Multi-layered golf balls made with a thiol-ene composition

Abstract

Methods for making multi-layered golf balls having at least one layer or coating made from a thiol-ene composition and the resultant golf balls are provided. A polymerizable composition comprising multifunctional thiol and -ene compounds is used to form the layer or coating. In one embodiment, the outer cover layer is made from the thiol-ene material. In another embodiment, a thiol-ene composition is applied as a protective coating over the outer cover layer. The thiol-ene layer or coating helps provide the ball with good impact durability and, toughness.

We claim: 
     
         1 . A golf ball having an outer coating comprising a polymerized thiol-ene composition, wherein the ball is formed by a method comprising the steps of:
 i) providing a golf ball comprising a spherical inner core and outer cover layer;   ii) coating a polymerizable composition comprising a multifunctional thiol compound and multifunctional ene compound over the outer cover, wherein the compounds react so that a golf ball comprising a polymerized thiol-ene outer coating is formed.   
     
     
         2 . The golf ball of  claim 1 , wherein the molar ratio of thiol functional groups from the thiol monomer relative to the ene functional groups from the ene monomer is about 1:1 or greater. 
     
     
         3 . The golf ball of  claim 1 , wherein the molar ratio of thiol functional groups from the thiol monomer relative to the ene functional groups from the ene monomer is about 1:1 or less. 
     
     
         4 . The golf ball of  claim 1 , wherein the composition further comprises a polymerization initiator selected from the group consisting of thermal initiators, photoinitiators, and mixtures thereof. 
     
     
         5 . The golf ball of  claim 4 , wherein the composition further comprises a polymerization accelerator. 
     
     
         6 . The golf ball of  claim 4 , wherein the composition further comprises a polymerization inhibitor. 
     
     
         7 . The golf ball of  claim 1 , wherein the thiol compounds is an alkyl thiol selected from the group consisting of 1,2-dimercaptoethane, 1,6-dimercaptohexane, neopentanetetrathiol, and the like, pentaerythritol tetra(3-mercapto propionate), 2,2-bis(mercaptomethyl)-1,3-propanedithiol, and the like, aryl thiol compounds such as 4-ethylbenzene-1,3-dithiol, 1,3-diphenylpropane-2,2-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 1,3,5-benzenetrithiol, glycol dimercaptoacetate, glycol dimercaptopropionate, pentaerythritol tetrathioglycolate, and trimethylolpropane trithioglycolate, and mixtures thereof. 
     
     
         8 . The golf ball of  claim 1 , wherein the ene compound is selected from the group consisting of tri-allyl isocyanurate; tri-vinyl isocyanurate; diallyl maleate; diallylether bisphenol A; ortho diallyl bisphenol A; triallyl trimellitate; tri(meth)acryl triols such as trimethylolpropane tri(meth)acrylate; triallyl triols such as 1-(allyloxy)-2,2-bis((allyloxy)methyl)butane; polyvinyl polyols such as 1-(vinyloxy)-2,2-bis((vinyloxy)methyl)butane; polyallyl polyols; polyvinyl polyetherpolyols; polyallyl polyetherpolyol; and mixtures thereof. 
     
     
         9 . The golf ball of  claim 1 , wherein the coating has a thickness of less than 0.005 inches. 
     
     
         10 . A golf ball having an outer cover layer comprising a polymerized thiol-ene composition, wherein the ball is formed by a method comprising the steps of:
 i) providing a spherical inner core;   ii) molding a polymerizable composition comprising a multifunctional thiol compound and multifunctional ene compound over the core, wherein the compounds react so that a golf ball comprising a core and polymerized thiol-ene outer cover layer is formed.   
     
     
         11 . The golf ball of  claim 10 , wherein the cover formed from the polymerizable composition is an outer cover, and the ball further comprises an inner cover, the inner cover being disposed between the inner core and outer cover. 
     
     
         12 . The golf ball of  claim 11 , wherein the inner cover is formed from an ethylene acid copolymer ionomer composition. 
     
     
         13 . The golf ball of  claim 10 , wherein the outer cover has a surface hardness in the range of about 40 to about 90 Shore C. 
     
     
         14 . The golf ball of  claim 10 , wherein the composition further comprises a polymerization initiator selected from the group consisting of thermal initiators, photoinitiators, and mixtures thereof. 
     
     
         15 . The golf ball of  claim 14 , wherein the polymerization initiator is a photoinitiator selected from the group consisting of 2-benzyl-2-(dimethylamino)-4′-morpholinobutyrophenone; 2-hydroxy-2-methylpropiophenone; benzophenone; trimethylbenzophenone; methylbenzophenone; 1-hydroxycyclohexylphenyl ketone; isopropyl thioxanthone; 2,2-dimethyl-2-hydroxy-acetophenone; 2,2-dimethoxy-2-phenylacetophenone; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one; 2,4,6-trimethylbenzyl-diphenyl-phosphine oxide; 1-chloro-4-propoxythioxanthone; benzophenone; bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl pentyl phosphine oxide; 1-phenyl-2-hydroxy-2-methyl propanone; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide; camphorquinone; and combinations thereof. 
     
     
         16 . The golf ball of  claim 10 , wherein the coating has a thickness of greater than 0.040 inches.