Amine co-accelerator for acrylic adhesives

Patent metadata

Field	Value
Publication number	US-9896607-B2
Application number	US-201514661324-A
Country	US
Kind code	B2
Filing date	Mar 18, 2015
Priority date	Mar 19, 2014
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

An acrylic adhesive composition is provided comprising a free-radical polymerizable monomer, an initiation system and a co-accelerator that enhances the reactivity of the initiation system by increasing the reaction rate between the oxidizing agent and the reducing agent. The free radical-polymerizable monomer preferably comprises methyl methacrylate (MMA), the initiator system preferably comprises N,N-diisopropanol-p-toluidine (DIIPT) and benzoyl peroxide (BPO), and the co-accelerator preferably comprises 1,4-diazabicyclo[2.2.2]octane (or triethylene diamine (TDA)).

First claim

What is claimed is:

1. A curable composition comprising a free-radical polymerizable acrylic monomer, an oxidizing agent, an aromatic tertiary amine reducing agent, and a tertiary amine co-accelerator comprising a bicyclic diaza compound that increases the reaction rate between the oxidizing agent and the reducing agent, wherein the curable composition is provided in two parts: in part A: (a) the at least one free radical-polymerizable acrylic monomer; and (b) the reducing agent and in part B: an oxidizing agent wherein the co-accelerator is present in at least one of part A or part B, and the weight ratio of part A to part B is from about 1:1 to about 15:1.

2. The composition of claim 1 , wherein the reducing agent comprises at least one of N,N-diisopropanol-p-chloroaniline; N,N-diisopropanol-p-bromoaniline; N,N-diisopropanol-p-bromo-m-methylaniline; N,N-dimethyl-p-chloroaniline; N,N-dimethyl-p-bromoaniline; N,N-diethyl-p-chloroaniline; N,N-diethyl-p-bromoaniline; N,N-dimethyl-p-aniline; or N,N-diisopropanol-p-toluidine.

3. The composition of claim 2 , wherein the aromatic tertiary amine reducing agent comprises N,N-diisopropanol-para-toluidine.

4. The composition of claim 1 , wherein the co-accelerator comprises 1,4-diazabicyclo[2.2.2]octane.

5. The composition of claim 1 , wherein the tertiary amine reducing agent comprises N—N-diisopropanol-para-toluidine and the co-accelerator comprises 1,4-diazabicyclo[2.2.2]octane and the composition is otherwise free of amine compounds.

6. The composition of claim 1 , wherein the composition is free of isocyanate compounds.

7. The composition of claim 1 , wherein the free radical-polymerizeable monomer comprises at least one of methylmethacrylate, or tetrahydrofurfuryl methacrylate.

8. The composition of claim 1 , further comprising a toughener.

9. The composition of claim 8 , wherein the toughener comprises at least one of glycidyl methacrylate/carboxyl terminated butadiene (GMA/CTB) adducts, core-shell impact modifiers, or block copolymer elastomers.

10. The composition of claim 1 , further comprising an adhesion promoter.

11. The composition of claim 10 , wherein the adhesion promoter comprises hydroxyethyl methacrylate phosphate.

12. The composition of claim 1 , further comprising methacrylic acid.

13. The composition of claim 1 , wherein the oxidizing agent comprises benzoyl peroxide.

14. The composition of claim 1 disposed between two substrates and cured so as to provide a bond therebetween having a bond strength of at least 1000 psi as measured by lap shear strength.

15. The composition of claim 14 wherein at least one of the two substrates comprises aluminum.

Assignees

• Lord Corp

Inventors

• Hill John E
• Abbey Kirk J

Classifications

• Y10T428/31699

  Ester, halide or nitrile of addition polymer · CPC title

• C09J4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C09J133/12 Primary

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C09J143/02

  Homopolymers or copolymers of monomers containing phosphorus · CPC title

• C08K5/3462

  Six-membered rings · CPC title