Furan-based amines as curing agents for epoxy resins in low VOC applications

• US 10,287,389 B2
• Filed: 02/24/2015
• Issued: 05/14/2019
• Est. Priority Date: 02/24/2014
• Status: Active Grant

• Current Assignee: Sika Technology Ag (Compagnie de Saint-Gobain SA)
• Original Assignee: Sika Technology Ag (Compagnie de Saint-Gobain SA)
• Inventors: Urban, Claus, Schaffeler, Nina
• Primary Examiner(s): McCulley, Megan
• Application Number:
  US15/121,155
• Publication Number:
  US 20170009005A1
• Time in Patent Office: 1,540 Days
• Field of Search: None
• CPC Class Codes: C08G 59/184 with amines
• CPC Class Codes: C08G 59/223 together with monoepoxy compounds
• CPC Class Codes: C08G 59/5046 heterocyclic
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09J 163/00 Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins

Abstract

A room temperature or low temperature curable epoxy formulation including a) an epoxy component including at least one epoxy resin and b) a hardener component including at least one compound of formula (I)

• • wherein X is a divalent hydrocarbon group, which optionally contains one or more heteroatoms, and n is 0, 1, 2 or 3, preferably 0 or 1, and/or at least one epoxy-amine adduct, which is a reaction product of the compound of formula (I) and an epoxy compound selected from at least one of a monoepoxide and a polyepoxide, as a curing agent. The compounds of formula (I) and the epoxy-amine adduct are suitable as curing agents for epoxy formulations which provide good surface properties and good cure speed, even at low temperature curing. In particular, amine blushing can be avoided or reduced to a large extent, when these curing agents are used.

Claims

1. A room temperature or low temperature curable epoxy formulation comprising

a) an epoxy component comprising at least one epoxy resin and

b) a hardener component comprising

at least one epoxy-amine adduct, which is a reaction product of a compound of formula (I) and an epoxy compound selected from at least one of a monoepoxide and/or a polyepoxide,

as a curing agent

2. The room temperature or low temperature curable epoxy formulation according to claim 1, wherein for the epoxy-amine adduct, the compound of formula (I) is a compound of formula (I), wherein n is 0, or a compound of formula (II)

3. The room temperature or low temperature curable epoxy formulation according to claim 2, wherein the compound of formula (I) is the compound of formula (II) in which R¹ is H and R² is methyl (IIb);

R¹ is H and R² is phenyl (IIc);

R¹ and R² are both methyl (IId);

R¹ is methyl and R² is ethyl (IIe);

or R¹ is methyl and R² is isobutyl (IIf).

4. The room temperature or low temperature curable epoxy formulation according to claim 2, wherein R¹ and R² in formula (II) are the same or different and selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, pentyl, hexyl, benzyl, or phenyl, which may be substituted, provided that R¹ and R² are not both hydrogen.

5. The room temperature or low temperature curable epoxy formulation according to claim 1, wherein the epoxy formulation has a TVOC content after 3 days (TVOC₃) of less than 50 mg/m³, when measured as defined in the AgBB evaluation scheme of 2010, wherein TVOC means Total Volatile Organic Compounds which is defined as the sum of the concentration of all individual substances with concentrations equal to or greater than 5 μ

g/m³ within the retention range C₆-C₁₆, and the AgBB evaluation scheme of 2010 is an evaluation scheme developed by AgBB (German Committee for Health-related Evaluation of Building Products).

6. The room temperature or low temperature curable epoxy formulation according to claim 1, wherein the epoxy formulation has a benzyl alcohol content of less than 5% by weight.

7. The room temperature or low temperature curable epoxy formulation according to claim 1, wherein the amine hydrogen to epoxy equivalent ratio is 0.8 to 1.2.

8. The room temperature or low temperature curable epoxy formulation according to claim 1, wherein the hardener component further comprises at least one further polyamine, and/or at least one epoxy-amine adduct thereof, and/or at least one accelerator.

9. The room temperature or low temperature curable epoxy formulation according to claim 1, wherein the epoxy formulation is an epoxy coating composition, an epoxy flooring material, an epoxy adhesive, an epoxy grout or potting material, an epoxy sealant, a waterproofing coating composition or an epoxy composite material.

10. A method for coating or adhering substrates or for preparing composites using a room temperature or low temperature curable epoxy formulation according to claim 1, the method comprising

a) mixing the epoxy component and the hardener component of the room temperature or low temperature curable epoxy formulation,

b) b1) applying the mixed epoxy formulation on a substrate;

b2) applying the mixed epoxy formulation on a surface of a first substrate and contacting the coated surface with a second substrate to obtain an adhesive bond;

or b3) laminating one or more substrates with the mixed epoxy formulation or embedding one or more substrates in the mixed epoxy formulation, and subsequently

c) curing the epoxy formulation at a temperature of not more than 50°

C.

11. Cured article obtainable according to the method of claim 10.