Nitrogen-containing heterocyclic epoxy curing agents, compositions and methods

Patent metadata

Field	Value
Publication number	US-10556985-B2
Application number	US-201615343632-A
Country	US
Kind code	B2
Filing date	Nov 4, 2016
Priority date	Nov 17, 2015
Publication date	Feb 11, 2020
Grant date	Feb 11, 2020

Abstract

Amine-epoxy curing agents are disclosed including at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (I) and at least one saturated fused bicyclic heterocyclic compound having three nitrogen heteroatoms according to formula (II):

wherein X is independently 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 or a divalent polyethylene polyamine derivative having 1 to 8 nitrogen atoms, Y 2 is a direct bond or a divalent polyethylene polyamine group having 1 to 7 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.

First claim

We claim:

1. An amine-epoxy curing agent comprising the contact product of:
(a) an amine epoxy curing agent having at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (I):

wherein X is independently 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 groups; and
(b) at least one multifunctional amine having three or more active amine hydrogens per molecule.

2. The amine-epoxy curing agent of claim 1 , wherein the at least one multifunctional amine is selected from the group consisting of an aliphatic amine, a cycloaliphatic amine, an aromatic amine, a poly(alkylene oxide) diamine or triamine, 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 with a dimer fatty acid or a mixture of a dimer fatty acid and fatty acid, an amidoamine derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine with a fatty acid, an amine adduct derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine with a glycidyl ether of bisphenol A or bisphenol F or an epoxy novolac resin, and combinations thereof.

3. A method for forming an epoxy comprising reacting an amine epoxy curing agent with at least one multifunctional epoxy resin, where:
the amine-epoxy curing agent comprises at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (I)

where X is independently selected from a hydrogen atom, a linear or branched C 1 to C 4 alkyl groups 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 groups.

4. The amine-epoxy curing agent of claim 1 , wherein X and R are H.

5. An amine-epoxy composition comprising an amine-epoxy curing agent and at least one multifunctional epoxy resin, wherein the amine-epoxy curing agent comprises at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (I):

wherein X is independently 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 groups, and further comprises at least one multifunctional amine having three or more active amine hydrogens per molecule.

6. The amine-epoxy composition of claim 5 , wherein X and R are H.

7. The amine-epoxy composition of claim 5 , wherein the at least one multifunctional amine is selected from the group consisting of an aliphatic amine, a cycloaliphatic amine, an aromatic amine, a poly(alkylene oxide) diamine or triamine, 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 with a dimer fatty acid or a mixture of a dimer fatty acid and fatty acid, an amidoamine derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine with a fatty acid, an amine adduct derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine with a glycidyl ether of bisphenol A or bisphenol F or an epoxy novolac resin, and combinations thereof.

8. A cured epoxy resin obtained from the composition of claim 5 .

Assignees

• Evonik Operations Gmbh

Inventors

• Zheng Shiying
• Ananthachar Sudhir
• Fazel Shafiq Nisarali
• Cook Michael Ian
• Rasing Robert Marjo Theodoor
• Cao Wei
• Tijsma Edze Jan

Classifications

• C08G59/508

  having three nitrogen atoms in the ring · CPC title

• C08K5/3445 Primary

  Five-membered rings · CPC title

• C07D233/02

  having no double bonds between ring members or between ring members and non-ring members · CPC title

• C08G59/5073 Primary

  having two nitrogen atoms in the ring · CPC title

• C08G59/5086

  Triazines; Melamines; Guanamines · CPC title