CN101519484A - 预聚物 - Google Patents

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CN101519484A
CN101519484A CN200910129200A CN200910129200A CN101519484A CN 101519484 A CN101519484 A CN 101519484A CN 200910129200 A CN200910129200 A CN 200910129200A CN 200910129200 A CN200910129200 A CN 200910129200A CN 101519484 A CN101519484 A CN 101519484A
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M·莱门斯托尔
B·科勒
C·卡拉菲利迪斯
M·温特曼特尔
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Covestro Deutschland AG
Bayer Intellectual Property GmbH
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Abstract

本发明涉及预聚物，即新的预聚物，其可以由低聚的二或多胺的甲酰胺(甲酰胺封端的低聚物)和二或多异氰酸酯得到。

Description

预聚物
相关申请
本申请要求于2008年2月27日申请的德国专利申请号102008011472的权益，为了所有有用的目的将该申请全文并入此处作为参考。
技术领域
本发明涉及新的预聚物，其可以由低聚的二或多胺的甲酰胺(甲酰胺封端的低聚物)和二或多异氰酸酯得到。
背景技术
多元醇和多异氰酸酯的异氰酸酯官能化预聚物已经公知很长时间了，并且是许多现有商业产品的基础。
对于许多应用，尤其是在漆和粘合剂领域中，具有低粘度的预聚物是所希望的。
二异氰酸酯和甲酰胺封端的低聚物的预聚物是新的，且在文献中是未知的。
现在已经发现以低粘度著称的酰基脲预聚物可以由甲酰胺封端的低聚物和多异氰酸酯得到。
发明内容
本发明的一个实施方案是二异氰酸酯和甲酰胺封端的低聚物的预聚物。
本发明的另一个实施方案是上述预聚物，其中所述预聚物具有式(I)
X-[-N(CHO)-CO-NH-R1-NCO]n   (I)
其中
X是n价的有机基团。
本发明的另一个实施方案是上述预聚物，其中X是式(II)的基团
Y-[-(CH2-CHR3-(CH2)p-O)m-CH2-CHR4-(CH2)o-]n-     (II)
其中
Y是n官能化的饱和C2-C6基团；
R1是C6-C13芳烷基基团或C4-C13亚烷基基团；
R3是氢或甲基；
R4代表氢或甲基；
m是2-30的自然数；
n是2-4的自然数；
o是0或1；和
p是0、1或2。
本发明的另一个实施方案是上述预聚物，其中
R4是甲基；
o是0；和
p是0。
本发明的另一个实施方案是制备上述预聚物的方法，包括使二异氰酸酯与甲酰胺封端的低聚物反应并通过蒸馏分离除去任何过量的所述二异氰酸酯。
本发明的另一个实施方案是制备上述预聚物的方法，包括使n到(n×10)摩尔的式(III)的二异氰酸酯
OCN-R1-NCO      (III)
其中
R1是C6-C13芳烷基基团或C4-C13亚烷基基团；和
n是2-4的自然数；
与1摩尔的式(IV)的甲酰胺封端的低聚物反应
X-[-NH(CHO)]n   (IV)
其中X是式(II)的基团
Y-[-(CH2-CHR3-(CH2)p-O)m-CH2-CHR4-(CH2)o-]n-    (II)
其中
Y是n官能化的饱和C2-C6基团；
R1是C6-C13芳烷基基团或C4-C13亚烷基基团；
R3是氢或甲基；
R4代表氢或甲基；
m是2-30的自然数；
n是2-4的自然数；
o是0或1；和
p是0、1或2；和
n是2-4的自然数；
并通过蒸馏分离除去任何过量的所述二异氰酸酯。
本发明的另一个实施方案是包含权利要求1的预聚物的PU成形制品或发泡制品。
本发明的另一个实施方案是包含任一种上述预聚物的粘合剂。
本发明的另一个实施方案是包含任一种上述预聚物的密封剂。
本发明的另一个实施方案是包含任一种上述预聚物的漆。
具体实施方式
本发明因此提供二异氰酸酯和甲酰胺封端的低聚物的预聚物。
它们优选是通式I的预聚物
X-[-N(CHO)-CO-NH-R1-NCO]n   (I)
其中
X代表n价的有机基团，优选式II的基团
Y-[-(CH2-CHR3-(CH2)p-O)m-CH2-CHR4-(CH2)o-]n-     (II)
其中
Y代表n官能化的饱和C2-C6基团；
R1代表C6-C13芳烷基基团或C4-C13亚烷基基团；
R3代表氢或甲基；
R4代表氢或甲基，优选甲基；
m代表2-30的自然数；
n代表2-4的自然数；
o代表0或1，优选0，和
p代表0、1或2，优选0。
本发明还提供制备根据本发明的预聚物的方法，其特征在于使二异氰酸酯与甲酰胺封端的低聚物反应并通过蒸馏分离除去可能存在的过量的二异氰酸酯。
优选地，根据本发明使n到(n×10)摩尔的式(III)的二异氰酸酯
OCN-R1-NCO     (III)
其中R1和n具有上述含义，
与1摩尔的式(IV)的甲酰胺封端的低聚物反应
X-[-NH(CHO)]n        (IV)
其中X和n具有上述含义，
并通过蒸馏分离除去可能存在的过量的二异氰酸酯。
甲酰胺封端的低聚物，尤其是式(IV)的甲酰胺封端的低聚物，可以例如通过甲酸C1-C4-烷基酯与式(V)的胺反应得到
X-[NH2]n       (V)，
其中X和n具有上述含义。
反应优选在过量的甲酸C1-C4-烷基酯，优选甲酸甲酯或甲酸乙酯中在甲酸酯的沸点温度反应，并且在氨基发生反应得到甲酰胺基团之后，蒸馏除去过量的物质和同样形成的链烷醇，优选甲醇或乙醇。多胺V与甲酸或其它甲酸衍生物，例如一氧化碳、混合的甲酸-羧酸酐、甲酸的低分子量酰胺或活性酯、或者甲酸与酰胺偶联剂，例如碳二亚胺或缩合的磷酸衍生物的前体反应产物反应得到甲酰胺封端的低聚物IV也是可能的，但是并不优选。甲酰胺或由强碱产生的甲酰胺阴离子与式(VI)的烷基化试剂反应同样是可能的，但并不优选，
X-[A]n(VI)
其中X和n具有上述含义，A代表离去基团，例如氯、溴、碘、甲磺酰酯、甲苯磺酰酯或三氟甲磺酸。
所采用的式(V)的胺优选是BASF的聚醚胺或Huntsman的Jeffamines。这些是聚乙二醇，优选用下述结构氨基官能化了的聚乙二醇或聚四氢呋喃：
-CH2-CH(CH3)-NH2
或
-CH2-CH2-CH2-NH2。
在存在或不存在，优选不存在催化剂如锌或锡的化合物的条件下，于40-120℃的温度下进行甲酰胺封端的低聚物与异氰酸酯的反应。二异氰酸酯优选以基于甲酰胺封端的低聚物3-8倍摩尔量使用，在反应得到酰基脲预聚物后通过真空下的薄膜蒸馏除去过量物。
根据本发明使用的二异氰酸酯是例如2，4-TDI、2，6-TDI、2，4’-MDI、4，4’-MDI、1，3-二异氰酸根合苯、1，4-二异氰酸根合苯、HDI、IPDI、4，4-二异氰酸根合环己基甲烷、二异氰酸根合甲基降冰片烷、二异氰酸根合甲基苯或二异氰酸根合甲基环己烷。
根据本发明的预聚物可以用于其中也使用对应于现有技术的预聚物的所有领域，例如粘合剂、漆、PU成形制品或发泡制品或者密封剂。在本文中，它们具有尤其是相对低粘度的优势。
低粘度例如在“软包装”或“反应性聚氨酯热熔粘合剂”(热熔体)的应用是非常有利的。软包装在这里理解为通过用基于聚氨酯的粘合剂粘合制备的复合膜。在这种情况中，粘合剂典型地以液体形式施涂到膜上并随后直接与第二层膜结合。反应性聚氨酯热熔粘合剂理解为在高温下是熔体形式并在该温度下以液体形式施涂的粘合剂体系。在施涂并结合之后，仍然具有反应性的粘合剂冷却，并因此建立了快速的初始强度。在环境中的湿气下完全固化后达到最终的强度。
所有上面描述的参考文献为了所有有用的目的全文并入作为参考。
虽然显示和描述了实施本发明的某些具体结构，但是本领域技术人员明白，在不偏离本发明构思的精神和范围下可以进行各部分的修改和重排，并且本发明构思并不限于这里显示和描述的具体形式。
实施例
使用的起始物质：
Desmodur
Figure A200910129200D0008182341QIETU
 T80(Bayer MaterialScience AG，Leverkusen，DE)，2，4-和2，6-TDI80∶20的混合物，
Desmophen
Figure A200910129200D0008182341QIETU
 1262 BD(Bayer MaterialScience AG，Leverkusen，DE)，摩尔质量Mn＝400的双官能聚丙烯氧化物，
Jeffamine
Figure A200910129200D0008182341QIETU
ED600(Huntsman，UK)，双官能的氨基封端的聚亚乙基-共-亚丙基二醇(poly-ethylene-co-propyleneglycol)，摩尔质量Mn＝600，
Jeffamine
Figure A200910129200D0008182341QIETU
D400(Huntsman，UK)，双官能的氨基封端的聚丙二醇，摩尔质量Mn＝400和
Irganox
Figure A200910129200D0008182341QIETU
1076(Ciba，CH)，空间位阻酚。
实施例1
将400g甲酸乙酯在4小时期间内在25℃滴入400g Jeffamine
Figure A200910129200D0008182341QIETU
ED600中，随后将混合物搅拌4小时。然后将过量的甲酸乙酯和形成的乙醇蒸馏除去。将所形成的甲酰胺封端的低聚物在2小时期间内在80℃滴入2，088g Desmodur
Figure A200910129200D0008182341QIETU
T80、1g Irganox
Figure A200910129200D0008182341QIETU
1076和2g苯甲酰氯中，随后将混合物在80℃下搅拌8小时。然后在130℃下用薄膜蒸馏除去过量的Desmodur
Figure A200910129200D0008182341QIETU
T80。
得到的酰基脲预聚物具有NCO含量9.2％，粘度如表1所示。
实施例2
将400g甲酸乙酯在4小时期间内在25℃滴入400gJeffamine
Figure A200910129200D0008182341QIETU
D400中，随后将混合物搅拌4小时。然后将过量的甲酸乙酯和形成的乙醇蒸馏除去。将所形成的甲酰胺封端的低聚物在2小时期间内在80℃滴入2，088g Desmodur
Figure A200910129200D0008182341QIETU
T80和2g苯甲酰氯中，随后将混合物在80℃下搅拌8小时。然后在130℃下用薄膜蒸馏除去过量的Desmodur
Figure A200910129200D0008182341QIETU
T80。
得到的酰基脲预聚物具有NCO含量10.4％，粘度如表1所示。
对比实施例
265.98g Desmophen
Figure A200910129200D0008182341QIETU
1262BD在2小时期间内在80℃滴入535.02gDesmodur
Figure A200910129200D0008182341QIETU
T80中，随后将混合物搅拌8小时。然后在130℃下用薄膜蒸馏除去过量的Desmodur
Figure A200910129200D0008182341QIETU
T80。
得到的酰基脲预聚物具有NCO含量10.4％，粘度如表1所示。
表1：在不同温度下实施例1和2以及对比实施例的粘度

Claims (18)

1、二异氰酸酯和甲酰胺封端的低聚物的预聚物。
2、权利要求1的预聚物，其中所述预聚物具有式(I)
X-[-N(CHO)-CO-NH-R1-NCO]n   (I)
其中
X是n价的有机基团。
3、权利要求2的预聚物，其中X是式(II)的基团
Y-[-(CH2-CHR3-(CH2)p-O)m-CH2-CHR4-(CH2)o-]n-   (II)
其中
Y是n官能化的饱和C2-C6基团；
R1是C6-C13芳烷基基团或C4-C13亚烷基基团；
R3是氢或甲基；
R4代表氢或甲基；
m是2-30的自然数；
n是2-4的自然数；
o是0或1；和
p是0、1或2。
4、权利要求3的预聚物，其中，
R4是甲基；
o是0；和
p是0。
5、制备权利要求1的预聚物的方法，包括使二异氰酸酯与甲酰胺封端的低聚物反应并通过蒸馏分离除去任何过量的所述二异氰酸酯。
6、制备权利要求2的预聚物的方法，包括使n到(n×10)摩尔的式(III)的二异氰酸酯
OCN-R1-NCO   (III)，
其中
R1是C6-C13芳烷基基团或C4-C13亚烷基基团；和
n是2-4的自然数；
与1摩尔式(IV)的甲酰胺封端的低聚物反应
X-[-NH(CHO)]n   (IV)
其中
X是式(II)的基团
Y-[-(CH2-CHR3-(CH2)p-O)m-CH2-CHR4-(CH2)o-]n-   (II)
其中
Y是n官能化的饱和C2-C6基团；
R1是C6-C13芳烷基基团或C4-C13亚烷基基团；
R3是氢或甲基；
R4代表氢或甲基；
m是2-30的自然数；
n是2-4的自然数；
o是0或1；和
p是0、1或2；和
n是2-4的自然数；
并通过蒸馏分离除去任何过量的所述二异氰酸酯。
7、包含权利要求1的预聚物的PU成形制品或发泡制品。
8、包含权利要求1的预聚物的粘合剂。
9、包含权利要求1的预聚物的密封剂。
10、包含权利要求1的预聚物的漆。
11、包含权利要求2的预聚物的PU成形制品或发泡制品。
12、包含权利要求2的预聚物的粘合剂。
13、包含权利要求2的预聚物的密封剂。
14、包含权利要求2的预聚物的漆。
15、包含权利要求3的预聚物的PU成形制品或发泡制品。
16、包含权利要求3的预聚物的粘合剂。
17、包含权利要求3的预聚物的密封剂。
18、包含权利要求3的预聚物的漆。
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* Cited by examiner, † Cited by third party
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CN101955574A (zh) * 2009-07-17 2011-01-26 拜尔材料科学股份公司 基于二或多异氰酸酯和甲酰胺封端的低分子量化合物的预聚物、其制备方法及其用途
CN114269805A (zh) * 2019-08-23 2022-04-01 韩华思路信(株) 制备聚异氰酸酯组合物的方法

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DE102009033636A1 (de) * 2009-07-17 2011-01-20 Bayer Materialscience Ag Formamide enthaltende Reaktivsysteme

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DE2436740A1 (de) 1974-07-30 1976-02-12 Bayer Ag Verfahren zur herstellung von polyharnstoffen
US4282330A (en) * 1979-08-03 1981-08-04 Texaco Inc. Energy management polyether polyurethane foam
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101955574A (zh) * 2009-07-17 2011-01-26 拜尔材料科学股份公司 基于二或多异氰酸酯和甲酰胺封端的低分子量化合物的预聚物、其制备方法及其用途
CN101955574B (zh) * 2009-07-17 2015-09-23 拜尔材料科学股份公司 基于二或多异氰酸酯和甲酰胺封端的低分子量化合物的预聚物、其制备方法及其用途
CN114269805A (zh) * 2019-08-23 2022-04-01 韩华思路信(株) 制备聚异氰酸酯组合物的方法

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ATE517135T1 (de) 2011-08-15
EP2098547A2 (de) 2009-09-09

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