Biogenic oligomers as reactive additives for the curing of reactive resins

Patent metadata

Field	Value
Publication number	US-10934378-B2
Application number	US-201815733075-A
Country	US
Kind code	B2
Filing date	Nov 19, 2018
Priority date	Nov 28, 2017
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

A reactive resin includes a vinyl ester resin as a base resin and an oligomeric itaconic acid ester as a reactive diluent.

First claim

The invention claimed is:

1. A reactive resin, comprising:
i) a base resin comprising at least one vinyl ester resin, and
ii) at least one itaconic acid ester of formula (I),

in which
R represents hydrogen or a C 1 -C 6 alkyl group,
X represents a C 2 -C 10 alkylene group, and
n is ≥2.

2. The reactive resin according to claim 1 , wherein the at least one itaconic acid ester of the formula (I) has a weight-average molar mass M W , of at least 500 g/mol.

3. The reactive resin according to claim 1 , wherein the at least one itaconic acid ester of the formula (I) is completely obtainable from a renewable raw material.

4. The reactive resin according to claim 1 , wherein the at least one vinyl ester resin is a vinyl urethane ester resin.

5. The reactive resin according to claim 1 , further comprising at least one inhibitor.

6. The reactive resin according to claim 5 , wherein the at least one inhibitor is selected from the group consisting of 2-methoxyphenol, 4-methoxyphenol, 2,6-di-tert-butyl-4-methylphenol, 2,4-di-tert-butylphenol, 2,6-di-tert-butylphenol, 2,4,6-trimethylphenol, 2,4,6-tris(dimethylaminomethyl)phenol, 4,4′-thio-bis(3-methyl-6-tert-butylphenol 4,4′-isopropylidenediphenol, 6,6′-di-tert-butyl-4,4′-bis (2,6-di-tert-butylphenol), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 2,2′-methylene-di-p-cresol, pyrocatechol, 4-tert-butyl pyrocatechol, 4,6-di-tert-butyl pyrocatechol, hydroquinone, 2-methylhydroquinone, 2-tert-butylhydroquinone, 2,5-di-tert-butylhydroquinone, 2,6-di-tert-butylhydroquinone, 2,6-dimethylhydroquinone, 2,3,5-trimethylhydroquinone, benzoquinone, 2,3,5,6-tetrachloro-1,4-benzoquinone, methylbenzoquinone, 2,6-dimethylbenzoquinone, naphthoquinone, and mixtures thereof.

7. The reactive resin according to claim 5 , comprising:
i) 50.0 to 95.0 wt. % of the base resin, comprising the at least one vinyl ester resin,
ii) 5.0 to 40.0 wt. % of the at least one itaconic acid ester of the formula (I), and
iii) up to 1.0 wt. % of the at least one inhibitor,
based on a total weight of the reactive resin.

8. A reactive resin component, comprising:
the reactive resin according to claim 1 , and
at least one inorganic or organic aggregate.

9. The reactive resin component according to claim 8 , wherein the at least one inorganic or organic aggregate is selected from the group consisting of fillers, thickeners, thixotropic agents, non-reactive solvents, agents for improving flowability, wetting agents, and mixtures thereof.

10. The reactive resin component according to claim 8 , comprising:
30 to 80 wt. % of the at least one inorganic or organic aggregate, based on a total weight of the reactive resin component.

11. A multi-component system, comprising:
the reactive resin component according to claim 8 , and
B) a hardener component.

12. The multi-component system according to claim 11 , wherein the hardener component comprises:
a radical initiator as a curing agent, and
optionally inorganic and/or organic aggregates.

13. The multi-component system according to claim 11 , wherein a weight ratio of the reactive resin component to the hardener component is in a range of approximately 3:1 to approximately 7:1.

14. A method for chemical fastening, comprising:
fastening with the reactive resin of claim 1 .

15. The method according to claim 14 , wherein the chemical fastening is fastening of an anchor in a borehole.

16. The method according to claim 15 , wherein the anchor comprises steel or iron.

17. The method according to claim 14 , wherein the reactive resin further comprises:
a base resin comprising at least one vinyl ester resin, and
at least one inhibitor.

18. The method according to claim 17 , wherein the at east one vinyl ester resin is a vinyl urethane ester resin.

19. The method according to claim 17 , wherein the at least one inhibitor is selected from the group consisting of 2-methoxyphenol, 4-methoxyphenol, 2,6-di-tert-butyl-4-methylphenol, 2,4-di-tert-butylphenol, 2,6-di-tert-butylphenol, 2,4,6-trimethylphenol, 2,4,6-tris(dimethylaminomethyl)phenol, 4,4′-thio-bis(3-methyl-6-tert-butylphenol), 4,4′-isopropylidenediphenol, 6,6′-di-tert-butyl-4,4′-bis (2,6-di-tert-butylphenol), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 2,2′-methylene-di-p-cresol, pyrocatechol, 4-tert-butyl pyrocatechol, 4,6-di-tea-butyl pyrocatechol, hydroquinone, 2-methylhydroquinone, 2-tert-butylhydroquinone, 2,5-di-tert-butylhydroquinone, 2,6-di-tert-butylhydroquinone, 2,6-dimethylhydroquinone, 2,3,5-trimethylhydroquinone, benzoquinone, 2,3,5,6-tetrachloro-1,4-benzoquinone, methylbenzoquinone, 2,6-dimethylbenzoquinone, naphthoquinone, and mixtures thereof.

20. The method according to claim 17 , wherein the reactive resin comprises:
50.0 to 95.0 wt. % of the base resin, comprising the at least one vinyl ester resin,
ii) 5.0 to 40.0 wt. % of the at least one itaconic acid ester of formula (I), and
iii) up to 1.0 wt. % of the at least one inhibitor,
based on the total weight of the reactive resin.

Assignees

• Hilti Ag

Inventors

• Bunzen Jens
• Bürgel Thomas
• Gnass Beate
• Jaehnichen Klaus
• Voit Brigitte

Classifications

• C04B26/18

  Polyesters; Polycarbonates · CPC title

• C04B26/10

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C08F222/14 Primary

  Esters having no free carboxylic acid groups {, e.g. dialkyl maleates or fumarates} · CPC title

• C04B26/16 Primary

  Polyurethanes · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title