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Compounds containing aldimine

A technology containing aldimines and compounds, which is applied in the field of aldimines and aldimine-containing compounds, and can solve problems such as limited use, unusable compositions, limited storage stability, etc.

Active Publication Date: 2008-11-19
SIKA TECH AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compositions described in said document have the disadvantage that they have significantly limited storage stability
This is due to the fact that the protected amino groups, which are contained in the said aldimines or their reaction products in the form of aldimino groups or cyclic aminal groups, do not appear completely inert towards isocyanate groups, but rather react with these , especially reactive aromatic isocyanate groups, react slowly even in the absence of moisture, causing a viscosity increase that renders the composition unusable after a short time
A further disadvantage of said aldimines containing active hydrogen, as well as their reaction products and compositions prepared therefrom, is that they, when brought into contact with moisture, are determined by the strong-smelling aldehydes released upon hydrolysis of the aldimino groups, Shows a strong odor formation and can therefore only be used to a limited extent, especially indoors

Method used

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  • Compounds containing aldimine
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  • Compounds containing aldimine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0197] Example 1 (aldimine-containing compound AV1)

[0198] In a round bottom flask, add 1.74 g (13.9 mmol NCO) 4,4'-diphenylmethane-diisocyanate (MDI; 44MC L, Bayer) and heated to 50°C. From the dropping funnel, 10.00 g (13.9 mmol) of aldimine AL3 are added within 5 minutes with good stirring, and the mixture is stirred at 50° C. for one hour. A colorless, viscous liquid at room temperature, a clear and odorless liquid with an amine content of 2.37 mmol NH 2 / g, which reacts neutrally on wetted pH test paper.

[0199] IR: 3300(N-H), 2952sh, 2922, 2851, 1735(C=O), 1664(C=N), 1647sh, 1595, 1527sh, 1513, 1466, 1416, 1395, 1375, 1305, 1244, 1215, 1196 , 1162, 1112, 1056, 1018, 1000, 939, 918sh, 851, 813, 777, 751, 721.

Embodiment 2

[0200] Embodiment 2 (compound AV2 containing aldimine)

[0201] In a round bottom flask, add 3.47g (27.7mmol NCO) 4,4'-diphenylmethane-diisocyanate (MDI; 44MC L, Bayer) and heated to 50°C. From the dropping funnel, 10.00 g (13.9 mmol) of aldimine AL3 are added within 5 minutes with good stirring, and the mixture is stirred at 50° C. for one hour. This gave a pale yellow, viscous liquid at room temperature, a clear and odorless liquid which reacted neutrally on moistened pH paper.

[0202] IR: 3308(N-H), 2954sh, 2922, 2852, 2266(N=C=O), 1735(C=O), 1665(C=N), 1596, 1526sh, 1514, 1467, 1415, 1395, 1374, 1306, 1244, 1216, 1197, 1162, 1110, 1059, 1018, 1000, 940, 918sh, 854, 813, 781, 751, 721.

Embodiment 3

[0203] Embodiment 3 (compound AV3 containing aldimine)

[0204] In a round bottom flask, charge 12.94 g (103.4 mmol NCO) 4,4'-diphenylmethane-diisocyanate (MDI; 44MC L, Bayer) and heated to 50°C. From the dropping funnel, 42.16 g (51.7 mmol) of aldimine AL4 are added within 10 minutes with good stirring, and the mixture is stirred at 50° C. for one hour. This gave a yellowish, viscous liquid at room temperature, a clear and odorless liquid which reacted neutrally on moistened pH paper.

[0205]IR: 3336(N-H), 2922, 2852, 2265(N=C=O), 1736(C=O), 1666(C=N), 1640, 1594, 1513, 1488, 1465, 1416, 1394, 1373, 1307, 1237, 1169, 1110, 1065, 1018, 1000sh, 932, 918sh, 848, 812, 776, 754, 723.

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Abstract

The invention relates to compounds of formula (I) which contain aldimine, and to the use thereof. Said compounds which contain aldimines are characterised in that they are odour-less and during hydrolysis the odour-free aldehydes are separated. They are used, therefor, as sources for aldehydes. They can also be used in cross-linking reactions.

Description

technical field [0001] The present invention relates to the field of aldimines and aldimine-containing compounds. Background technique [0002] Aldimines are condensation products of amines and aldehydes and are a class of substances which has been known for a long time. Aldimines can be hydrolyzed to the corresponding amines and aldehydes when in contact with water, whereas they are stable in the absence of water. Due to this property, it can be used in amine or aldehyde bonded or protected form. For example, aldimines are used, for example, in polyurethane chemistry, where they serve as moisture-activatable crosslinkers, so-called “latent amines” or “latent curing agents”, for isocyanate-containing plastic precursors. The use of aldimines as latent curing agents in isocyanate-containing systems has advantages of two types here: On the one hand, undesired formation of air bubbles in the cured plastic can be avoided, since the curing takes place via latent amines - which r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C275/42C07C273/18C07C251/08C08G18/32
CPCC08G18/3256C08G18/089C07C251/08C08G18/12C07C275/42C07C273/18
Inventor U·布尔克哈特
Owner SIKA TECH AG
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