US 12,742,041 B2Granted

Dual catalyst system for mass vinyl addition and cationic polymerizable compositions

AssigneePromerus, LLC

InventorGuodong Deng

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Abstract

Embodiments in accordance with the present invention encompass compositions comprising an organopalladium compound, a photoacid generator, a photosensitizer, one or more epoxy group containing olefinic monomers. The compositions of this invention may additionally contain one or more olefinic monomers and a stabilizer, such as for example a hindered amine. The compositions undergo simultaneous vinyl addition polymerization and cationic polymerization when exposed to a suitable actinic radiation to form a substantially transparent film. The compositions of this invention are stable at room temperature for several days to several months and undergo mass polymerization only when subjected to suitable actinic radiation. The monomers employed therein have a range of optical and mechanical properties, and thus these compositions can be tailored to form films having various opto-electronic properties. More specifically, the compositions of this invention undergo much faster mass polymerization and exhibit superior thermo-mechanical properties when compared with the compositions containing only the olefinic monomers. Accordingly, compositions of this invention are useful in various applications, including as coatings, encapsulants, fillers, leveling agents, sealants, adhesives, among others.

Claims20

Dependent claims

A thermoset film forming composition selected from the group consisting of:

2-(4-(bicyclo[2.2.1]hept-5-en-2-yl)butyl) oxirane (EHNB), palladium hexafluoroacetylacetonate (Pd520), tolylcumyliodonium-tetrakis pentafluorophenylborate and 2-isopropyl-9H-thioxanthen-9-one (ITX);
3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), tolylcumyliodonium-tetrakis pentafluorophenylborate and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), tolylcumyliodonium-tetrakis pentafluorophenylborate and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB), 2-(4-(bicyclo[2.2.1]hept-5-en-2-yl)butyl) oxirane (EHNB), palladium hexafluoroacetylacetonate (Pd520), tolylcumyliodonium-tetrakis pentafluorophenylborate and 2-isopropyl-9H-thioxanthen-9-one (ITX);
3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1), 2-isopropyl-9H-thioxanthen-9-one (ITX) and bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate (HALS-1);
5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 3-(1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEpTD), palladium hexafluoroacetylacetonate (Pd520), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium (hexafluoroacetylacetonate) methyl tri-isopropylphosphine (Pd489), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX);
and
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium (hexafluoroacetylacetonate) methyl tri-isopropylphosphine (Pd489), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX).

8 more elements

A kit for forming a thermoset film, comprising a composition selected from the group consisting of:

2-(4-(bicyclo[2.2.1]hept-5-en-2-yl)butyl) oxirane (EHNB), palladium hexafluoroacetylacetonate (Pd520), tolylcumyliodonium-tetrakis pentafluorophenylborate and 2-isopropyl-9H-thioxanthen-9-one (ITX);
3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), tolylcumyliodonium-tetrakis pentafluorophenylborate and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), tolylcumyliodonium-tetrakis pentafluorophenylborate and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB), 2-(4-(bicyclo[2.2.1]hept-5-en-2-yl)butyl) oxirane (EHNB), palladium hexafluoroacetylacetonate (Pd520), tolylcumyliodonium-tetrakis pentafluorophenylborate and 2-isopropyl-9H-thioxanthen-9-one (ITX);
3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium hexafluoroacetylacetonate (Pd520), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEpNB), palladium hexafluoroacetylacetonate (Pd520), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1), 2-isopropyl-9H-thioxanthen-9-one (ITX) and bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate (HALS-1);
5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 3-(1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEpTD), palladium hexafluoroacetylacetonate (Pd520), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX);
5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium (hexafluoroacetylacetonate) methyl tri-isopropylphosphine (Pd489), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX);
and
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB), 3-(bicyclo[2.2.1]hept-5-en-2-yl)-7-oxabicyclo[4.1.0]heptane (CHEPNB), palladium (hexafluoroacetylacetonate) methyl tri-isopropylphosphine (Pd489), bis(4,4′-di-C10-C13-alkylphenyl) iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate (PAG1) and 2-isopropyl-9H-thioxanthen-9-one (ITX).

8 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/110,906Filed 17 Feb 2023 · us provisional application
Priority: 18 Feb 2022
Published: US 2023/0265243 A124 Aug 2023
Granted: 22 Sep 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification13 codes

C08G 65/12
Characterised by the catalysts used: containing organo-metallic compounds or metal hydrides
B01J 31/12
Containing organic compounds or metal hydrides: containing organo-metallic compounds or metal hydrides
C08G 65/266
Metals or compounds thereof, e.g. salts: metallic elements not covered by group C08G65/2648 - C08G65/2645, or compounds thereof
C08K 5/45
Sulfur-, selenium-, or tellurium-containing compounds: heterocyclic compounds having sulfur in the ring