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Polyisocyanate containing acyl urea group, its producing process and its application

A polyisocyanate and acyl urea-containing technology, which is applied in the application field of crosslinking agents and can solve problems such as yellowing of product batches

Inactive Publication Date: 2008-01-23
BAYER AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Basic tertiary amines, amidines, especially imidazoles, are easily oxidized and may cause yellowing of the product batch during longer reaction times

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0040] 1411.2 g of hexamethylene diisocyanate, 54 mg of magnesium trifluorosulfonate, and 150 mg each of lonol and Tinuvin 770 were charged into a 2L three-necked flask. 51.15 g of adipic acid and 21.96 g of azelaic acid, both previously dissolved in 282 g of triethyl phosphate, were added to the above mixture over a period of 30 min. During the addition, the temperature was 60°C. After the addition was complete, the mixture was heated to 110°C. Continue heating for 15h. Then, let the mixture cool. The NCO content of this solution was 36.1% (theoretical NCO content for conversion to tetrafunctional acylurea: 36.3%). The reaction solution carried out thin film distillation (130 ℃ of temperature, pressure 1.5 * 10 -2 bar). 334 g of product were obtained with a color value of 60 [APHA] and a viscosity of 3870 mPa.s (yield 23%, based on acid and isocyanate). The amount of monomeric hexamethylene diisocyanate is about 0.1%.

example 2

[0042] 604.8 g of hexamethylene diisocyanate, 11 mg of zinc acetate, and 60 mg each of lonol and Tinuvin 770 were put into a 1 L three-necked flask. To this mixture was added 21.92 g of adipic acid and 9.41 g of azelaic acid. After the addition was complete, the temperature was adjusted to 120°C. Continue heating for 12h. Then, let the mixture cool. The NCO content of this solution was 43.4% (theoretical NCO content for conversion to tetrafunctional acylurea: 43.5%). The reaction solution carried out thin film distillation (130 ℃ of temperature, pressure 1.5 * 10 -2 bar). 143.4 g of product were obtained with a color value of 65 [APHA] and a viscosity of 2250 mPa.s (yield 23.2%, based on acid and isocyanate). The amount of monomeric hexamethylene diisocyanate is about 0.1%.

example 3

[0044] 75.68 g of cyclohexanedicarboxylic acid, 20.7 g of azelaic acid, 50 mg of zinc acetate, and 260 mg each of lonol and Tinuvin 770 were charged into a 2.5 L three-necked flask. To this mixture was added 1663.2 g of hexamethylene diisocyanate. After the addition was complete, the temperature was adjusted to 120°C. Continue heating for 12h. Then, let the mixture cool. The NCO content of this solution was 42.2% (theoretical NCO content for conversion to tetrafunctional acylurea: 42.01%). The reaction solution carried out thin film distillation (130 ℃ of temperature, pressure 1.5 * 10 -2 bar). 400 g of product were obtained with a color value of 65 [APHA] and a viscosity of 7150 mPa.s (yield 22.7%, based on acid and isocyanate). The NCO content of the product was 24.7%. The amount of monomeric hexamethylene diisocyanate is about 0.1%.

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Abstract

The present invention relates to a process for preparing polyisocyanates containing acylurea groups by reacting isocyanates corresponding to formula (I) R-(NCO)n, wherein R represents an n-valent linear or branched aliphatic group or cycloaliphatic group having 4 to 30 carbon atoms or an aromatic group having 6 to 24 carbon atoms and n is 1, 2, 3 or 4, with aliphatic and / or aromatic carboxylic acids in the presence of a metal salt catalyst at a temperature of 20 to 220 DEG C. The present invention also relates to the reaction products (polyisocyanates) prepared by this process and to their use as binders for polyurethane coating compositions.

Description

technical field [0001] The invention relates to polyisocyanates containing acylurea groups, their preparation and their use as raw material components for the production of polyurethane plastics, in particular as crosslinkers for binders for coating compositions containing isocyanate-reactive groups Applications. Background technique [0002] The reaction of isocyanates with carboxylic acids is a reaction that has not been extensively studied before. The formation of isocyanate polyaddition reaction products containing acylurea groups is described, for example, in P. Babusiaux, R. Longeray, J. Dreux, "Liebigs Ann. Chem. " 1976, (3), 487; A.H.M. Schotmann, W.J.Mijs , Recl.Trav.Chim.PaysBas ("Holland Chemical Papers") 1992, 111, 88; DE-A 2 436 740 and in the literature cited therein. The condensation reaction of isocyanate and carboxylic acid has also been studied by I.S.Blagbrough, N.E.Mackenzie, C.Ortiz, A. and I.Scott ("Tetrahedron Lett." (Tetrahedron Lett.) 1986, 27 (11)...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C263/16C07C265/00C09D175/04C07C273/18C07B61/00C07C275/50C08G18/22C08G18/34C08G18/72C08G18/78
CPCC08G18/222C08G18/7818C08G18/341C08G18/34
Inventor C·居特勒M·布拉姆
Owner BAYER AG