Accelerators for two step adhesive systems

Patent metadata

Field	Value
Publication number	US-9371473-B2
Application number	US-201313785007-A
Country	US
Kind code	B2
Filing date	Mar 5, 2013
Priority date	Jun 27, 2012
Publication date	Jun 21, 2016
Grant date	Jun 21, 2016

Abstract

Benzoylthiourea or benzoylthiourethane derivatives as cure accelerators in primers for two step adhesive systems are provided.

First claim

What is claimed is:

1. A process for preparing a reaction product from a curable composition, comprising the steps of:
applying a benzoyl thiourea or benzoyl thiourethane compound within structure I or IA

wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or

wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, to a desired substrate surface,
applying a composition comprising a (meth)acrylate component and an oxidant to that desired substrate surface,
mating a second surface to that substrate surface to form an assembly, and
exposing the assembly to appropriate conditions for a time sufficient to cure the composition.

2. A process for preparing a reaction product from a curable composition, comprising the steps of:
applying a composition comprising a (meth)acrylate component and an oxidant to a desired substrate surface,
applying a benzoyl thiourea or benzoyl thiourethane compound within structure I or IA

wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or

wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, to that desired substrate surface,
mating a second surface to that substrate surface to form an assembly, and
exposing the assembly to appropriate conditions for a time sufficient to cure the composition.

3. A process for preparing a reaction product from a curable composition, comprising the steps of:
applying an oxidant to a desired substrate surface,
applying a composition comprising a (meth)acrylate component and a benzoyl thiourea or benzoyl thiourethane compound within structure I or IA

wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or

wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2 to that desired substrate surface,
mating a second surface to that substrate surface to form an assembly, and
exposing the assembly to appropriate conditions for a time sufficient to cure the composition.

4. A process for preparing a reaction product from a curable composition, comprising the steps of:
applying a composition comprising a (meth)acrylate component and a benzoyl thiourea or benzoyl thiourethane compound within structure I or IA

wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or

wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is

Assignees

• Henkel Corp
• Henkel Ireland Ltd
• Henkel IP & Holding GmbH
• Henkel Ag & Co Kgaa

Inventors

• Birkett David P
• Jacobine Anthony F
• Messana Andrew D
• Schall Joel D
• Mullen David
• Wyer Martin
• Hurlburt Lynnette
• Ouyang Jiangbo
• Shah Smita

Classifications

• C08K5/405

  Thioureas; Derivatives thereof · CPC title

• C08K5/39

  Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates · CPC title

• C09J11/06 Primary

  organic · CPC title

• C09J133/08 Primary

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title