Reactive resin composition and use of the same

Patent metadata

Field	Value
Publication number	US-10273186-B2
Application number	US-201515535551-A
Country	US
Kind code	B2
Filing date	Dec 18, 2015
Priority date	Dec 19, 2014
Publication date	Apr 30, 2019
Grant date	Apr 30, 2019

Abstract

A reactive resin composition is described, with a resin component, which contains a radical-polymerizable compound, and an initiator system, which contains an α-halocarboxylic acid and a catalyst system, which comprises a nitrogen-containing ligand and Cu(0) or an inorganic Cu(I) compound, as is the use of the same for construction purposes.

First claim

The invention claimed is:

1. A reactive resin composition, comprising:
a resin component, which comprises a radical-polymerizable compound, and an initiator system, which comprises an α-halocarboxylic acid ester and a catalyst system,
wherein the catalyst system comprises at least one nitrogen-containing ligand and Cu(0) or an inorganic Cu(I) compound
wherein said initiator system further comprises an accelerator which is a phenol or a phenol derivative.

2. The reactive resin composition according to claim 1 , wherein the α-halocarboxylic acid ester is selected from the group consisting of compounds of the general formula (I)

in which
X denotes chlorine, bromine or iodine;
R 1 is a straight-chain or branched C 1 -C 20 alkyl group, optionally substituted, an aryl group; or
a radical of an acylated, branched, trihydric alcohol, a radical of a completely or partly acylated, linear or branched tetrahydric alcohol, a radical of a completely or partly acylated, linear pentahydric or hexahydric alcohol, a radical of a completely or partly acylated, linear or cyclic C 4 -C 6 aldose or C 4 -C 6 ketose or a radical of a completely or partly acylated disaccharide, or isomers of these compounds;

R 2 and R 3 , independently of one another, is hydrogen, a C 1 -C 20 alkyl group, a C 3 -C 8 cycloalkyl group, C 2 -C 20 alkenyl or alkynyl group, oxiranyl group, glycidyl group, aryl group, heterocyclyl group, aralkyl group or aralkenyl group.

3. The reactive resin composition according to claim 2 , wherein the α-halocarboxylic acid ester is a C 1 -C 6 alkyl ester of an α-halo-C 1 -C 6 carboxylic acid.

4. The reactive resin composition according to claim 3 , wherein the α-halo-C 1 -C 6 carboxylic acid is an α-bromo-C 1 -C 6 carboxylic acid.

5. The reactive resin composition according to claim 1 , wherein the nitrogen-containing ligand contains two or more nitrogen atoms and is able to form a chelate complex with copper(I).

6. The reactive resin composition according to claim 5 , wherein the nitrogen-containing ligand is selected from the group consisting of i) amino compounds with at least two primary, secondary and/or tertiary amino groups and ii) amino compounds with at least one heterocyclic nitrogen atom.

7. The reactive resin composition according to claim 5 , wherein the nitrogen-containing ligand is present in excess relative to the Cu(0) or an inorganic Cu(I) compound.

8. The reactive resin composition according to claim 1 , wherein the inorganic Cu(I) compound is a Cu(I) compound with elements of Group VI.

9. The reactive resin composition according to claim 8 , wherein the inorganic Cu(I) compound is at least one selected from the group consisting of Cu 2 O, Cu 2 S, Cu 2 Se and Cu 2 Te.

10. The reactive resin composition according to claim 1 , wherein the radical-polymerizable compound is an unsaturated polyester resin, a vinyl ester resin and/or a vinyl ester-urethane resin.

11. The reactive resin composition according to claim 1 , wherein the radical-polymerizable compound is a (meth)acrylate-functionalized resin and the α-halocarboxylic acid ester is an α-halocarboxylic acid ester of isobutanoic acid or propanoic acid.

12. The reactive resin composition according to claim 1 , further comprising a non-phenolic inhibitor.

13. The reactive resin composition according to claim 12 , wherein the non-phenolic inhibitor is a stable N-oxyl radical.

14. The reactive resin composition according to claim 1 , wherein the resin component further comprises at least one reactive diluent.

15. The reactive resin composition according to claim 1 , further comprising an inorganic aggregate.

16. The reactive resin composition according to claim 15 , wherein the inorganic aggregate is an additive and/or a filler.

17. A two-component or multicomponent system, comprising:
the reactive resin composition according to claim 1 , wherein the nitrogen-containing ligand and the Cu(0) or the inorganic Cu(I) compound are stored separately from one another in a way that inhibits reaction.

18. The two-component system according to claim 17 ,
wherein
the Cu(0) or the inorganic Cu(I) compound and optionally an accelerator are contained in a first component, and
the nitrogen-containing ligand and the initiator are contained in a second component,
the radical-polymerizable compound and optionally the inhibitor are distributed among the two components, wherein the two components are kept separate from one another in a way that inhibits reaction.

19. The two-component system according to claim 18 , wherein the reactive resin composition further comprises at least one reactive diluent and/or inorganic aggregates, which are contained in one or in both components.

20. A method for anchoring of an anchoring elements in a drilled hole, said method comprising:
applying in said drilled hole the reactive resin composition according to claim 1 .

Assignees

• Hilti Ag

Inventors

• Pfeil Armin

Classifications

• C08F4/50

  selected from alkaline earth metals, zinc, cadmium, mercury, copper or silver · CPC title

• C04B26/06 Primary

  Acrylates · CPC title

• C08F2438/01

  Atom Transfer Radical Polymerization [ATRP] or reverse ATRP · CPC title

• C09J4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C04B26/16

  Polyurethanes · CPC title