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

Patent metadata

Field	Value
Publication number	US-9550852-B2
Application number	US-201314437959-A
Country	US
Kind code	B2
Filing date	Oct 22, 2013
Priority date	Oct 24, 2012
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

Disclosed is 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. The resins are suitable as binding agents in chemical fixing engineering.

First claim

The invention claimed is:

1. A method for producing a vinyl ester urethane resin, comprising the steps of:
(I) reacting a dianhydrohexitol compound with a diisocyanate in a presence of a monomeric radically copolymerizable compound as a solvent to produce a product; and
(II) reacting the product with a hydroxy-substituted (meth)acrylate.

2. The method according to claim 1 , wherein the monomeric radically copolymerizable compound is 1,4-butanedioldi(meth)acrylate, propyleneglycol(meth)acrylate, tetrahydrofuryl(meth)acrylate, or (2,2-dimethyl-1,3-di oxol ane-4-yl)m ethyl (m eth)acryl ate.

3. The method according to claim 1 , wherein at least two moles of diisocyanate are used per mole of the dianhydrohexitol compound.

4. The method according to claim 1 , wherein the dianhydrohexitol compound is isosorbide, isomannite, or isoidide.

5. The method according to claim 1 , wherein the diisocyanate is an aliphatic diisocyanate.

6. The method according to claim 1 , wherein the hydroxy-substituted (meth)acrylate is a hydroxyalkyl(meth)acrylate.

7. The method according to claim 1 , wherein the reaction is continued in step (I) until a residual isocyanate content has dropped to less than 0.2% measured according to DIN EIN 1242.

8. The method according to claim 1 , wherein starting compounds are obtained from chemicals based on renewable raw materials.

9. A vinyl ester urethane resin obtained using the method according to claim 1 .

10. The vinyl ester urethane resin of claim 9 , wherein the vinyl ester urethane resin is a binding agent in radically curable resin mixtures.

11. The vinyl ester urethane resin of claim 9 , wherein the vinyl ester urethane resin is a binding agent in radically curable reaction resin mortar compositions.

12. The vinyl ester urethane resin according to claim 10 wherein the resin mixtures are used for chemical fixing.

13. The vinyl ester urethane resin according to claim 11 wherein the resin mortar compositions are used for chemical fixing.

Assignees

• Hilti Ag

Inventors

• Leitner Michael
• Gnass Beate

Classifications

• C08G18/3218

  containing cyclic groups having at least one oxygen atom in the ring · CPC title

• C08L75/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08G18/68

  Unsaturated polyesters · CPC title

• C08G18/10 Primary

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08F290/067

  Polyurethanes; Polyureas · CPC title