Golf balls comprising light stable materials and methods of making the same

• US 6,835,794 B2
• Filed: 08/27/2002
• Issued: 12/28/2004
• Est. Priority Date: 12/17/1999
• Status: Expired due to Term

• Current Assignee: Acushnet Company (FILA Holdings Corp.)
• Original Assignee: Acushnet Company (FILA Holdings Corp.)
• Inventors: Rajagopalan, Murali, Wu, Shenshen, Wilson, Craig A.
• Primary Examiner(s): Buttner, David J.
• Application Number:
  US10/228,311
• Publication Number:
  US 20030096936A1
• Time in Patent Office: 854 Days
• Field of Search: 528/53, 528/56, 528/58, 528/61, 528/64, 528/65, 528/76, 473/374, 473/377, 473/378
• US Class Current: 528/64
• CPC Class Codes: A63B 37/0003 Golf balls
• CPC Class Codes: A63B 37/0006 Arrangement or layout of dimples
• CPC Class Codes: A63B 37/0018 Specified number of dimples
• CPC Class Codes: A63B 37/0021 Occupation ratio, i.e. percentage surface occupied by dimples
• CPC Class Codes: A63B 37/0022 Coatings, e.g. paint films; Markings
• CPC Class Codes: A63B 37/0027 Polyurea
• CPC Class Codes: A63B 37/0031 Hardness
• CPC Class Codes: A63B 37/0033 Thickness
• CPC Class Codes: A63B 37/0037 Flexural modulus; Bending stiffness
• CPC Class Codes: A63B 37/0039 characterised by the material
• CPC Class Codes: A63B 37/0043 Hardness
• CPC Class Codes: A63B 37/0045 Thickness
• CPC Class Codes: A63B 37/0064 Diameter
• CPC Class Codes: A63B 37/0065 Deflection or compression
• CPC Class Codes: A63B 37/0073 Solid, i.e. formed of a single piece
• CPC Class Codes: A63B 37/0074 Two piece balls, i.e. cover and core
• CPC Class Codes: A63B 37/0075 Three piece balls, i.e. cover, intermediate layer and core
• CPC Class Codes: A63B 37/0076 Multi-piece balls, i.e. having two or more intermediate layers
• CPC Class Codes: A63B 37/0083 Weight; Mass
• CPC Class Codes: A63B 37/0084 Initial velocity
• CPC Class Codes: A63B 37/0087 : Deflection or compression
• CPC Class Codes: A63B 37/00922 : whereby hardness of the cover is lower than hardness of the intermediate layers
• CPC Class Codes: A63B 37/12 : Special coverings , i.e. outer layer material balls with finger holes A63B37/0001, golf ball covers A63B37/0023
• CPC Class Codes: A63B 45/00 : Apparatus or methods for manufacturing balls working of plastics or substances in a plastic state B29

Abstract

Golf equipment having improved cut and shear resistance that includes a polyurea composition, preferably saturated, formed of a polyurea prepolymer and a curing agent, wherein the polyurea prepolymer includes an isocyanate and a polyether amine, and wherein the curing agent includes a hydroxy-terminated curing agent, amine-terminated curing agent, or a mixture thereof.

Claims

1. A golf ball comprising at least one light stable cover layer formed from a polyurea composition consisting of a prepolymer and an amine-terminated curing agent, wherein the prepolymer is the reaction product of a diisocyanate selected from the group consisting of ethylene diisocyanate;

propylene-1,2-diisocyanate;

tetramethylene diisocyanate;

tetramethylene-1,4-diisocyanate;

1,6-hexamethylene-diisocyanate;

octamethylene diisocyanate;

decamethylene diisocyanate;

2,2,4-trimethylhexamethylene diisocyanate;

2,4,4-trimethylhexamethylene diisocyanate;

dodecane-1,12-diisocyanate;

dicyclohexylmethane diisocyanate;

cyclobutane-1,3-diisocyanate;

cyclohexane-1,2-diisocyanate;

cyclohexane-1,3-diisocyanate;

cyclohexane-1,4-diisocyanate;

methyl-cyclohexylene diisocyanate;

2,4-methylcyclohexane diisocyanate;

2,6-methylcyclohexane diisocyanate;

4,4′

-dicyclohexyl diisocyanate;

2,4′

-dicyclohexyl diisocyanate;

1,3,5-cyclohexane triisocyanate;

isocyanatomethylcyclohexane isocyanate;

1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane;

isocyanatoethylcyclohexane isocyanate;

bis(isocyanatomethyl)-cyclohexane diisocyanate;

4,4′

-bis(isocyanatomethyl)dicyclohexane;

2,4′

-bis(isocyanatomethyl)dicyclohexane;

isophoronediisocyanate;

triisocyanate of HDI;

triisocyanate of 2,2,4-trimethyl-1,6-hexane diisocyanate;

4,4′

-dicyclohexylmethane diisocyanate;

2,4-hexahydrotoluene diisocyanate;

2,6-hexahydrotoluene diisocyanate; and

mixtures thereof and a polyether amine selected from the group consisting of polytetramethylene ether diamines, polyoxypropylene diamines, poly(ethylene oxide capped oxypropylene) ether diamines, triethyleneglycoldiamines, propylene oxide-based triamines, trimethylolpropane-based triamines, glycerin-based triamines, and mixtures thereof.

2. The golf ball of claim 1, wherein the saturated diisocyanate is selected from the group consisting of isophoronediisocyanate, 4,4′

-dicyclohexylmethane diisocyanate, 1,6-hexamethylene diisocyanate, or a combination thereof.

3. The golf ball of claim 1, wherein the diisocyanate is selected from the group consisting of aromatic aliphatic isocyanate;

meta-tetramethylxylene diisocyanate;

para-tetramethylxylene diisocyanate;

trimerized isocyanurate of polyisocyanate;

dimerized uredione of polyisocyanate;

modified polyisocyanate; and

mixtures thereof.

4. The golf ball of claim 1, wherein the polyether amine has a molecular weight of about 1000 to about 3000.

5. The golf ball of claim 1, wherein the amine-terminated curing agent is saturated.

6. The golf ball of claim 1, wherein the amine-terminated curing agent has a molecular weight of about 2000 or less.

7. The golf ball of claim 1, wherein the amine-terminated curing agents are selected from the group consisting of ethylene diamine;

hexamethylene diamine;

1-methyl-2,6-cyclohexyl diamine;

tetrahydroxypropylene ethylene diamine;

2,2,4- and 2,4,4-trimethyl-1,6-hexanediamine;

4,4′

-bis-(sec-butylamino)-dicyclohexylmethane;

1,4-bis-(sec-butylamino)-cyclohexane;

1,2-bis-(sec-butylamino)-cyclohexane;

derivatives of 4,4′

-bis-(sec-butylamino)-dicyclohexylmethane;

4,4′

-dicyclohexylmethane diamine;

1,4-cyclohexane-bis-(methylamine);

1,3-cyclohexane-bis-(methylamine);

diethylene glycol di-(aminopropyl)ether;

2-methylpentamethylene-diamine;

diaminocyclohexane;

diethylene triamine;

triethylene tetramine;

tetraethylene pentamine;

propylene diamine;

1,3-diaminopropane;

dimethylamino propylamine;

diethylamino propylamine;

imido-bis-propylamine;

monoethanolamine, diethanolamine;

triethanolamine;

monoisopropanolamine, diisopropanolamine;

isophoronediamine; and

mixtures thereof.

8. The golf ball of claim 1, wherein the cover layer has a difference in yellowness index of about 12 or less after 5 days of ultraviolet light exposure.

9. The golf ball of claim 1, wherein the cover layer has a difference in b chroma dimension of about 6 or less after 5 days of ultraviolet light exposure.

10. The golf ball of claim 1, wherein the cover layer is formed from casting, injection molding, or reaction injection molding.

11. A golf ball comprising:

a core;

a layer disposed about the core forming a center; and

a cover cast onto the center, wherein the cover comprises a light stable polyurea material consisting essentially of a diisocyanate selected from the group consisting of ethylene diisocyanate;

propylene-1,2-diisocyanate;

tetramethylene diisocyanate;

tetramethylene-1,4-diisocyanate;

1,6-hexamethylene-diisocyanate;

octamethylene diisocyanate;

decamethylene diisocyanate;

2,2,4-trimethylhexamethylene diisocyanate;

2,4,4-trimethylhexamethylene diisocyanate;

dodecane-1,12-diisocyanate;

dicyclohexylmethane diisocyanate;

cyclobutane-1,3-diisocyanate;

cyclohexane-1,2-diisocyanate;

cyclohexane-1,3-diisocyanate;

cyclohexane-1,4-diisocyanate;

methyl-cyclohexylene diisocyanate;

2,4-methylcyclohexane diisocyanate;

2,6-methylcyclohexane diisocyanate;

4,4′

-dicyclohexyl diisocyanate;

2,4′

-dicyclohexyl diisocyanate;

1,3,5-cyclohexane triisocyanate;

isocyanatomethylcyclohexane isocyanate;

1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane;

isocyanatoethylcyclohexane isocyanate;

bis(isocyanatomethyl)-cyclohexane diisocyanate;

4,4′

-bis(isocyanatomethyl)dicyclohexane;

2,4′

-bis(isocyanatomethyl)dicyclohexane;

isophoronediisocyanate;

triisocyanate of HDI;

triisocyanate of 2,2,4-trimethyl-1,6-hexane diisocyanate;

4,4′

-dicyclohexylmethane diisocyanate;

2,4-hexahydrotoluene diisocyanate;

2,6-hexahydrotoluene diisocyanate; and

mixtures thereof, a polyether amine selected from the group consisting of polytetramethylene ether diamines, polyoxypropylene diamines, poly(ethylene oxide capped oxypropylene) ether diamines, triethyleneglycoldiamines, propylene oxide-based triamines, trimethyloipropane-based triamines, glycerin-based triamines, and mixtures thereof, and an amine-terminated curing agent.

12. The golf ball of claim 11, wherein the layer comprises ionomers, polyamides, highly neutralized polymers, polyesters, polycarbonates, polyimides, polyolefins, acid copolymers, polyurethanes, vinyl resins, acrylic resins, polyphenylene oxide resins, metallocene catalyzed polymers, and mixtures thereof.

13. The golf ball of claim 11, wherein the layer is a moisture barrier layer.

14. The golf ball of claim 11, wherein the cover has a thickness of about 0.02 inches to about 0.035 inches.

15. The golf ball of claim 11, wherein the layer has a first Shore D hardness and the cover has a second Shore D hardness, and wherein the ratio of second Shore D hardness to the first Shore D hardness is about 0.7 or less.

16. The golf ball of claim 11, wherein the core comprises polybutadiene, and wherein the core has a diameter of about 1.55 or greater.

17. The golf ball of claim 16, wherein the core comprises a cis-to-trans catalyst, a resilient polymer component, and a free radical source.

18. The golf ball of claim 17, wherein the cis-to-trans catalyst comprises an organosulfur component, a Group VIA component, an inorganic sulfide component, an aromatic organic compound, or mixtures thereof.

19. The golf ball of claim 11, wherein at least one of the core, the layer, the cover, or combinations thereof comprise a density-adjusting filler.

20. A golf ball comprising a cover layer formed from a polyurea composition consisting essentially of:

a polyurea prepolymer formed from the reaction product of;

an isocyanate having the structure O═

C═

N—

R—

N═

C═

O, wherein R consists of a cyclic, aromatic, or linear or branched hydrocarbon moiety containing from about 1 to about 20 carbon atoms; and

a polyether amine selected from the group consisting of

wherein the repeating unit x has a value ranging from about 1 to about 70,

wherein x and z have combined values from about 3.6 to about 8, y ranges from about 9 to about 50, and wherein R is —

(CH₂)_a— and

a ranges from about 1 to about 10,

21. The golf ball of claim 20, wherein the isocyanate is saturated.

22. The golf ball of claim 20, wherein the amine-terminated curing agent is saturated.

23. The golf ball of claim 20, wherein the golf ball further comprises a core and an intermediate layer.

24. The golf ball of claim 23, wherein the intermediate layer comprises an ionomer.

25. The golf ball of claim 20, wherein the cover layer has a thickness of about 0.02 inches to about 0.035 inches.

26. The golf ball of claim 20, wherein the isocyanate is selected from the group consisting of ethylene diisocyanate;

propylene-1,2-diisocyanate;

tetramethylene diisocyanate;

tetramethylene-1,4-diisocyanate;

1,6-hexamethylene-diisocyanate;

octamethylene diisocyanate;

decamethylene diisocyanate;

2,2,4-trimethylhexamethylene diisocyanate;

2,4,4-trimethylhexamethylene diisocyanate;

dodecane-1,12-diisocyanate;

dicyclohexylmethane diisocyanate;

cyclobutane-1,3-diisocyanate;

cyclohexane-1,2-diisocyanate;

cyclohexane-1,3-diisocyanate;

cyclohexane-1,4-diisocyanate;

methyl-cyclohexylene diisocyanate;

2,4-methylcyclohexane diisocyanate;

2,6-methylcyclohexane diisocyanate;

4,4′

-dicyclohexyl diisocyanate;

2,4′

-dicyclohexyl diisocyanate;

1,3,5-cyclohexane triisocyanate;

isocyanatomethylcyclohexane isocyanate;

1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane;

isocyanatoethylcyclohexane isocyanate;

bis(isocyanatomethyl)-cyclohexane diisocyanate;

4,4′

-bis(isocyanatomethyl)dicyclohexane;

2,4′

-bis(isocyanatomethyl)dicyclohexane;

isophoronediisocyanate;

triisocyanate of HDI;

triisocyanate of 2,2,4-trimethyl-1,6-hexane diisocyanate;

4,4′

-dicyclohexylmethane diisocyanate;

2,4-hexahydrotoluene diisocyanate;

2,6-hexahydrotoluene diisocyanate; and

mixtures thereof.

27. The golf ball of claim 20, wherein the amine-terminated curing agent is selected from the group consisting of ethylene diamine;

hexamethylene diamine;

1-methyl-2,6-cyclohexyl diamine;

tetrahydroxypropylene ethylene diamine;

2,2,4- and 2,4,4-trimethyl-1,6-hexanediamine;

4,4′

-bis-(sec-butylamino)-dicyclohexylmethane;

1,4-bis-(sec-butylamino)-cyclohexane;

1,2-bis-(sec-butylamino)-cyclohexane;

derivatives of 4,4′

-bis-(sec-butylamino)dicyclohexylmethane;

4,4′

-dicyclohexylmethane diamine;

1,4-cyclohexane-bis-(methylamine);

1,3-cyclohexane-bis-(methylamine);

diethylene glycol di-(aminopropyl)ether;

2-methylpentamethylene-diamine;

diaminocyclohexane;

diethylene triamine;

triethylene tetramine;

tetraethylene pentamine;

propylene diamine;

1,3-diaminopropane;

dimethylamino propylamine;

diethylamino propylamine;

imido-bis-propylamine;

monoethanolamine, diethanolamine;

triethanolamine;

monoisopropanolamine, diisopropanolamine;

isophoronediamine; and

mixtures thereof.