 “(环)脂族的二异氰酸酯”是指在分子中同时存在在环上连接的NCO基团和在脂族基团上连接的NCO基团，例如异佛尔酮二异氰酸酯的情况。在一个优选的实施方案中，本文中使用的术语 “环脂族的二异氰酸酯” 是指仅具有直接在环脂族的环上连接的NCO基团的二异氰酸酯，例如二异氰酸根合二环己基甲烷(H12MDI)。
优选适用作二异氰酸酯 B) 的脂族二异氰酸酯包含直链的和/或支化的、优选具有3至16个碳原子，更优选4至12个碳原子的亚烷基。优选合适的环脂族的或 (环)脂族的二异氰酸酯包含优选具有4至18个碳原子，更优选 6至15个碳原子的环亚烷基。合适的二异氰酸酯的优选实例包括环己烷二异氰酸酯、甲基环己烷二异氰酸酯、乙基环己烷二异氰酸酯、丙基环己烷二异氰酸酯、甲基二乙基环己烷二异氰酸酯、丙烷二异氰酸酯、丁烷二异氰酸酯、戊烷二异氰酸酯、己烷二异氰酸酯、庚烷二异氰酸酯、辛烷二异氰酸酯、壬烷二异氰酸酯例如4-异氰酸根合甲基-1,8-辛烷二异氰酸酯 (TIN)、癸烷二-和三异氰酸酯、十一烷二-和三异氰酸酯、十二烷二-和三异氰酸酯。同样优选合适的是4-甲基环己烷-1,3-二异氰酸酯、2-丁基-2-乙基五亚甲基二异氰酸酯、3(4)-异氰酸根合甲基-1-甲基环己基异氰酸酯、2-异氰酸根合丙基环己基异氰酸酯、2,4'-亚甲基双(环己基)二异氰酸酯和/或1,4-二异氰酸根合-4-甲基戊烷。
优选的二异氰酸酯 B) 是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)、戊烷二异氰酸酯、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)、四甲基苯二亚甲基二异氰酸酯 (TMXDI)、苯二亚甲基二异氰酸酯 (MXDI)，单独地或以混合物的形式。
在一个特别优选的实施方案中，所述二异氰酸酯 B) 是IPDI和/或4,4'-H12MDI和/或HDI和/或2,2,4-TMDI与2,4,4-TMDI的混合物。
本发明还涉及制备烷氧基硅烷官能化的脲基甲酸酯的方法，其通过
A) 至少一种，优选一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 A)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
B) 至少一种二异氰酸酯 B)，
以A)与B)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1；
C)任选地在至少一种催化剂 C) 的存在下反应，
和
D) 任选地，源自B)的残余量的NCO基团与醇D)反应。
本发明的脲基甲酸酯的制备通常在无溶剂的情况下或在使用非质子性溶剂的情况下进行，其中所述反应可以不连续地或连续地进行。所述反应在合适的设备中进行，例如搅拌釜、挤出机、静态混合机、捏合室。所述反应可以在室温下，即在15至40℃，特别是15至25℃的温度下进行。然而优选地，使用80至220℃，特别是80至120℃的较高温度。所述反应在不含水的情况下进行。优选地，所述反应在无溶剂的情况下进行。
为了加速所述反应，可以有利地使用在氨基甲酸酯化学中已知的催化剂 C)，例如金属有机化合物，如含锡或锌的化合物，盐，如氯化锌(II)和/或碱。合适的是例如Sn、Bi、Zn和其它金属的羧酸盐，如二月桂酸二丁基锡、辛酸锡、乙基己酸锌、新癸酸铋，叔胺，如1,4-二氮杂双环[2.2.2]辛烷(DABCO)、1,8-二氮杂双环[5.4.0]十一-7-烯 (DBU)、1,5-二氮杂双环[4.3.0]壬-5-烯 (DBN)，三乙胺，脒，胍，以及季铵盐，优选四烷基铵盐，和/或季鏻盐。
作为催化剂 C)，也可以使用金属-乙酰丙酮化物。其实例是乙酰丙酮锌、乙酰丙酮锂、乙酰丙酮铁和乙酰丙酮锡，单独地或以混合物的形式。优选使用乙酰丙酮锌或乙基己酸锌。作为催化剂还可以使用季铵-乙酰丙酮化物或季鏻-乙酰丙酮化物。
在含有烷氧基硅烷基团的单氨基甲酸酯 A) 与二异氰酸酯 B) 的根据本发明的反应之后，NCO含量优选为 <3重量%，特别优选 <1重量%，非常特别优选 <0.2重量%。在NCO含量为3重量%至0.2重量%的情况下，源自B)的残余量的NCO基团与醇D)以NCO基团与醇D)的OH基团的比例为 0.8:1至1.2:1，优选0.9:1至1.1:1反应，其中特别优选化学计量反应，即1:1的比例。优选地，源自B)的残余量的NCO基团与醇D)的反应在30 - 150℃，特别是50 -150℃的温度下进行。所述反应在不含水的情况下进行。优选地，所述反应在无溶剂的情况下进行。
优选使用的醇 D) 是直链或支化的醇，其羟基官能团连接在伯、仲或叔碳原子上。也可以使用二元醇或多元醇。特别优选甲醇、乙醇、丙醇、异丙醇、1-丁醇、2-丁醇、戊醇、乙基-2-己醇、1-己醇。非常特别优选乙醇、丙醇和1-丁醇。
本发明还涉及涂覆剂和胶粘剂，其包含或由如下组成：
烷氧基硅烷官能化的脲基甲酸酯，其包含A)与B)的反应产物：
A) 至少一种，优选一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 A)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
B) 至少一种二异氰酸酯 B)，
其中A)与B)的摩尔比为3:1至1.5:1。
本发明还涉及根据本发明的烷氧基硅烷官能化的脲基甲酸酯在用于金属、塑料、玻璃、木材、MDF (中密度纤维板) 或皮革基材或其它耐热基底的涂料组合物和漆料组合物中的用途。
本发明还涉及所述烷氧基硅烷官能化的脲基甲酸酯在用于粘合金属、塑料、玻璃、木材、MDF或皮革基材或其它耐热基底的胶粘剂组合物中的用途。
本发明接下来通过下面的非受限的实施例阐述，从中可以看出本发明的其它特征、实施方案、方面和优点。
具体实施方式
原材料：
Vestanat® EP-UPMS：三甲氧基甲硅烷基丙基甲基氨基甲酸酯 (Evonik ResourceEfficiency GmbH)
Vestanat® IPDI：异佛尔酮二异氰酸酯 (Evonik Resource Efficiency GmbH)
Vestanat® TMDI：2,2,4-三甲基六亚甲基二异氰酸酯 (2,2,4-TMDI)和2,4,4-三甲基六亚甲基二异氰酸酯的混合物 (Evonik Resource Efficiency GmbH)
Vestanat® HT 2500/100：六亚甲基-1,6-二异氰酸酯，均聚物 (异氰脲酸酯类型)(Evonik Resource Efficiency GmbH)
Vestanat® EP Cat 11 B：在丁醇中的四乙基苯甲酸铵 (Evonik ResourceEfficiency GmbH)
Tegoglide® 410：基于聚醚硅氧烷共聚物的滑动和防粘连添加剂 (Evonik ResourceEfficiency GmbH)。
1. 制备
实施例1
烷氧基硅烷官能化的脲基甲酸酯 1
在具有回流冷凝器的三颈烧瓶中，预先加入340.2 g的Vestanat® EP-UPMS、0.3 g的乙基己酸锌(II)和159.7 g的Vestanat® IPDI，填充氮气和在搅拌下加热至100℃。在加热20小时之后，获得的NCO含量为1.4重量% NCO。然后加入10.84 g的丁醇，并且在100℃下加入1小时，直至达到NCO含量为 <0.1重量% NCO。在冷却至室温之后，获得透明液体的本发明烷氧基硅烷官能化的脲基甲酸酯 1，其粘度为14.3 Pas (在23℃下)。
实施例2
烷氧基硅烷官能化的脲基甲酸酯 2
在具有回流冷凝器的三颈烧瓶中，预先加入474.6 g的Vestanat® EP-UPMS、0.22 g的乙基己酸锌(II)和211.8 g的Vestanat® TMDI，填充氮气和在搅拌下加热至100℃。在加热24小时之后，获得的NCO含量为0.8重量% NCO。然后加入10.35 g的丁醇，并且在65℃下加热3小时，直至达到NCO含量为 <0.1重量% NCO。在冷却至室温之后，获得透明液体的本发明烷氧基硅烷官能化的脲基甲酸酯 2，其粘度为1170 mPas (在23℃下)。
对比例3A
烷氧基硅烷官能化的脲基甲酸酯 3A (对比例)
在具有回流冷凝器的三颈烧瓶中，预先加入44.3 g的Vestanat® EP-UPMS、0.01 g的乙基己酸锌(II)和35.7 g的Vestanat® HT 2500/100，填充氮气和在搅拌下加热至100℃，直至达到NCO含量为 <0.1重量%。然后，为了降低粘度，趁热加入20 g的乙酸丁酯。如此获得的烷氧基硅烷官能化的脲基甲酸酯 3a 是透明液体，其粘度为750 mPas (在23℃下)。
对比例3B
烷氧基硅烷官能化的脲基甲酸酯 3B (对比例)
在具有回流冷凝器的三颈烧瓶中，预先加入335.7 g的Vestanat® EP-UPMS、0.076 g的乙基己酸锌(II)、273.8 g的Vestanat® HT 2500/100和152 g 二甲苯，填充氮气和在搅拌下加热至100℃，直至达到NCO含量为1.0重量%。然后加入13.58 g的丁醇并且在100℃下加热0.5小时，直至达到NCO含量为 <0.1重量% NCO。如此获得的烷氧基硅烷官能化的脲基甲酸酯 3b 是透明液体，其粘度为542 mPas (在23℃下)。
2. 由烷氧基硅烷官能化的脲基甲酸酯作为涂覆剂制造透明漆料
为了配制本发明的透明漆料和对比例，将在表1和表2中所述的组合物的组分在加工前直接彼此混合。
所述配制品的粘度为大约60秒，作为在23℃下在DIN 4 杯中的流出时间测定。
为了测定机械表征数据，将所有漆料以100 µm刮涂到磷化钢板 (ChemetallGardobond 26S/60/OC) 上，并且在室温 (23℃)（表3）或在140℃（表4）下固化。
表3：在23℃ (7天)下固化之后的组合物I-III的漆料性能
包含根据本发明的烷氧基硅烷官能化的脲基甲酸酯 1或2 的涂层I和II的漆料性能相比于对比例III a和b表现出明显更高的摆锤硬度。特别是在漆料III a和b中的三倍官能化的产物的情况下，由于更高的交联度而会期望更高的硬度。
表4：在140℃ (22 min)下固化之后的组合物IV-V的漆料性能
包含本发明的烷氧基硅烷官能化的脲基甲酸酯 1 的涂层IV的漆料性能相比于对比例V a和b表现出明显更高的摆锤硬度。特别是在漆料V a和b中的三倍官能化的产物的情况下，由于更高的交联度而会期望更高的硬度。此外，具有光泽的表面的涂层IV相比于无光泽的涂层Va表现出更好的外观。
表3和4的结果证明了，可以使用本发明的烷氧基硅烷官能化的脲基甲酸酯用于研发高度交联的、特别是硬质的涂层，并且只有这些可以作为单一的粘合剂用在冷固化和热固化中，甚至在需要无溶剂的情况下使用。

Claims (21)

1.烷氧基硅烷官能化的脲基甲酸酯，其包含A)与B)的反应产物：
A) 至少一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 A)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
B) 至少一种二异氰酸酯 B)，
其中A)与B)的摩尔比为3:1至1.5:1。
2.烷氧基硅烷官能化的脲基甲酸酯，其通过下列物质的反应获得：
A) 至少一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 A)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
和
B) 至少一种二异氰酸酯 B)，
其中A)与B)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1；
C)任选地在至少一种催化剂 C) 的存在下，
和
D) 任选地，源自B)的残余量的NCO基团与醇D)反应。
3.根据权利要求1或2的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，所述A)与B)的摩尔比为2.5:1至1.8:1，特别优选 2:1。
4.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，R、R1、R2 和R3同时或彼此独立地表示甲基、乙基、正丙基、异丙基、正丁基、仲丁基或叔丁基。
5.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，n等于0，R1 和R3 同时或彼此独立地表示甲基或乙基，和R2 同时或彼此独立地表示甲基或丙基。
6.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，n等于0和R2表示甲基或丙基，和R1表示甲基或乙基和R3 = R1 。
7.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，n等于0，R1 和R3 表示甲基和R2 表示丙基。
8.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，所述二异氰酸酯 B) 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)、戊烷二异氰酸酯、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)、四甲基苯二亚甲基二异氰酸酯 (TMXDI)、苯二亚甲基二异氰酸酯(MXDI)，单独地或以混合物的形式。
9.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，所述二异氰酸酯 B) 选自IPDI、4,4'-H12MDI、HDI和2,2,4-TMDI与2,4,4-TMDI的混合物，单独地或以混合物的形式。
10.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，所述组分C) 选自金属羧酸盐，叔胺，脒，胍，季铵盐，四烷基铵盐，季鏻盐，金属-乙酰丙酮化物，季铵-乙酰丙酮化物，季鏻-乙酰丙酮化物，单独地或以混合物的形式。
11.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，所述组分C)是乙酰丙酮锌和/或乙基己酸锌。
12.根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯，其特征在于，所述醇D) 选自甲醇、乙醇、丙醇、异丙醇、1-丁醇、2-丁醇、戊醇、乙基-2-己醇、1-己醇。
13.制备根据前述权利要求至少一项的烷氧基硅烷官能化的脲基甲酸酯的方法，其通过
A) 至少一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 A)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1,
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
B) 至少一种二异氰酸酯 B)，
以A)与B)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1；
C)任选地在至少一种催化剂 C) 的存在下反应，
和
D) 任选地，源自B)的残余量的NCO基团与醇D)反应。
14.根据权利要求13的方法，其特征在于，所述反应在15至40℃，尤其在15至25℃的温度下进行。
15.根据权利要求13的方法，其特征在于，所述反应在80至220℃，尤其在80至120℃的温度下进行。
16.根据权利要求13-15任一项的方法，其特征在于，源自B)的残余量的NCO基团与醇D) 的反应在30至150℃，尤其在50至150℃的温度下进行。
17.根据权利要求13-16任一项的方法，其特征在于，所述反应在存在乙酰丙酮锌和/或乙基己酸锌作为催化剂 C) 的情况下进行。
18.根据权利要求13-17任一项的方法，其特征在于，源自B)的残余量的NCO基团与醇D)以NCO基团与醇D)的OH基团的比例为0.8:1至1.2:1，优选0.9:1至1.1:1而反应，特别优选以1:1的比例的化学计量反应进行。
19.根据权利要求1-12的烷氧基硅烷官能化的脲基甲酸酯在用于金属、塑料、玻璃、木材、MDF (中密度纤维板) 或皮革基材或其它耐热基底的涂料组合物和漆料组合物中的用途。
20.根据权利要求1-12的烷氧基硅烷官能化的脲基甲酸酯在用于粘合金属、塑料、玻璃、木材、MDF或皮革基材或其它耐热基底的胶粘剂组合物中的用途。
21.涂覆剂、胶粘剂或密封剂，其包含至少一种根据权利要求1-12任一项的烷氧基硅烷官能化的脲基甲酸酯。
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Application publication date: 20180105