# US 8,772,409 B2 · Compositions for sports equipment > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,772,409 B2 - Document ID: US8772409B2 - Status: Granted - Kind: B2 - Application number: 13/619,593 - Filed: 2012-09-14 - Published: 2013-01-10 - Granted: 2014-07-08 - Earliest claimed: 2008-12-23 - Assignees: Taylor Made Golf Company, Inc. - Applicants: Hyun J. Kim; Hong G. Jeon - Inventors: Hyun J. Kim; Hong G. Jeon - Web page: https://patentgrep.com/patent/US8772409B2 ## CPC - C08L 19/006: {Rubber characterised by functional groups, e.g. telechelic diene polymers} - A63B 37/0024: {Materials other than ionomers or polyurethane} - A63B 37/0031: {Hardness} - A63B 37/0033: {Thickness} - A63B 37/0037: {Flexural modulus; Bending stiffness} - A63B 37/0039: {characterised by the material} - A63B 37/0043: {Hardness} - A63B 37/0045: {Thickness} - A63B 37/0046: {Deflection or compression} - A63B 37/0049: {Flexural modulus; Bending stiffness} - A63B 37/0051: {Materials other than polybutadienes; Constructional details} - A63B 37/0064: {Diameter} - A63B 37/0065: {Deflection or compression} - A63B 37/0069: {Flexural modulus; Bending stiffness} - A63B 37/0075: {Three piece balls, i.e. cover, intermediate layer and core} - A63B 37/0076: {Multi-piece balls, i.e. having two or more intermediate layers} - A63B 37/0082: {Density; Specific gravity} - A63B 37/0084: {Initial velocity} - A63B 37/0087: {Deflection or compression} - A63B 45/00: Apparatus or methods for manufacturing balls (working of plastics or substances in a plastic state B29) - C08L 13/00: Compositions of rubbers containing carboxyl groups - C08L 51/04: grafted on to rubbers - C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers - A63B 37/0003: {Golf balls} - C08G 2261/3322: derived from cyclooctene - C08G 2261/418: Ring opening metathesis polymerisation [ROMP] - C08G 2261/76: crosslinking - C08K 5/098: Metal salts of carboxylic acids - C08K 5/14: Peroxides - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - A63B: APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT (apparatus for passive exercising, massage A61H) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract Compositions comprising the reaction product of: (a) a polyalkenamer; and (b) an organic modifier that includes at least one carbon to carbon unsaturated bond and at least one functional group selected from carboxyl, hydroxyl, amino, epoxy, (meth)acrylate, vinyl, ester, isocyanate, carbonyl, urethane, anhydride, or a metal salt thereof. Also disclosed are golf balls that include (i) a core, (ii) at least one intermediate layer, and (iii) at least one cover layer, wherein at least one of the core, intermediate layer or cover layer includes the polyalkenamer/functionalized organic modifier composition as a majority ingredient. ## Claims ### Claim 1 A composition comprising a reaction product of: (a) a polyalkenamer; and (b) an organic modifier that includes a urethane containing unsaturated polymer or is selected from a carboxyl-terminated polybutadiene, an amine-terminated polybutadiene, a hydroxyl-terminated polybutadiene, an isocyanate-terminated polybutadiene, a carboxyl-functionalized polyisoprene, a hydrogenated liquid isoprene rubber functionalized with at least one moiety selected from the group consisting of carboxyl, hydroxyl, amino, epoxy, (meth)acrylate, vinyl, ester, isocyanate, carbonyl, urethane, anhydride or a metal salt thereof; and (c) a crosslinking agent; and (d) a co-crosslinking agent comprising an unsaturated fatty acid having from about 3 to about 8 carbon atoms, or a metal salt thereof. ### Claim 2 (depends on 1) The composition of claim 1, wherein the polyalkenamer is a polyoctenamer. ### Claim 3 (depends on 1) The composition of claim 1, wherein the organic modifier is a carboxyl-functionalized polybutadiene or carboxyl-functionalized polyisoprene or a metal salt thereof. ### Claim 4 (depends on 1) The composition of claim 1, wherein the metal salt includes a metal cation selected from Li+, Na+, K+, Zn2+, Ca2+, Co2+, Ni2+, Cu2+, Pb2+, Mg+ or a mixture thereof. ### Claim 5 (depends on 1) The composition of claim 1, wherein the reaction product is prepared via thermal energy, e-beam radiation, gamma-radiation, irradiation, or a combination thereof. ### Claim 6 (depends on 1) The composition of claim 1 wherein the organic modifier is partially hydrogenated. ### Claim 7 (depends on 1) The composition of claim 1, wherein the crosslinking agent comprises zinc oxide, sulfur, sulfur compounds, organic peroxide, zinc peroxide, azo compounds, magnesium oxide, benzothiazole sulfenamide accelerator, benzothiazyl disulfide, phenolic curing resin, m-phenylene bis-maleimide, thiuram disulfide, dipentamethylene-thiuram hexasulfide, or a mixture thereof. ### Claim 8 (depends on 1) The composition of claim 1 wherein the composition comprises from about 5 to about 70 wt % of polyalkenamer, based on the combined weight of components (a) and (b). ### Claim 9 (depends on 1) A sports equipment article comprising the composition of claim 1 wherein the sports equipment article is selected from a recreation ball, a golf club or component thereof, running shoes, walking shoes, golf shoes, glove, grips, helmet, protective gear, bicycle, ski, and a skate. ### Claim 10 (depends on 1) The composition of claim 1, wherein the organic modifier is a metal salt of carboxyl-terminated polybutadiene or a metal salt of a carboxyl-functionalized polyisoprene, and wherein the reaction product is a crosslinked ionomer. ### Claim 11 (depends on 1) The composition of claim 1, wherein the co-crosslinking agent comprises a zinc salt of acrylic acid or a zinc salt of methacrylic acid. ### Claim 12 A method for making a composition comprising reacting together: (a) a polyalkenamer; and (b) an organic modifier that includes a urethane containing unsaturated polymer or is selected from a carboxyl-terminated polybutadiene, an amine-terminated polybutadiene, a hydroxyl-terminated polybutadiene, an isocyanate-terminated polybutadiene, a carboxyl-functionalized polyisoprene, a hydrogenated liquid isoprene rubber functionalized with at least one moiety selected from the group consisting of carboxyl, hydroxyl, amino, epoxy, (meth)acrylate, vinyl, ester, isocyanate, carbonyl, urethane, anhydride or a metal salt thereof; and (c) a crosslinking agent; and (d) a co-crosslinking agent comprising an unsaturated fatty acid having from about 3 to about 8 carbon atoms, or a metal salt thereof. ### Claim 13 (depends on 12) The method of claim 12, wherein the polyalkenamer is a polyoctenamer and the organic modifier is a carboxyl-functionalized polybutadiene or carboxyl-functionalized polyisoprene or a metal salt thereof. ### Claim 14 (depends on 12) The method of claim 12, wherein the organic modifier is a metal salt of carboxyl-terminated polybutadiene or a metal salt of a carboxyl-functionalized polyisoprene, and wherein the reaction product is a crosslinked ionomer. ### Claim 15 (depends on 12) The method of claim 12, wherein the organic modifier is a carboxyl-functionalized polybutadiene or a carboxyl-functionalized polyisoprene, and the method comprises mixing the polyalkenamer with the organic modifier and subsequently neutralizing the carboxyl moiety of the organic modifier with a metal cation. ### Claim 16 A golf ball comprising: (i) a core; (ii) and at least one additional layer, wherein at least one of the core or the at least one additional layer comprises a reaction product of: (a) a polyalkenamer; and (b) an organic modifier that includes a urethane containing unsaturated polymer or is selected from a carboxyl-terminated polybutadiene, an amine-terminated polybutadiene, a hydroxyl-terminated polybutadiene, an isocyanate-terminated polybutadiene, a carboxyl-functionalized polyisoprene, a hydrogenated liquid isoprene rubber functionalized with at least one moiety selected from the group consisting of carboxyl, hydroxyl, amino, epoxy, (meth)acrylate, vinyl, ester, isocyanate, carbonyl, urethane, anhydride or a metal salt thereof; and (c) a crosslinking agent; and (d) a co-crosslinking agent comprising an unsaturated fatty acid having from about 3 to about 8 carbon atoms, or a metal salt thereof. ### Claim 17 A golf ball comprising: (i) a core; (ii) at least one intermediate layer; and (iii) at least one cover layer, wherein at least one of the core, the at least one intermediate layer or cover layer comprises a reaction product of: (a) a polyalkenamer; and (b) an organic modifier that includes a urethane containing unsaturated polymer or is selected from a carboxyl-terminated polybutadiene, an amine-terminated polybutadiene, a hydroxyl-terminated polybutadiene, an isocyanate-terminated polybutadiene, a carboxyl-functionalized polyisoprene, a hydrogenated liquid isoprene rubber functionalized with at least one moiety selected from the group consisting of carboxyl, hydroxyl, amino, epoxy, (meth)acrylate, vinyl, ester, isocyanate, carbonyl, urethane, anhydride or a metal salt thereof; and (c) a crosslinking agent; and (d) a co-crosslinking agent comprising an unsaturated fatty acid having from about 3 to about 8 carbon atoms, or a metal salt thereof. ### Claim 18 (depends on 17) The golf ball of claim 17, wherein the reaction product is a majority ingredient in the respective core, intermediate layer or cover layer. ### Claim 19 A golf ball comprising: (i) a core; (ii) at least one intermediate layer; and (iii) at least one cover layer, wherein at least one of the core, the at least one intermediate layer, or the at least one cover layer comprises a reaction product of: (a) a polyalkenamer; (b) an organic modifier selected from a carboxyl-terminated polybutadiene, an amine-terminated polybutadiene, a hydroxyl-terminated polybutadiene, an isocyanate-terminated polybutadiene, a carboxyl-functionalized polyisoprene, a hydrogenated liquid isoprene rubber functionalized with at least one moiety selected from the group consisting of carboxyl, hydroxyl, amino, epoxy, (meth)acrylate, vinyl, ester, isocyanate, carbonyl, urethane, anhydride, or a metal salt thereof; (c) a crosslinking agent; and (d) a co-crosslinking agent. ### Claim 20 (depends on 19) The golf ball of claim 19, wherein the co-crosslinking agent comprises an unsaturated fatty acid having from about 3 to about 8 carbon atoms, or a metal salt thereof. ### Claim 21 (depends on 20) The golf ball of claim 20, wherein the co-crosslinking agent comprises a zinc salt of acrylic acid or a zinc salt of methacrylic acid.