Photolabile barbiturate compounds
US-11897977-B2 · Feb 13, 2024 · US
US12552974B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-12552974-B2 |
| Application number | US-202017626944-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jul 16, 2020 |
| Priority date | Jul 26, 2019 |
| Publication date | Feb 17, 2026 |
| Grant date | Feb 17, 2026 |
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A method of disposing an adhesive composition onto a first surface of a first substrate comprises: a) disposing a photoactivatable adhesive precursor composition onto at least a portion of the first surface of the first substrate according to a predetermined pattern, and b) exposing the photoactivatable adhesive precursor composition to actinic electromagnetic radiation, thereby providing an adhesive precursor composition that spontaneously cures to provide the adhesive composition. The photoactivatable adhesive precursor composition comprises: at least one free-radically polymerizable compound and a photoactivatable redox initiation system comprising: (i) at least one photoactivatable reducing agent precursor; (ii) at least one transition metal compound comprising at least one metal selected from groups 5 to 11 in the Periodic Table of the Elements; (iii) optional organic peroxide; and (iv) optional quaternary ammonium halide. An article preparable according to the method is also disclosed.
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What is claimed is: 1 . A method of disposing an adhesive composition onto a first surface of a first substrate, the method comprising steps: a) disposing a photoactivatable adhesive precursor composition onto a portion of the first surface of the first substrate according to a predetermined pattern, wherein the photoactivatable adhesive precursor composition comprises: at least one free-radically polymerizable compound; and a photoactivatable redox initiation system comprising: (i) at least one photoactivatable reducing agent precursor; (ii) at least one transition metal compound comprising at least one metal selected from groups 5 to 11 in the Periodic Table of the Elements; and b) exposing the photoactivatable adhesive precursor composition to actinic electromagnetic radiation, thereby providing an adhesive precursor composition that spontaneously cures to provide the adhesive composition, wherein the at least one photoactivatable reducing agent precursor is represented by: wherein each R 1 , R 2 , and R 3 independently represents H or a hydrocarbyl group having from 1 to 18 carbon atoms; and each R Photo independently represents a photoremovable group. 2 . The method of claim 1 , wherein the at least one metal selected from groups 5 to 11 in the Periodic Table of the Elements comprises at least one of copper, iron, ruthenium, chromium, molybdenum, palladium, nickel, platinum, manganese, rhodium, rhenium, cobalt, vanadium, gold, niobium, or silver. 3 . The method of claim 1 , wherein the at least one free-radically polymerizable compound comprises at least one (meth)acrylic monomer or oligomer. 4 . The method of claim 1 , wherein the photoremovable group is an o-nitrobenzyl group. 5 . The method of claim 1 , further comprising organic peroxide. 6 . A method of disposing an adhesive composition onto a first surface of a first substrate, the method comprising steps: a) disposing a photoactivatable adhesive precursor composition onto a portion of the first surface of the first substrate according to a predetermined pattern, wherein the photoactivatable adhesive precursor composition comprises: at least one free-radically polymerizable compound; and a photoactivatable redox initiation system comprising: (i) at least one photoactivatable reducing agent precursor; (ii) at least one transition metal compound comprising at least one metal selected from groups 5 to 11 in the Periodic Table of the Elements; and (iii) quaternary ammonium halide; and b) exposing the photoactivatable adhesive precursor composition to actinic electromagnetic radiation, thereby providing an adhesive precursor composition that spontaneously cures to provide the adhesive composition. 7 . The method of claim 1 , wherein said disposing the photoactivatable adhesive precursor composition comprises screen printing or stencil printing the photoactivatable adhesive precursor composition. 8 . The method of claim 1 , further comprising contacting the adhesive precursor composition with at least a portion of a second surface of a second substrate prior to sufficient curing to provide the adhesive composition. 9 . An article comprising: a first surface of a first substrate adhered to a second surface of a second substrate by an adhesive layer having a predetermined pattern that contacts less than the entire first surface, wherein the adhesive layer comprises an adhesive composition preparable by exposing a photoactivatable adhesive precursor composition to actinic electromagnetic radiation, thereby providing an adhesive precursor composition that spontaneously cures to provide the adhesive composition, and wherein the photoactivatable adhesive precursor composition comprises: at least one free-radically polymerizable compound; and a photoactivatable redox initiation system comprising: (i) at least one photoactivatable reducing agent precursor; and (ii) at least one transition metal compound comprising at least one metal selected from groups 5 to 11 in the Periodic Table of the Elements, wherein the at least one photoactivatable reducing agent precursor is represented by: wherein each R 1 , R 2 , and R 3 independently represents H or a hydrocarbyl group having from 1 to 18 carbon atoms; and each R Photo independently represents a photoremovable group. 10 . The article of claim 9 , wherein the at least one metal selected from groups 5 to 11 in the Periodic Table of the Elements comprises at least one of copper, iron, ruthenium, chromium, molybdenum, palladium, nickel, platinum, manganese, rhodium, rhenium, cobalt, vanadium, gold, niobium, or silver. 11 . The article of claim 9 , wherein the at least one free-radically polymerizable compound comprises at least one (meth)acrylic monomer or oligomer. 12 . The article of claim 9 , wherein the photoremovable group is an o-nitrobenzyl group. 13 . The article of claim 9 , further comprising organic peroxide. 14 . An article comprising: a first surface of a first substrate adhered to a second surface of a second substrate by an adhesive layer having a predetermined pattern that contacts less than the entire first surface, wherein the adhesive layer comprises an adhesive composition preparable by exposing a photoactivatable adhesive precursor composition to actinic electromagnetic radiation, thereby providing an adhesive precursor composition that spontaneously cures to provide the adhesive composition, and wherein the photoactivatable adhesive precursor composition comprises: at least one free-radically polymerizable compound; and a photoactivatable redox initiation system comprising: (i) at least one photoactivatable reducing agent precursor; (ii) at least one transition metal compound comprising at least one metal selected from groups 5 to 11 in the Periodic Table of the Elements; and iii) quaternary ammonium halide. 15 . The article of claim 9 , wherein the article comprises at least one of a smartphone, a tablet computer, or an electronic display monitor. 16 . The article of claim 14 , wherein the article comprises at least one of a smartphone, a tablet computer, or an electronic display monitor.
Presence of (meth)acrylic polymer · CPC title
use of irradiation · CPC title
Vinyl aromatic monomers and methacrylates as the only monomers · CPC title
and containing two or more oxygen atoms · CPC title
Homopolymers or copolymers of esters {(C09J143/04 takes precedence)} · CPC title
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