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US 7,001,590 B1Granted
Metathesis-curable composition
AssigneeKerr Corporation
InventorChristos Angeletakis
Life of this patent
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Abstract
One-part and two-part compositions curable by a metathesis reaction comprising a resin containing a substrate with at least two cycloolefin groups per molecule curable by a metathesis reaction with a metathesis catalyst. These compositions may optionally contain a reaction control agent for slowing the progress of the metathesis reaction. The metathesis catalyst can be a ruthenium carbene complex catalyst. The substrate may be, for example, a difunctional or trifunctional carboxylate ester containing norbornenyl end groups.
Claims45
A composition comprising at least 0.1 wt. % of a substrate containing at least two cycloolefin groups capable of undergoing a metathesis reaction and a metal carbene complex catalyst capable of initiating the metathesis reaction, wherein the substrate has the formula:
- wherein:
- a=1–100, c=0 or 1 and d=2–4,
- when d=2 or 3, Z and Q are the same or different and are each a linear, branched, cyclic or polycyclic organic residue optionally containing siloxane groups (Si—O—Si) and optionally containing heteroatoms selected from the group consisting of B, N, O, Si, P, and S,
- when d=4, Z is C and Q is a linear, branched, cyclic or polycyclic organic residue optionally containing siloxane groups (Si—O—Si) and optionally containing heteroatoms selected from the group consisting of B, N, O, Si, P, and S, and
- D is a cycloolefinic residue and is different than Q or Z;
- and
- wherein the catalyst has a structure selected from:
- wherein:
- M is ruthenium or osmium,
- X is an alkylidene ligand with basicity higher than that of tricyclohexylphosphine (PCy3),
- X1 is either PCy3 or a neutral electron donor ligand with basicity lower than that of PCy3,
- X2 and X3 are either the same or different and are any anionic ligand,
- Z is oxygen (O) or sulfur (S),
- R1 and R2 are either the same or different and are each independently hydrogen or a substituent selected from the group consisting of C1–C20 alkyl, C2–C20 alkenyl, C2–C20 alkynyl, aryl, C1–C20 carboxylate, C1–C20 alkoxy, C2–C20 alkenyloxy, C2–C20 alkynyloxy, aryloxy, C2–C20 alkoxycarbonyl, C1–C20 alkylthio, C1–C20 alkylsulfonyl and C1–C20 alkylsulfinyl, wherein each of the substituents is substituted or unsubstituted
- R4 is a substituent selected from the group consisting of C1–C20 alkyl, C2–C20 alkenyl, C2–C20 alkynyl, aryl, C1–C20 carboxylate, C1–C20 alkoxy, C2–C20 alkenyloxy, C2–C20 alkynyloxy, aryloxy, C2–C20 alkoxycarbonyl, C1–C20 alkylthio, C1–C20 alkylamino, C1–C20 alkylsulfonyl and C1–C20 alkylsulfinyl, wherein each of the substituents is substituted or unsubstituted, and
- R5, a, b, c, and d are either the same or different and are each independently hydrogen or a substituent selected from the group consisting of C1–C20 alkyl, C2–C20 alkenyl, C2–C20 alkynyl, aryl, C1–C20 carboxylate, C1–C20 alkoxy, C2–C20 alkenyloxy, C2–C20 alkynyloxy, aryloxy, C2–C20 alkoxycarbonyl, C1–C20 alkylthio, C1–C20 alkylsulfonyl and C1–C20 alkylsulfinyl, wherein each of the substituents is substituted or unsubstituted.
13 more elements
A composition capable of undergoing a metathesis reaction upon mixing of its components, the components comprising:
- a resin having a carboxylate ester backbone functionalized with at least two cycloolefin groups capable of undergoing a metathesis reaction;
- a ruthenium carbene complex catalyst capable of initiating the metathesis reaction in the composition, wherein the catalyst has the formula:
- wherein Ph is phenyl, X is an alkylidene ligand having a basicity higher than that of tricyclohexylphosphine (PCy3), and X1 is a phosphine, phosphite, phosphinite or phosphonite having a basicity lower than that of PCy3;
- and
- a reaction control agent for preventing completion of the metathesis reaction after mixing the composition components at a mixing temperature and until exposing the composition to an elevated temperature above the mixing temperature, the reaction control agent having the structure:
- wherein:
- G is selected from the group consisting of:
- L3,
- L is a hydrocarbon fragment containing an allyl group, a vinyl group, an ethynyl group or a propargyl group,
- L1–L9 are each independently selected from the group consisting of L, alkyl, aryl, aralkyl or haloalkyl,
- A is a Group 14 atom,
- n=0–20, and
- m=0–20.
10 more elements
A two-paste composition capable of undergoing a metathesis reaction at room temperature upon mixing the two pastes together, the composition comprising:
- (a) a base paste comprising a base resin having a carboxylate ester backbone functionalized with at least two cycloolefin groups capable of undergoing a metathesis reaction;
- (b) a catalyst paste comprising a metal carbene complex catalyst dissolved in a catalyst solvent that is miscible with the base paste and capable of initiating the metathesis reaction in the composition, wherein the catalyst has the structure:
- wherein:
- M is ruthenium or osmium,
- X is an alkylidene ligand with basicity higher than that of tricyclohexylphosphine (PCy3),
- Z is oxygen (O) or sulfur (S)
- X2 and X3 are either the same or different and are any anionic ligand,
- R4 is a substituent selected from the group consisting of C1–C20 alkyl, C2–C20 alkenyl, C2–C20 alkynyl, aryl, C1–C20 carboxylate, C1–C20 alkoxy, C2–C20 alkenyloxy, C2–C20 alkynyloxy, aryloxy, C2–C20 alkoxycarbonyl, C1–C20 alkylthio, C1–C20 alkylamino, C1–C20 alkylsulfonyl and C1–C20 alkylsulfinyl, wherein each of the substituents is substituted or unsubstituted, and
- R5, a, b, c, and d are either the same or different and are each independently hydrogen or a substituent selected from the group consisting of C1–C20 alkyl, C2–C20 alkenyl, C2–C20 alkynyl, aryl, C1–C20 carboxylate, C1–C20 alkoxy, C2–C20 alkenyloxy, C2–C20 alkynyloxy, aryloxy, C2–C20 alkoxycarbonyl, C1–C20 alkylthio, C1–C20 alkylsulfonyl and C1–C20 alkylsulfinyl, wherein each of the substituents is substituted or unsubstituted.
6 more elements
Dependencies are inferred from the claim text.