Coating Composition

Abstract

The present invention relates to compositions suitable for use as coatings. More specifically, the present invention relates to compositions suitable for use as industrial coatings, such as anticorrosion coatings, protective coatings, and adhesive coatings. The present invention relates to compositions and methods for coating substrates. More specifically, the present invention relates to coating compositions and methods for coating substrates, wherein the coating compositions comprise polymerized olefins and cyclic olefins via different chemical transformations. The present invention also relates to methods for applying coatings to substrates.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Patent Application No. 62 / 778,901, filed December 13, 2018, and U.S. Patent Application No. 62 / 845,052, filed May 8, 2019, the disclosures of which are incorporated herein by reference.

[0002] The present invention relates to compositions suitable for use as coatings. More specifically, the present invention relates to compositions suitable for use as industrial coatings, such as anticorrosion coatings and protective coatings. The present invention relates to compositions and methods for coating substrates. More specifically, the present invention relates to coating compositions and methods for coating substrates, wherein the coating compositions comprise polymerized olefins and cyclic olefins via different chemical transformations. The present invention also relates to methods for applying coatings to substrates.

[0003] The coating compositions of the present invention can be utilized on a wide variety of substrates, particularly those used in petrochemical and chemical manufacturing operations. The present invention has utility in the fields of polymers, materials, and manufacturing. [Background technology]

[0004] Materials deteriorate from interaction with the environment by mechanisms including corrosion, erosion, and other processes. Protective coatings can provide protection against deterioration of the surface properties of a wide range of substrates. Protective coatings can protect metal substrates from corrosion, polymer and composite substrates from ice, acid rain, salt water, weathering, and UV degradation, and wood, concrete, and brick substrates from deterioration due to moisture intrusion and decomposition.

[0005] According to the National Association of Corrosion Engineers International, corrosion is a naturally occurring phenomenon generally defined as the deterioration of a material (usually a metal) resulting from a chemical or electrochemical reaction with the environment. Corrosion can cause severe damage and be very expensive to repair. Protective coatings are an effective method of providing protection from corrosion. Metal corrosion occurs through either chemical or electrochemical reactions. Electrochemical corrosion is the most common form of metal corrosion. Metals such as iron and / or steel begin to corrode and form rust when they come into contact with oxygen and moisture (e.g., humidity, steam, immersion).

[0006] Exposure to water (e.g., groundwater, seawater, atmospheric water, etc.), corrosive chemicals, ultraviolet radiation, ozone, and other harmful agents can cause changes in the quality over time of unprotected surfaces of objects such as, for example, automobiles, buses, boats, trains, other vehicles, aircraft, bridges, signs, buildings, sidewalks, roads, underground pipelines and facilities, and petrochemical and chemical manufacturing facilities, resulting in deterioration or failure of the objects.

[0007] Because corrosion can be very widespread and expensive to repair, effective preventative measures are recommended to prevent corrosion.

[0008] One of the best ways to prevent corrosion is to apply a protective coating, which protects the substrate by preventing contact between it and the harsh environment (air, chemicals, etc.).

[0009] Thus, there has been a continuing need for coating compositions (eg, anti-corrosion coating compositions) that provide surface protection to objects from corrosive materials or damaging environmental conditions.

[0010] Most pipes and pipelines used in petrochemical and chemical manufacturing operations are constructed of metal, typically some grade of steel, and many are insulated. If, during pipe or pipeline installation, the insulating material covering the pipe or pipeline is damaged or deteriorates over time, there is a risk that the underlying surface of the pipe or pipeline will come into direct contact with the atmospheric environment, which can result in a number of problems, including premature failure of the pipe or pipeline, and increased repair and / or replacement costs.

[0011] Therefore, there is a need for an undercoat coating on the pipe or pipeline surface that will be applied between the pipe or pipeline surface and the insulating material and act as a corrosion barrier if the insulating material becomes damaged or deteriorated. This need has led to the introduction of numerous coating compositions intended to protect steel pipelines and structures.

[0012] Epoxy, polyamide, and polyurethane-based coating compositions are widely used to prevent corrosion of steel pipelines and structures.

[0013] The industry has relied on 2K epoxies, but liquid two-part epoxies typically require long cure cycles and are not very conducive to rapid coating operations that facilitate manufacturing.

[0014] Despite the advances made in the art in the field of coating compositions, particularly anticorrosion coating compositions for coating pipelines and structures, there is a continuing need for further improvements. Summary of the Invention

[0015] The present invention is directed to addressing one or more of the aforementioned concerns and relates to coating compositions and methods for coating substrates. The coating compositions of the present invention can be used for a variety of purposes, including, but not limited to, decoration, improving the barrier properties of packaging, protecting substrate materials, which may be metals such as steel, stainless steel, aluminum, copper, iron, nickel, titanium, silver, etc., or non-metals such as glass, concrete, ceramic, porcelain, brick, stone, plastic, rubber, wood, cloth, fabric, or reinforced plastic, composite materials such as electronic assemblies, and / or protecting substrate surfaces from changes in quality over time or degradation due to environmental exposure. In other words, the coating compositions of the present invention can be applied to substrate surfaces to provide protection, including anticorrosion protection, from degradation of the substrate material and / or substrate surface due to environmental exposure.

[0016] The coating composition of the present invention can also be used as an adhesive.

[0017] In particular, the present invention provides a coating composition for coating pipes, pipelines, and structures used in petrochemical and chemical manufacturing operations to provide a corrosion barrier against deterioration of the underlying pipe, pipeline, equipment, structure, or object due to environmental exposure and other corrosive materials. The coating of the present invention provides a protective lining that helps protect the pipe from the harmful effects of corrosion. Pipeline coating is one of the most reliable corrosion protection methods used in industry today.

[0018] The coating compositions of the present invention offer several advantages over prior art materials used to provide protective coatings on pipes, pipelines, equipment, structures, and objects used in petrochemical and chemical manufacturing operations.

[0019] In particular, the coating compositions of the present invention can be formulated to meet a wide variety of application conditions and needs.

[0020] As an example of one advantage, the coating compositions of the present invention are designed to provide long-term corrosion inhibition by acting as an impermeable barrier to oxygen, water, ions, etc. The coating compositions of the present invention are not porous. The coating compositions of the present invention can be applied and cured under higher humidity conditions and at lower temperatures than typical coatings.

[0021] As another example of an advantage, the coating compositions of the present invention can be formulated to have widely adjustable cure times.

[0022] For example, the coating compositions of the present invention may be formulated to cure quickly so that they dry to the touch quickly after application to a substrate surface ("fast cure"). The fast-curing coating compositions of the present invention have a fast dry-to-the-touch time of less than 20 minutes, preferably less than 10 minutes, more preferably less than 1 minute, and even within a few seconds after application to a surface. Articles coated with the fast-curing compositions of the present invention are handleable and have a durable coating in less than 60 minutes, preferably less than 30 minutes, and more preferably 10 minutes or less after application. In comparison, liquid epoxies typically take several hours to cure.

[0023] As another example of an advantage, the coating compositions of the present invention are solvent-free.

[0024] As another example of an advantage, the coating compositions of the present invention are resistant to cracking and spalling in high temperature / humid aqueous environments.

[0025] The coating compositions of the present invention can be prepared by different chemical transformations and processed by a variety of methods.

[0026] In one embodiment, the present invention provides a coating composition that is cured by ring-opening metathesis polymerization (ROMP), which comprises reacting at least one cyclic olefin with at least one metal carbene olefin metathesis catalyst.

[0027] The coating compositions of the present invention may also be cured by vinyl / addition copolymerization of cyclic olefins, optionally with at least one linear olefin, with at least one organometallic catalyst (Progress in Polymer Science 84(2018)1-46, Coordination Chemistry Reviews 253(2009)827-861). Organometallic complexes suitable for such vinyl / addition copolymerization of the cyclic olefins of the present invention consist of transition metals, generally late transition metals, typically palladium or nickel, linked by monodentate coordination or by chelating nitrogen, oxygen, or phosphorus ligands. These complexes may be activated by cocatalysts such as methylaluminoxane (MAO), tris(pentafluorophenyl)borane, or other Lewis acids.

[0028] Alternatively, the coating composition of the present invention may be cured by free radical polymerization (The Journal of American Science, 4(1), 2008, 1545-1003). Suitable initiators for such radical addition polymerization of the cyclic olefins of the present invention include azo compounds including azobisisobutyronitrile (AIBN), organic hydroperoxides including tert-butyl hydroperoxide and cumene hydroperoxide, organic diperoxides including benzoyl peroxide and tert-butyl peroxide, alkoxyamines including (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) and N-tert-butyl-N-(2-methyl-1-phenylpropyl)-O-(1-phenylethyl)hydroxylamine, and boron amine complexes such as triethylborane-1,3-diaminopropane complex and tri-n-butylborane-3-methoxy-1-propylamine complex. Radical cationic initiators may also be used, as well as expensive iodine activators such as diaryliodonium salts and (diacetoxyiodo)benzene.

[0029] In another embodiment, the coating composition of the present invention can be cured by cationic polymerization of at least one cyclic olefin, optionally at least one linear olefin, and at least one radical or cationic initiator (Macromolecules 47 (2014) 5470-5483). Suitable activators for such cationic polymerization of the cyclic olefins of the present invention are Lewis acids including boron trifluoride, aluminum trichloride, titanium tetrachloride, and tin tetrachloride, optionally activated by an initiator including water, hydrogen chloride, and octanoic acid. Suitable organometallic catalysts for promoting the cationic polymerization of the monomers of the present invention are metallocene catalysts including Cp*TiCl3 and Cp2AlMe activated by a Lewis acid including tris(pentafluorophenyl)borane.

[0030] The coating compositions of the present invention can comprise, consist essentially of, or consist of at least one cyclic olefin selected from the group consisting of formulas (I), (II), and (III), optionally at least one linear olefin of formula (IV), at least one coating additive, and at least one curing agent selected from organometallic complexes, free radical initiators, and cationic initiators, preferably at least one metal carbene metathesis catalyst curing agent. The cyclic olefins of formulas (I), (II), and (III), and the linear olefin of formula (IV), have the following structures: [ka] Cyclic olefins of formula (I), (II), and (III), and linear olefins of formula (IV) are described below.

[0031] The present invention also provides a method for coating a substrate material, comprising the steps of: optionally applying an adhesion promoter to the substrate surface; applying to the substrate surface a coating composition comprising, consisting essentially of, or consisting of at least one cyclic olefin selected from the group consisting of Formulas (I), (II), and (III); optionally at least one linear olefin of Formula (IV); at least one coating additive; and at least one curing agent selected from organometallic complexes, free radical initiators, and cationic initiators, preferably at least one metal carbene metathesis catalyst curing agent; and curing the coating applied to the substrate surface.

[0032] The present invention further relates to articles of manufacture made by the methods of the present invention.The articles of manufacture of the present invention have a substrate coated with the cured coating composition of the present invention. Although overlapping with other descriptions, various aspects of the present invention are described below, however, the present invention is not limited to the following. [1] 1. A coating composition comprising: at least one cyclic olefin selected from the group consisting of formulas (I), (II), and (III); Optionally, at least one linear olefin of formula (IV), at least one coating additive; at least one curing agent selected from an organometallic complex, a free radical initiator, and a cationic initiator; The cyclic olefins of formulas (I), (II), and (III) and the linear olefins of formula (IV) have the following structure: [C1] JPEG0007752048000002.jpg39132 During the ceremony, R a is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , -CN, -NO 2 , -CF 3 , -P(O)(ORh ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R b is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -Si(OR k ) 3 , -S(O) 2 OR h , OS(O) 2 R h , optionally substituted heterocycle, optionally substituted spiroheterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NRo R p , -C(R h )(R i )C(O)NR o OR n and R c is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , CN, NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(Rh )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R d is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , CN, NO 2 , -CF 3 -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(Ri )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and Each R s are independently optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and t is 0, 1, 2, 3, 4, 5, or 6; R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 Aryl, optionally substituted straight or branched chain C 2-24 alkenyl, -C(O)-(optionally substituted C 5-24 aryl), -C(O)-(optionally substituted straight or branched chain C 2-24 alkenyl), or optionally substituted C 3-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R j is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R l is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, Rm is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, The coating composition wherein z is 0, 1, 2, or 3. [2] R a H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-12 is cycloalkenyl, R b H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-12 is cycloalkenyl, R c H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-12 is cycloalkenyl, R d H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C2-6 Alkenyl, halogen, -C(O)R f , -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-12 is cycloalkenyl, t is 0, R f But, OH, OR k , N.R. g R h , optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R g is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R h is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, z is 2, R i is H, optionally substituted C1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R j is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R k optionally replaced by C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R l is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R m is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R n is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R o is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R p is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 The coating composition according to [1], wherein the alkyl group is cycloalkenyl. [3] the cyclic olefin of formula (I) is ENB-DDA, HNB-DDA, or a mixture thereof; the cyclic olefin of formula (II) is HENB, NBCbSi, ONB, NB-methanol, NB-dimethanol, NB-epoxide, NB-triethoxysilane, NB-fluorocarbon (1), NB-fluorocarbon (2), NB-fluorocarbon (3), or a mixture thereof; The coating composition according to [1] or [2], wherein the cyclic olefin of formula (III) is TCPD, DCPD, or a mixture thereof. [4] the at least one curing agent has a structure of formula (1): [C2] JPEG0007752048000003.jpg4245 During the ceremony, M is ruthenium; L 1 、L 2 , and L 3 are independently a neutral electron donor ligand; n is 0 or 1, m is 0, 1, or 2; k is 0 or 1, X 1 and X 2 are independently an anionic ligand; R 1 and R 2 is independently hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl, or R 1 and R 2 and are linked together to form one or more cyclic groups. [5] the at least one curing agent has a structure of formula (2): [C3] JPEG0007752048000004.jpg4650 During the ceremony, M is ruthenium; L 1 is a neutral electron donor ligand, X 1 and X 2 are independently an anionic ligand; W is O, halogen, NR 33 , or S, R 19 is H, optionally substituted C 1-24 Alkyl, -C(R 34 )(R 35 )COOR 36 , -C(R 34 )(R 35 )C(O)H, -C(R 34 )(R 35 )C(O)R 37 , -C(R 34 )(R 35 )CR 38 (OR 39 )(OR 40 ), -C(R 34 )(R 35 )C(O)NR 41 R 42 , -C(R 34 )(R 35 )C(O)NR 41 OR 40 , -C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or W is NR 33 If R 19 is R 33 together can form an optionally substituted heterocycle, or when W is halogen, R 19 is nothing, R 20 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 21 together can form a polycyclic ring, R 21 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 20 with or R 22 can form a polycyclic ring together with R 22 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 21 with or R 23 can form a polycyclic ring together with R 23 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 22 together can form a polycyclic ring, R 24 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) xR 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 is cycloalkenyl, R 25 But, OH, OR 30 , N.R. 27 R 28 , optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-24 Alkyl, OR 26 , -NR 27 R28 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 optionally replaced by C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 33 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 34 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 35 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 36 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 37 optionally replaced by C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 38 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 39 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 40 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 41 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 42 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, The coating composition according to any one of [1] to [4], wherein x is 1 or 2 and the at least one metal carbene metathesis catalyst is a metal carbene metathesis catalyst. [6] The coating composition according to any one of [1] to [4], wherein the coating composition contains at least one cyclic olefin selected from the group consisting of formulas (I) and (II): [7] The coating composition according to any one of [1] to [4], wherein the coating composition comprises at least one cyclic olefin selected from the group consisting of formulas (I) and (III). [8] The coating composition according to any one of [1] to [4], wherein the coating composition contains at least one cyclic olefin selected from the group consisting of formulas (II) and (III). [9] The coating composition according to any one of [1] to [8], wherein the coating additive is selected from the group consisting of gel modifiers, hardness modifiers, impact modifiers, antioxidants, antiozonants, fillers, binders, thixotropes, rheology modifiers, dispersants, wetting agents, plasticizers, pigments, flame retardants, dyes, fibers, reinforcing materials, coupling agents, UV absorbers, UV light stabilizers, film formers, lubricants, adhesion promoters, and mixtures thereof.

[10] The coating composition according to any one of [1] to [8], wherein the coating additive is selected from the group consisting of a filler, a rheology modifier, a coupling agent, a UV absorber, a UV light stabilizer, an adhesion promoter, and a mixture thereof.

[11] The coating composition according to any one of [1] to

[10] , wherein the coating composition contains a filler, and the filler is an inorganic filler present in an amount of about 0.01 to about 95% by weight.

[12] 1. A method of coating a substrate material, comprising: Optionally, applying an adhesion promoter onto the surface of the substrate; On the surface of the substrate, at least one cyclic olefin selected from the group consisting of formula (I), (II), and (III), and optionally at least one linear olefin of formula (IV); at least one coating additive; at least one curing agent selected from organometallic complexes, free radical initiators, and cationic initiators; The cyclic olefins of formulas (I), (II), and (III) and the linear olefins of formula (IV) have the following structure: [C4] JPEG0007752048000005.jpg39132 During the ceremony, R a is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2R h , optionally substituted heterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R b is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -Si(OR k ) 3 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted spiroheterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o ORn and R c is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , CN, NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(Rh )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R d is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , CN, NO 2 , -CF 3 -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(Ri )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and Each R s are independently optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH 2 -C(O)R f , -OR g , -CH 2 -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, -CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 Cycloalkyl, -CH 2 -(Optionally replaced C 3-10 cycloalkyl), optionally substituted C 5-24 Aryl, -CH 2 -(Optionally replaced C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH 2 -(Optionally replaced C3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and t is 0, 1, 2, 3, 4, 5, or 6; R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 Aryl, optionally substituted straight or branched chain C 2-24 alkenyl, -C(O)-(optionally substituted C 5-24 aryl), -C(O)-(optionally substituted straight or branched chain C 2-24 alkenyl), or optionally substituted C 3-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R j is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R l is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R m is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, a coating composition wherein z is 0, 1, 2, or 3; and applying at least one metal carbene metathesis catalyst and at least one additive; and curing the coating applied onto the substrate surface.

[13] R a H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-12 is cycloalkenyl, R b H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-12 is cycloalkenyl, R c H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-12 is cycloalkenyl, R d H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -OR g , -CN, -NO 2 , -CF 3 , -P(O)(OR h ) 2 , -OP(O)(OR h ) 2 , -S(O) 2 OR h , -OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-12 is cycloalkenyl, t is 0, R f But, OH, OR k , N.R. g R h , optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R g is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R h is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, z is 2, R i is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C3-12 is cycloalkenyl, R j is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R k optionally replaced by C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R l is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R m is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R n is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R o is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 is cycloalkenyl, R p is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 The method according to

[12] , wherein the alkyl group is cycloalkenyl.

[14] the cyclic olefin of formula (I) is ENB-DDA, HNB-DDA, or a mixture thereof; the cyclic olefin of formula (II) is HENB, NBCbSi, ONB, NB-methanol, NB-dimethanol, NB-epoxide, NB-triethoxysilane, NB-fluorocarbon (1), NB-fluorocarbon (2), NB-fluorocarbon (3), or a mixture thereof; The method according to

[12] or

[13] , wherein the cyclic olefin of formula (III) is TCPD, DCPD, or a mixture thereof.

[15] the at least one curing agent has a structure of formula (1): [5] JPEG0007752048000006.jpg4245 During the ceremony, M is ruthenium; L 1 、L 2 , and L 3 are independently a neutral electron donor ligand; n is 0 or 1, m is 0, 1, or 2; k is 0 or 1, X 1 and X 2 are independently an anionic ligand; R 1 and R 2 are independently hydrogen, unsubstituted hydrocarbyl, substituted hydrocarbyl, unsubstituted heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl, or R 1 and R 2 and are linked together to form one or more cyclic groups.

[16] L 1 but, [6] JPEG0007752048000007.jpg2957 and R 1 is H, optionally substituted C1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 2 can form a spiro compound with R 3 with or R 4 can form a polycyclic ring together with R 2 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 1 can form a spiro compound with R 3 with or R 4 can form a polycyclic ring together with R 3 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 2 with or R 1 can form a polycyclic ring together with R 4 can form a spiro compound with R 4 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 3 can form a spiro compound with R 2 with or R 1 can form a polycyclic ring together with R 5 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 together can form an optionally substituted polycyclic ring, R 6 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 5 with or R 7 together can form an optionally substituted polycyclic ring, R 7 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 with or R 8 together can form an optionally substituted polycyclic ring, R 8 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 7 with or R 9 together can form an optionally substituted polycyclic ring, R 9 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R8 together can form an optionally substituted polycyclic ring, R 10 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 together can form an optionally substituted polycyclic ring, R 11 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 10 with or R 12 together can form an optionally substituted polycyclic ring, R 12 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 with or R 13 together can form an optionally substituted polycyclic ring, R 13 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 14 with or R 12 together can form an optionally substituted polycyclic ring, R 14 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O)x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 13 can form a polycyclic ring together with R 25 -OH, -OR 30 , -NR 27 R 28 , optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-24 Alkyl, -OR 26 , -NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 optionally replaced by C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, The method according to

[15] , wherein x is 1 or 2.

[17] L 2 But PR H1 R H2 R H3 where R H1 、R H2 , and R H3 each independently represents an optionally substituted C 6 -C 10 Aryl, optionally substituted C 1 -C 10 alkyl, or optionally substituted C 3 -C 10 The method according to

[15] or

[16] , wherein the cycloalkyl is cycloalkyl.

[18] R 1 is hydrogen and R 2 is phenyl, or R 1 is hydrogen and R 2 is 3-methyl-1-propenyl, or R 1 and R 2 are linked together to form 3-phenylindenylide-1-ene.

[19] R H1 is phenyl, ethyl, or cyclohexyl, and R H2 is phenyl or cyclohexyl, and R H3

[18] The method according to

[18] , wherein is phenyl, ethyl, or cyclohexyl.

[20] the at least one curing agent has a structure of formula (2): [7] JPEG0007752048000008.jpg4952 During the ceremony, M is ruthenium; L 1 is a neutral electron donor ligand, X 1 and X 2 are independently an anionic ligand; W is O, halogen, NR 33 , or S, R 19 is H, optionally substituted C 1-24 Alkyl, -C(R 34 )(R 35 )COOR 36 , -C(R 34 )(R 35 )C(O)H, -C(R 34 )(R 35 )C(O)R 37 , -C(R 34 )(R 35 )CR 38 (OR 39 )(OR 40 ), -C(R 34 )(R 35 )C(O)NR 41R 42 , -C(R 34 )(R 35 )C(O)NR 41 OR 40 , -C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or W is NR 33 If R 19 is R 33 together can form an optionally substituted heterocycle, or when W is halogen, R 19 is nothing; R 20 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 21 together can form a polycyclic ring, R 21 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) xR 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 20 with or R 22 can form a polycyclic ring together with R 22 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 21 with or R 23 can form a polycyclic ring together with R 23 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 22 together can form a polycyclic ring, R 24 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 is cycloalkenyl, R 25 But, OH, OR 30 , N.R. 27 R 28 , optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-24 Alkyl, OR 26 , -NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 optionally replaced by C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 33 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 34 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 35 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 36 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 37 optionally replaced by C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 38 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 39 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 40 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R41 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 42 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, The method according to any one of

[12] to

[19] , wherein x is 1 or 2, and the at least one metal carbene metathesis catalyst is a metal carbene metathesis catalyst.

[21] The method according to any one of

[12] to

[20] , wherein the coating composition comprises at least one cyclic olefin selected from the group consisting of formulas (I) and (II):

[22] The method according to any one of

[12] to

[20] , wherein the coating composition comprises at least one cyclic olefin selected from the group consisting of formulas (I) and (III).

[23] The method according to any one of

[12] to

[20] , wherein the coating composition comprises at least one cyclic olefin selected from the group consisting of formulas (II) and (III).

[24] 23. The method according to any one of

[12] to

[23] , wherein the coating composition additive is selected from the group consisting of gel modifiers, hardness modifiers, impact modifiers, antioxidants, antiozonants, fillers, binders, thixotropes, rheology modifiers, dispersants, wetting agents, plasticizers, pigments, flame retardants, dyes, fibers, reinforcing materials, coupling agents, UV absorbers, UV light stabilizers, film formers, lubricants, adhesion promoters, and mixtures thereof.

[25] The method according to any one of

[12] to

[23] , wherein the coating composition additive is selected from the group consisting of fillers, rheology modifiers, coupling agents, UV absorbers, UV light stabilizers, adhesion promoters, and mixtures thereof.

[26] The method according to any one of

[12] to

[23] , wherein the coating composition contains a filler, and the filler is an inorganic filler present in an amount of about 0.01 to about 95% by weight.

[27] The method according to any one of

[12] to

[26] , further comprising the step of adhering a second substrate by placing a second substrate on the coated substrate and adhering the two substrates together.

[28] An article of manufacture produced by the method according to any one of

[12] to

[27] .

[29] A manufactured article comprising a substrate coated with a cured coating composition, wherein the coating composition is the coating composition according to any one of [1] to

[11] .

[30] 29. The article of manufacture according to claim 29, wherein the substrate is a metal surface.

[31] 29. The article of manufacture according to claim 29, wherein the substrate is a non-metallic surface.

[32] L 1 but, [8] JPEG0007752048000009.jpg2957 and R 1 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 2 can form a spiro compound with R 3 with or R 4 can form a polycyclic ring together with R 2 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 1 can form a spiro compound with R 3 with or R 4 can form a polycyclic ring together with R 3 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 2 with or R 1 can form a polycyclic ring together with R 4 can form a spiro compound with R 4 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 3 can form a spiro compound with R 2 with or R 1 can form a polycyclic ring together with R 5 is H, optionally substituted C1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 together can form an optionally substituted polycyclic ring, R 6 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 5 with or R 7 together can form an optionally substituted polycyclic ring, R 7 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 with or R 8 together can form an optionally substituted polycyclic ring, R 8 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 7 with or R 9 together can form an optionally substituted polycyclic ring, R 9 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 8 together can form an optionally substituted polycyclic ring, R 10 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 together can form an optionally substituted polycyclic ring, R 11 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 10 with or R 12 together can form an optionally substituted polycyclic ring, R 12 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 with or R 13 together can form an optionally substituted polycyclic ring, R 13 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 14 with or R 12 together can form an optionally substituted polycyclic ring, R 14 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR26 , -CN, -NR 27 R 28 , -NO 2 , -CF 3 , -S(O) x R 29 , -P(O)(OH) 2 , -OP(O)(OH) 2 , -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 13 can form a polycyclic ring together with R 25 -OH, -OR 30 , -NR 27 R 28 , optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-24 Alkyl, -OR 26 , -NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 optionally replaced by C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, [4] The coating composition according to [4], wherein x is 1 or 2.

[33] L 2 But PR H1 R H2 R H3 where R H1 、R H2 , and R H3 each independently represents an optionally substituted C 6 -C 10 Aryl, optionally substituted C 1 -C 10 alkyl, or optionally substituted C 3 -C 10 The coating composition according to [4] or

[32] , wherein the alkyl is cycloalkyl.

[34] R1 is hydrogen and R 2 is phenyl, or R 1 is hydrogen and R 2 is 3-methyl-1-propenyl, or R 1 and R 2 are linked together to form 3-phenylindenylide-1-ene.

[35] R H1 is phenyl, ethyl, or cyclohexyl, and R H2 is phenyl or cyclohexyl, and R H3

[34] The coating composition according to

[34] , wherein is phenyl, ethyl, or cyclohexyl. DETAILED DESCRIPTION OF THE INVENTION

[0033] Terms and Definitions Unless otherwise indicated, the present invention is not limited to particular reactants, substituents, catalysts, metal carbene olefin metathesis catalysts, catalyst compositions, olefins, cyclic olefin compositions, coating compositions, reaction conditions, etc., as such may vary. It is also understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to be limiting.

[0034] In this specification and in the claims that follow, reference will be made to a number of terms that shall be defined to have the meaning set forth herein.

[0035] As used herein, the term "alkyl" refers to a straight-chain, branched, saturated hydrocarbon group typically containing 1 to 24 carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms: for example, methyl (Me), ethyl (Et), n-propyl (Pr or n-Pr), iso-propyl (i-Pr), n-butyl (Bu or n-Bu), iso-butyl (i-Bu), tert-butyl (t-Bu), octyl (Oct), decyl, and the like.

[0036] The term "cycloalkyl" refers to a cyclic alkyl group, which may be monocyclic, bicyclic, or polycyclic, and typically has 3 to 10, preferably 5 to 7, carbon atoms; common cycloalkyl groups are cyclopentyl (Cp), cyclohexyl (Cy), and adamantyl.

[0037] The term "substituted alkyl" refers to an alkyl that is substituted with one or more substituents, and the terms "heteroatom-containing alkyl" and "heteroalkyl" refer to an alkyl in which at least one carbon atom is replaced with a heteroatom.

[0038] As used herein, the term "alkylene" refers to a difunctional, straight-chain, branched-chain alkyl group, where "alkyl" is defined above.

[0039] As used herein, the term "alkenyl" refers to a straight or branched chain hydrocarbon group of 2 to 24 carbon atoms containing at least one double bond, such as ethenyl, n-propenyl, iso-propenyl, n-butenyl, iso-butenyl, octenyl, decenyl, tetradecenyl, hexadecenyl, etc. Preferred alkenyl groups herein contain 2 to 12 carbon atoms, and more preferred alkenyl groups herein contain 2 to 6 carbon atoms.

[0040] The term "substituted alkenyl" refers to an alkenyl substituted with one or more substituents, and the terms "heteroatom-containing alkenyl" and "heteroalkenyl" refer to an alkenyl in which at least one carbon atom is replaced with a heteroatom.

[0041] The term "cycloalkenyl" refers to cyclic alkenyl groups preferably having from 3 to 12 carbon atoms.

[0042] As used herein, the term "alkenylene" refers to a difunctional straight-chain, branched group, where "alkenyl" is defined above.

[0043] As used herein, the term "alkynyl" refers to a straight or branched chain hydrocarbon group of 2 to 24 carbon atoms containing at least one triple bond, such as ethynyl, n-propynyl, etc. Preferred alkynyl groups herein contain 2 to 12 carbon atoms, and more preferred alkynyl groups herein contain 2 to 6 carbon atoms.

[0044] The term "substituted alkynyl" refers to an alkynyl substituted with one or more substituents, and the terms "heteroatom-containing alkynyl" and "heteroalkynyl" refer to an alkynyl in which at least one carbon atom is replaced with a heteroatom.

[0045] As used herein, the term "alkynylene" refers to a difunctional alkynyl group, where "alkynyl" is defined above.

[0046] As used herein, the term "alkoxy" refers to an alkyl group bonded through a single, terminal ether linkage; i.e., an "alkoxy" group may be represented as -O-alkyl, where "alkyl" is as defined above. Similarly, "alkenyloxy" refers to an alkenyl group bonded through a single, terminal ether linkage, and "alkynyloxy" refers to an alkynyl group bonded through a single, terminal ether linkage.

[0047] As used herein, and unless otherwise specified, the term "aryl" refers to an aromatic substituent containing a single aromatic ring or multiple aromatic rings that are fused together, directly linked, or indirectly linked (such that different aromatic rings are bonded to a common group such as a methylene or ethylene moiety). Preferred aryl groups contain 5 to 24 carbon atoms, and particularly preferred aryl groups contain 6 to 10 carbon atoms. Exemplary aryl groups include one aromatic ring, or two fused or linked aromatic rings, such as phenyl (Ph), naphthyl, biphenyl, diphenylether, diphenylamine, benzophenone, phenanthryl, and the like.

[0048] "Substituted aryl" refers to an aryl moiety substituted with one or more substituents, and the terms "heteroatom-containing aryl" and "heteroaryl" refer to an aryl substituent in which at least one carbon atom is replaced with a heteroatom, as described in more detail herein.

[0049] As used herein, the term "aryloxy" refers to an aryl group bonded through a single, terminal ether bond, where "aryl" is as defined above. An "aryloxy" group may also be represented as -O-aryl, where aryl is as defined above. Preferred aryloxy groups contain 5 to 24 carbon atoms, and particularly preferred aryloxy groups contain 6 to 10 carbon atoms. Examples of aryloxy groups include, but are not limited to, phenoxy, o-halo-phenoxy, m-halo-phenoxy, p-halo-phenoxy, o-methoxy-phenoxy, m-methoxy-phenoxy, p-methoxy-phenoxy, 2,4-dimethoxy-phenoxy, 3,4,5-trimethoxy-phenoxy, and the like.

[0050] The term "alkaryl" refers to an aryl group having an alkyl substituent, and the term "aralkyl" refers to an alkyl group having an aryl substituent, where "aryl" and "alkyl" are defined above. Preferred alkaryl and aralkyl groups contain 6 to 24 carbon atoms, with particularly preferred alkaryl and aralkyl groups containing 6 to 16 carbon atoms. Alkaryl groups include, but are not limited to, p-methylphenyl, 2,4-dimethylphenyl, p-cyclohexylphenyl, 2,7-dimethylnaphthyl, 7-cyclooctylnaphthyl, 3-ethyl-cyclopenta-1,4-diene, and the like. Examples of aralkyl groups include, but are not limited to, benzyl, 2-phenyl-ethyl, 3-phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4-benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.

[0051] The terms "alkaryloxy" and "aralkyloxy" refer to a substituent of the formula -OR, where R is alkaryl or aralkyl, respectively, as defined herein.

[0052] The term "acyl" refers to a substituent having the formula -(CO)-alkyl, -(CO)-aryl, -(CO)-aralkyl, -(CO)-alkaryl, -(CO)-alkenyl, or -(CO)-alkynyl; the term "acyloxy" refers to a substituent having the formula -O(CO)-alkyl, -O(CO)-aryl, -O(CO)-aralkyl, -O(CO)-alkaryl, -O(CO)-alkenyl, or -(CO)-alkynyl, where "alkyl," "aryl," "aralkyl," "alkaryl," "alkenyl," and "alkynyl" are as defined above. The acetoxy group (-O(CO)CH, often abbreviated as -OAc) is a common example of an acyloxy group.

[0053] The terms "cyclic" and "ring" refer to an alicyclic or aromatic group which may or may not be substituted and / or heteroatom-containing, and which may be monocyclic, bicyclic, or polycyclic. The term "alicyclic" is used in the conventional sense to refer to an alicyclic moiety, as opposed to an aromatic cyclic moiety, which may be monocyclic, bicyclic, or polycyclic.

[0054] The term "polycyclic ring" refers to an aliphatic or aromatic group that may or may not be substituted and / or heteroatom-containing and that has at least two closed rings connected by tethers, fused, single bonds, or bridges. Polycyclic rings include, but are not limited to, naphthyl, biphenyl, phenanthryl, and the like.

[0055] The term "spiro compound" refers to a compound that presents a twisted structure of two or more rings (ring systems), where two or three rings are linked together by one common atom.

[0056] The terms "halo" and "halide" and "halide" are used in the conventional sense to refer to a fluorine (F), chlorine (Cl), bromine (Br), or iodine (I) substituent.

[0057] "Hydrocarbyl" refers to monovalent hydrocarbyl moieties containing 1 to 24 carbon atoms, preferably 1 to 12 carbon atoms, and includes straight-chain, branched, cyclic, saturated and unsaturated species, such as alkyl, alkenyl, alkynyl, aryl, etc. "Substituted hydrocarbyl" refers to a hydrocarbyl substituted with one or more substituents.

[0058] "Hydrocarbylene" refers to a divalent hydrocarbyl moiety containing 1 to 24 carbon atoms, preferably 1 to 12 carbon atoms, and includes straight-chain, branched, cyclic, saturated, and unsaturated species formed by removing two hydrogens from a hydrocarbon. "Substituted hydrocarbylene" refers to a hydrocarbylene substituted with one or more substituents.

[0059] The term "heteroatom-containing" in "heteroatom-containing hydrocarbyl group" refers to a hydrocarbon molecule or hydrocarbyl molecule fragment in which one or more carbon atoms are replaced with atoms other than carbon, such as nitrogen, oxygen, sulfur, phosphorus, or silicon, typically nitrogen, oxygen, or sulfur. The terms "heteroatom-containing hydrocarbylene" and "heterohydrocarbylene" refer to hydrocarbylene in which at least one carbon atom is replaced with a heteroatom. Similarly, the term "heteroalkyl" refers to a heteroatom-containing alkyl substituent, the term "heterocyclic" refers to a heteroatom-containing cyclic substituent, and the terms "heteroaryl" and "heteroaromatic" refer to heteroatom-containing "aryl" and "aromatic" substituents, respectively. Note that a "heterocyclic" group or compound may or may not be aromatic, and further, a "heterocycle" may be monocyclic, bicyclic, or polycyclic, as described above for the term "aryl." Examples of heteroalkyl groups include, but are not limited to, alkoxyaryl, alkylsulfanyl-substituted alkyl, N-alkylated aminoalkyl, and the like. Examples of heteroaryl substituents include, but are not limited to, pyrrolyl, pyrrolidinyl, pyridinyl, quinolinyl, indolyl, pyrimidinyl, imidazolyl, 1,2,4-triazolyl, tetrazolyl, etc. Examples of heteroatom-containing alicyclic groups include, but are not limited to, pyrrolidino, morpholino, piperazino, piperidino, etc.

[0060] In addition, the aforementioned substituents may, where a particular group allows, be further substituted with one or more additional substituents or with one or more hydrocarbyl moieties such as those specifically listed above. Similarly, the above hydrocarbyl moieties may be further substituted with one or more substituents or with additional hydrocarbyl moieties such as those specifically mentioned above. Similarly, the above hydrocarbylene moieties may be further substituted with one or more substituents or additional hydrocarbyl moieties as described above.

[0061] As referenced in some of the definitions above, such as in "substituted hydrocarbyl," "substituted alkyl," "substituted aryl," etc., "substituted" means that at least one hydrogen atom bonded to a carbon (or other) atom in a hydrocarbyl, alkyl, aryl, or other moiety is replaced with one or more non-hydrogen substituents. Examples of such substituents include, but are not limited to, halo, hydroxyl, sulfhydryl, C-C 24 Alkoxy, C2-C 24 Alkenyloxy, C2-C 24 Alkynyloxy, C5-C 24 Aryloxy, C6-C 24 Aralkyloxy, C6-C 24 Alkyloxy, acyl (C2-C 24 Alkylcarbonyl (-CO-alkyl) and C6-C 24 arylcarbonyl (-CO-aryl), acyloxy (-O-acyl, C2-C 24 Alkylcarbonyloxy (-O-CO-alkyl) and C6-C 24 Arylcarbonyloxy (including -O-CO-aryl), C2-C 24 Alkoxycarbonyl (-(CO)-O-alkyl), C6-C 24 Aryloxycarbonyl (—(CO)—O-aryl), halocarbonyl (—CO—X, where X is halo), C2-C 24 Alkyl carbonate (-O-(CO)-O-alkyl), C6-C 24 Aryl carbonate (-O-(CO)-O-aryl), carboxylic acid (-COOH), carbamoyl (-(CO)-NH), mono-(C1-C 24 Alkyl)-substituted carbamoyl (-(CO)-NH(C1-C 24 alkyl), di-(C1-C 24 Alkyl)-substituted carbamoyl (-(CO)-N(C1-C 24 alkyl)2), mono-(C1-C 24 haloalkyl)-substituted carbamoyl (-(CO)-NH(C-C 24 haloalkyl), di-(C1-C 24Haloalkyl)-substituted carbamoyl (-(CO)-N(C-C 24 haloalkyl)2), mono-(C5-C 24 aryl)-substituted carbamoyl (-(CO)-NH-aryl), di-(C5-C 24 Aryl)-substituted carbamoyl (-(CO)-N(C5-C 24 aryl), N(C1-C 24 Alkyl)(C5-C 24 Aryl)-substituted carbamoyl (-(CO)-N(C1-C 24 Alkyl)(C5-C 24 aryl), thiocarbamoyl (-(CS)-NH), mono-(C1-C 24 Alkyl)-substituted thiocarbamoyl (-(CS)-NH(C1-C 24 alkyl), di-(C1-C 24 Alkyl)-substituted thiocarbamoyl (-(CS)-N(C1-C 24 alkyl)2), mono-(C5-C 24 aryl)-substituted thiocarbamoyl (-(CS)-NH-aryl), di-(C5-C 24 Aryl)-substituted thiocarbamoyl (-(CS)-N(C5-C 24 aryl), N(C1-C 24 Alkyl)(C5-C 24 Aryl)-substituted thiocarbamoyl (-(CS)-N(C1-C 24 Alkyl)(C5-C 24 aryl), -C(O)-NH(alkyl) optionally substituted with a silyl group, -C(O)-N(alkyl)2 optionally substituted with a silyl group, carbamido (-NH-(CO)-NH2), cyano (-C≡N), cyanato (-OC≡N), thiocyanato (-SC≡N), isocyanato (-NCO), thioisocyanato (-NCS), formyl (-(CO)-H), thioformyl (-(CS)-H), amino (-NH2), mono-(C1-C 24 alkyl)-substituted amino (-NH(C-C 24 alkyl), di-(C1-C 24 Alkyl)-substituted amino ((-N(C-C 24 alkyl)2), mono-(C5-C24 aryl)-substituted amino (-NH(C5-C 24 aryl), di-(C5-C 24 Aryl)-substituted amino (-N(C5-C 24 Aryl)2), C2-C 24 Alkylamide (-NH-(CO)-alkyl), C6-C 24 Arylamide (—NH—(CO)-aryl), imino (—CRNH, where R is, but is not limited to, H, C-C 24 Alkyl, C5-C 24 Aryl, C6-C 24 Alkaryl, C6-C 24 aralkyl, etc.), C2-C 20 Alkylamino (-CRN(alkyl), where R is, but is not limited to, H, C-C 24 Alkyl, C5-C 24 Aryl, C6-C 24 Alkaryl, C6-C 24 aralkyl, etc.), arylimino (-CRN(aryl), where R is, but is not limited to, H, C-C 20 Alkyl, C5-C 24 Aryl, C6-C 24 Alkaryl, C6-C 24 aralkyl, etc.), nitro (-NO2), nitroso (-NO), sulfo (-S(O)2OH), C1-C 24 Alkylsulfanyl (-S-alkyl; also called "alkylthio"), C5-C 24 Arylsulfanyl (-S-aryl; also called "arylthio"), C1-C 24 Alkylsulfinyl (-(SO)-alkyl), C5-C 24 Arylsulfinyl (-(SO)-aryl), C1-C 24 Alkylsulfonyl (-SO2-alkyl), C1-C 24 Monoalkylaminosulfonyl (-SO2-N(H) alkyl), C1-C 24 Dialkylaminosulfonyl (-SO2-N(alkyl)2), C5-C 24Arylsulfonyl (-SO2-aryl), boryl (-BH2), borono (-B(OH)2), boronato (-B(OR)2, where R includes, but is not limited to, alkyl or other hydrocarbyl), phosphono (-P(O)(OH)2), phospho (-PO2), phosphino (-PH2), silyl (-SiR3, where R is H, hydrocarbyl, or C1-C6 alkoxy), and silyloxy (-O-silyl); hydrocarbyl moieties C1-C6 24 Alkyl (preferably C1-C 12 alkyl, more preferably C1-C6 alkyl), C2-C 24 Alkenyl (preferably C2-C 12 alkenyl, more preferably C2-C6 alkenyl), C2-C 24 Alkynyl (preferably C2-C 12 alkyl, more preferably C2-C6 alkynyl), C5-C 24 Aryl (preferably C6-C 10 aryl), C6-C 24 Alkaryl (preferably C6-C 16 Alkaryl), or C6-C 24 Aralkyl (preferably C6-C 16 The hydrocarbyl, alkyl, and aryl groups in the above moieties may themselves be substituted.

[0062] "Functionalized," as in "functionalized hydrocarbyl," "functionalized alkyl," "functionalized olefin," "functionalized cyclic olefin," etc., means that at least one H atom bonded to a carbon (or other) atom in a hydrocarbyl, alkyl, olefin, cyclic olefin, or other moiety has been replaced with one or more functional group(s), such as those described above. The term "functional group" is meant to include any functional species suitable for use as described herein. In some cases, "substituent" and "functional group" are used interchangeably.

[0063] "Optional" or "optionally" means that the subsequently described circumstance may or may not occur, i.e., the description includes cases where the circumstance occurs and cases where it does not occur. For example, the phrase "optionally substituted" means that a non-hydrogen substituent may or may not be present on a given atom, and thus the description includes structures where the non-hydrogen substituent is present and structures where the non-hydrogen substituent is not present.

[0064] As used herein, the term "absent" means absent or non-existent.

[0065] As used herein, the term "sulfhydryl" refers to a group of the formula "-SH".

[0066] As used herein, the term "hydroxyl" refers to a group of the formula "-OH".

[0067] As used herein, the term "carbonyl" refers to a group of the formula "-C(O)-".

[0068] As used herein, the term "ketone" refers to a -C(O)R x1 represents an organic compound having a carbonyl group bonded to a carbon atom, such as x1 may be alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle as defined above.

[0069] As used herein, the term "ester" refers to an ester of -C(O)OR x1 represents an organic compound having a carbonyl group bonded to a carbon atom, such as x1 may be alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle as defined above.

[0070] As used herein, the term "amine" refers to a group of the formula "-NR x R y " group, wherein R x and Ry may be the same or independently H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle as defined above.

[0071] As used herein, the term "carboxyl" refers to a group of the formula "-C(O)O-".

[0072] As used herein, the term "sulfonyl" refers to a group of the formula "-SO2 - " represents the group.

[0073] As used herein, the term "sulfate" refers to a group of the formula "-OS(O)2-O-".

[0074] As used herein, the term "sulfonate" refers to a group of formula "-S(O)2-O-".

[0075] As used herein, the term "amide" refers to a group of the formula "-C(O)NR x R y " group, wherein R x and R y may be the same or independently H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle as defined above.

[0076] As used herein, the term "sulfonamide" refers to a group of the formula "-S(O)NR x R y " group, wherein R x and R y may be the same or independently H, alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle as defined above.

[0077] As used herein, the term "sulfoxide" refers to a group of the formula "-S(O)-".

[0078] As used herein, the term "phosphonic acid" refers to a group of formula "-P(O)(OH)2".

[0079] As used herein, the term "phosphonate ester" refers to a phosphonate ester of the formula "-P(O)(OR x1 )2" group, where R x1 may be alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle as defined above.

[0080] As used herein, the term "phosphate" refers to a group of formula "-OP(O)(OH)2".

[0081] As used herein, the term "phosphate ester" refers to a group of esters of the formula "-OP(O)(OR x1 )2" group, where R x1 may be alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycle as defined above.

[0082] As used herein, the term "sulfonic acid" refers to a group of formula "-S(O)2OH".

[0083] As used herein, the formula "H" represents a hydrogen atom.

[0084] As used herein, the formula "O" represents an oxygen atom.

[0085] As used herein, the formula "N" represents a nitrogen atom.

[0086] As used herein, the formula "S" represents a sulfur atom.

[0087] Functional groups may be protected if they interfere with metal carbene olefin metathesis catalysts, and any of the protecting groups commonly used in the art may be used. Acceptable protecting groups can be found, for example, in Greene et al., Protective Groups in Organic Synthesis, 5th Ed. (New York: Wiley, 2014). Examples of protecting groups include acetals, cyclic acetals, boronic acid esters (boronates), cyclic boronic acid esters (cyclic boronates), carbonates, etc. Examples of protecting groups include cyclic acetals or cyclic boronic acid esters.

[0088] As used herein, the term "coating" refers to a material temporarily or permanently applied to a surface or substrate for decorative purposes, to impart functionality to the surface or substrate, such as electrical passivity or conductivity, or to protect the surface or substrate from deterioration or decomposition as a result of its reaction with the environment or corrosive substances. In particular, the coating of the present invention is suitable for industrial coatings, such as protective coatings, especially anticorrosion coatings. The coating can be applied as a liquid, gas (vapor deposition), or solid.

[0089] As used herein, the term "adhesive" or "adhesive coating composition" refers to a substance that is applied between two substrates to create a bond or joint.

[0090] As used herein, the term "adhesion promoter" refers to an additive or primer that promotes adhesion of a coating to a target substrate. Adhesion promoters typically have an affinity for the substrate and the applied coating.

[0091] As used herein, the term "dispersant" refers to an agent capable of preventing settling or flocculation and is used interchangeably with "dispersing agent."

[0092] The term "antioxidant" is used interchangeably with the term "antiozonant" and is a type of "stabilizer."

[0093] In the context of the present invention, the term "substrate(s)" refers to an object or surface of an object that may be subject to deterioration or corrosion of properties and whose surface may be protected by a coating. The substrate may be a metal, such as steel, stainless steel, aluminum, copper, alloys, or a non-metal, such as glass, concrete, ceramic, porcelain, brick, plastic, rubber, wood, fabric, textiles, or a composite material, such as reinforced plastics, electronic assemblies, etc.

[0094] As used herein, the term "substrate material(s)" refers to the material(s) of construction of the substrate.

[0095] Cyclic Olefin Monomers In general, any cyclic olefin suitable for the reactions disclosed herein can be used in the present invention. Such cyclic olefins can be monocyclic, bicyclic, or polycyclic, optionally substituted, optionally heteroatom-containing, mono-, di-, or polyunsaturated C5-C 24 It can be a hydrocarbon. When the cyclic olefin contains more than one ring, the rings can be fused or unfused.

[0096] The cyclic olefin may generally be any strained or unstrained cyclic olefin, provided that the cyclic olefin is capable of participating in the polymerization reaction either individually or as part of a cyclic olefin composition.

[0097] In one embodiment of the present invention, the cyclic olefin is represented by the structure of formula (I): [ka] During the ceremony, R a is H, optionally substituted straight or branched chain C 1-24Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , -CN, -NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, optionally substituted spiroheterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2- (optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and Each R s are independently optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)Rf , -CH2-C(O)R f , -OR g , -CH2-OR g , -CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2- (optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and t is 0, 1, 2, 3, 4, 5, or 6; R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-24 Alkyl, optionally substituted C 3-10Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 Aryl, optionally substituted straight or branched chain C 2-24 alkenyl, -C(O)-(optionally substituted C 5-24 aryl), -C(O)-(optionally substituted straight or branched chain C 2-24 alkenyl), or optionally substituted C 3-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R j is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R kis an optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R l is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R m is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 It is a cycloalkenyl.

[0098] In one embodiment of the present invention, the cyclic olefin is represented by formula (I): R a is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-12 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted spiroheterocycle, optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2- (optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NRo R p , -C(R h )(R i )C(O)NR o OR n and Each R s are independently optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-12 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , -CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2- (optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o ORn and t is 0, 1, 2, 3, or 4; R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, optionally substituted straight or branched chain C 2-12 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted straight or branched chain C 2-12 alkenyl), or optionally substituted C 5-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R jis H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R l is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R m is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 It is a cycloalkenyl.

[0099] In one embodiment of the present invention, the cyclic olefin is represented by formula (I): R a is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, optionally substituted spiroheterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2- (optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-7 cycloalkenyl), t is 0, R f OH, OR k , N.R. g Rh , optionally substituted linear or branched C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, optionally substituted straight or branched chain C 2-6 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted straight or branched chain C 2-6 alkenyl), or optionally substituted C 5-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 It is a cycloalkenyl.

[0100] The cyclic olefin of formula (I) is represented by R on the tetracyclododec-3-ene moiety. s Depending on the position of [ka] where t is 1 and R a and R s is as defined herein, and R a and R s can form an optionally substituted polycyclic ring with the rest of the molecule.

[0101] In one embodiment of the present invention, the cyclic olefin is represented by formula (I), wherein R a teeth, [ka] [ka] and t=0.

[0102] Non-limiting examples of monomers of formula (I) are: [ka] [ka] [ka] It can be represented by:

[0103] In one embodiment of the present invention, the cyclic olefin is represented by the structure of formula (II): [ka] During the ceremony, R b is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f, -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -Si(OR k )3, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, optionally substituted spiroheterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2-(optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and Each R s are independently optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g, -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH-(optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and t is 0, 1, 2, 3, 4, 5, or 6; R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 Aryl, optionally substituted straight or branched chain C 2-24 alkenyl, -C(O)-(optionally substituted C 5-24 aryl), -C(O)-(optionally substituted straight or branched chain C 2-24 alkenyl), or optionally substituted C 3-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R j is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R l is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R m is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12It is a cycloalkenyl.

[0104] In one embodiment of the present invention, the cyclic olefin is represented by the structure of formula (II), wherein: R b is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-12 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, optionally substituted spiroheterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2- (optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NRo OR n and Each R s are independently optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-12 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH-(optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and t is 0, 1, 2, 3, or 4; Rf OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, optionally substituted straight or branched chain C 2-12 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted straight or branched chain C 2-12 alkenyl), or optionally substituted C 5-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R j is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R l is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R m is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 It is a cycloalkenyl.

[0105] In one embodiment of the present invention, the cyclic olefin is represented by formula (II): R b is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, optionally substituted spiroheterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH-(optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), t is 0, R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-6 Alkyl, optionally substituted C 5-7Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, optionally substituted straight or branched chain C 2-6 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted straight or branched chain C 2-6 alkenyl), or optionally substituted C 5-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 It is a cycloalkenyl.

[0106] The cyclic olefin structure of formula (II) is represented by R on the 2-norbornene moiety. s Depending on the position of , it can be expressed as [ka] In the formula, t=1, R s and R bis as defined herein, and R s and R b can be taken together with the rest of the molecule to form an optionally substituted polycyclic structure.

[0107] In one embodiment of the present invention, the cyclic olefin is represented by formula (II): R b teeth, [ka] [ka] and t=0.

[0108] Non-limiting examples of monomers of formula (II) are: [ka] [ka] [ka] [ka] [ka] It can be expressed as:

[0109] In one embodiment of the present invention, the cyclic olefin is represented by the structure of formula (III): [ka] wherein z is 0, 1, 2, or 3.

[0110] In one embodiment of the present invention, the cyclic olefin is represented by the structure of formula (III), wherein z is 1 or 2.

[0111] In one embodiment of the present invention, the cyclic olefin is represented by the structure of formula (III), wherein z is 2.

[0112] Non-limiting examples of monomers of formula (III) are: [ka] It can be expressed as:

[0113] Thus, examples of cyclic olefins include dicyclopentadiene, tricyclopentadiene, tetracyclopentadiene, norbornene, 5-isobutyl-2-norbornene, 5,6-dimethyl-2-norbornene, 5-phenyl-2-norbornene, 5-benzyl-2-norbornene, 5-methoxycarbonyl-2-norbornene, 5-methyl-5-methoxycarbonyl-2-norbornene, 5-cyano-2-norbornene, 5,5,6-trimethyl-2-norbornene, 5-isobutyl-2-norbornene, 5,6-dimethyl-2-norbornene, 5-phenyl-2-norbornene, 5-benzyl-2-norbornene, 5-methoxycarbonyl-2-norbornene, 5-methyl-5-methoxycarbonyl-2-norbornene, 5-cyano-2-norbornene, 5,5,6-trimethyl-2-norbornene, 5-methyl-5-methyl-2-norbornene, ... C1-C methyl-2-norbornene, endo,exo-5,6-dimethoxy-2-norbornene, endo,endo-5,6-dimethoxy-2-norbornene, endo,exo-5,6-dimethoxycarbonyl-2-norbornene, endo,endo-5,6-dimethoxycarbonyl-2-norbornene, norbornadiene, tricycloundecene, tetracyclododecene, 8-methoxycarbonyl-tetracyclodecene, 8-cyanotetracyclodecene C1-C 12 Hydrocarbyl-substituted norbornenes, such as 5-methyl-2-norbornene, 5-ethyl-2-norbornene, 5-butyl-2-norbornene, 5-hexyl-2-norbornene, 5-octyl-2-norbornene, 5-decyl-2-norbornene, 5-dodecyl-2-norbornene, 5-vinyl-2-norbornene, 5-ethylidene-2-norbornene, 5-isopropenyl-2-norbornene, 5-propenyl-2-norbornene, and 5-butenyl-2-norbornene, C2-C 12Hydrocarbyl-substituted tetracyclododecenes include, for example, 8-methyl-tetracyclododec-3-ene, 8-ethyl-tetracyclododec-3-ene, 8-butyl-tetracyclododec-3-ene, 8-hexyl-tetracyclododec-3-ene, 8-octyl-2-tetracyclododec-3-ene, 8-decyl-2-tetracyclododec-3-ene, 8-dodecyl-2-tetracyclododec-3-ene, 8-vinyl-tetracyclododec-3-ene, 8-ethylidene-2-tetracyclododec-3-ene, 8-isopropenyl-tetracyclododec-3-ene, 5-propenyl-tetracyclododec-3-ene, and 5-butenyl-tetracyclododec-3-ene.

[0114] It will be appreciated by those skilled in the art that the bicyclic and polycyclic olefins disclosed herein can consist of various structural and / or stereoisomers, any and all of which are suitable for use in the present invention. References herein to such bicyclic and polycyclic olefins include mixtures of any and all such structural and / or stereoisomers, unless otherwise specified.

[0115] Linear Olefins The linear olefins used in the present invention may be optionally substituted, optionally heteroatom-containing, monounsaturated, or polyunsaturated.

[0116] In one embodiment of the present invention, the linear olefin is represented by the structure of formula (IV), where R c and R d may be in cis or trans configuration, [ka] During the ceremony, R c is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)Rf , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH-(optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R d is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h)2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2- (optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 Aryl, optionally substituted straight or branched chain C 2-24 alkenyl, -C(O)-(optionally substituted C 5-24 aryl), -C(O)-(optionally substituted straight or branched chain C 2-24 alkenyl), or optionally substituted C 3-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R j is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R lis H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R m is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 It is a cycloalkenyl.

[0117] In one embodiment of the present invention, the linear olefin is represented by the structure of formula (IV), wherein: Rc is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-12 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH-(optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R d is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-12Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2- (optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10aryl, or optionally substituted C 5-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, optionally substituted straight or branched chain C 2-12 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted straight or branched chain C 2-12 alkenyl), or optionally substituted C 5-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R j is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R l is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R m is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C5-12 It is a cycloalkenyl.

[0118] In one embodiment of the present invention, the linear olefin is represented by formula (IV), wherein: R c is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2(optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH-(optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), R d is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C5-7 cycloalkyl, -CH- (optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2- (optionally substituted C 6-10 aryl), optionally substituted C 5-12 Cycloalkenyl, -CH- (optionally substituted C 5-12 cycloalkenyl), R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, optionally substituted straight or branched chain C 2-6 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted straight or branched chain C 2-6 alkenyl), or optionally substituted C 5-7 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-6Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-12 It is a cycloalkenyl.

[0119] In one embodiment of the present invention, the linear olefin is represented by formula (IV), wherein: R c H, [ka] and R d teeth, [ka] [ka] is.

[0120] Non-limiting examples of monomers of formula (IV) can be represented by the following: [ka] [ka]

[0121] In a separate embodiment, in the coating composition of the present invention, the composition may comprise, consist essentially of, or consist of, as its olefin component, at least one cyclic olefin selected from the group consisting of formulas (I) and (II), at least one cyclic olefin selected from the group consisting of formulas (I) and (III), or at least one cyclic olefin selected from the group consisting of formulas (II) and (III). The coating composition of the present invention may contain only cyclic monomers of formulas (I), (II), and (III) or mixtures thereof, or, as described above, may contain at least one specific cyclic olefin selected from one of formulas (I), (II), and (III), but may not contain a linear olefin of formula (IV). In the coating composition of the present invention, the olefin component may comprise 0-100%, preferably 25-100%, and most preferably 50-100% or 70-85% of at least one cyclic olefin of formula (I), 0-100%, preferably 20-80% or 15-50% of at least one cyclic olefin of formula (II), 0-10%, preferably 10-80% or 20-75% of at least one cyclic olefin of formula (III), and 0-20%, preferably 0-10% or 1-5% of at least one linear olefin of formula (IV), such that the olefin component comprising the olefin component is added to 100% of the coating composition of the present invention.

[0122] Metal Carbene Olefin Metathesis Catalysts Metal carbene olefin metathesis catalysts suitable for catalyzing the ring-opening metathesis polymerization of cyclic olefins of the present invention are represented by the general structure of formula (1): During the ceremony, [ka] M is a Group 8 transition metal, generally M is ruthenium or osmium, typically M is ruthenium; L 1 , L 2 , and L3 are independently a neutral electron donor ligand; n is 0 or 1, typically n is 0; m is 0, 1, or 2, typically m is 0; k is 0 or 1, typically k is 1; X 1 and X 2 are independently anionic ligands, and generally, X 1 and X 2 are independently halogens, trifluoroacetates, perfluorophenols, or can form nitrates together therewith, and are typically 1 and X 2 are independently Cl, Br, I, or F; R 1 and R 2 are independently hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl, and are typically 1 is hydrogen and R 2 is optionally substituted phenyl, C1-C6 alkyl or substituted 1-propenyl, or R 1 and R 2 are linked together to form one or more cyclic groups, for example, a substituted indenylidene, specifically 3-phenylindenylide-1-ene.

[0123] In one embodiment, L 1 and L 2 are independently selected from phosphines, sulfonated phosphines, phosphites, phosphinites, phosphonites, arsines, stibines, ethers (including cyclic ethers), amines, amides, imines, sulfoxides, carboxyls, nitrosyls, pyridines, substituted pyridines, imidazoles, substituted imidazoles, pyrazines, substituted pyrazines, and thioethers. An exemplary ligand is a trisubstituted phosphine. A preferred trisubstituted phosphine is of the formula PR H1 R H2 R H3 wherein R H1 , RH2 , and R H3 each independently represents an optionally substituted C 6-10 Aryl or C1-C 10 Alkyl, or C 3-10 Most preferably, L 1 and L 2 are independently selected from the group consisting of trimethylphosphine (PMe), triethylphosphine (PEt), tri-n-butylphosphine (PBu), tri(ortho-tolyl)phosphine (Po-tolyl), tri-tert-butylphosphine (P-tert-Bu), tricyclopentylphosphine (PCp), tricyclohexylphosphine (PCy), triisopropylphosphine (Pi-Pr), trioctylphosphine (POct), triisobutylphosphine (Pi-Bu), triphenylphosphine (PPh), tri(pentafluorophenyl)phosphine (P(CF)), methyldiphenylphosphine (PMePh), dimethylphenylphosphine (PMePh), and diethylphenylphosphine (PEtPh).

[0124] In one embodiment, L 1 teeth [ka] wherein X and Y are independently C, CR 3a , N, O, S, or P, and only one of X or Y is C or CR 3a Typically, X and Y are independently N and Q 1 , Q 2 , R 3 , R 3a , and R 4 are independently hydrogen, optionally substituted hydrocarbylene, or optionally substituted heteroatom-containing hydrocarbylene, and generally, Q 1 , Q 2 , R 3 , R 3a , and R 4is optionally linked to X or Y via a linker such as an optionally substituted hydrocarbylene, an optionally substituted heteroatom-containing hydrocarbylene, or -(CO)-, and is typically 1 , Q 2 , R 3 , R 3a , and R 4 is directly linked to X or Y, p is 0 when X is O or S, and p is 0 when X is N, P, or CR 3a and p is 1 when X is C, q is 2 when Y is O or S, and q is 0 when Y is N, P, or CR. 3a and q is 2 when X is C.

[0125] In one embodiment, L 1 teeth [ka] wherein Q is a group having the structure -[CR 11 R 12 ] s -[CR 13 R 14 ] t -or- [CR 11 =CR 13 ]-, and typically Q is -[CR 11 R 12 ] s -[CR 13 R 14 ] t -, wherein R 11 , R 12 , R 13 , and R 14 are independently hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl, and are typically 11 , R 12 , R 13 , and R 14 are independently hydrogen, optionally substituted C-C 12 Alkyl, optionally substituted C-C 12Heteroalkyl, optionally substituted C-C 14 aryl, and "s" and "t" are independently 1, or typically, "s" and "t" are independently 1, or R 11 , R 12 , R 13 , and R 14 Any two of can be optionally linked to form an optionally substituted, saturated or unsaturated polycyclic ring structure.

[0126] In one embodiment, L 1 teeth, [ka] wherein: X is -CR 1a R 2a - and a is 1 or 2, R 1a is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, halogen, optionally substituted C5-C 24 Aryl, optionally substituted C-C 24 Aralkyl, optionally substituted C-C 20 Heteroalkyl, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 or R 2a and optionally substituted spiromonocyclic or spiropolycyclic C 3-10 form a cycloalkyl or spiro heterocyclic ring together with the carbon atom to which they are attached, or R 3 With or R 4 together form an optionally substituted polycyclic ring, R 2ais H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, halogen, optionally substituted C5-C 24 Aryl, optionally substituted C-C 24 Aralkyl, optionally substituted C-C 20 Heteroalkyl, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 or R 1a and spiromonocyclic or spiropolycyclic C 3-10 together with the carbon atoms to which they are attached, form a cycloalkyl or spiro heterocycle, or R 3 With or R 4 together form an optionally substituted polycyclic ring, Y is -CR 1b R 2b - and b is 0, 1, or 2; R 1b is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, halogen, optionally substituted C5-C 24 Aryl, optionally substituted C-C 24 Aralkyl, optionally substituted C-C 20 Heteroalkyl, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 or R 2b together with the carbon atom to which they are attached form a 5-, 6-, or 10-membered cycloalkyl or heterocyclic ring; R2b is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, halogen, optionally substituted C5-C 24 Aryl, optionally substituted C-C 24 Aralkyl, optionally substituted C-C 20 Heteroalkyl, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 or R 1b together with the carbon atom to which they are attached form a 5-, 6-, or 10-membered cycloalkyl or heterocyclic ring; R 3 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-12 cycloalkenyl, or R 1a with or R 2a together with R to form an optionally substituted polycyclic ring, or R 3a and optionally substituted spiromonocyclic or spiropolycyclic C 3-10 can form a cycloalkyl, R 3a is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR 22 , CN, -NR23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-12 cycloalkenyl, or R 1a with or R 2a together with R to form an optionally substituted polycyclic ring, or R 3 and optionally substituted spiromonocyclic or spiropolycyclic C 3-10 can form a cycloalkyl, R 4 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-12 cycloalkenyl, or R 1a with or R 2a together with R to form an optionally substituted polycyclic ring, or R 4a and optionally substituted spiromonocyclic or spiropolycyclic C 3-10 can form a cycloalkyl, R 4a is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O)x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-12 cycloalkenyl, or R 1a with or R 2a together with R to form an optionally substituted polycyclic ring, or R 4 and optionally substituted spiromonocyclic or spiropolycyclic C 3-10 can form a cycloalkyl, R 5 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-12 cycloalkenyl, or R 6 together can form an optionally substituted polycyclic ring, R 6 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24Aryl, optionally substituted C 3-12 cycloalkenyl, or R 5 with or R 7 together can form an optionally substituted polycyclic ring, R 7 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-12 cycloalkenyl, or R 6 With or R 8 together can form an optionally substituted polycyclic ring, R 8 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR 22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-12 cycloalkenyl, or R 7 with or R 9 together can form an optionally substituted polycyclic ring, R 9 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 21 , -OR22 , CN, -NR 23 R 24 , NO2, -CF3, -S(O) x R 25 , -P(O)(OH)2, -OP(O)(OH)2, -SR 27 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-12 is cycloalkenyl, or R 8 together can form a polycyclic ring, R 21 OH, OR 26 , N.R. 23 R 24 , optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R 22 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R 23 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R 24 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C3-12 is cycloalkenyl, R 25 is H, optionally substituted C 1-24 Alkyl, OR 22 , -NR 23 R 24 , optionally substituted heterocycle, optionally substituted C 3-8 Cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R 26 is an optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R 27 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-8 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, x is 1 or 2, provided that: a. when a is 2, the "XX" bond may be saturated or unsaturated; b. When b is 2, the "YY" bond can be saturated or unsaturated; c. If a is 2 and the "XX" bond is unsaturated, R 2a is nothing, d. If b is 1, then R 3a and R 4a Both are nothing, e. If b is 2, R 3a and R 4a Both are nothing, f. When b is 2 and the "YY" bond is unsaturated, R 2b There is nothing.

[0127] In one embodiment, L 1 teeth, [ka] where: Z is N or CR 32 and R 1 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 2 can form a spiro compound with R 3 with or R 4 can form a polycyclic ring together with R 2 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 1 can form a spiro compound with R 3 with or R 4can form a polycyclic ring together with R 3 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl or optionally substituted C 3-8 cycloalkenyl, or R 2 with or R 1 can form a polycyclic ring together with R 4 can form a spiro compound with R 4 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 3 can form a spiro compound with R 2 with or R 1 can form a polycyclic ring together with R 5 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 together can form an optionally substituted polycyclic ring, R 6 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 5 together with or R 7 together can form an optionally substituted polycyclic ring, R 7 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 with or R8 together can form an optionally substituted polycyclic ring, R 8 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 7 together with or R 9 together can form an optionally substituted polycyclic ring, R 9 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 8 together can form an optionally substituted polycyclic ring, R 10 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29, -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 together can form an optionally substituted polycyclic ring, R 11 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 10 together with or R 12 together can form an optionally substituted polycyclic ring, R 12 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 together with or R 13 together can form an optionally substituted polycyclic ring, R 13 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 14 together with or R 12 together can form an optionally substituted polycyclic ring, R 14 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 13 together can form a polycyclic ring, R 32 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 25 OH, OR 30 , N.R. 27 R28 , optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-24 Alkyl, OR 26 , -NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 is optionally substituted C alkyl, optionally substituted C 3-10Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl, where x is 1 or 2.

[0128] In one embodiment, L 1 teeth, [ka] wherein: R 1 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 2 can form a spiro compound with R 3 together with or R 4 can form a polycyclic ring together with R 2 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O)x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 1 can form a spiro compound with R 3 with or R 4 can form a polycyclic ring together with R 3 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl or optionally substituted C 3-8 cycloalkenyl, or R 2 with or R 1 can form a polycyclic ring together with R 4 can form a spiro compound with R 4 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10Aryl, optionally substituted C 3-8 cycloalkenyl, or R 3 can form a spiro compound with R 2 with or R 1 can form a polycyclic ring together with R 5 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 together can form an optionally substituted polycyclic ring, R 6 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 5 together with or R 7 together can form an optionally substituted polycyclic ring, R 7 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 with or R 8 together can form an optionally substituted polycyclic ring, R 8 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 7 together with or R 9 together can form an optionally substituted polycyclic ring, R 9 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10Aryl, optionally substituted C 5-7 cycloalkenyl, or R 8 together can form an optionally substituted polycyclic ring, R 10 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 together can form an optionally substituted polycyclic ring, R 11 is H, optionally substituted C 1-124 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 10 together with or R 12 together can form an optionally substituted polycyclic ring, R 12 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28, NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 together with or R 13 together can form an optionally substituted polycyclic ring, R 13 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 14 together with or R 12 together can form an optionally substituted polycyclic ring, R 14 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R13 together can form a polycyclic ring, R 25 OH, OR 30 , N.R. 27 R 28 , optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-12 Alkyl, OR 26 , -NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 is an optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, x is 1 or 2.

[0129] In one embodiment, L 1 teeth [ka] wherein: R 1 is H, phenyl, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, R 2 is H, phenyl, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, R 3 is H, phenyl, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, R 4 is H, phenyl, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, R 5 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 6 together can form an optionally substituted polycyclic ring, R 6 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 5 with or R 7 together can form an optionally substituted polycyclic ring, R 7 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 6 with or R 8 together can form an optionally substituted polycyclic ring, R 8 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 7 with or R 9 together can form an optionally substituted polycyclic ring, R 9 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 8 can form a polycyclic ring together with R 10 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 11 together can form an optionally substituted polycyclic ring, R 11 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 10 with or R 2 together can form an optionally substituted polycyclic ring, R 12is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 11 with or R 13 together can form a polycyclic ring, R 13 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 12 with or R 14 together can form an optionally substituted polycyclic ring, R 14 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 13 together can form an optionally substituted polycyclic ring.

[0130] In one embodiment, L 2 teeth [ka] where R a2 is hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl, and generally R a2 is an optionally substituted C1-C 10 Alkyl, optionally substituted C-C 10 Cycloalkyl, optionally substituted C5-C 24 aryl, typically R a2 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, or phenyl, and R b2 is hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl, and generally R b2 is an optionally substituted C1-C 10 Alkyl, optionally substituted C-C 10Cycloalkyl, optionally substituted C5-C 24 aryl, typically R b2 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, or phenyl, or R a2 and R b2 are linked together to form a 5- or 6-membered heterocycle together with the sulfoxide group [—S(O)—].

[0131] In one embodiment, L 2 teeth, [ka] wherein R is an optionally substituted hydrocarbyl, an optionally substituted heteroatom-containing hydrocarbyl, and generally R is an optionally substituted C-C 10 Alkyl, optionally substituted C-C 10 Cycloalkyl, optionally substituted C5-C 24 aryl, typically R is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, or phenyl.

[0132] In one embodiment, L 2 teeth, [ka] where R 1p , R 2p , R 3p are each independently an optionally substituted C-C 10 aryl, or optionally substituted C-C 10 Alkyl or optionally substituted C-C 10 is cycloalkyl. R 8p , R 9p , R 10p are each independently an optionally substituted C-C 10 aryl, or optionally substituted C-C 10Alkyl or optionally substituted C-C 10 It is cycloalkyl.

[0133] In one embodiment, L 2 is PR H1 R H2 R H3 where R H1 , R H2 , R H3 are each independently an optionally substituted C-C 10 aryl, or optionally substituted C-C 10 Alkyl or optionally substituted C-C 10 In one embodiment, R H1 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl. H2 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl. H3 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl. 2 are P(cyclohexyl)3, P(Et)2Ph, and P(Ph)3.

[0134] In one embodiment, X 1 and X 2 are independently halogens, trifluoroacetates, perfluorophenols, or can form nitrates together therewith, and are typically 1 and X 2 is independently Cl, Br, I, or F. In a preferred embodiment, X 1 and X 2 are both Cl.

[0135] In one embodiment, R 1 is hydrogen and R 2is an optionally substituted phenyl, C1-C6 alkyl, or substituted 1-propenyl, or R 1 and R 2 are linked together to form one or more cyclic groups such as substituted indenylidene, particularly 3-phenylindenylide-1-ene.

[0136] In another embodiment, R 1 is hydrogen and R 2 is 2-methyl-1-propenyl. In another embodiment, R 1 and R 2 together form 3-phenylindenylide-1-ene. In another embodiment, R 1 is hydrogen and R 2 is phenyl.

[0137] In one embodiment, L 2 teeth [ka] where R a3 is optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl; generally, R a3 is an optionally substituted C1-C 10 Alkyl, optionally substituted C-C 10 Cycloalkyl, optionally substituted C5-C 24 aryl; typically, R a3 is methyl, ethyl, n-propyl, n-butyl, tert-butyl, cyclohexyl, benzyl or phenyl; R b3 is optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl; generally, R b3 is an optionally substituted C1-C 10 Alkyl, optionally substituted C-C 10 Cycloalkyl, optionally substituted C5-C 24 aryl; typically, R b3is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, benzyl, or phenyl; or R a3 and R b3 can be linked to form a 5-, 6-, or 7-membered heterocyclic ring with the nitrogen atom to which they are attached; R c3 is an optionally substituted hydrocarbyl, an optionally substituted heteroatom-containing hydrocarbyl, and generally R c3 is an optionally substituted C1-C 10 Alkyl, optionally substituted C-C 10 Cycloalkyl, optionally substituted C5-C 24 aryl, typically R c3 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, benzyl, or phenyl, and R d3 is an optionally substituted hydrocarbyl, an optionally substituted heteroatom-containing hydrocarbyl, and generally R d3 is an optionally substituted C1-C 10 Alkyl, optionally substituted C1-C 10 Cycloalkyl, optionally substituted C-C 24 aryl; typically, R d3 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, benzyl, or phenyl; or R c3 and R d3 can be linked to form a 5-, 6-, or 7-membered heterocyclic ring with the nitrogen atom to which they are attached; or R b3 and R c3 can be linked to form a 5-, 6-, or 7-membered heterocyclic ring with the nitrogen atom to which they are attached.

[0138] In one embodiment, the moiety [ka] wherein X3 and X 4 are independently O or S, and typically X 3 and X 4 are independently S and R x , R y , R w , and R z are independently hydrogen, halogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl, and generally R x , R y , R w , and R z are independently hydrogen, halogen, optionally substituted C-C 12 Alkyl, optionally substituted C-C 10 Cycloalkyl, optionally substituted C5-C 24 aryl, typically R x1 , R y , R w , and R z are independently C1-C6 alkyl, hydrogen, optionally substituted phenyl, or halogen, or R x1 and R y are linked together to form an optionally substituted bicyclic or polycyclic aryl, or R w and R z are linked together to form an optionally substituted bicyclic or polycyclic aryl, or R y and R w are linked together to form an optionally substituted bicyclic or polycyclic aryl.

[0139] In another embodiment, metal carbene olefin metathesis catalysts suitable for ring-opening the monomers of the present invention are represented by the general structure of formula (2): [ka] During the ceremony, M is ruthenium; L 1 , X 1 , and X2 is as defined herein; W is O, halogen, NR 33 , or S, R 19 is H, optionally substituted C 1-24 Alkyl, -C(R 34 )(R 35 )COOR 36 , -C(R 34 )(R 35 )C(O)H, -C(R 34 )(R 35 )C(O)R 37 , -C(R 34 )(R 35 )CR 38 (OR 39 )(OR 40 ), -C(R 34 )(R 35 )C(O)NR 41 R 42 , -C(R 34 )(R 35 )C(O)NR 41 OR 40 , -C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or W is NR 33 If R 19 is R 33 together can form an optionally substituted heterocycle, or when W is halogen, R 19 is nothing, R 20 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 21 together can form a polycyclic ring, R 21 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 20 with or R 22 can form a polycyclic ring together with R 22 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 21 with or R 23 can form a polycyclic ring together with R 23 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26, CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 22 together can form a polycyclic ring, R 24 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 is cycloalkenyl, R 25 OH, OR 30 , N.R. 27 R 28 , optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-24 Alkyl, OR 26 , -NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 is an optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 33 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 34 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 35 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 36 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 37 is an optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 38 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 39 is H, optionally substituted C1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 40 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 41 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 42 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, x is 1 or 2.

[0140] In one embodiment, metal carbene olefin metathesis catalysts suitable for ring-opening the monomers of the present invention are represented by the general structure of formula (2): [ka] During the ceremony, M is ruthenium; L 1 , X 1 , and X 2 is as defined herein; W is O, halogen, NR 33, or S, R 19 is H, optionally substituted C 1-12 Alkyl, -C(R 34 )(R 35 )COOR 36 , -C(R 34 )(R 35 )C(O)H, -C(R 34 )(R 35 )C(O)R 37 , -C(R 34 )(R 35 )CR 38 (OR 39 )(OR 40 ), -C(R 34 )(R 35 )C(O)NR 41 R 42 , -C(R 34 )(R 35 )C(O)NR 41 OR 40 , -C(O)R 25 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or W is NR 33 If R 19 is R 33 together can form an optionally substituted heterocycle, or when W is halogen, R 19 is nothing, R 20 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C3-8 cycloalkenyl, or R 21 together can form a polycyclic ring, R 21 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 20 with or R 22 can form a polycyclic ring together with R 22 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 21 with or R 23 can form a polycyclic ring together with R 23 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 22 together can form a polycyclic ring, R 24 is H, optionally substituted C 1-12 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 Aryl, optionally substituted C 3-8 is cycloalkenyl, R 25 OH, OR 30 , N.R. 27 R 28 , optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-12 Alkyl, optionally substituted C5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-12 Alkyl, OR 26 , -NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 5-7 Cycloalkyl, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 is an optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 33 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C3-8 is cycloalkenyl, R 34 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 35 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 36 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 37 is an optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 38 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 39 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 40 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 41 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 42 is H, optionally substituted C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-8 is cycloalkenyl, x is 1 or 2.

[0141] In one embodiment, the metal carbene olefin metathesis catalyst is represented by the structure of formula (2): [ka] During the ceremony, M is ruthenium; L 1 , X 1 , and X 2 is as defined herein; W is O, R 19is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 20 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 21 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 20 with or R 22 can form a polycyclic ring together with R 22 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 23 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 24 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 25 OH, OR 30 , N.R. 27 R 28 , methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R26 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 27 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 28 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 29 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, OR 26 , -NR 27 R 28 , cyclohexyl, cyclopentyl, or phenyl; R 30 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 31 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; x is 1 or 2.

[0142] In one embodiment, L 1 teeth, [ka] and R 1 is H, phenyl, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, R 2 is H, phenyl, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, R 3is H, phenyl, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, R 4 is H, phenyl, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, R 5 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 6 together can form an optionally substituted polycyclic ring, R 6 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 5 with or R 7 together can form an optionally substituted polycyclic ring, R 7 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 6 with or R 8 together can form an optionally substituted polycyclic ring, R 8 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 7 with or R 9 together can form an optionally substituted polycyclic ring, R 9 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 8 can form a polycyclic ring together with R 10is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 11 together can form an optionally substituted polycyclic ring, R 11 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 10 with or R 2 together can form an optionally substituted polycyclic ring, R 12 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 11 with or R 13 together can form a polycyclic ring, R 13 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, F, optionally substituted phenyl, or R 12 with or R 14 together can form an optionally substituted polycyclic ring, R 14 is H, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, optionally substituted phenyl, or R 13 together can form an optionally substituted polycyclic ring. R 19 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 20 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 21 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 20 with or R 22 can form a polycyclic ring together with R 22 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 23 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 24 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 25 OH, OR 30 , N.R. 27 R 28 , methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 26 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 27 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 28is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 29 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, OR 26 , -NR 27 R 28 , cyclohexyl, cyclopentyl, or phenyl; R 30 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; R 31 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, or phenyl; x is 1 or 2.

[0143] In one embodiment, L 1 teeth, [ka] wherein: R 1 is H, R 2 is H, R 3 is H, R 4 is H, R 5 is H, methyl, isopropyl, R 6 is H, R 7 is H, methyl, R 8 is H, R 9 is H, methyl, isopropyl, R 10 is H, methyl, isopropyl, R 11 is H, R12 is H, methyl, R 13 is H, R 14 is H, methyl, isopropyl, X 1 and X 2 is Cl, W is O, R 19 is isopropyl, R 20 is H, R 21 is H, R 22 is H, R 23 is H, R 24 is H.

[0144] In some embodiments, the metal carbene olefin metathesis catalysts used in the present invention can be represented by the following general structure: [ka] [ka] [ka] [ka] [ka] In the formula, Q, Q 1 , Q 2 , p, q, X 1 , X 2 , X 3 , X 4 , R, R 1 , R 2 , R 3 , R 4 , R5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 20 , R 21 , R 22 , R 23 , R 24 , R a2 , R b2 , R a3 , R b3 , R c3 , R d3 , R 1p , R 2p , R 3p , R H1 , R H2 , R H3 , -(L 2 ) n -, and R 42 is as defined herein.

[0145] Preferred metal carbene olefin metathesis catalysts for use in the present invention are encompassed by the formula: [ka] In the formula, X 1 , X 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R13 , R 14 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R H1 , R H2 , R H3 , and R 42 is as defined herein.

[0146] The most preferred metal carbene olefin metathesis catalysts for use in the present invention are encompassed by the formula: [ka] [ka] In the formula, R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , Cy, R H1 , R H2 , R H3 , and R 42 is as defined herein.

[0147] It will be understood that the amount of catalyst used in a reaction (i.e., "catalyst loading") will depend on various factors, such as the identity of the reactants and the reaction conditions used. It will therefore be understood that the catalyst loading can be optimally and independently selected for each reaction. However, in general, the catalyst will be present in an amount ranging from a low of 0.1 ppm, 1 ppm, or 5 ppm to a high of 10 ppm, 15 ppm, 25 ppm, 50 ppm, 100 ppm, 200 ppm, 500 ppm, or 1000 ppm, relative to the amount of olefin substrate.

[0148] The catalyst is generally present in an amount ranging from a low of about 0.00001 mol%, 0.0001 mol%, or 0.0005 mol%, to a high of about 0.001 mol%, 0.0015 mol%, 0.0025 mol%, 0.005 mol%, 0.01 mol%, 0.02 mol%, 0.05 mol%, or 0.1 mol%, based on the olefin substrate.

[0149] When expressed as a molar ratio of olefin to catalyst ("olefin to catalyst ratio"), the catalyst loading is generally present in an amount ranging from a low of about 10,000,000:1, 1,000,000:1, 500,000:1, or 200,000:1 to a high of about 100,000:1, 60,000:1, 50,000:1, 45,000:1, 40,000:1, 30,000:1, 20,000:1, 10,000:1, 5,000:1, or 1,000:1.

[0150] Coating composition of the present invention In one embodiment, the present invention provides a coating composition comprising a ring-opening metathesis polymerization composition comprising at least one cyclic olefin and at least one metal carbene olefin metathesis catalyst. In the fast-curing coating composition of the present invention, the at least one metal carbene olefin metathesis catalyst is preferably a catalyst of formula (1), wherein L 1 is defined above as [ka] and L 2 is a triarylphosphine, and / or L 1 but [ka] The catalyst is represented by formula (2): L 1 and L 2 Preferred embodiments of the catalysts containing them are described above and illustrated in the examples.

[0151] The coating composition comprises at least one cyclic olefin represented by formula (I), by formula (II), and by formula (III), and may optionally comprise a linear olefin represented by formula (IV), and comprises at least one metal carbene olefin metathesis catalyst represented by formula (1), wherein formulas (I), (II), (III), (IV), and (1) are as defined herein.

[0152] The coating composition comprises at least one cyclic olefin represented by formula (I), by formula (II), by formula (III), and at least one metal carbene olefin metathesis catalyst represented by formula (1), wherein formulas (I), (II), (III), and (1) are as defined herein.

[0153] The coating composition comprises at least one cyclic olefin represented by Formula (I) and by Formula (II), and at least one metal carbene olefin metathesis catalyst represented by Formula (1), wherein Formulas (I), (II), and (1) are as defined herein.

[0154] The coating composition comprises at least one cyclic olefin represented by Formula (I) and by Formula (III), and at least one metal carbene olefin metathesis catalyst represented by Formula (1), wherein Formulas (I), (III), and (1) are as defined herein.

[0155] The coating composition comprises at least one cyclic olefin represented by formula (II) and by formula (III), and at least one metal carbene olefin metathesis catalyst represented by formula (1), wherein formulas (II), (III), and (1) are as defined herein.

[0156] The coating composition of the present invention contains at least one coating additive known in the art. Suitable coating additives include, but are not limited to, gel modifiers, hardness modifiers, impact modifiers, fillers, binders, thixotropes, rheology modifiers, dispersants, wetting agents, plasticizers, pigments, flame retardants, dyes, fibers, reinforcing materials, coupling agents, adhesion promoters, film formers, lubricants, and stabilizers such as antioxidants, antiozonants, UV absorbers, and UV light stabilizers, as well as other stabilizers known in the art. Furthermore, the amount of additive added to the resin composition may vary depending on the specific type of additive. The coating additive and coating additive loading should not interfere with the curing of the coating composition of the present invention. Caution is advised when using chemicals known to inhibit ring-opening polymerization. The concentration of the coating additive in the coating composition typically ranges, for example, from 0.001 to 95 wt %, specifically from 0.1 to 75 wt %, or more specifically from 1 to 60 wt %, 5 to 70 wt %, 10 to 60 wt %, or 20 to 60 wt %.

[0157] Suitable impact modifiers or elastomers include, but are not limited to, natural rubber, butyl rubber, polyisoprene, polybutadiene, polyisobutylene, ethylene-propylene copolymer, styrene-butadiene-styrene triblock rubber, random styrene-butadiene rubber, styrene-isoprene-styrene triblock rubber, styrene-ethylene / butylene-styrene copolymer, styrene-ethylene-ethylene / propylene-styrene copolymer, ethylene-propylene-diene terpolymer, ethylene-vinyl acetate rubber, and nitrile rubber.

[0158] Suitable antioxidants or antiozonants include primary antioxidants such as 2,6-di-tert-butyl-4-methylphenol (BHT), styrenated phenols such as Wingstay® S (Goodyear), 2 and 3-tert-butyl-4-methoxyphenol, alkylated hindered phenols such as Wingstay C (Goodyear), 4-hydroxymethyl-2,6-di-tert-butylphenol, 2,6-di-tert-butyl-4-sec-butylphenol, 2,2′-methylenebis(4-methyl-6-tert-butylphenol), 2,2′-methylenebis(4-ethyl-6-tert-butylphenol), 4,4′-methylenebis(2,6-di-tert-butylphenol), and miscellaneous bisphenols such as Cyanox® 53 and Permanax®. WSO, 2,2'-ethylidenebis(4,6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-(1-methylcyclohexylphenol), 4,4'-butylidenebis(6-tert-butyl-3-methylphenol), polybutylated bisphenol A, 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-methylenebis(2,6-dimethylphenol), 1,1'-thiobis(2-naphthol), methylene-bridged polyacrylphenols, e.g., Ethyl antioxidant 738, 2,2'-thiobis(4-methyl-6-tert-butylphenol), 2,2'-isobutylidenebis(4,6-dimethylphenol), 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), butylated reaction products of p-cresol and dicyclopentadiene, e.g., Wingstay L, tetrakis(methylene-3,5-di-tert-butyl-4-hydroxyhydrocinnamate)methane, i.e., Irganox 1010, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, e.g., Ethanox 330, 4,4'-methylenebis(2,6-di-tert-butylphenol), e.g., Ethanox 4702 or Ethanox 4710, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, i.e., Good-rite 3114, 2,5-di-tert-amylhydroquinone, tert-butylhydroquinone, 1,6-hexamethylenebis(3-(3,5-di-tert-butyl-4-hydroxyphenylpropionate), e.g., Irganox 259, octadecyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, i.e., Irganox 1076, diphenylamine, 4,4'-dimethoxydiphenylamine, secondary antioxidants, e.g., tris(nonylphenylphosphite), bis(2,4-di-tert-butyl)pentaerythritol) diphosphate, distearyl pentaerythritol diphosphite, phosphated phenols and bisphenols, e.g., Naugard 492, phosphite / phenolic antioxidant blends, e.g., Irganox Examples of suitable esters of thiodipropionic acid include, but are not limited to, B215, di-n-octadecyl(3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, such as Irganox 1093, tetrakis(2,4-di-tert-butylphenyl)4,4'-biphenylylene diphosphonite, and esters of thiodipropionic acid, such as Irganox PS 802, Irganox PS 800, and Cyanox MTDP. Such materials are typically used in the compositions of the present invention at levels of about 0.10% to 10% by weight, or more preferably at levels of about 0.1% to 5% by weight.

[0159] As mentioned above, UV absorbers and UV light stabilizers are two examples of types of stabilizers that can be used in the coating compositions of the present invention. Suitable UV absorbers include nickel quenchers, benzophenones, benzotriazoles, benzyl dene malonates, triazines, and the like. Suitable UV stabilizers include hindered amines, and the like. Blends of various UV absorbers and UV light stabilizers are also suitable for providing UV protection. Some suitable UV absorbers include 2-(2H-benzotriazol-2-yl)-p-cresol, 2-(6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], 2-hydroxy-4-methoxybenzophenone, and 2-hydroxy-4-octyloxybenzophenone, such as 2-(4,6-diphenyl-1, 3,5-triazin-2-yl)-5-[(hexyl)oxy]-phenol, oxanilide UV absorbers such as N-(2-ethoxyphenyl)-N'-(2-ethylphenyl)oxamide, dimethyl 2-(4-methoxybenzylidene)malonate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, methyl 1,2,2,6,6-pentamethyl-4-piperidylsebacate, bis(1-octyloxy-2,2,6,6-Tetramethyl-4-piperidyl)sebacate, LOWILITE® Q84 and POLYBATCH®, LLUVS 110, Tinuvin 1130, Tinuvin 171, Tinuvin 328, Tinuvin 384-2, Tinuvin 900, Tinuvin 928, Tinuvin 99, Tinuvin 5050, Tinuvin 5060, Tinuvin 5151, Tinuvin 5248, Tinuvin 5251, Tinuvin 5350, Tinuvin 123, Tinuvin 144, Tinuvin 152, Tinuvin 249, Tinuvin 292, Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479 (BASF), Chimassorb 81, Chimassorb 944, Chimassorb 2020 (BASF), KEMISORB 10, KEMISORB 11, KEMISORB 111 (Chemipro Kasei Ksisha), BP-2, BP-3, BP-6, BP-9 (Dalian Richfortune Chemicals), Ultra V 301 (Dover, ICI Industries), Grandsorb BP-1, Grandsorb Examples include BP-2, Grandsorb BP-4, Grandsorb BP-6 (Hongkun Group), SpeedBlock UV-6 (Lamsson), Maxgard 1000, Maxgard 300, Maxgard 400, Maxgard 500, Maxgard 600, Maxgard 700 (Lycus), Cyasorb UV-3346, Hostavin N 30, etc. Such stabilizers may be used as individual components or in combination with other stabilizers known in the art for coating compositions. Such materials are typically used in the compositions of the present invention at levels of about 0.10% to 10% by weight, more preferably at levels of about 0.1% to 5% by weight.

[0160] Suitable fillers include, for example, particulate density adjusters, such as microspheres, or macroparticle density adjusters, such as glass or ceramic beads. Other suitable fillers include, for example, aluminum powder, aluminum flakes (e.g., aluminum flake paste), glass flakes, mica-like iron oxide, calcium carbonate, dolomite, silica, silicates, talc, kaolin, mica, feldspar, barium sulfate, and inorganic fillers such as wollastonite, carbon nanotubes, and graphene. Preferred inorganic fillers include aluminum powder, aluminum flakes, mica-like iron oxide, mica, glass fiber, wollastonite, calcium carbonate, silica, and mixtures thereof, with flaky fillers also being preferred. Preferably, the filler is aluminum powder or aluminum flakes (e.g., aluminum flake paste), or an alloy thereof. Aluminum powder or aluminum flakes can be used alone or in combination with other fillers, such as those mentioned above. For example, aluminum flake paste can be used alone or in combination with mica-like iron oxide. Fillers, particularly preferred fillers, may be present in the coating compositions of the present invention in any suitable amount, such as about 0.01% to about 95% by weight, about 1% to about 95% by weight, about 5% to about 95% by weight, about 1% to about 30% by weight, preferably about 0.01% to about 25% by weight, preferably about 10% to about 80% by weight, preferably about 5% to about 70% by weight, preferably about 10% to about 60% by weight, preferably about 20% to about 50% by weight, and most preferably about 15% to about 40% by weight. Aluminum flakes may have particle sizes ranging from about 2 to about 50 microns, preferably from about 5 to about 30 microns, and most preferably from about 10 to about 20 microns. Metal flakes, such as zinc, aluminum, magnesium, and nickel, may be added as inorganic fillers to the coating as sacrificial anodes to provide cathodic protection. They may also be used in combination with electrically conductive fillers as taught in US Pat. No. 7,794,626 to provide galvanic protection to the substrate.

[0161] Suitable dyes or pigments include MO 02294 black, MO-80406BV-Yellow from Chromaflo, and white pigment powder TI-PURE from Dupont.

[0162] Suitable adhesion promoters include isocyanates and their derivatives, phosphorus-containing compounds such as phosphoric acid and phosphate ester-containing compounds, sulfonic acids, sulfonic acid and sulfate-containing compounds, carboxylic acids and carboxylate-containing compounds, maleic acid-modified esters, organofunctional silanes, zirconates, zirconoaluminates, and organometallic compounds such as titanic acid chlorinated olefins. Some suitable adhesion promoters include carbamic acid [3-(triethoxysilyl)propyl]-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (NBCbSi), 3-(trimethoxysilyl)propyl methacrylate, [(5-bicyclo[2.2.1]hept-2-enyl)ethyl]trimethoxysilane, 5-bicyclo[2.2.1]hept-2-enyl)methyldichlorosilane, (5-bicyclo[2.2.1]hept-2-enyl)methyldichlorosilane, (2.2.1)hept-2-enyl)triethoxysilane, (5-bicyclo[2.2.1]hept-2-enyl)methyldiethoxysilane, (5-bicyclo[2.2.1]hept-2-enyl)dimethyldiethoxysilane, (3-acryloxypropyl)trimethoxysilane, n-(2-aminoethyl)-3-aminopropyltrimethoxysilane, (3-triethoxysilyl)propylsuccinic anhydride, 2-( Examples of suitable silanes include (3,4-epoxycyclohexyl)ethyltriethoxysilane, (chloromethylphenyl)trimethoxysilane, (3-guanidinyl)propyltrimethoxysilane, n,n-bis(2-hydroxyethyl)-3-aminopropyltriethoxysilane, styrylethyltrimethoxysilane, methacryloxymethyltrimethoxysilane, vinyltriethoxysilane, ureidopropyltriethoxysilane, 3-isocyanatopropyltriethoxysilane, triethoxysilyl-modified poly-1,2-butadiene, bis(methyldiethoxysilylpropyl)amine, [2-(3-cyclohexenyl)ethyl]triethoxysilane, hexadecafluorododec-11-en-1-yltrimethoxysilane, or a mixture of 2-hydroxyethylbicyclo[2.2.1]hept-2-ene-5-carboxylate (HENB).Other typical adhesion promoters include organosilanes (3-isocyanatopropyltriethoxysilane, bicyclo[2.2.1]hept-5-en-2-yl)ethyltrimethoxysilane), organozirconates, organotitanates (Manchem® products (Manchem® Zircoaluminates) (FedChem, LLC) (e.g., Manchem® A, Manchem® APG-X, Manchem® APG-1, Manchem® APG-2, Manchem® APG-3, Manchem® C, Manchem® CPG, Manchem® CPM, Manchem® F, Manchem® FPM, Manchem® M, Manchem® S, Manchem® 376, Manchem® 441), and Kenrich Petrochemicals products, e.g., KR 55 (Titanium IV) tetrakis(bis 2-propenolatomethyl)-1-butanolate adduct with 2 moles of (di-tridecyl) hydrogen phosphite), KZ® TPPJ (Zirconium IV (2-ethyl, 2-propenomethyl) 1,3-propandiolate, cyclobis 2-dimethylaminopyrophosphato-O, adduct with 2 moles of methanesulfonic acid), KZ® 55 (Zirconium IV tetrakis 2,2(bis-2propenolatomethyl)butanolate, adduct with 2 moles of ditridecyl hydrogen phosphite), phosphoric acid and phosphate ester-containing resins (Sipomer PAM products from Solvay) (e.g., Sipomer PAM-100 (phosphate ester of polyethylene glycol monomethacrylate), Sipomer PAM-200).Also included are Sipomer products from Solvay, such as Sipomer WAM products, Sipomer WAM II products, Sipomer COPS-1 products, Sipomer β-CEA, SIPOMER BEM, Sipomer IBOA, Sipomer IBOMA, Sipomer SEM-25, which contain other polar functional groups; carboxylic acid and anhydride-containing resins (Nucrel (ethylene acrylic acid copolymer) from DuPont, Escor EAA copolymer from ExxonMovil Chemicals, POLYBOND (acrylic acid grafted polypropylene) from Addivant).Anhydride-containing resins, such as FG1901, FG1924 (SEBS grafted with maleic anhydride) from Kraton, ROYALTUF 485, ROYALTUF 498 (EPDM polymer modified with maleic anhydride) from Addivant; isocyanate-containing resins (hexamethylene diisocyanate (HDI), 5-isocyanato-1-(isocyanatomethyl)-1,3,3,3-trimethylcyclohexane (commonly known as isophorone diisocyanate or IPDI), tetramethyloxylendiisocyanate (TMXDI), methylene diphenyl diisocyanate (MDI - its three isomers 2,2'-MDI, 2,4'-MDI, and 4'-MDI) 4,4' methylenebis(cyclohexyl isocyanate) (H12MDI), hexamethylene diisocyanate (HDIt), toluene isocyanate (TDI - may include any mixture of 2,4-TDI and 2,6-TDI); 2-biphenylyl isocyanate, 4-benzylphenyl isocyanate, toluene diisocyanate, PM200 (polyMDI), Lupranate® (polyMDI from BASF), Krasol® ) isocyanate-terminated polybutadiene prepolymer, Krasol® LBD2000 (TDI system), Krasol® LBD3000 (TDI system), Krasol® NN-22 (MDI system), Krasol® NN-23 (MDI system), Krasol® NN-25 (MDI system), MDI prepolymer (Lupranate® 5080), liquid carbodiimide-modified 4,4'-MDI (Lupranate® MM103, liquid M Also included are DI (Lupranate® MI), liquid MDI (e.g., Mondur® ML or Mondur® MLQ, which are 50 / 50 blends of 4,4'-MDI and 2,4-MDI), or 2-hydroxyethyl acrylate (HEA) and liquid MDI (Mondur® MLQ), or 9-decen-1-ol and liquid MDI (Mondur® MLQ), or oleyl alcohol and liquid MDI (Mondur® MLQ).The ratio of alcohol to liquid MDI varies from 1:1 to 1:10. Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, and 2-[[[[4-[(4-isocyanatophenyl)methyl]phenyl]amino]carbonyl]oxy]ethyl ester), chlorinated polyolefins such as Eastman CP343-1, CP343-3, CP515-2, CP-164-1 (Eastman Chemical), Hardlen 13LP (Advanced Polymer), KEPRADH949, 951, 958, 980, 982 (Kito Chemical), Lanco Intercoat VPP 154, 555 (Lubrizol), HARDLEN 15-LP, BS-40, CY-1132, CY-9122P, CY-9124P, TRAPYLEN Other examples include 112X, 130X, 135X, 137X, 138S (Tramaco), and Special-Primer PP 7560 (Worlee).

[0163] Suitable rheology modifiers and anti-settling agents include inorganic and organic rheology modifiers, such as clays and organoclays, hectorite, bentonite, attapulgite, kaolin, pyrophyllite, and talc; minerals, such as fumed silica, precipitated silica, precipitated calcium carbonate, and montmorillonite; and metal organic gelants, such as zirconates and aluminates. Organic rheology modifiers include castor oil derivatives, modified polyureas, polyamides, calcium sulfonates, cellulose, hydrophobic ethoxylated urethane resins, and examples of suitable rheology modifiers include fumed silica, such as Cab-O-Sil TS610 and TS720 from Cabot Corp, AEROSIL 972 and AEROSIL 974 from Evonik, organoclays, such as BENTOLITE L-10, BENTOLITE-WH, CLAYTONE 40, CLAYTONE AF, MINERAL COLLOID BP, and Garamite 7303 from BYK Chemie, USA, and Bentonite 149, Bentonite 329, Bentonite 331, and Bentonite 344 from BASF, polyaminoamide phosphates, polymeric carboxylates of polyamides, and alkyleneamine salts of unsaturated fatty acids (all of which are marketed by BYK under the trademark ANTI TERRA). Chemie USA), polyamide modified castor oil derivatives such as Luvotix ZH5, Luvitix ZH50 from Lehmann & Voss, micronized amide waxes such as Crayvallac SUPER from Arkema.

[0164] The coating composition of the present invention may contain additives such as dispersants / dispersants (surfactants) known in the art. Examples of dispersants and surfactants include sodium bis(tridecyl)sulfosuccinate, sodium di(2-ethylhexyl)sulfosuccinate, sodium dihexylsulfosuccinate, sodium dicyclohexylsulfosuccinate, sodium diamylsulfosuccinate, sodium diisobutylsulfosuccinate, sodium isodecylsulfosuccinate, disodium isodecylsulfosuccinate, disodium ethoxylated alcohol half ester of sulfosuccinic acid, disodium alkylamidopolyethoxysulfosuccinate, tetrasodium N-(1,2-dicarboxy-ethyl)-N-oxadecylsulfosuccinamate, disodium N-octasulfosuccinamate, sulfated ethoxylated nonylphenol, 2-amino-2-methyl-1-propanol, etc.

[0165] The compositions of the present invention containing functional monomers can optionally be formulated with other reactive chemicals to form co-cured coatings. The co-curing process may form interpenetrating polymer networks; for example, co-cured polyurethanes may be formed from polyols and diisocyanates, and co-cured epoxies may be formed from bisepoxides and curing agents such as anhydrides, amines, or thiols. Care should be taken when using chemicals known to inhibit ring-opening polymerization. Copolymer coatings can be formed when difunctional monomers are incorporated. For example, isocyanate- or alcohol-containing olefin comonomers can copolymerize urethanes with the compositions of the present invention, and epoxide-containing comonomers can copolymerize epoxies with the compositions of the present invention. Other polymers, such as polysiloxanes, polyureas, and acrylics, can be incorporated into the compositions of the present invention.

[0166] (Embodiments of the present invention) In one embodiment, the present invention provides a method for coating at least a portion of at least one surface of a substrate with a coating composition, the method comprising: contacting at least a portion of at least one surface of the substrate with a coating composition, the coating composition comprising at least one cyclic olefin, at least one curing agent, e.g., a metal carbene olefin metathesis catalyst, and at least one coating additive; and subjecting the coated substrate to conditions effective to promote an olefin metathesis reaction of the at least one cyclic olefin in the presence of the at least one curing agent, e.g., a metal carbene olefin metathesis catalyst. The substrate surface is preferably a clean surface, although the coating composition of the present invention can be applied to "dirtier" surfaces than conventional epoxy-based coating compositions. The method of the present invention may also apply a UV-resistant topcoat to the coating to protect against UV degradation, as is known in the art. Thus, the method of the present invention produces an article of manufacture coated with the cured coating composition of the present invention.

[0167] Adhesion to the substrate can be achieved by priming the substrate with an adhesion promoter, by adding an adhesion promoter to the coating formulation as a coating additive, or by substituting the cyclic olefin with a functional group that promotes adhesion to the substrate.

[0168] In one embodiment, the present invention provides a method of coating a steel substrate material, comprising: Blasting the steel surface with blasting media in accordance with SSPC SP10 standard; Optionally, applying an adhesion promoter uniformly onto the steel surface; applying a coating composition comprising at least one cyclic olefin, at least one metal carbene metathesis catalyst, and at least one additive (preferably aluminum powder or aluminum flake); and curing the applied coating on the steel surface at a temperature between 5°C and 150°C.

[0169] In one embodiment, the present invention provides a method of coating a steel substrate material, comprising: Blasting the steel surface with blasting media in accordance with SSPC SP10 standard; uniformly applying an optional adhesion promoter onto the steel surface; at least one cyclic olefin represented by formula (I), by formula (II), and by formula (III), and optionally a linear olefin represented by formula (IV); [ka] (In the formula, R a is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , -CN, -NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2- (optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(Rh )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R b is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , -CN, -NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, optionally substituted spiroheterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH-(optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i)C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R c is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2- (optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m)(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and R d is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2- (optionally substituted C 5-24 aryl), optionally substituted C 3-12 Cycloalkenyl, -CH- (optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p, -C(R h )(R i )C(O)NR o OR n and Each R s are independently optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted straight or branched chain C 2-24 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , -CN, -NO2, -CF3, --P(O)(OR h )2, -OP(O)(OR h )2, -S(O)2OR h , -OS(O)2R h , optionally substituted heterocycle, -CH2- (optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH- (optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH-(optionally substituted C 5-24 aryl), optionally substituted C 3-12 cycloalkenyl, -CH2-(optionally substituted 3-12 cycloalkenyl), C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , -C(R h )(R i )C(O)NR o OR n and t is 0, 1, 2, 3, 4, 5, or 6; R f OH, OR k , N.R. g R h , optionally substituted linear or branched C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R g is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 Aryl, optionally substituted straight or branched chain C 2-24 alkenyl, -C(O)-(optionally substituted C 5-24 aryl), -C(O)-(optionally substituted straight or branched chain C 2-24 alkenyl), or optionally substituted C 3-12 is cycloalkenyl, R h is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R i is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R j is H, optionally substituted straight or branched chain C1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R k is an optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R l is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R m is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R n is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R o is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, R p is H, optionally substituted straight or branched chain C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 is cycloalkenyl, z is 0, 1, 2, or 3; and applying a coating composition comprising at least one metal carbene metathesis catalyst and at least one additive (preferably aluminum powder or aluminum flake); and curing the applied coating on the steel surface at a temperature between 5°C and 150°C.

[0170] In one embodiment, the present invention provides a method for coating a steel substrate material with a coating composition, the coating comprising at least one metal carbene olefin metathesis catalyst represented by formula (1): [ka] During the ceremony, M is ruthenium; L 1 , L 2 , and L 3 are independently neutral electron donor ligands, n is 0 or 1, m is 0, 1, or 2; k is 0 or 1, X 1 and X 2 are independently an anionic ligand; R 1 and R 2are independently hydrogen, unsubstituted hydrocarbyl, substituted hydrocarbyl, unsubstituted heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl, or R 1 and R 2 and are at least one metal carbene olefin metathesis catalyst linked together to form one or more cyclic groups.

[0171] In one embodiment, the present invention provides a method for coating a steel substrate material with a coating composition, the coating comprising at least one metal carbene olefin metathesis catalyst represented by formula (1): L 1 teeth [ka] and R 1 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 2 can form a spiro compound with R 3 with or R 4 can form a polycyclic ring together with R 2 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28, -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 1 can form a spiro compound with R 3 with or R 4 can form a polycyclic ring together with R 3 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl or optionally substituted C 3 -8 cycloalkenyl, or R 2 with or R 1 together with R can form a polycyclic ring, or R 4 can form a spiro compound with R 4 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 3 can form a spiro compound with R 2 together with or R 1 can form a polycyclic ring together with R 5 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 together can form an optionally substituted polycyclic ring, R 6 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 5 with or R 7 together can form an optionally substituted polycyclic ring, R 7 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25, -OR 26 , -CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 6 with or R 8 together can form an optionally substituted polycyclic ring, R 8 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 7 with or R 9 together can form an optionally substituted polycyclic ring, R 9 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , CN, -NR 27 R 28 , NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 8 together can form an optionally substituted polycyclic ring, R 10 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 together can form an optionally substituted polycyclic ring, R 11 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 10 with or R 12 together can form an optionally substituted polycyclic ring, R 12 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28, -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 11 with or R 13 together can form an optionally substituted polycyclic ring, R 13 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R 14 with or R 12 together can form an optionally substituted polycyclic ring, R 14 is H, optionally substituted C 1-24 Alkyl, halogen, -C(O)R 25 , -OR 26 , -CN, -NR 27 R 28 , -NO2, -CF3, -S(O) x R 29 , -P(O)(OH)2, -OP(O)(OH)2, -SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 Aryl, optionally substituted C 3-8 cycloalkenyl, or R13 can form a polycyclic ring together with R 25 -OH, -OR 30 , -NR 27 R 28 , optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 26 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 27 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 28 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 29 is H, optionally substituted C 1-24 Alkyl, -OR 26 , -NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-10 Cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 30 is an optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, R 31 is H, optionally substituted C 1-24 Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 is cycloalkenyl, x is 1 or 2.

[0172] In one embodiment, the present invention provides a method for coating a steel substrate material with a coating composition, the coating comprising at least one metal carbene olefin metathesis catalyst represented by formula (1), L 2 is PR H1 R H2 R H3 where R H1 , R H2 , R H3 are each independently an optionally substituted C-C 10 aryl, or optionally substituted C-C 10 Alkyl or optionally substituted C-C 10 It is cycloalkyl.

[0173] In one embodiment, the present invention provides a method for coating a steel substrate material with a coating composition, the coating comprising at least one metal carbene olefin metathesis catalyst represented by formula (1), wherein R 1 is hydrogen and R 2 is optionally substituted phenyl, C alkyl, or substituted 1-propenyl, or R 1 and R 2are linked together to form one or more cyclic groups such as substituted indenylidene, particularly 3-phenylindenylide-1-ene.

[0174] In one embodiment, the present invention provides a method of coating a steel substrate material with a coating composition, wherein the coating composition comprises at least one cyclic olefin represented by formula (I), at least one cyclic olefin represented by formula (II), and at least one cyclic olefin represented by formula (III), a coating additive, and at least one metal carbene olefin metathesis catalyst represented by formula (1).

[0175] In one embodiment, the present invention provides a method for coating a steel substrate material with a coating composition, wherein the coating composition comprises at least one cyclic olefin represented by Formula (I) and by Formula (II), a coating additive, and at least one metal carbene olefin metathesis catalyst represented by Formula (1).

[0176] In one embodiment, the present invention provides a method for coating a steel substrate material with a coating composition, the coating composition comprising at least one cyclic olefin represented by Formula (I) and by Formula (III), a coating additive, and at least one metal carbene olefin metathesis catalyst represented by Formula (1).

[0177] In one embodiment, the present invention provides a method for coating a steel substrate material with a coating composition, wherein the coating composition comprises at least one cyclic olefin represented by Formula (II) and by Formula (III), a coating additive, and at least one metal carbene olefin metathesis catalyst represented by Formula (1).

[0178] The substrate to be coated may be of any configuration, weight, size, thickness, and / or geometric shape. Furthermore, the substrate to be coated may be constructed from any material, including, but not limited to, metals such as steel, stainless steel, aluminum, copper, metal alloys, iron, nickel, titanium, and silver, as well as stone, plastic, rubber, polymers, wood, ceramic, glass, carbon, brick, fabric, cement, or concrete.

[0179] The substrate surface to be coated may be partially or completely coated.

[0180] Methods for applying the coating compositions of the present invention The coating compositions of the present invention can be applied to the substrate material to be coated / protected by several methods, including, but not limited to, spraying, brushing, dipping, or rolling.

[0181] In one embodiment of the present invention, the coating composition can be applied onto the substrate material to be coated with a paint brush.

[0182] In one embodiment of the present invention, the coating composition can be sprayed onto the substrate material to be coated with a film spray gun, a conventional spray gun, a multi-component sprayer, a high volume low pressure (HVLP), or an airless applicator.

[0183] While the present invention has been described in connection with specific embodiments thereof, it is to be understood that the foregoing description and the following examples are intended to illustrate, but not to limit, the scope of the invention. Other aspects, advantages, and modifications within the scope of the invention will be apparent to those skilled in the art to which the invention pertains.

[0184] experiment In the following examples, efforts have been made to ensure accuracy with respect to numbers used (e.g., amounts, temperatures, etc.), but some experimental error and deviation should be accounted for. Unless otherwise indicated, temperatures are in degrees Celsius (°C) and pressures are at or near atmospheric pressure. Weight percent (wt%) and percent by weight are used interchangeably herein. Weight percent of cyclic olefin compositions were determined from area percent values ​​obtained by gas chromatography.

[0185] GC method used: Column: DB-5, 30 m x 250 μm x 0.25 μm film thickness or equivalent 5% phenylmethylsiloxane, Manufacturer: Agilent; GC and column conditions: Injector temperature: 280 °C, Detector temperature: 310 °C, Oven temperature: Starting temperature: 50 °C, Hold time: 0.5 min, Ramp rate 20 °C / min to 210 °C; Ramp rate 5 °C / min to 240 °C; Ramp rate 20 °C / min to 280 °C, Hold time 2.5 min; Carrier gas: Helium 23.5 mL / min, Split ratio: 20.0:1.0.

[0186] All glassware was oven-dried and reactions were carried out under ambient conditions unless otherwise noted. All solvents and reagents were purchased from commercial suppliers and used as received unless otherwise noted.

[0187] The ruthenium catalysts used in the experimental procedures were prepared using known methods.

[0188] Irganox® 1076 antioxidant (BASF) was used where indicated. Butylated hydroxytoluene (BHT) was used where indicated. Kraton 1901FG, CAB-O-SIL® Ultrabond, CAB-O-SIL TS610, CAB-O-SIL TS720 (Cabot Corporation), 2-hydroxyethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate (HENB), and liquid methylene diphenyl diisocyanate (MDI) (sold as Mondur® MLQ) were used where indicated.

[0189] DCPD (Ultrene® 99) The resin was obtained from Ultrene® 99 Tech Corporation. A typical lot of Ultrene® 99 contained DCPD (99 wt%) and TCPD (1 wt%). Modified DCPD-based resins containing 20-25 wt% TCPD (and small amounts of higher cyclopentadiene homologs) were prepared by heat treatment of Ultrene® 99 as described in U.S. Pat. No. 4,899,005.

[0190] TCPD was prepared as described in European Patent No. EP0271007B2 and purified to greater than 95% by vacuum distillation.

[0191] Following this procedure, a HNB-DDA / TCPD (70 / 30) blend was prepared. 1-octene (2.2 equiv.) and DCPD (1.0 equiv.) containing a small amount of BHT were transferred to a reactor with a rupture disk rating of 50 psi. The reactor was evacuated and refilled with nitrogen three times. The solution was placed under full vacuum and the reactor was closed. The solution was gently stirred and heated to 170 °C, where it was held for 24 h. The reactor was then cooled to room temperature. The filtrate, consisting of the 1-octene and DCPD starting materials, was flash distilled at 70 °C under high vacuum. Flash distillation at 70-120 °C produced an HNB-enriched fraction. The fraction was further purified in a metal-packed distillation column under high vacuum to yield 98% pure HNB.

[0192] HNB (2.0 equiv.) and DCPD (1.0 equiv.) containing a small amount of BHT were placed in a reactor with a rupture disk rating of 50 psi. The solution was cycled through three vacuum / nitrogen cycles. The solution was placed under full vacuum and the reactor was closed. The mixture was heated to 170°C with gentle stirring. The solution was held at 170°C for 20 hours and then cooled to room temperature. Unreacted HNB and DCPD were recovered by flash distillation at 120°C. The HNB-DDA enriched fraction in TCPD was flash distilled at 160-165°C.

[0193] NBCbSi was prepared according to Polymer Bulletin (1996) 37: 289-295.

[0194] HENB was prepared according to the following procedure: HEA (2-hydroxyethyl acrylate) (640 g, 1.0 mol equivalent) was added to a 3 L round-bottom flask containing toluene (1 kg). DCPD (dicyclopentadiene) (1.5 kg) was added to a separate 3 L round-bottom flask, and the 3 L flask containing DCPD was fitted with a distillation head connected to a Vigreaux column and a condenser. The 3 L flask containing HEA and toluene was connected to a condenser. DCPD was heated to over 160 °C under an inert atmosphere to "crack" DCPD and form CPD (cyclopentadiene). CPD (740 g, 2.0 mol equivalent) was added dropwise to the HEA / toluene mixture at 10-40 °C under an inert atmosphere. The conversion of HEA to HENB (2-hydroxyethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate) was monitored by GC (gas chromatography). Toluene and reformed DCPD (364 g) were removed from the reaction mixture by vacuum distillation to give the desired HENB product (1,004 g, quantitative yield, approximately 98% purity) as a colorless liquid.

[0195] NB-Fluorocarbon (2) [ka]

[0196] 2,2,3,3,4,4,5,5,6,7,7-Dodecafluoroheptylbicyclo[2,2,1]hept-5-ene-2-carboxylate (39.5 g, 102 mmol) was placed in a 100 mL round-bottom flask equipped with a stir bar under a nitrogen blanket. The flask was placed in an ice-water bath on a magnetic stirrer. Cyclopentadiene (8.87 g, 134 mmol) was added portionwise to the acrylate over a 2-hour period. The mixture temperature rose to 5-10°C. The ice / water bath was removed. The reaction was allowed to stir overnight. The next day, more cyclopentadiene (5 g, 76 mmol) was added. The reaction mixture was allowed to stir overnight. The product was purified by short-path distillation under high vacuum (120 mtorr). The distillation was carried out at a head temperature of 60-70°C and the product was collected. Yield: 42 g, 93%. Purity: 99% by GC.

[0197] Following this procedure, a 77 / 23 ONB / TCPD blend was prepared. 1-Decene (3 equivalents) and modified DCPD containing 20-25% tricyclopentadiene (1 equivalent) were combined in a three-neck flask and heated to 160 °C on a heating mantle under argon for 12 hours. The temperature was then increased to 170 °C for an additional 24 hours. After completion of the reaction, residual 1-decene and DCPD were removed from the reaction mixture by vacuum distillation at 70-80 °C. After removal of 1-decene and DCPD, the remaining mixture was heated to 100 °C, and a 3:1 mixture of octylnorbornene:tricyclopentadiene was distilled overhead and collected as a homogeneous liquid. The collected octylnorbornene / tricyclopentadiene liquid mixture was treated with a small amount of butylated hydroxytoluene and stored under argon.

[0198] Low carbon steel, grade ASTM 4130, was purchased from McMaster Carr in 6" x 6" x 1 / 4" panels. Each sheet was ground using a working mix of G18 / G25 steel grinding wheels. The grind profile was 2-3 mils for each sample. After grinding, the steel substrate surface was cleaned with high-pressure compressed air to remove fine particles.

[0199] The following examples should not be construed as limiting the invention described herein, but instead are provided as representative examples of the present compositions and methods of their use.

[0200] The following abbreviations are used in the examples: phr Weight in grams of component per 100 grams of cyclic olefin composition g grams(s) [ka] Dichloro[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene](3-methyl-2 -butenylidene)(tricyclohexylphosphine)ruthenium(II) [CAS 253688-91-4] [ka] [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylindenylidene) (Diethylphenylphosphine)ruthenium(II) [CAS 1624610-17-8] [ka] (1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium [CAS 246047-72-3] [ka] (1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium [CAS 301224-40-8] [ka] (1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(3-phenyl-1H-inden-1-ylidene)(triphenylphosphine)ruthenium [CAS 340810-50-6] [ka] 2-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylate [CAS 37503-42-7] [ka] Carbamic acid, [3-(triethoxysilyl)propyl]-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester [CAS 187161-66-6] [ka] 2-Ethylidene-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene [CAS 38233-76-0] [ka] Tricyclopentadiene [CAS 7158-25-0] [ka] Octylnorbornene [CAS 22094-84-4] [ka] 2-Hexyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene [CAS 344396-70-9] [ka] Dicyclopentadiene [CAS 77-73-6] [ka] 5-Norbornene-2-methanol [CAS 95-12-5] [ka] 5-Norbornene-2-exo,3-exo-dimethanol [CAS 699-95-6] [ka] 2-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylate [CAS 37503-42-7] [ka] Norbornene-triethoxysilane [CAS 18401-43-9] [ka] 5-(Perfluorobutyl)bicyclo[2.2.1]hept-2-ene [CAS 118777-97-2] [ka] Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ester [CAS 391248-29-6]

[0201] Preparation of coating formulation The coating formulations of the present invention were prepared by starting with the preparation of a pre-catalyst formulation and then combining a base monomer package with additives. The base monomer package includes at least one cyclic olefin of formula (I), a cyclic olefin of formula (II), and a cyclic olefin of formula (III). At least one metal carbene olefin metathesis catalyst was added to the monomer and additive mixture to form the coating composition described herein.

[0202] The monomer compositions were prepared from mixtures of ENB-DDA / TCPD (70 / 30), HNB-DDA / TCPD (70 / 30), ONB / TCPD (77 / 23), and DCPD / TCPD (43 / 57), respectively, by combining specific amounts of these mixtures to obtain the desired ratios of individual monomers. The monomer mixture of the present invention was first mixed in a plastic cup using a magnetic stir bar for 5 minutes or an overhead high-speed mixer for 1 minute, depending on the target amount of base monomer package, to prepare the base monomer package. The composition of the monomer package [MP] is listed in Table 1. [Table 1]

[0203] When additional comonomers were used, they were added according to the compositions set forth in Table 2. [Table 2]

[0204] The additive package was added to the monomer / comonomer package as described in Table 3 to form the pre-catalyst formulations tabulated in Table 4. Irganox was added first to the monomer package, followed by Kraton 1901 FG or CAB-O-SIL®. For formulations with Kraton 1901 FG, a high-shear mixer was used at 3000-5000 rpm until a homogeneous Kraton solution was formed in the base monomer package (45 minutes to 1.5 hours). For formulations with CAB-O-SIL®, a high-speed overhead mixer with a Cowles blade was used to disperse the fumed silica at 350-2000 rpm for 20-30 minutes until no agglomerates were visually observed in the dispersion. Formulations with comonomer were made by adding 10 wt. % comonomer (formulations contained only 90% base monomer package) using a high-speed mixer at 600-800 rpm for 2-3 minutes. A dispersant (W980 from BYK), a silane coupling agent (A174 from Momentive Performance Materials), or dicumyl peroxide (from Sigma-Aldrich) was then added. Fillers such as aluminum paste (STAPA 4 nl from EcKart Effect Pigments), mica-like iron oxide (MIOX SG from Kish Co.), aluminum powder (120 atomized aluminum powder from EcKart Effect Pigments), or ceramic particulates (W-410 from 3M) were then slowly added to the homogenized dispersion using a plastic scoop or spatula, and the formulation was continuously mixed in a high-speed mixer at 850-1100 rpm until filler addition was complete. The formulation with monomer, comonomer, rheology modifier, dispersant, coupling agent, peroxide, and filler was further mixed at 1800-2000 rpm for 15-20 minutes to ensure no agglomeration of the rheology modifier or filler occurred. Finally, HENB / MDI or NBCbSi was added to the mixture, which was then degassed in a FlackTek high-speed mixer for 3 min at a rotation speed of 500–1600 rpm. [Table 3]

[0205] The precatalyst formulation was prepared at room temperature. [Table 4-1] [Table 4-2]

[0206] A catalyst suspension (2 phr in mineral oil) was added to all formulations in Table 4. Catalyst C827 was used in all examples unless otherwise indicated. The catalyst formulations were simultaneously mixed and degassed using a FlackTek high-speed mixer at 1000 rpm for 30 seconds to form the uncured coating compositions.

[0207] Several commercially available coating samples were purchased and tested under the same conditions for comparison. These commercial formulations are listed in Table 5. The commercial samples were prepared according to their manufacturer's guidelines, applied to metal panel substrates, and tested in an adhesion pull-off test. [Table 5]

[0208] General Procedure for Coating Metallic Substrate Panels Metal panel surface treatment (NACE SSPC SP10 standard) Carbon steel panels (6 in x 6 in x 1 / 4 in, 4 in x 4 in x 1 / 4 in, and 1 in x 8 in x 1 / 4 in) were ground using a steel grinding wheel according to NACE SSPC SP10 standards with a surface profile of 2-3 mils. The uncured coating composition was then applied onto the panels within 4 hours after sandblasting.

[0209] For low-viscosity coating compositions, yellow silicone adhesive tape (from Airtech Industries) was used to construct a dam around the edge of the previously ground panel to prevent leakage. 12.50 g of coating composition was then dispensed onto the panel to achieve a theoretical wet film coating thickness of 30 mils. Higher viscosity formulations (including Kraton 1901FG and CAB-O-SIL) were applied directly onto the panel using a film applicator to a wet film thickness of 20-25 mils. The coating composition was allowed to gel at ambient temperature for 30 minutes to 1 hour and then cured in an oven at 150°C for 1 hour. Some examples using the C931 catalyst were cured at room temperature.

[0210] The thickness of the dry film coating was measured using an Elcometer ultrasonic thickness gauge. A total of three measurements were taken for each coating.

[0211] Testing of coated steel panels Pull-off adhesion test per ASTM D4541 This test method covers the procedure for evaluating the pull-off strength (commonly referred to as adhesion) of a coating system from a metal substrate. The main components of a pull-off adhesion tester are a pressure source, a pressure gauge, and an actuator. During operation, the flat side of the pull stub (dolly) adheres to the coating being evaluated.

[0212] Prior to adhesion testing, an industrial-grade 2K epoxy adhesive was prepared by mixing the two components in a 10:4.4 ratio in a FlackTek SpeeedMixer. Glass beads (0.5–0.6 mm) were incorporated into the adhesive to maintain the adhesive bondline thickness between the metal dolly and the cured coating. Test areas were prepared on the cured coating by scoring using a 14 mm diameter circular hole saw, forming an isolated 14 mm diameter coated circle with the exposed steel surface around the perimeter of the circle. The aluminum (14 mm) dolly was ground in the same manner as the carbon steel substrate, and the coated circle was roughened using sandpaper (100 grit).

[0213] Epoxy adhesive was then applied to the roughened dolly, covering the roughened base of the dolly. The dolly was then carefully placed on the coating circle, ensuring that the dolly was perfectly perpendicular to the substrate. Excess adhesive was carefully removed to prevent adhesion to the bare substrate surrounding the dolly. The coating, including the dolly, was cured at 75°C for 4 hours to ensure complete cure of the epoxy adhesive. Three test areas were used per coating. The dolly was then peeled from the coating using an automated PosiTest adhesion tester. Adhesion strength was reported as the average of three adhesion values ​​required to completely peel the dolly from the coating.

[0214] Hot water immersion test according to ASTM D870 This test covers the basic principles and operating procedures for testing the water resistance of coatings by partial or complete immersion of coated specimens in distilled or demineralized water at ambient or elevated temperatures.

[0215] The cured coating was placed in a sealed water bath. The water bath was then filled with deionized water, completely submerging the cured coating. The temperature was increased to 95°C. After 7 days, the panels were removed from the water bath. Visual observations were made to identify any changes in the coating after testing. Peel adhesion tests (ASTM D4541) were also performed on the panels according to the procedure described above. Adhesion performance data for the coated panels before and after hot water immersion are shown in Table 7. Qualitative failure morphology was recorded to identify the failure mechanism: A = adhesive failure of the coating to the steel substrate; C = cohesive failure of the coating; G = adhesive or cohesive failure of the epoxy resin between the coating and the dolly. Peel strength data are presented using a ranking system, as described in Table 6. [Table 6] [Table 7-1] [Table 7-2]

[0216] Reverse impact strength (effect of rapid deformation according to ASTM D2794) This test method demonstrates the effect of rapid impact on the integrity (resistance to cracking and delamination) of organic coatings. A Gardner Universal Impact Tester with a maximum drop height of 48 inches and a drop weight (ball and indenter combination) of 4 pounds was used to test the resistance to deformation of cured coatings. Care was taken to ensure that the drop weight fell freely through a calibrated vertical gravity tube (with slots for raising and lowering the drop weight) attached to the impact tester. Selected coating formulations and commercial coatings were applied to bare 3" x 5" x 0.032" carbon steel Q panels using a film applicator at a 20 mil wet film thickness. The coating formulations and commercial coatings were cured according to the procedures described in the previous section and in the technical data sheets, respectively. Once cured, the Q panels were placed on the magnetic holder of the impact tester, with the bare metal surface in contact with the drop weight. The drop weight was raised to different heights within the gravity tube of the tester, starting at the 25" mark on the gravity tube, and released onto the panel. The drop weight was released from different heights (above and below 25 inches) (depending on performance at 25 inches) until the coating showed no damage (crazing, cracking, peeling). The reverse impact height of the coating was recorded as the maximum height that damaged the coating. Additionally, the reverse impact strength of the coating was calculated as the maximum height that damaged the coating times the drop weight. Higher values ​​(in-lb) indicated better impact performance. The reverse impact strength data are listed in Table 8. Some formulations showed much higher reverse impact strength than the comparative products. [Table 8]

[0217] Mandrel Bend Testing per ASTM D522 The following test provides a general procedure for testing the flexibility and resistance to crazing, cracking, or delamination of organic coatings under strain or extension.

[0218] Selected coating formulations and commercial coatings were applied to milled 1 in. x 8 in. x 0.25 in. carbon steel strips using a film applicator with a wet film thickness equivalent to 20 mils. All coatings were cured according to the procedure described above. A custom-made electric hydraulic mandrel bend tester (Model FRMB1X-1HP from Partech) was used to bend the coated metal strips. Prior to using the equipment, the machine's hydraulic reservoir was filled with approximately 9.5 gallons of medium-weight petroleum-based hydraulic oil (R&O or AW32). One at a time, mandrels with different radii (3.5 in. (most aggressive) to 50 in. (least aggressive)) were placed into the tester's mandrel holder. One coated metal strip was placed on the curved mandrel so that the coating was exposed to air and the milled metal side was in contact with the mandrel. To prevent slippage of the strip on the mandrel, the strip was firmly secured at one end with a "hold-down" bolt. The strips were mechanically bent at fixed speeds on different mandrels by manually pulling the machine's directional control valve. The results were recorded as the minimum mandrel radius that did not damage the coating. Lower mandrel radius values ​​indicated improved coating flexibility performance. Mandrel bending test data are listed in Table 9. Formulation F43 showed better flexibility at much lower mandrel bending radii than the comparative products. [Table 9]

[0219] Heat / dry heat aging test Carbon steel panels (6 in x 6 in x 1 / 4 in, 4 in x 4 in x 1 / 4 in, and 1 in x 8 in x 1 / 4 in) were ground using a steel grinding wheel according to NACE SSPC SP10 standards with a surface profile of 2 to 3 mils. The uncured coating composition was then applied to the panels within 4 hours after sandblasting. The coating was then cured at 150°C for 1 hour unless otherwise specified. The cured panels were then placed in a forced air oven heated sequentially to 190°C and 205°C. The panels were removed from the oven, cooled to room temperature, and inspected periodically. The time at which the first crack was observed in the coating was recorded. [Table 10] [Table 11]

[0220] The addition of fillers to the formulation generally improved the hot / dry heat aging performance of the coatings. However, the addition of STAPA 4 nl aluminum paste in the formulation showed a significant improvement in the hot / dry heat aging cracking performance of the coatings across a wide range of monomer compositions.

[0221] QUV testing according to ASTM G154 In general, the UV stability of a coating composition can be improved by adding appropriate UV absorbers and UV light stabilizers to the coating. Alternatively, a UV-resistant top coat can be applied over the coating to provide protection against UV degradation. In addition, pigmentation and fillers can also improve the UV resistance of clear coatings.

[0222] Monomer package composition MP3 was used in the testing. Table 12 lists the coating compositions with different fillers and pigmentation. The coatings were applied to bare 3" x 5" x 0.032" carbon steel Q panels using a film applicator. The coating formulations were cured at 150°C for 1 hour according to the procedure. [Table 12]

[0223] The cured panels were then placed in a QUV test chamber for testing according to the modified ASTM G154 Cycle 1 method. The only modification from ASTM G154 Cycle 1 was the cycle duration. UVA exposure was performed for 12 hours and condensation was performed for 2 hours per cycle. The panels were removed after 22 cycles and checked for changes in the coating (discoloration, cracking, peeling). No cracking or peeling was observed, but differences in discoloration were observed. Table 13 summarizes the results. The addition of fillers or pigmentation was shown to improve the UV resistance of the coating. [Table 13]

[0224] Multi-component spray experiments for fast-curing systems Component A in the multi-component spray experiments used a coating formulation consisting of the MP3 monomer from Table 1 and the AP33 additive package from Table 2, while component B in the multi-component spray experiments used 0.15 wt.% C627 catalyst and 0.65 wt.% C931 catalyst in a mineral oil suspension. A Binks Century External Mix Gel Coat System (Model CX2017HC) was used as the multi-component spray equipment. The ratio of component A to component B was 100:3. The environmental conditions during multi-component spraying were 55°F and 50% relative humidity. The article used for multi-component spray coating was a carbon pipe with a 2-inch diameter and a 12-inch length. The surface preparation was sandblasted according to SSPC SP10 with a 2-3 mil surface profile. A 14-16 mil coating was applied to the carbon steel pipe in a single coat using the Binks multi-component spray equipment. No sagging or dripping was observed after the high-film-thick liquid coating was applied to the substrate. The multiple component spray combined with a fast-reacting catalyst achieves a rapid dry-to-touch time of less than 3 minutes, and the spray-coated article can be easily handled in less than 10 minutes.

[0225] In comparison, commercially available phenolic epoxy coating systems, such as those listed in Table 5, require premixing of two resin and curing components and spraying via conventional spray equipment. Each coat requires at least 4 to 8 hours of air drying to become tack-dry, and two coats are required to achieve the required dry film thickness. Furthermore, these commercially available phenolic epoxy coating systems have a pot life of only 2 to 3 hours once the resin and curing components are mixed. Furthermore, unused portions must be discarded, whereas multi-component spray systems eliminate the pot life issue by simply mixing the resin and catalyst externally as needed.

[0226] Preparation of adhesive formulations The adhesive coating formulations of the present invention were prepared by starting with the preparation of a pre-catalyst formulation and combining a base monomer package with additives. The base monomer package includes at least one cyclic olefin of formula (I), a cyclic olefin of formula (II), and a cyclic olefin of formula (III). At least one metal carbene olefin metathesis catalyst was then added to the monomer and additive mixture to form the coating composition described herein.

[0227] The monomer compositions were prepared from mixtures of TCPD / DCPD (25 / 75), TCPD / DCPD (40 / 60), TCPD / ONB / DCPD (57 / 30 / 13), and ONB / TCPD (60 / 40), respectively, by combining specific amounts of these mixtures to obtain the desired ratios of individual monomers. The monomer mixture of the present invention was first mixed in a plastic cup using a magnetic stir bar for 5 minutes or an overhead high-speed mixer for 1 minute, depending on the target amount of base monomer package, to prepare the base monomer package. The composition of the monomer package [MP] is listed in Table 14. [Table 14]

[0228] The additive package was added to the monomer / comonomer package as described in Table 15 to form the pre-catalyst formulations tabulated in Table 16. Irganox was added first to the monomer package, followed by Kraton 1901 FG or CAB-O-SIL®, if utilized. For formulations with Kraton 1901 FG, a high-shear mixer was used at 3000-5000 rpm until a homogeneous Kraton solution was formed in the base monomer package (45 minutes to 1.5 hours). For formulations with CAB-O-SIL®, a high-speed overhead mixer with a Cowles blade was used to disperse the fumed silica at 350-2000 rpm for 20-30 minutes until no agglomerates were visually observed in the dispersion. Finally, the other additives were added to the mixture, which was then degassed in a FlackTek high-speed mixer at 500-1600 rpm for 3 minutes.

[0229] A catalyst suspension containing 0.7-1.2 wt. % ROMP catalyst in a white mineral oil carrier was added to all formulations in Table 16 at 2 phr based on formulation weight. Catalyst C827 was used in all examples. The catalyst formulations were simultaneously mixed and degassed using a FlackTek high-speed mixer at 1000 rpm for 30 seconds to form the uncured adhesive compositions. [Table 15] [Table 16]

[0230] General procedure for preparation of lap-shear specimens surface preparation Lap shear specimens were prepared according to ASTM D1102-05 and ASTM D3161. Lap shear panels were prepared by grinding using steel grit before use. The adhesive bond thickness was set at 0.005 inches with either glass beads, steel wire, or shim tabs.

[0231] Once the lap shear specimen surfaces are prepared, the formulations listed in Table 16 are applied to the surfaces listed in Table 17. [Table 17]

[0232] Bonded lap shear samples to be subjected to different cure profiles as described in Table 18. [Table 18]

[0233] Lap shear specimen testing Overhead Tensile Lap Shear Testing per ASTM D1102-05 or ASTM D3161 This test method encompasses a procedure for evaluating the overhead lap shear strength of bonded metal or plastic substrates. Data was collected using a universal testing machine with Lab Works software. Lab shear strength was reported as the average of the required three to five values. [Table 19]

[0234] The adhesive performance data for the lap shear specimens is shown in Table 20. The peel strength data is presented in a ranking system as described in Table 19. [Table 20]

Claims

1. A coating composition comprising or consisting of the following components (A) to (C): (A) 5 to 94.999 wt. % of an olefin-based resin composition, based on the total weight of the coating composition; (B) 5 to 80 wt. %, based on the total weight of the coating composition, of an inorganic filler selected from aluminum powder or alloys thereof, aluminum flake or alloys thereof, mica-like iron oxide, and mixtures thereof; The olefin resin composition comprises An olefin component, 0 to 100 wt. % of at least one cyclic olefin selected from the group consisting of formulas (I), (II), and (III), based on the total weight of the olefin component; Optionally, 0 to 20 wt. %, based on the total weight of the olefin component, of at least one linear olefin of formula (IV): The olefin component comprises the weight percent of olefins of formula (I), (II), (III), and optionally (IV) add up to 100 weight percent of the olefin component; (C) at least one curing agent selected from organometallic complexes, free radical initiators, and cationic initiators; The cyclic olefins of formula (I), (II), and (III) and the linear olefins of formula (IV) have the following structure: 【Chemical 1】 During the ceremony, R ａ is H, linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ ,or 【Chemistry 2】 and R ｂ is H, linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -Si(OR ｋ ) ３ , -S(O) ２ OR ｈ , OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ and R ｃ is H, linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , C.N., N.O. ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ and R ｄ is H, linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , C.N., N.O. ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ and Each R ｓ are independently linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ and t is 0, 1, 2, 3, 4, 5, or 6; R ｆ OH, OR ｋ , N.R. ｇ R ｈ , linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｇ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ Aryl, linear or branched C ２－２４ Alkenyl, —C(O)—(C ５－２４ aryl), —C(O)—(straight or branched C ２－２４ alkenyl), or C ３－１２ is cycloalkenyl, R ｈ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｉ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｊ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｋ is a linear or branched chain C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｌ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｍ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｎ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｏ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｐ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, A coating composition wherein z is 0, 1, 2, or 3.

2. A coating composition comprising the following components (A) to (C): (A) an olefin component, at least one cyclic olefin selected from the group consisting of formulas (I), (II), and (III); Optionally, 0 to 20 wt. %, based on the total weight of the olefin component, of at least one linear olefin of formula (IV): the olefin component, wherein the olefins constituting the olefin component are added up to 100% by weight of the olefin component; (B) 0.001 to 95 wt. % of at least one coating additive, based on the total weight of the coating composition, of an inorganic filler selected from aluminum powder or alloys thereof, aluminum flake or alloys thereof, mica-like iron oxide, and mixtures thereof; (C) at least one curing agent selected from organometallic complexes, free radical initiators, and cationic initiators; The cyclic olefins of formula (I), (II), and (III) and the linear olefins of formula (IV) have the following structure: 【Chemistry 3】 During the ceremony, R ａ is H, linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ ,or 【Chemistry 4】 and R ｂ is H, linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -Si(OR ｋ ) ３ , -S(O) ２ OR ｈ , OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ and R ｃ is H, linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , C.N., N.O. ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ and R ｄ is H, linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , C.N., N.O. ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ and Each R ｓ are independently linear or branched C １－２４ Alkyl, linear or branched C ２－２４ Alkenyl, halogen, —C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, —CH ２ -(C ３－１０ cycloalkyl), C ５－２４ Aryl, —CH ２ -(C ５－２４ aryl), C ３－１２ Cycloalkenyl, —CH ２ -(C ３－１２ cycloalkenyl), C(R ｈ ) (R ｉ ) COOR ｊ , -C(R ｈ ) (R ｉ )C(O)H, -C(R ｈ ) (R ｉ ) C(O)R ｋ , -C(R ｈ ) (R ｉ )CR ｌ (OR ｍ ) (OR ｎ ), -C(R ｈ ) (R ｉ )C(O)NR ｏ R ｐ , -C(R ｈ ) (R ｉ )C(O)NR ｏ OR ｎ and t is 0, 1, 2, 3, 4, 5, or 6; R ｆ OH, OR ｋ , N.R. ｇ R ｈ , linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｇ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ Aryl, linear or branched C ２－２４ Alkenyl, —C(O)—(C ５－２４ aryl), —C(O)—(straight or branched C ２－２４ alkenyl), or C ３－１２ is cycloalkenyl, R ｈ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｉ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｊ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｋ is a linear or branched chain C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｌ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｍ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｎ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｏ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, R ｐ is H, linear or branched C １－２４ Alkyl, C ３－１０ Cycloalkyl, C ５－２４ aryl, or C ３－１２ is cycloalkenyl, A coating composition wherein z is 0, 1, 2, or 3.

3. R ａ is H, linear or branched C １－１２ Alkyl, linear or branched C ２－６ Alkenyl, halogen, —C(O)R ｆ , -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, C ６－１０ Aryl, C ３－１２ cycloalkenyl, or 【Chemistry 5】 and R ｂ is H, linear or branched C １－１２ Alkyl, linear or branched C ２－６ Alkenyl, halogen, —C(O)R ｆ , -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, C ６－１０ Aryl, C ３－１２ is cycloalkenyl, R ｃ is H, linear or branched C １－１２ Alkyl, linear or branched C ２－６ Alkenyl, halogen, —C(O)R ｆ , -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ Rh, C ３－１０ Cycloalkyl, C ６－１０ Aryl, C ３－１２ is cycloalkenyl, R ｄ is H, linear or branched C １－１２ Alkyl, linear or branched C ２－６ Alkenyl, halogen, —C(O)R ｆ , -OR ｇ , -CN, -NO ２ , -CF ３ , -P(O)(OR ｈ ) ２ , -OP(O)(OR ｈ ) ２ , -S(O) ２ OR ｈ , -OS(O) ２ R ｈ , C ３－１０ Cycloalkyl, C ６－１０ Aryl, C ３－１２ is cycloalkenyl, t is 0, R ｆ But, OH, OR ｋ , N.R. ｇ R ｈ , C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｇ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｈ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, z is 2, R ｉ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｊ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｋ But C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｌ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｍ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｎ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｏ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ is cycloalkenyl, R ｐ But H, C １－１２ Alkyl, C ３－８ Cycloalkyl, C ６－１０ aryl, or C ３－１２ 3. The coating composition of claim 1 or claim 2, wherein the alkyl group is cycloalkenyl.

4. the cyclic olefin of formula (I) is ENB-DDA, HNB-DDA, or a mixture thereof; 【Chemistry 6】 【Chemistry 7】 the cyclic olefin of formula (II) is HENB, NBCbSi, ONB, NB-methanol, NB-dimethanol, NB-epoxide, NB-triethoxysilane, NB-fluorocarbon (1), NB-fluorocarbon (2), NB-fluorocarbon (3), or a mixture thereof; 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 The coating composition of any one of claims 1 to 3, wherein the cyclic olefin of formula (III) is tricyclopentadiene (TCPD), dicyclopentadiene (DCPD), or a mixture thereof.

5. the at least one curing agent has a structure of formula (1): 【Chemistry 18】 During the ceremony, M is ruthenium; L １ , L ２ , and L ３ are independently a neutral electron donor ligand; n is 0 or 1; m is 0, 1, or 2; k is 0 or 1; X １ and X ２ are independently an anionic ligand; R １ and R ２ is independently hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl, or R １ and R ２ and are linked together to form one or more cyclic groups.

6. L １ but, 【Chemistry 19】 and R １ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ２ can form a spiro compound with R ３ together with or R ４ can form a polycyclic ring together with R ２ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R １ or can form a spiro compound with R ３ together with or R ４ can form a polycyclic ring together with R ３ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ２ together with or R １ can form a polycyclic ring together with R ４ can form a spiro compound with R ４ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ３ or can form a spiro compound with R ２ together with or R １ can form a polycyclic ring together with R ５ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ６ together can form an optionally substituted polycyclic ring, R ６ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ５ together with or R ７ together can form an optionally substituted polycyclic ring, R ７ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ６ together with or R ８ together can form an optionally substituted polycyclic ring, R ８ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ７ together with or R ９ together can form an optionally substituted polycyclic ring, R ９ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ８ together can form an optionally substituted polycyclic ring, R １０ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R １１ together can form an optionally substituted polycyclic ring, R １１ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R １０ together with or R １２ together can form an optionally substituted polycyclic ring, R １２ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R １１ together with or R １３ together can form an optionally substituted polycyclic ring, R １３ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R １４ together with or R １２ together can form an optionally substituted polycyclic ring, R １４ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , -CN, -NR ２７ R ２８ , -NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R １３ can form a polycyclic ring together with R ２５ But -OH, -OR ３０ , -NR ２７ R ２８ , optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ２６ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ２７ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ２８ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ２９ is H, optionally substituted C １－２４ Alkyl, -OR ２６ , -NR ２７ R ２８ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３０ is optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３１ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, 6. The coating composition of claim 5, wherein x is 1 or 2.

7. L ２ But PR Ｈ１ R Ｈ２ R Ｈ３ wherein R Ｈ１ , R Ｈ２ , and R Ｈ３ each independently represents an optionally substituted C ６ -C １０ Aryl, optionally substituted C １ -C １０ alkyl, or optionally substituted C ３ -C １０ 7. The coating composition of claim 5 or claim 6, wherein the alkyl group is cycloalkyl.

8. R １ is hydrogen and R ２ is phenyl, or R １ is hydrogen and R ２ is 3-methyl-1-propenyl, or R １ and R ２ The coating composition of any one of claims 5 to 7, wherein are linked together to form 3-phenylindenylide-1-ene.

9. R Ｈ１ is phenyl, ethyl, or cyclohexyl, and R Ｈ２ is phenyl or cyclohexyl, and R Ｈ３ The coating composition of claim 8 , wherein is phenyl, ethyl, or cyclohexyl.

10. the at least one curing agent has a structure of formula (2): 【Chemistry 20】 During the ceremony, M is ruthenium; L １ is a neutral electron donor ligand, X １ and X ２ are independently an anionic ligand; W is O, halogen, NR ３３ , or S, R １９ is H, optionally substituted C １－２４ alkyl, —C(R ３４ ) (R ３５ ) COOR ３６ , -C(R ３４ ) (R ３５ )C(O)H, -C(R ３４ ) (R ３５ ) C(O)R ３７ , -C(R ３４ ) (R ３５ )CR ３８ (OR ３９ ) (OR ４０ ), -C(R ３４ ) (R ３５ )C(O)NR ４１ R ４２ , -C(R ３４ ) (R ３５ )C(O)NR ４１ OR ４０ , -C(O)R ２５ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or W is NR ３３ If R １９ is R ３３ together to form an optionally substituted heterocycle, or when W is halogen, R １９ is nothing, R ２０ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ２１ together can form a polycyclic ring, R ２１ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ２０ together with or R ２２ can form a polycyclic ring together with R ２２ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ２１ together with or R ２３ can form a polycyclic ring together with R ２３ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ cycloalkenyl, or R ２２ together can form a polycyclic ring, R ２４ is H, optionally substituted C １－２４ Alkyl, halogen, —C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ is cycloalkenyl, R ２５ But, OH, OR ３０ , N.R. ２７ R ２８ , optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ２６ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ２７ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ２８ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ２９ is H, optionally substituted C １－２４ Alkyl, OR ２６ , -NR ２７ R ２８ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３０ is optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３１ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３３ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３４ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３５ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３６ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３７ is optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３８ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ３９ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ４０ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ４１ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, R ４２ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl, 10. The coating composition of any one of claims 1 to 9, wherein x is 1 or 2 and the at least one metal carbene olefin metathesis catalyst is a metal carbene olefin metathesis catalyst.

11. 11. The coating composition of any one of claims 1 to 10, wherein the coating composition comprises at least one cyclic olefin represented by one selected from the group consisting of formulas (I) and (II):

12. The coating composition of any one of claims 1 to 10, wherein the coating composition comprises at least one cyclic olefin selected from the group consisting of formulas (I) and (III):

13. The coating composition of any one of claims 1 to 10, wherein the coating composition comprises at least one cyclic olefin selected from the group consisting of formulas (II) and (III):

14. The coating composition of any one of claims 1 to 10, wherein the coating composition comprises at least one cyclic olefin selected from formula (III):

15. 15. The coating composition of any one of claims 1 to 14, wherein the coating composition further comprises a coating additive selected from the group consisting of gel modifiers, hardness modifiers, impact modifiers, antioxidants, antiozonants, fillers, binders, thixotropes, rheology modifiers, dispersants, wetting agents, plasticizers, pigments, flame retardants, dyes, fibers, reinforcing materials, coupling agents, UV absorbers, UV light stabilizers, film formers, lubricants, adhesion promoters, and mixtures thereof.

16. 16. The coating composition of any one of claims 1 to 15, wherein the coating additive is selected from the group consisting of fillers, rheology modifiers, coupling agents, UV absorbers, UV light stabilizers, adhesion promoters, and mixtures thereof. Composition.

17. The coating composition according to any one of claims 1 to 16, wherein the inorganic filler is selected from aluminum powder or alloys thereof, aluminum flakes or alloys thereof, and mixtures thereof.

18. 1. A method of coating a substrate material, comprising: Optionally, applying an adhesion promoter onto the surface of the substrate; Applying the coating composition according to any one of claims 1 to 17 onto the surface of the substrate; and curing the coating applied onto the substrate surface.

19. 20. The method of claim 18, further comprising adhering a second substrate by placing the second substrate on the coated substrate and adhering the two substrates together.

20. 20. The method of claim 18, wherein the coating applied onto the substrate surface is cured at room temperature.

21. 18. An article of manufacture comprising a substrate coated with a cured coating composition, wherein the coating composition is a coating composition according to any one of claims 1 to 17.

22. 22. The article of manufacture of claim 21, wherein the substrate is a metal surface.

23. 22. The article of manufacture of claim 21, wherein the substrate is a non-metallic surface.

24. 1. A method of coating a substrate material, comprising: Optionally, applying an adhesion promoter onto the surface of the substrate; Applying the coating composition according to any one of claims 1 to 17 onto the surface of the substrate; and curing the coating applied onto the substrate surface.

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