Polymerizable composition including a benzoxazine and an acid-forming peroxide catalyst, article, and method

Patent metadata

Field	Value
Publication number	US-9371477-B2
Application number	US-201314437052-A
Country	US
Kind code	B2
Filing date	Dec 11, 2013
Priority date	Dec 27, 2012
Publication date	Jun 21, 2016
Grant date	Jun 21, 2016

Abstract

A polymerizable composition, articles, and methods are provided, wherein the polymerizable composition includes a benzoxazine, an acid-forming peroxide catalyst and optionally a film-forming polymer, a co-catalyst, a curative, or a combination thereof.

First claim

What is claimed is:

1. A polymerizable composition comprising:
a 3,4-dihydro-1,3-benzoxazine;
an acid-forming peroxide catalyst;
a non-reactive film-forming material,
wherein the composition is polymerizable by ionic ring opening of the benzoxazine;
and optionally a co-catalyst, a curative, or a combination thereof.

2. The polymerizable composition of claim 1 wherein the acid-forming peroxide catalyst is present in an amount of 0.1 wt-% to 10 wt-%, based on the total weight of the benzoxazine.

3. The polymerizable composition of claim 1 wherein the film-forming material is present in an amount of 10 wt-% to 75 wt-%, based on the total weight of the polymerizable composition.

4. The polymerizable composition of claim 1 wherein the acid-forming peroxide catalyst comprises a carboxyl group, acetyl group, phthalyl group, sulfonyl group, or a combination thereof.

5. The polymerizable composition of claim 4 wherein the acid-forming peroxide catalyst is selected from the group of a diacyl peroxide, a peroxydicarbonate, a peroxy ester, and a combination thereof.

6. The polymerizable composition of claim 1 free of a chlorinated organic solvent.

7. The polymerizable composition of claim 1 wherein the composition comprises a co-catalyst, wherein the co-catalyst is selected from the group of elemental sulfur, elemental selenium, a sulfide of a Group VA element, a sulfide of a Group VIA element, a selenide of a Group VA element, a selenide of a Group VIA element, and a combination thereof.

8. The polymerizable composition of claim 1 wherein the composition comprises a co-catalyst, wherein the co-catalyst is a salt of an organometallic complex cation.

9. The polymerizable composition of claim 1 wherein the composition comprises a curative, wherein the curative is selected from the group of a thiol compound, an amine compound, and a combination thereof.

10. The polymerizable composition of claim 1 comprising:
a 3,4-dihydro-1,3-benzoxazine; and
an acid-forming peroxide catalyst;
wherein the polymerizable composition is free of a chlorinated organic solvent.

11. An article comprising a substrate and an adhesive film disposed thereon comprising a polymerizable composition of claim 1 .

12. A method of forming an adhesive, the method comprising:
providing a polymerizable composition of claim 1 ; and
heating the polymerizable composition at a temperature and for a time effective to at least partially polymerize the benzoxazine.

13. A method of forming an adhesive, the method comprising:
providing the polymerizable composition of claim 1 ; and
heating the polymerizable composition at a temperature of at least 150° C. for a time effective to at least partially polymerize the benzoxazine by ionic ring opening of the benzoxazine.

Assignees

• 3M Innovative Properties Co

Inventors

• Gorodisher Ilya
• Salnikov Dmitriy

Classifications

• C09J179/02

  Polyamines · CPC title

• C08G73/0233

  Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups · CPC title

• C09J179/04 Primary

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• C09D179/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/06

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule · CPC title