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Method for producing vinyl ester urethane resins based on dianhydrohexitol compounds and use thereof

A technology of dianhydrohexitol and polyurethane resin, which is applied in the field of vinyl ester polyurethane resin and can solve problems such as failure

Inactive Publication Date: 2015-07-08
HILTI AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In particular the reaction of C4-diisocyanates with dianhydrohexitol-compounds has so far been unsuccessful in bulk

Method used

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  • Method for producing vinyl ester urethane resins based on dianhydrohexitol compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0049] A) Synthesis of resin masterbatch

[0050] A1) Application of Tetramethylene Diisocyanate (TMDI)

Embodiment A11

[0052] In a 500 mL three-necked flask, 260 g of 1,3-propanediol dimethacrylate (Sarbio6200) and 50 g of TMDI were placed in advance and mixed with 30 mg of dioctyltin dilaurate (Tegokat216), 20 mg of BHT and 40 mg of Tempol. The solution was tempered at 70°C. 20 g of isosorbide were then added to the stirred solution in 20 equal portions over 60 minutes. After the addition of isosorbide was complete, the mixture was heated to 80° C. and stirred at this temperature for 5 hours. The reaction of isosorbide was controlled by thin layer chromatography. After 5 hours, the isosorbide was completely reacted. Subsequently, 50 g of HPMA were added dropwise over 60 minutes and further stirred at 80° C. until the NCO content determined according to DIN EN 1242 was less than 0.2%. This gives a ready-to-use resin masterbatch.

Embodiment A12

[0054] 250 g of 1,4-butanediol dimethacrylate and 40 g of TMDI were pre-charged into a 500 mL three-necked flask, and mixed with 60 mg of dioctyltin dilaurate (Tegokat216), 40 mg of BHT and 90 mg of Tempol. The temperature of the solution was adjusted at 70°C. 20 g of isosorbide were then added to the stirred solution in 20 equal portions over 60 minutes. After the addition of isosorbide was complete, the mixture was heated to 80° C. and stirred at this temperature for 5 hours. The reaction of isosorbide was controlled by thin layer chromatography. After 5 hours, the isosorbide was completely reacted. Subsequently, 40 g of HPMA were added dropwise over 60 minutes and further stirred at 80° C. until the NCO content determined according to DIN EN 1242 was less than 0.2%. This gives a ready-to-use resin masterbatch.

[0055] A2) Application of hexamethylene diisocyanate (HMDI)

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PUM

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Abstract

The invention relates to a method for producing vinyl ester urethane resins, in which a dianhydrohexitol-compound is reacted with a diisocyanate in the presence of a monomeric radically co-polymerizable compound as a solvent and the product is reacted with a hydroxy-substituted (meth)acrylate. As a result, vinyl ester urethane resins based on dianhydrohexitol-compounds and also based on renewable raw materials can be obtained in a simple manner with high yields. Said resins are suitable as binding agents in chemical fixing engineering.

Description

technical field [0001] The present invention relates to a process for the preparation of vinyl ester polyurethane resins based on dianhydrohexitol compounds, vinyl ester polyurethane resins prepared according to this process and their use as free radical curable binders, especially those for chemical curing the use of. Background technique [0002] The use of reactive resin mortars based on radically curable compounds as binders has long been known. In the field of fastening technology, resin mixtures are used as organic binders for chemical fastening technology, for example as pinning compositions. What is meant here is a jointing composition, which is formulated as a multi-component system, wherein one component comprises a resin mixture and the other component comprises a curing agent. Other conventional ingredients such as solvents including reactive solvents (reactive diluents) may be contained in the one component and / or in the other component. By mixing the two com...

Claims

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Application Information

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IPC IPC(8): C08G18/67C08F290/06C08G18/32C08L75/16
CPCC08G18/672C08G18/3218C08L75/16C08F290/067C04B26/16C08G18/10C08G18/68C08G18/73C08F283/008
Inventor M·莱特纳B·尼亚斯
Owner HILTI AG
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