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US007888432B2

(12) United States Patent

Voorheis

(io) Patent No.: (45) Date of Patent:

US 7,888,432 B2 *Feb. 15, 2011

(54) HIGH COR GOLF BALL USING ZINC DIMETHACRYLATE

(75) Inventor: Peter R. Voorheis, New Bedford, MA (US)

(73) Assignee: Acushnet Company, Fairhaven, MA (US)

( * ) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 U.S.C. 154(b) by 295 days.

This patent is subject to a terminal disclaimer.

(21) Appl.No.: 12/073,088

(22) Filed: Feb. 29, 2008

(65) Prior Publication Data

US 2008/0214739 Al Sep. 4, 2008

Related U.S. Application Data

(63) Continuation of application No. 10/740,530, filed on Dec. 22, 2003, now Pat. No. 7,342,073.

(51) Int. CI.

A63B 37/00 (2006.01)
A63B 37/12 (2006.01)
C08F 279/02 (2006.01)

(52) U.S. CI 525/261; 525/274; 473/373;

473/376

(58) Field of Classification Search None

See application file for complete search history.

(56) References Cited

U.S. PATENT DOCUMENTS

4,560,168 A 12/1985 Aoyama 273/232

4,925,193 A 5/1990 Melvin et al 273/232

4,960,281 A 10/1990 Aoyama 273/232

5,006,297 A 4/1991 Brown etal 264/234

5,248,878 A 9/1993 Ihara 219/121.69

5,249,804 A 10/1993 Sanchez 273/232

5,252,652 A 10/1993 Egashiraetal 524/392

5,334,673 A 8/1994 Wu 273/235 R

5,484,870 A 1/1996 Wu 528/28

5,562,552 A 10/1996 Thurman 473/379

5,575,477 A 11/1996 Hwang 473/379

5,605,968 A 2/1997 Egashiraetal 525/221

5,688,191 A 11/1997 Cavallaro et al 473/373

5,697,856 A 12/1997 Moriyamaetal 473/374

5,713,801 A 2/1998 Aoyama 473/354

5,733,428 A 3/1998 Calabria etal 264/134

5,776,012 A 7/1998 Moriyamaetal 473/372

5,803,831 A 9/1998 Sullivan et al 473/374

5,816,944 A 10/1998 Asakuraetal 473/372

5,820,488 A 10/1998 Sullivan et al 473/374

5,849,168 A 12/1998 Lutz 264/755

5,885,172 A 3/1999 Hebertetal 473/354

5.919.100 A 7/1999 Boehm et al 473/354

5.919.101 A 7/1999 Yokotaetal 473/374

5,929,171 A 7/1999 Sanoetal 525/261

5,957,787 A 9/1999 Hwang 473/379

5,965,669 A 10/1999 Cavallaro et al 525/221

5,981,654 A 11/1999 Rajagopalan 525/66

5,981,658 A 11/1999 Rajagopalan et al 525/72

6,056,842 A 5/2000 Daltonetal 156/243

6,075,223 A 6/2000 Harrison 219/121.85

6,121,357 A 9/2000 Yokota 524/406

6,129,881 A 10/2000 Puniello 264/278

6,149,535 A 11/2000 Bissonnette et al 473/354

6,162,135 A 12/2000 Bulpettetal 473/373

6,180,040 Bl 1/2001 Laddetal 264/248

6,180,722 Bl 1/2001 Daltonetal 525/193

6,184,301 Bl 2/2001 Shindo et al 525/261

6,207,784 Bl 3/2001 Rajagopalan 528/71

6,213,898 Bl 4/2001 Ogg 473/383

6,235,230 Bl 5/2001 Puniello 264/278

6,241,625 Bl 6/2001 Yokotaetal 473/373

6,287,218 Bl 9/2001 Ohama 473/377

6,290,615 Bl 9/2001 Ogg 473/378

6,315,915 Bl 11/2001 Hebertetal 216/67

6,338,684 Bl 1/2002 Winfieldetal 473/378

6,358,161 Bl 3/2002 Aoyama 473/383

6,379,138 Bl 4/2002 Puniello etal 425/116

6,383,092 Bl 5/2002 Ogg 473/378

6,386,993 Bl 5/2002 Yokota 473/373

6,409,615 Bl 6/2002 McGuire et al 473/383

6,462,303 Bl 10/2002 Brown 219/121.69

(Continued)

FOREIGN PATENT DOCUMENTS

JP 10192446 7/1998

OTHER PUBLICATIONS

Thain, Science and Golf IV; p. 319-327.

Primary Examiner—David Buttner

(74) Attorney, Agent, or Firm—Murphy & King, PC.

(57) ABSTRACT

The present invention is directed to resilient golf balls and portions thereof including compositions containing zinc dimethacrylate and zinc pentachlorothiophenol, and methods for making same. In particular, the present invention is directed to a golf ball having at least one of a center, cover, or intermediate layer that includes a reaction product that includes a resilient polymer component, a free radical source, zinc dimethacrylate and at least one halogenated organosulfur compound having the following general formula I:

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BACKGROUND OF THE INVENTION

1

HIGH COR GOLF BALL USING ZINC
DIMETHACRYLATE

CROSS-REFERENCE TO RELATED

APPLICATIONS 5

This application is a continuation of U.S. patent application Ser. No. 10/740,530, filed Dec. 22, 2003, now U.S. Pat. No. 7,342,073, the disclosure of which is incorporated by 10 reference herein in its entirety.

where R^Rs can be substituted or unsubstituted Cj-Cg alkyl groups; halogen groups; thiol groups (—SH), carboxy

FIELD OF THE INVENTION lated groups; sulfonated groups; and hydrogen; in any order.

In one embodiment, the at least one structural layer is a

The present invention relates to the use of zinc dimethacry- core, an intermediate layer or a cover, wherein the composi

late in golf ball compositions. In particular, the invention tion is disposed in at least a portion of the at least one struc

relates to resilient golf balls and portions thereof including mral layer- ^ zinc dimethacrylate may be present in an

compositions containing zinc dimethacrylate and zinc pen- 20 amount from about 0.01 pph to about 100 pph and the at least

^ ,, ^ • , , , ^ , j- , • one halogenated organosulfur compound ol formula I is tachlorothiophenol, and methods for making same. . . f „ 1+^^11+1+^1

r ° present in an amount from about 0.01 pph to about 50 pph.

In one embodiment, the at least one halogenated organosulfur compound of formula I is selected from the group

25 consisting of pentafluorothiophenol; 2-fluorothiophenol;

Conventional golf balls can be divided into several general 3-fluorothiophenol; 4-fluorothiophenol; 2,3-fluorothiophe

classes: (a) solid golf balls having one or more layers, and (b) nol; 2,4-fluorothiophenol; 3,4-fluorothiophenol; 3,5-fluo

wound golf balls. Solid golf balls include one-piece balls, rothiophenol 2,3,4-fluorothiophenol; 3,4,5-fluorothiophenol;

which are easy to construct and relatively inexpensive, but 2,3,4,5-tetrafluorothiophenol; 2,3,5,6-tetrafluorothiophenol;

have poor playing characteristics and are thus generally lim- 30 4-chlorotetrafluorothiophenol; pentachlorothiophenol;

.+ , .. . „ . ^ . 2-chlorotmophenol; 3-chlorothiophenol; 4-chlorothiophe

lted for use as range balls. Iwo-piece balls are constructed , ,. ,. , , „ . , , . , , - . , ,

,, ,. , , nol; 2,3-chlorothiophenol; 2,4-chlorothiophenol; 3,4-chlo

with a generally solid core and a cover and are generally rothiophenol; 3,5-chlorothiophenol; 2,3,4-chlorothiophenol;

popular with recreational golfers because they are very 3,4,5-chlorothiophenol; 2,3,4,5-tetrachlorothiophenol; 2,3,5,

durable and provide maximum distance. Balls having a two- 35 6-tetrachlorothiophenol; pentabromothiophenol; 2-bro

piece construction are commonly formed of a polymeric core mothiophenol; 3-bromothiophenol; 4-bromothiophenol; 2,3

encased by a cover. Solid golf balls also include multi-layer bromothiophenol; 2,4-bromothiophenol; 3,4

golf balls that are comprised of a solid core of one or more bromothiophenol; 3,5-bromothiophenol; 2,3,4

layers and/or a cover of one or more layers. These balls are bromothiophenol; 3,4,5-bromothiophenol; 2,3,4,5

regarded as having an extended range of playing characteris- 40 tetrabromothiophenol; 2,3,5,6-tetrabromothiophenol;

tics. These balls are generally easy to manufacture, but are pentaiodothiophenol; 2-iodothiophenol; 3-iodothiophenol;

, ^ . ^. 4-iodothiophenol; 2,3-iodothiophenol; 2,4-iodothiophenol;

regarded as having limited playing characteristics. , . . , ^ . , , ' . . , ^ . , ,' . . , I. ,

3,4-iodothiophenol; 3,5-iodothiophenol; 2,3,4-iodothiophe

A variety of golf balls designed to provide a wide range of noi; 3,4,5-iodothiophenol; 2,3,4,5-tetraiodothiophenol; 2,3, playing characteristics, i.e., the compression, velocity, "feel," 45 5,6-tetraiodothiophenol; and their metal salts. In a preferred and spin, that can be optimized for various playing ability, are embodiment, the at least one halogenated organosulfur cornknown in the prior art. Typical golf ball construction includes pound of formula I is a metal salt of Zn, Ca, Ba, Cd, Sn, Mg, a core formed from polybutadiene that is chemically and Mn. In another preferred embodiment, the at least one crosslinked with zinc diacrylate and/or other similar halogenated organosulfur compound of formula I is a metal crosslinking agents 50 salt of Zn'In yet another preferred embodiment, the at least

one halogenated organosulfur compound of formula I is zinc

However, it is desirable to have golf ball compositions that pentachlorothiophenol alternative crosslinkers, such as zinc dimethacrylate, without xhe free radical source may be di.tert.amyl per0xide, di(2

compromising golf ball payability. The compositions of the tert-butylperoxyisopropyl)benzene peroxide or a,a-bis(tert

present invention provided golf balls with improved coeffi- 55 butylperoxy) diisopropylbenzene, l,l-bis(tert-butylperoxy)

cient of restitution ("CoR") and increased compression using 3,3,5-trimethylcyclohexane or l,l-di(tert-butylperoxy) 3,3,

zinc dimethacrylate. 5-trimethyl cyclohexane, dicumyl peroxide, di-tert-butyl

peroxide, 2,5-di-(tert-butylperoxy)-2,5-dimethyl hexane,

SUMMARY OF THE INVENTION n-butyl-4,4-bis(tert-butylperoxy)valerate, lauryl peroxide,

60 benzoyl peroxide, tert-butyl hydroperoxide, or any mixture thereof.

The present invention is directed to a golf ball comprising in one embodiment, the composition further comprises one

at least one structural layer formed from a composition that ormore additional crosslinking agent selected from the group

comprises a resilient polymer component, a free radical consisting of a metallic salt of an unsaturated acid monomer

source, zinc dimethacrylate and at least one halogenated 65 and a metallic salt of a monocarboxylic acid. In another

organosulfur compound having the following general for- embodiment, the cover comprises one or more homopoly

mula I: meric or copolymeric cover materials selected from the group

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