Golf balls comprising polytrimethylene ether amine-based polyurea compositions

Abstract

Golf balls having at least one layer made from a composition comprising a polytrimethylene ether amine (PTMEA)-based polyurea or polyurea/urethane are provided. The composition is the reaction product of a polyisocyanate with polytrimethylene ether amine and a hydroxyl and/or amine curing agent. In a preferred version, a functionalized PTMEA-based polyurea or polyurea/urethane hybrid is produced using iscoyanates, polytrimethylene ether amines, or curing agents containing acid, ester, or ionic groups. Blends of polytrimethylene ether amine with other amine compounds such as amine-terminated hydrocarbons, polyethers, polyesters, polycarbonates, and polycaprolactones 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;   an intermediate layer, the intermediate layer being formed from a polytrimethylene ether amine-based polyurea or polyurea/urethane hybrid composition that is produced by a reaction of i) an isocyanate compound, ii) a polytrimethylene ether amine compound, and iii) a curing agent selected from the group consisting of hydroxyl-terminated curing agents, amine-terminated curing agents, and mixtures thereof, and   a cover layer overlying the intermediate layer.   
     
     
         2 . The golf ball of  claim 1 , wherein the core has a first Shore D surface hardness of H 1  in the range of about 10 to about 60; the intermediate layer overlying the core has a second Shore D surface hardness of H 2  in the range of about 50 to about 75; and the cover layer overlying the intermediate layer has 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 
     
     
         3 . The golf ball of  claim 1 , wherein the polytrimethylene ether amine compound is a blend of polytrimethylene ether amine and amine-terminated compound elected from amine-terminated hydrocarbons, polyethers, polyesters, polycarbonates, polycaprolactones; and mixtures thereof. 
     
     
         4 . The golf ball of  claim 1 , wherein at least one of the isocyanate compound, polytrimethylene ether amine compound, or curing agent contains acid, ester or ionic groups; 
     
     
         5 . The golf ball of  claim 4 , wherein the acid, ester, or ionic groups are derived from the isocyanate compound. 
     
     
         6 . The golf ball of  claim 4 , wherein the acid, ester, or ionic groups are derived from the polytrimethylene ether amine compounds. 
     
     
         7 . The golf ball of  claim 4 , 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 amine-based polyurea 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 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. 
     
     
         17 . 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. 
     
     
         18 . 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. 
     
     
         19 . The golf ball of  claim 1 , wherein the core is a single-piece core comprising a polybutadiene or a highly neutralized olefin-based copolymer. 
     
     
         20 . 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. 
     
     
         21 . The golf ball of  claim 1 , wherein the cover layer is formed from a thermoplastic or thermoset composition. 
     
     
         22 . The golf ball of  claim 21 , 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. 
     
     
         23 . The golf ball of  claim 21 , wherein the thermoset composition is selected from the group consisting of polyurethanes, polyureas, and polyurethane-polyurea hybrids, epoxy and mixtures thereof. 
     
     
         24 . A multi-layered golf ball, comprising:
 a core;   an intermediate layer overlying the core;   a cover layer overlying the intermediate layer, the cover layer being formed from a polytrimethylene ether amine-based polyurea or polyurea/urethane hybrid composition that is produced by a reaction of: i) an isocyanate compound, ii) a polytrimethylene ether amine compound, and iii) a curing agent selected from the group consisting of hydroxyl-terminated curing agents, amine-terminated curing agents, and mixtures thereof.   
     
     
         25 . 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;   a cover layer overlying the intermediate layer, at least one of the cover layer and intermediate layer being formed from a polytrimethylene ether amine-based polyurea or polyurea/urethane hybrid composition that is produced by a reaction of: i) an isocyanate compound, ii) a polytrimethylene ether amine compound, and iii) a curing agent selected from the group consisting of hydroxyl-terminated curing agents, amine-terminated curing agents, and mixtures thereof.