US 12,043,573 B2 · Adhesion promoters and gel-modifiers for olefin metathesis compositions

Abstract

This invention relates to compositions and methods for improving the adhesion of resin compositions to substrate materials, pre-treating substrate materials to improve the adhesion of resin compositions to the substrate materials, and/or controlling gel formation of resin compositions. More particularly, the invention relates to compositions and methods for improving the adhesion of ring opening metathesis polymerization (ROMP) compositions to substrate materials using adhesion promoters containing isocyanate groups in a resin composition. The invention also relates to methods for improving the adhesion of resin compositions to substrate materials by pre-treating substrate materials with adhesion promoters containing isocyanate groups. The invention further relates to a method of providing a gel-modified ROMP composition, in which a hydroperoxide is added to a ROMP polymerizable resin composition in order to control gel formation of the polymerizing resin. An improved ROMP composition is further disclosed, comprising a cyclic olefin, a ROMP metathesis catalyst, an adhesion promoter, and an added hydroperoxide gel modifier. The polymer products produced via ROMP reactions of the invention may be utilized for a wide range of materials and composite applications. The invention has utility in the fields of catalysis, organic synthesis, and polymer and materials chemistry and manufacture.

Claims24

Dependent claims

A method for improving the adhesion of a resin composition to a substrate material, comprising:

combining at least one adhesion promoter, at least one cyclic olefin, and at least one olefin metathesis catalyst to form the resin composition;
contacting the resin composition with the substrate material;
and
subjecting the resin composition to conditions effective to promote an olefin metathesis reaction of the at least one cyclic olefin,
wherein the at least one adhesion promoter comprises at least one compound containing at least two isocyanate groups and a compound containing a heteroatom-containing functional group and a metathesis-active olefin,
wherein the at least one compound containing at least two isocyanate groups is selected from the group consisting of methylene diphenyl diisocyanate (MDI) including any mixture of its three isomers 2,2′-MDI, 2,4′-MDI and 4,4′-MDI;
liquid MDI;
solid MDI;
hexamethylene diisocyanate trimer;
isophorone diisocyanate, 4,4′methylene bis(cyclohexyl isocyanate);
polymeric MDI;
MDI prepolymer;
and liquid carbodiimide modified 4,4′-MDI;
tetramethylxylene diisocyanate;
and isomers of isocyanato-[(isocyanatocyclohexyl)methyl] cyclohexane;
and
wherein the compound containing a heteroatom-containing functional group and a metathesis-active olefin is selected from the group consisting of 5-norbornene-2-methanol (NB-MeOH);
2-hydroxyethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate (HENB);
and allyl alcohol.

16 more elements

Dependencies are inferred from the claim text.

Adhesion promoters and gel-modifiers for olefin metathesis compositions

Life of this patent

Adhesion promoters and gel-modifiers for olefin metathesis compositions

Life of this patent

Abstract

Claims24