IP Library › Granted Patent US 11,542,363
Granted Patent B2
US 11,542,363 · App. 16/755,512 · Granted Jan 3, 2023

Multicomponent epoxide resin composition and curing agent component therefor

Inventors: Nicole Behrens (Munich, DE); Alexander Bornschlegl (Munich, DE)
Assignee: Hilti Aktiengesellschaft
C08G59/4014C08G59/38C08G59/5033C08G59/621C08K5/132C08K5/17
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Quick Facts
Patent No.
US 11,542,363
App. No.
16/755,512
Granted
Jan 3, 2023
Kind
B2
Abstract

A curing agent component is useful for a multicomponent epoxide resin composition. An epoxide resin composition produced using the curing agent component, wherein the curing agent component includes, as a curing agent, at least one Mannich base and an amine that is reactive with respect to epoxide groups, as well as at least one polyphenol from the group of novolac resins as an accelerant. The Mannich base can he obtained by reacting a phenolic compound selected from phenol, styrenated phenol, catechol, resorcinol, hydroquinone, hydroxyhydroquinone, phloroglucinol, pyrogallol, o-cresol, m-cresol, p-cresol and bisphenols, with an aldehyde or an aldehyde precursor and an amine having at least two active hydrogen atoms in the molecule which are bonded to a nitrogen atom. The novolac resin is contained in the curing agent component in a proportion of 5-30 wt. %, based on the organic proportions of the curing agent component.

Claims (34)

1. A curing agent component for a multicomponent epoxide resin composition, comprising:

as a curing agent, at least one Mannich base and at least one amine that is reactive with respect to epoxide groups, and

at least one polyphenol selected from the group consisting of novolac resins as an accelerant,

wherein the at least one Mannich base can be obtained by:

reacting at least one phenolic compound selected from the group consisting of phenol, styrenated phenol, catechol, resorcinol, hydroquinone, hydroxyhydroquinone, phloroglucinol, pyrogallol, o-cresol, m-cresol, p-cresol, bisphenols, and mixtures thereof, with at least one aldehyde or at least one aldehyde precursor and at least one amine having at least two active hydrogen atoms in the molecule which are bonded to a nitrogen atom,

said Mannich base is contained in the curing agent component in a proportion of from 10 to 70 wt. %, based on the organic proportion of the curing agent component,

said at least one polyphenol is contained in the curing agent component in a proportion of from 5 to 30 wt. %, based on organic proportions of the curing agent component,

said at least one polyphenol corresponds to the following formula:

in which

R 1 and R 2 represent, independently of one another, H or —CH 3 ;

R 3 , R 4 , R 5 , and R 6 represent, independently of one another, H, —CH 3 , an aliphatic radical, or an alkaryl radical: and where n is 0 to 20: and

said at least one amine is contained in the curing agent component in a proportion of from 60 to 80 wt. % based on the organic proportion of the curing agent component.

2. The curing agent component according to claim 1 , wherein the at least one amine that is reactive with respect to epoxide groups is at least one selected from the group consisting of aliphatic, alicyclic, araliphatic, and aromatic amines, the amine having on average at least two reactive hydrogen atoms per molecule which are bonded to a nitrogen atom.

3. The curing agent component according to claim 2 , wherein the at least one amine that is reactive with respect to epoxide groups is a polyamine having at least two amino groups in the molecule which are bonded to a nitrogen atom.

4. The curing agent component according to claim 1 , wherein the at least one phenolic compound is selected from the group consisting of phenol and styrenated phenol, and mixtures thereof.

5. The curing agent component according to claim 1 , wherein the at least one aldehyde is an aliphatic aldehyde, and wherein the at least one aldehyde precursor comprises trioxane or paraformaldehyde.

6. The curing agent component according to claim 5 , wherein the at least one aldehyde is formaldehyde.

7. The curing agent component according to claim 1 , wherein the at least one Mannich base is formed using the at least one amine that is reactive with respect to epoxide groups.

8. The curing agent component according to claim 7 , wherein the at east one amine is a polyamine.

9. The curing agent component according to claim 1 , wherein the at least one polyphenol corresponds to the following formula:

in which

R 1 represents H;

R 2 represents a C 1 -C 15 alkyl;

m is 0, 1, or 2; and

n is 0 to 15.

10. The curing agent component according to claim 9 , wherein R 2 represents —CH 3 and m is 1 or 2, or R 2 represents tert-butyl or a C 1 -C 15 alkyl and m is 1.

11. The curing agent component according to claim 1 , wherein the at least one polyphenol is contained in the curing agent component in a proportion of from 8 to 25 wt. %.

12. The curing agent component according to claim 1 , wherein the curing agent component further comprises at least one additive selected from the group consisting of diluents, solvents, accelerants, silanes, thickeners, and inorganic fillers.

13. A multicomponent epoxide resin composition, comprising:

at least one epoxide resin component (A) containing at least one curable epoxide resin and optionally a reactive diluent, and

at least one curing agent component (B) according to claim 1 ,

wherein the at least one epoxide resin component (A) and the curing agent component (B) are separate from one another.

14. The multicomponent epoxide resin composition according to claim 13 , wherein the multicomponent epoxide resin composition further comprises at least one additive selected from the group consisting of co-accelerants, adhesion promoters, reactive diluents, thickeners, and fillers.

15. The curing agent according to claim 1 , wherein n=1-20.

Priority Claims (1)
EP 17200077 · Nov 6, 2017 · regional
Continuity (1)
Related Publication 20210221943A1 · Jul 22, 2021