Golf balls comprising functionalized polyurethane compositions

Abstract

Golf balls having at least one layer made from a composition comprising a functionalized polytrimethylene ether-based polyurethane are provided. The composition is the reaction product of a polyisocyanate with polytrimethylene ether glycol and a hydroxyl and/or amine curing agent wherein at least one of the isocyanate compound, polytrimethylene ether glycol compound, or curing agent contains acid, ester, or ionic groups. Blends of polytrimethylene ether glycol with other glycols such as polyester glycol, polycaprolactone glycol, or polycarbonate glycol can be used. The composition can be prepared using prepolymer and one-shot manufacturing techniques. The composition may be used to form any layer in the golf ball structure and the resulting golf ball has improved resiliency and playing performance.

1 . A multi-layered golf ball, comprising:
 a core having a first Shore D surface hardness of H 1  in the range of about 10 to about 60;   an intermediate layer overlying the core having a second Shore D surface hardness of H 2  in the range of about 50 to about 75, the intermediate layer being formed from a functionalized polytrimethylene ether-based polyurethane or polyurethane/polyurea hybrid composition that is produced by a reaction of i) an isocyanate compound, ii) a polytrimethylene ether glycol compound, and iii) a curing agent selected from the group consisting of hydroxyl-terminated curing agents, amine-terminated curing agents, and mixtures thereof, wherein at least one of the isocyanate compound, polytrimethylene ether glycol compound, or curing agent contains acid, ester or ionic groups; the intermediate layer having a thickness in the range of about 0.010 to about 0.040 inches; and   a cover layer overlying the intermediate layer having a third Shore D surface hardness of H 3  in the range of about 30 to 60, wherein the ratio of H 3  to H 1  is in the range of about 0.6 to about 6.   
     
     
         2 . The golf ball of  claim 1 , wherein the polytrimethylene ether glycol compound is a blend of polytrimethylene ether glycol and a polyester glycol. 
     
     
         3 . The golf ball of  claim 1 , wherein the polytrimethylene ether glycol compound is a blend of polytrimethylene ether glycol and a polycaprolactone glycol. 
     
     
         4 . The golf ball of  claim 1 , wherein the polytrimethylene ether glycol compound is a blend of polytrimethylene ether glycol and a polyether glycol selected from the group consisting of polyethylene glycol, poly (1,3-propylene) glycol, polytetramethylene glycol, copolymers of tetrahydrofuran and ethylene oxide or propylene oxide glycol, and mixtures thereof. 
     
     
         5 . The golf ball of  claim 1 , wherein the acid, ester, or ionic groups are derived from the isocyanate compound. 
     
     
         6 . The golf ball of  claim 1 , wherein the acid, ester, or ionic groups are derived from the polytrimethylene ether glycol compounds. 
     
     
         7 . The golf ball of  claim 1 , wherein the acid, ester, or ionic groups are derived from the hydroxyl-terminated curing agents or amine-terminated curing agents. 
     
     
         8 . The golf ball of  claim 1 , wherein the acid or ester groups are about 0.5 to about 50 wt % based on the weight of functionalized polytrimethylene ether-based polyurethane or polyurethane/urea hybrid composition. 
     
     
         9 . The golf ball of  claim 8 , wherein the acid or ester groups are selected from carboxylic, sulfonic, or phosphonic acid groups. 
     
     
         10 . The golf ball of  claim 8 , wherein the acid or ester groups are neutralized by a cation source. 
     
     
         11 . The golf ball of  claim 10 , wherein the acid or ester groups are neutralized by a cation source such that the acid content of the composition is neutralized below 80%. 
     
     
         12 . The golf ball of  claim 10 , wherein the acid or ester groups are neutralized by a cation source such that the acid content of the composition is neutralized 80% or greater. 
     
     
         13 . The golf ball of  claim 12 , wherein the acid or ester groups are neutralized by a cation source in the presence of a melt flow modifier. 
     
     
         14 . The golf ball of  claim 10 , wherein the cation source is a metal cation selected from the group consisting of lithium, sodium, potassium, magnesium, calcium, barium, lead, tin, zinc, aluminum, manganese, nickel, chromium, copper, and combinations thereof. 
     
     
         15 . The golf ball of  claim 13 , wherein the melt flow modifier is a fatty acid or salt thereof selected from the group consisting of stearic, behenic, erucic, oleic, lineolic, or dimerized derivatives thereof. 
     
     
         16 . The golf ball of  claim 1 , wherein the ionic groups are selected from carboxylate, sulfonate, or phosphonate groups. 
     
     
         17 . The golf ball of  claim 1 , wherein the isocyanate compound is selected from the group consisting of monomeric or oligomeric or polymeric MDI, H 12 MDI, PPDI, TDI, IPDI, HDI, NDI, XDI, and TMXDI and their acid or ionic derivatives thereof. 
     
     
         18 . The golf ball of  claim 1 , wherein the curing agent is a hydroxyl-terminated curing agent selected from the group consisting of ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, PTMEG, polyethylene propylene glycol, polyoxypropylene glycol, 2-methyl-1,3-propanediol, 2-methyl-1,4-butanediol, and their acid, ester, or ionic derivatives thereof. 
     
     
         19 . The golf ball of  claim 1 , wherein the curing agent is an amine-terminated curing agent selected from the group consisting of 4,4′-diamino-diphenylmethane; 3,5-diethyl-(2,4- or 2,6-)toluenediamine; 3,5-dimethylthio-(2,4- or 2,6-)toluenediamine; 3,5-diethylthio-(2,4- or 2,6-)toluenediamine: 2,2′-dichloro-3,3′,5,5′-tetraethyl-4,4′-diamino-diphenylmethane; polytetramethyleneglycol-di(p-aminobenzoate); 4,4′-bis(sec-butylamino)-dicyclohexylmethane; their acid, ester, or ionic derivatives thereof. 
     
     
         20 . The golf ball of  claim 1 , wherein the core is a single-piece core comprising a polybutadiene or a highly neutralized olefin-based copolymer. 
     
     
         21 . The golf ball of  claim 1 , wherein the core is a multi-layered core and at least one layer comprises a polybutadiene or a highly neutralized olefin-based copolymer. 
     
     
         22 . The golf ball of  claim 1 , wherein the cover layer is formed from a thermoplastic or thermoset composition. 
     
     
         23 . The golf ball of  claim 22 , wherein the thermoplastic composition is selected from the group consisting of ionomers; polyesters; polyester-ether elastomers; polyester-ester elastomers; polyamides; polyamide-ether elastomers, and polyamide-ester elastomers; polyurethanes, polyureas, and polyurethane-polyurea hybrids and mixtures thereof. 
     
     
         24 . The golf ball of  claim 22 , wherein the thermoset composition is selected from the group consisting of polyurethanes, polyureas, and polyurethane-polyurea hybrids, epoxy and mixtures thereof. 
     
     
         25 . A multi-layered golf ball, comprising:
 a core having a first Shore D surface hardness of H 1  in the range of about 10 to about 60;   an intermediate layer overlying the core having a second Shore D surface hardness of H 2  in the range of about 50 to about 75,   a cover layer overlying the intermediate layer having a third Shore D surface hardness of H 3 , the cover layer being formed from a functionalized polytrimethylene ether-based polyurethane or polyurethane/urea hybrid composition that is produced by a reaction of: i) an isocyanate compound, ii) a polytrimethylene ether glycol compound, and iii) a curing agent selected from the group consisting of hydroxyl-terminated curing agents, amine-terminated curing agents, and mixtures thereof, wherein at least one of the isocyanate compound, polytrimethylene ether glycol compound, or curing agent contains acid, ester, or ionic groups; the cover layer having a thickness in the range of about 0.010 to about 0.030 inches and H 3  being in the range of about 45 to about 65.   
     
     
         26 . A multi-layered golf ball, comprising:
 a dual core having an inner core layer and an outer core layer overlying the inner core, the outer core layer having a thickness in the range of about 0.030 to about 0.070 inches and a Shore D surface hardness in the range of about 40 to about 70;   an intermediate layer overlying the outer core, the intermediate layer having a thickness in the range of about 0.010 to about 0.040 inches and a Shore D surface hardness in the range of about 50 to about 75;   a cover layer overlying the intermediate layer, the cover layer having a thickness in the range of about 0.010 to about 0.030 inches and a Shore D surface hardness in the range of about 45 to about 65; wherein at least one of the outer core, intermediate, or cover layers is formed from a polytrimethylene ether-based polyurethane or polyurethane/urea hybrid composition that is produced by a reaction of: i) an isocyanate compound, ii) a polytrimethylene ether glycol compound, and iii) a curing agent selected from the group consisting of hydroxyl-terminated curing agents, amine-terminated curing agents, and mixtures thereof, wherein at least one of the isocyanate compound, polytrimethylene ether glycol compound, or curing agent contains acid, ester, or ionic groups.   
     
     
         27 . A triple covered golf ball, comprising:
 a core;   an innermost cover layer overlying the core having a Shore D surface hardness of in the range of about 50 to about 75,   an intermediate cover layer and   an outer cover layer, wherein at least one of the innermost, intermediate, or outer cover layer is formed from a polytrimethylene ether-based polyurethane or polyurethane/urea hybrid composition that is produced by a reaction of: i) an isocyanate compound, ii) a polytrimethylene ether glycol compound, and iii) a curing agent selected from the group consisting of hydroxyl-terminated curing agents, amine-terminated curing agents, and mixtures thereof, wherein at least one of the isocyanate compound, polytrimethylene ether glycol compound, or curing agent contains acid, ester, or ionic groups; the inner cover layer having a thickness in the range of about 0.020 to about 0.050 inches and a Shore D surface hardness in the range of about 50 to about 70 and the outer cover layer having a thickness in the range of about 0.010 to about 0.030 inches and a Shore D surface hardness in the range of about 40 to about 60.