US 12,180,385 B2Granted

Shelf life stable and improved mass polymerizable polycyclic-olefinic compositions

AssigneePromerys, LLC

InventorPramod Kandanarachchi

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Abstract

Embodiments in accordance with the present invention encompass compositions containing one or more polycycloolefinic monomers, optionally at least one multifunctional olefinic monomer and a suitable solvent, which exhibits long shelf life stability and undergoes mass polymerization only when subjected to a suitable temperature to provide a three-dimensional insulating articles. Embodiments of this invention exhibit hitherto unattainable properties, such as for example, low dielectric constant and low loss properties, and very high thermal properties, among others. The compositions of this invention may additionally contain one or more organic or inorganic filler materials, which provide improved thermo-mechanical properties in addition to very low dielectric properties. In general the compositions are stable at room temperature for an extended period of time lasting up to a few weeks and undergo mass polymerization only when subjected to suitable higher temperatures generally above 100° C. The compositions of this invention are useful in various applications, including as insulating materials in millimeter wave radar antennas, among others.

Claims14

Dependent claims

A film forming composition comprising:

a) one or more olefinic monomers selected from the group consisting of:
2-hexyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (HexTD);
tetracyclododecene (TD);
5-butylbicyclo[2.2.1]hept-2-ene (BuNB);
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB);
2,2′-bi(bicyclo[2.2.1]heptan-5-ene (NBANB);
5-cyclohexylbicyclo[2.2.1]hept-2-ene (CyHexNB);
bicyclo[2.2.1]hepta-2,5-diene (NBD);
and
3a,4,4a,5,8,8a,9,9a-octahydro-1H-4,9:5,8-dimethanocyclopenta[b]naphthalene (CPD3);
b) an organopalladium compound selected from the group consisting of:
palladium (II) bis(tricyclohexylphosphine) dichloride;
palladium (II) bis(tricyclohexylphosphine) dibromide;
palladium (II) bis(tricyclohexylphosphine) diacetate (Pd785);
and
palladium (II) bis(tricyclohexylphosphine) bis(trifluoroacetate);
and
c) an activator selected from the group consisting of:
tolylcumyliodonium-tetrakis pentafluorophenylborate;
4,4′-di-(C10-C13) alkyldiphenyl iodonium tetrakis(2,3,4,5,6-pentafluorophenyl) borate;
lithium tetrakis(pentafluorophenyl)borate etherate (LiFABA);
and
dimethylanilinium tetrakis(pentafluorophenyl)borate (DANFABA);
and
d) a solvent selected from the group consisting of water, toluene, trifluorotoluene, tetrahydrofuran, ethyl acetate, cyclohexane, methylcyclohexane, and a mixture in any combination thereof;
and
wherein the composition exhibits shelf life stability from about one hour up to seven weeks at about 25° C. and undergoes mass polymerization only when subjected to a suitable temperature above 100° C.

24 more elements

A kit for forming a film comprising a composition comprising:

a) one or more olefinic monomers of formula (I) selected from the group consisting of:
2-hexyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (HexTD);
tetracyclododecene (TD);
5-butylbicyclo[2.2.1]hept-2-ene (BuNB);
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB);
2,2′-bi(bicyclo[2.2.1]heptan-5-ene (NBANB);
5-cyclohexylbicyclo[2.2.1]hept-2-ene (CyHexNB);
bicyclo[2.2.1]hepta-2,5-diene (NBD);
and
3a,4,4a,5,8,8a,9,9a-octahydro-1H-4,9:5,8-dimethanocyclopenta[b]naphthalene (CPD3);
b) an organopalladium compound selected from the group consisting of:
palladium (II) bis(tricyclohexylphosphine) dichloride;
palladium (II) bis(tricyclohexylphosphine) dibromide;
palladium (II) bis(tricyclohexylphosphine) diacetate (Pd785);
and
palladium (II) bis(tricyclohexylphosphine) bis(trifluoroacetate);
and
c) an activator selected from the group consisting of:
tolylcumyliodonium-tetrakis pentafluorophenylborate;
4,4′-di-(C10-C13)alkyldiphenyl iodonium tetrakis(2,3,4,5,6-pentafluorophenyl)borate;
lithium tetrakis(pentafluorophenyl)borate etherate (LiFABA);
and
dimethylanilinium tetrakis(pentafluorophenyl)borate (DANFABA);
and
d) a solvent selected from the group consisting of water, toluene, trifluorotoluene, tetrahydrofuran, ethyl acetate, cyclohexane, methylcyclohexane, and a mixture in any combination thereof;
and
wherein the composition exhibits shelf life stability from about one hour up to seven weeks at about 25° C. and undergoes mass polymerization only when subjected to a suitable temperature above 100° C.

24 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/514,579Filed 29 Oct 2021 · us provisional application
Priority: 30 Oct 2020
Published: US 2022/0135832 A15 May 2022
Granted: 31 Dec 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification13 codes

C08G 61/08
Prepared by ring-opening of carbocyclic compounds: of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
C09D 165/00
Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon
C08F 232/08
Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double…
C08F 2500/26
Characteristics or properties of obtained polyolefins; Use thereof: use as polymer for film forming

Family

Application63/107,522Us provisional application · filed 30 Oct 2020
US 2022/0135832 A1Pre-grant publication · published 5 May 2022
US 12,180,385 B2This patent

From the US filing history. Foreign family members aren’t listed.

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