US 12,227,612 B2
Ultrafast cyclic ether-amine photopolyaddition and uses thereof
Patxi Garra, Mulhouse (FR); Jacques Lalevée, Mulhouse (FR); Fabrice Morlet-Savary, Pfastatt (FR); Céline Dietlin, Mulhouse (FR); and Aurore Caron, Mulhouse (FR)
Assigned to CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, Paris (FR); and UNIVERSITE DE HAUTE-ALSACE, Mulhouse (FR)
Appl. No. 17/280,354
Filed by Centre National de la Recherche Scientifique, Paris (FR); and Université de Haute-Alsace, Mulhouse (FR)
PCT Filed Sep. 25, 2019, PCT No. PCT/EP2019/075871
§ 371(c)(1), (2) Date Mar. 26, 2021,
PCT Pub. No. WO2020/064839, PCT Pub. Date Apr. 2, 2020.
Claims priority of application No. 18306272 (EP), filed on Sep. 27, 2018.
Prior Publication US 2021/0363286 A1, Nov. 25, 2021
Int. Cl. C08F 2/46 (2006.01); C08F 2/50 (2006.01); C08G 59/02 (2006.01); C08G 59/22 (2006.01); C08G 59/38 (2006.01); C08G 59/50 (2006.01); C08G 61/04 (2006.01); C08J 5/24 (2006.01); C08K 5/03 (2006.01); C08K 5/45 (2006.01)
CPC C08G 59/022 (2013.01) [C08G 59/226 (2013.01); C08G 59/38 (2013.01); C08G 59/5006 (2013.01); C08G 59/5033 (2013.01); C08J 5/249 (2021.05); C08K 5/03 (2013.01); C08K 5/45 (2013.01); C08G 2150/00 (2013.01); C08G 2170/00 (2013.01)] 21 Claims
 
1. A composition curable on demand under the triggering action of UV-visible to near-infrared irradiation comprising:
(a) at least one polyfunctional cyclic ether component comprising at least two cyclic ether moieties, wherein the at least one polyfunctional cyclic ether component is selected from:
polyfunctional aromatic epoxy compounds selected from:

OG Complex Work Unit Chemistry
polyfunctional heteroaliphatic epoxy compounds selected from:

OG Complex Work Unit Chemistry
epoxy prepolymers obtained from reaction of diols with epichlorhydrine, selected from bisphenol A diglycidyl ether, 1,4-butanediol diglycidyl ether;
epoxy prepolymers obtained from reaction of diamines with epichlorhydrine, selected from 4,4′-diaminodiphenyl methane tetraglycidyl ether;
or a mixture of two or more of the above;
(b) at least one polyfunctional amine component comprising at least two primary or secondary amine moieties; and
(c) a photoinitiating system generating catalytic species comprising:
at least one suitable photoinitiator or photosensitizer that absorbs light at a UV-visible to near-infrared irradiation under which the composition is to be cured; and
at least one oxidation agent able to react with the photoinitiator or the photosensitizer, selected from iodonium salts, sulfonium salts, and thianthrenium salts.