Rubber compositions comprising benzoquinones and the use thereof in golf balls

Abstract

The present invention is directed to a golf ball having at least one layer formed from a rubber composition comprising a base rubber, at least 0.05 parts by weight of a free radical initiator, per 100 parts of the base rubber, and at least 0.1 parts by weight of a benzoquinone, per 100 parts of the base rubber. The rubber composition may be present in any one or more of a core layer, a cover layer, or an intermediate layer.

1 . A golf ball comprising a core and a cover, wherein the core has at least one layer formed from a rubber composition comprising: 
 (a) a base rubber;    (b) at least 0.05 parts by weight of a free radical initiator per 100 parts of the base rubber; and    (c) at least 0.15 parts by weight of a benzoquinone per 100 parts of the base rubber.    
   
   
       2 . The golf ball of  claim 1 , wherein a ratio (P BQ /P FRI ) of the amount of the benzoquinone present in the rubber composition (P BQ ), measured in parts by weight per 100 parts of the base rubber, to the amount of free radical initiator present in the rubber composition (P FRI ), measured in parts by weight per 100 parts of the base rubber, is from 0.05 to 2.  
   
   
       3 . The golf ball of  claim 2 , wherein P BQ /P FRI  is from 0.25 to 2.  
   
   
       4 . The golf ball of  claim 2 , wherein P BQ /P FRI  is at least 0.05 and less than 0.5.  
   
   
       5 . The golf ball of  claim 2 , wherein P BQ /P FRI  is at least 0.25 and less than 0.5.  
   
   
       6 . The golf ball of  claim 2 , wherein P BQ /P FRI  is from 0.25 to 0.45.  
   
   
       7 . The golf ball of  claim 1 , wherein the benzoquinone is selected from compounds represented by the following formula, and hydrates thereof:  
     
       
         
         
             
             
         
       
       wherein each R 1 , R 2 , R 3 , and R 4  is independently selected from the group consisting of hydrogen, a halogen group (F, Cl, Br, I), an alkyl group, a carboxyl group (—COOH) and metal salts thereof (e.g., —COO − M + ) and esters thereof (—COOR), an acetate group (—CH 2 COOH) and esters thereof (—CH 2 COOR), a formyl group (—CHO), an acyl group (—COR), an acetyl group (—COCH 3 ), a halogenated carbonyl group (—COX), a sulfo group (—SO 3 H) and esters thereof (—SO 3 R), a halogenated sulfonyl group (—SO 2 X), a sulfino group (—SO 2 H), an alkylsulfinyl group (—SOR), a carbamoyl group (—CONH 2 ), a halogenated alkyl group, a cyano group (—CN), an alkoxy group (—OR), a hydroxy group (—OH) and metal salts thereof (e.g., —O − M + ), an amino group (—NH 2 ), a nitro group (—NO 2 ), an aryl group (e.g., phenyl, tolyl, etc.), an aryloxy group (e.g., phenoxy, etc.), an arylalkyl group [e.g., cumyl (—C(CH 3 ) 2 phenyl); benzyl (—CH 2  phenyl)], a nitroso group (—NO), an acetamido group (—NHCOCH 3 ), and a vinyl group (—CH═CH 2 ).  
     
   
   
       8 . The golf ball of  claim 1 , wherein the benzoquinone is selected from methyl p-benzoquinone and tetrachloro p-benzoquinone.  
   
   
       9 . The golf ball of  claim 1 , wherein the rubber composition comprises one or more coagents selected from metal salts of acrylates, diacrylates, methacrylates, and dimethacrylates, wherein the metal is selected from magnesium, calcium, zinc, aluminum, lithium, and nickel; and wherein the total amount of metal salts of acrylates, diacrylates, methacrylates, and dimethacrylates present in the rubber composition is less than 20 parts per 100 parts of the base rubber.  
   
   
       10 . The golf ball of  claim 1 , wherein the rubber composition is substantially free of organosulfur compounds.  
   
   
       11 . The golf ball of  claim 1 , wherein the amount of the benzoquinone present in the rubber composition is at least 0.2 parts by weight per 100 parts of the base rubber.  
   
   
       12 . The golf ball of  claim 1 , wherein the core is a single layer.  
   
   
       13 . The golf ball of  claim 1 , wherein the core comprises an inner core layer and an outer core layer, and wherein the inner core layer is formed from the rubber composition.  
   
   
       14 . The golf ball of  claim 1 , wherein the core comprises an inner core layer and an outer core layer, and wherein the outer core layer is formed from the rubber composition  
   
   
       15 . A golf ball comprising a core and a cover, wherein the core has at least one layer formed from a rubber composition comprising: 
 (a) a base rubber;    (b) at least 0.05 parts by weight of a free radical initiator per 100 parts of the base rubber; and    (c) at least 0.1 parts by weight of a benzoquinone per 100 parts of the base rubber, wherein the benzoquinone is selected from compounds represented by the following formula, and hydrates thereof:                          wherein each R 1 , R 2 , R 3 , and R 4  is independently selected from the group consisting of: a metal salt of a carboxyl group (e.g., —COO − M + ), an acetate group (—CH 2 COOH) and esters thereof (—CH 2 COOR), a hydroxy group (—OH), a metal salt of a hydroxy group (e.g., —O − M + ), an amino group (—NH 2 ), a nitro group (—NO 2 ), an aryl group (e.g., phenyl, tolyl, etc.), an aryloxy group (e.g., phenoxy, etc.), an arylalkyl group [e.g., cumyl (—C(CH 3 ) 2 phenyl); benzyl (—CH 2  phenyl)], a nitroso group (—NO), an acetamido group (—NHCOCH 3 ), and a vinyl group (—CH═CH 2 ).    
   
   
       16 . The golf ball of  claim 15 , wherein the rubber composition comprises at least 0.2 parts by weight of the benzoquinone per 100 parts of the base rubber.  
   
   
       17 . The golf ball of  claim 15 , wherein a ratio (P BQ /P FRI ) of the amount of the benzoquinone present in the rubber composition (P BQ ), measured in parts by weight per 100 parts of the base rubber, to the amount of free radical initiator present in the rubber composition (P FRI ), measured in parts by weight per 100 parts of the base rubber, is at least 0.05.  
   
   
       18 . The golf ball of  claim 15 , wherein the rubber composition is substantially free of organosulfur compounds.  
   
   
       19 . A golf ball comprising a core and a cover, wherein the core has at least one layer formed from a rubber composition comprising: 
 (a) a base rubber;    (b) at least 0.05 parts by weight of a free radical initiator, per 100 parts of the base rubber; and    (c) at least 0.15 parts by weight of a benzoquinone, per 100 parts of the base rubber;    wherein the benzoquinone is selected from compounds represented by the following formula, and hydrates thereof:                          wherein each R 1 , R 2 , R 3 , and R 4  is independently selected from the group consisting of hydrogen, a halogen group (F, Cl, Br, I), an alkyl group, a carboxyl group (—COOH) and metal salts thereof (e.g., —COO − M + ) and esters thereof (—COOR), an acetate group (—CH 2 COOH) and esters thereof (—CH 2 COOR), a formyl group (—CHO), an acyl group (—COR), an acetyl group (—COCH 3 ), a halogenated carbonyl group (—COX), a sulfo group (—SO 3 H) and esters thereof (—SO 3 R), a halogenated sulfonyl group (—SO 2 X), a sulfino group (—SO 2 H), an alkylsulfinyl group (—SOR), a carbamoyl group (—CONH 2 ), a halogenated alkyl group, a cyano group (—CN), an alkoxy group (—OR), a hydroxy group (—OH) and metal salts thereof (e.g., —O − M + ), an amino group (—NH 2 ), a nitro group (—NO 2 ), an aryl group (e.g., phenyl, tolyl, etc.), an aryloxy group (e.g., phenoxy, etc.), an arylalkyl group [e.g., cumyl (—C(CH 3 ) 2 phenyl); benzyl (—CH 2  phenyl)], a nitroso group (—NO), an acetamido group (—NHCOCH 3 ), and a vinyl group (—CH═CH 2 );    wherein a ratio (P BQ /P FRI ) of the amount of the benzoquinone present in the rubber composition (P BQ ), measured in parts by weight per 100 parts of the base rubber, to the amount of free radical initiator present in the rubber composition (P FRI ), measured in parts by weight per 100 parts of the base rubber, is from 0.25 to 2; and    wherein the rubber composition is substantially free of organosulfur compounds.    
   
   
       20 . The golf ball of  claim 19 , wherein P BQ /P FRI  is at least 0.25 and less than 0.5.