Epoxy curing agents, compositions and uses thereof

Patent metadata

Field	Value
Publication number	US-10465039-B2
Application number	US-201715596996-A
Country	US
Kind code	B2
Filing date	May 16, 2017
Priority date	Nov 17, 2015
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

The present invention relates to epoxy curing agents which are obtained from the reaction of a polyalkylene polyether modified polyepoxide resin and a polyamine component. They polyamine component is a reaction product of a polyethylene polyamine having 3 to 10 nitrogen atoms, for example, diethylenetriamine (DETA), and at least one aldehyde having 1 to 8 carbon atoms, for example, formaldehyde. The epoxy curing agent may be used as part of a two component coating system in the curing of liquid or pre-dispersed curable epoxy resins.

First claim

The invention claimed is:

1. A curing agent composition comprising the reaction product of:
(a) a polyamine comprising at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (II)

wherein X is selected from a hydrogen atom, a linear or branched C 1 to C 4 alkyl group and a substituted or unsubstituted phenyl group, Y 1 is a direct bond or a divalent polyethylene polyamine group having 1 to 8 nitrogen atoms, and R is independently a hydrogen atom or a group selected from C 1 -C 8 linear, cyclic, and branched alkyl, alkenyl, and alkaryl groups; and
(b) a polyalkylene polyether modified polyepoxide resin.

2. The curing agent composition of claim 1 further comprises at least one multifunctional amine having 2 or more active amine hydrogens.

3. The curing agent composition of claim 2 further comprises water.

4. The curing agent composition of claim 2 , wherein the at least one multifunctional amine is an aliphatic amine, a cycloaliphatic amine, an aromatic amine, a Mannich base derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, a polyamide derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, an amidoamine derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, an amine adduct derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, or any combination thereof.

5. The curing agent composition of claim 1 , wherein X is hydrogen and R is hydrogen.

6. The curing agent composition of claim 1 , wherein the polyalkylene polyether modified polyepoxide resin comprises the reaction product of: a polyalkylene polyether polyol and a polyepoxide compound.

7. The curing agent composition of claim 6 wherein the polyalkylene polyether polyol comprises polyethylene glycol.

8. The curing agent composition of claim 1 , wherein the polyalkylene polyether modified polyepoxide resin comprises the reaction product of: a polyepoxide compound and a polyetheramine.

9. The curing agent composition of claim 1 , further comprises water.

10. The curing agent composition of claim 1 , further comprises isophorone diamine.

11. The curing agent composition of claim 1 , further comprises a co-curing agent selected from an amidoamine curing agent, an aliphatic curing agent, a polyamide curing agent, a cycloaliphatic curing agent, or a Mannich base curing agent.

12. An amine-epoxy composition comprising:
the reaction product of a curing agent and an epoxy composition, wherein the epoxy composition comprises at least one multifunctional epoxy resin, and wherein the curing agent comprises:
a reaction product of at least one polyamine and at least one polyalkylene polyether modified polyepoxide resin, wherein the at least one polyamine comprises at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (II)

wherein X is selected from a hydrogen atom, a linear or branched C 1 to C 4 alkyl group and a substituted or unsubstituted phenyl group Y 1 is a direct bond or a divalent polyethylene polyamine group having 1 to 8 nitrogen atoms, and R is independently a hydrogen atom or a group selected from C 1 -C 8 linear, cyclic, and branched alkyl, alkenyl and alkaryl groups.

13. The composition of claim 12 , wherein the composition further comprises water.

14. An article of manufacture comprising the composition of claim 12 .

15. The article of claim 14 , wherein the article is an adhesive, a coating, a primer, a sealant, a curing compound, a construction product, a flooring product, or a composite product.

16. A process for the preparation of a curing agent for aqueous epoxy resin compositions, comprising:
(a) reacting a polyethylene polyamine having 3 to 10 nitrogen atoms with at least one aldehyde having 1 to 8 carbon atoms to produce a polyethylene polyamine component, wherein the polyethylene polyamine component comprises at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (II)

wherein X is selected from a hydrogen atom, a linear or branched C 1 to C 4 alkyl group and a substituted or un-substituted phenyl group, Y 1 is a direct bond or a divalent polyethylene polyamine group having 1 to 8 nitrogen atoms, and R is independently a hydrogen atom or a group selected from C 1 -C 8 linear, cyclic, and branched alkyl, alkenyl, and alkaryl group; and
(b) reacting the polyethylene polyamine component with at least one polyalkylene polyether modified polyepoxide resin to produce a curing agent.

17. The process of claim 16 , further comprising
(c) mixing the curing agent with water.

18. An epoxy modified cement composition comprising:
(A) an epoxy composition comprising at least one multifunctional epoxy resin having at least two epoxide groups per molecule;
(B) a curing agent comprising water and the reaction product of: (1) a polyalkylene polyether modified polyepoxide resin component, and (2) a polyamine component comprising at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (II)

wherein X is selected from a hydrogen atom, a linear or branched C 1 to C 4 alkyl group and a substituted or unsubstituted phenyl group, Y 1 is a direct bond or a divalent polyethylene polyamine group having 1 to 8 nitrogen atoms, and R is independently a hydrogen atom or a group selected from C 1 -C 8 linear, cyclic, and branched alkyl alkenyl, and alkaryl groups; and
(C) a solid component comprising at least one hydraulic inorganic binder.

Assignees

• Evonik Degussa Gmbh

Inventors

• Zheng Shiying
• Ananthachar Sudhir
• Rasing Robert
• Bozok Nergiz
• Fazel Shafiq
• Oberlander Michael

Classifications

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C07D487/08

  Bridged systems · CPC title

• C04B28/04

  Portland cements · CPC title

• C08G59/508

  having three nitrogen atoms in the ring · CPC title

• C08G59/245

  aromatic · CPC title