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US 5,854,299 AGranted
Process for the polymerization of cyclic olefins and polymerizable composition
AssigneeCiba Specialty Chemicals Corporation
InventorsAndreas Muhlebach, Paul Bernhard, Andreas Hafner, Thomas Karlen, Martin Andreas Ludi
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Abstract
Process for the polymerization of cyclic olefins by photochemical ring-opening metathesis polymerization by irradiation, using catalytic amounts of a heat-stable ruthenium or osmium catalyst which has at least one photolabile ligand, the other coordination sites being occupied by non-photolabile ligands.
Claims44
A process for the photochemically induced polymerization of a cyclic olefin or at least two different cyclic olefins in the presence of a metal compound as catalyst, which comprises:
- a) initially activating a heat-stable ruthenium or osmium compound
- i) wherein at least two photolabile ligands are bonded to one metal atom and are selected from the group consisting of monocyclic, polycyclic and fused arenes having 6 to 24 C-atoms which are unsubstituted or substituted by substituents, from the group consisting of OH, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.6 -C.sub.12 -aryl and halogen;
- or
- ii) wherein one or more photolabile ligands are bonded to the metal atom and are selected from the group consisting of nitrogen, monocyclic heteroarenes, fused heteroarenes and fused arene-heteroarenes having 3 to 22 C-atoms and 1 to 3 heteroatoms selected from the group consisting of O, S, and N, which are unsubstituted or substituted by substituents selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy and halogen;
- or
- iii) wherein one or more photolabile ligands are bonded to one metal atom and are selected from the group consisting of aliphatic, cycloaliphatic, aromatic and araliphatic nitrites which are unsubstituted or substituted by substituents selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.-C.sub.4 -alkoxy and halogen;
- subject to the proviso that none of the photolabile ligands from the group i) are present in the catalyst together with photolabile ligands either from the group ii) or the group iii);
- the-remaining coordination sites being occupied by non-photolabile ligands;
- by exposing the compound to radiation from a light source, radiating in the range, selected from the ultraviolet, visible, and infrared range, and then mixing with at least one olefin ;
- or by activating a mixture of cyclic olefin and the ruthenium or osmium compound by exposing the mixture to radiation from the light source, and
- b) then ending the polymerization by heating and without radiation.
8 more elements
A composition comprising
- a cyclic olefin or at least two different cyclic olefins and a catalytically active amount of a heat-stable ruthenium or osmium compound
- i) wherein at least two photolabile ligands are bonded to one metal atom and are selected from the group consisting of monocyclic, polycyclic and fused arenes having 6 to 24 C-atoms which are unsubstituted or substituted by substituents selected from the group consisting of OH, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.6 -C.sub.12 -aryl and halogen;
- or
- ii) wherein one or more photolabile ligands are bonded to one metal atom and are selected from the group consisting of nitrogen, monocyclic heteroarenes, fused heteroarenes and fused arene-heteroarenes having 3 to 22 C-atoms and 1 to 3 heteroatoms selected from the group consisting of O, S, and N, which are unsubstituted or substituted by substituents selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy and halogen;
- or
- iii) wherein one or more photolabile ligands are bonded to one metal atom and are selected from the group consisting of aliphatic, cycloaliphatic, aromatic and araliphatic nitrites which are unsubstituted or substituted by substituents selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkoxy and halogen;
- subject to the proviso that none of the photolabile ligands from the group i) are present in the catalyst together with photolabile ligands either from the group ii) or the group iii);
- which ligands are photolabile by exposure of the compound to a light source radiating in the range selected from the ultraviolet, visible and infrared range;
- and then mixing with at least one olefin the remaining coordination sites being occupied by non-photolabile ligands.
6 more elements
Dependencies are inferred from the claim text.