Urethane golf ball

• US 6,392,002 B1
• Filed: 12/03/1999
• Issued: 05/21/2002
• Est. Priority Date: 05/14/1999
• Status: Expired due to Term

• Current Assignee: Acushnet Company (FILA Holdings Corp.)
• Original Assignee: Acushnet Company (FILA Holdings Corp.)
• Inventors: Wu, Shenshen
• Primary Examiner(s): Buttner, David J.
• Application Number:
  US09/453,960
• Time in Patent Office: 900 Days
• Field of Search: 528/76, 528/80, 528/83, 528/85, 525/467, 525/473, 525/460, 525/453, 473/354, 473/374, 473/378
• US Class Current: 528/76
• CPC Class Codes: A63B 2037/087 Wound cores or layers
• CPC Class Codes: A63B 37/0003 Golf balls
• CPC Class Codes: A63B 37/0066 Density; Specific gravity
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/3215 containing aromatic groups or benzoquinone groups
• CPC Class Codes: C08G 18/3865 containing groups having one sulfur atom between two carbon atoms
• CPC Class Codes: C08G 18/4854 Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
• CPC Class Codes: C08G 18/50 having heteroatoms other than oxygen
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

A golf ball comprising a center, a cover, and optionally, at least one intermediate layer disposed between the center and the cover, wherein at least one of the center, the cover, and the at least one intermediate layer is formed with a polyurethane composition comprising a reaction product of a prepolymer of at least one polyol and at least one polyisocyanate, and at least one curing agent. A polyurethane composition, suitable for forming golf equipment, said composition comprising a reaction product of a prepolymer of at least one polyol and at least one polyisocyanate, and at least one curing agent.

Claims

1. A golf ball comprising a center, a cover, and optionally, at least one intermediate layer disposed between the center and the cover, wherein at least one of the center, the cover, and the at least one intermediate layer is formed with a polyurethane composition comprising a reaction product of:

a prepolymer comprising para-phenylene diisocyanate and at least one polyol selected from the group consisting of polyether polyols having the structure;

where R₁ and R₂ are straight or branched hydrocarbon chains, each containing from 1 to 20 carbon atoms, and n ranges from 1 to about 45;

polyester polyols having the structure;

where R₁ and R₂ are straight or branched hydrocarbon chains, each containing from 1 to 20 carbon atoms, and n ranges from 1 to about 25;

polycaprolactone polyols having the structure;

where R₁ is a straight or branched hydrocarbon chain containing from 1 to 20 carbon atoms, and n ranges from 1 to about 20; and

polycarbonate polyols having the structure;

where R₁ is predominantly bisphenol A units -(p-C₆H₄)—

C(CH₃)₂-(p-C₆H₄)—

or derivatives thereof, and n is the chain length and ranges from 1 to about 20; and

at least one of a hydroxy-terminated curing agent selected from the group consisting of 1,3-bis(2-hydroxyethoxy)benzene and 1,3-bis-[2-(2-hydroxyethoxy)ethoxy]benzene, and 1,3-bis-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}benzene;

resorcinol-di-(β

-hydroxyethyl) ether;

hydroquinone-di-(β

-hydroxyethyl)ether;

ethylene glycol;

diethylene glycol;

polyethylene glycol;

polytetramethylene ether glycol having average molecular weights between about 250 to 4000; and

mixtures thereof or an amine curing agent.

2. The golf ball of claim 1, wherein the polyol is a polyether polyol selected from the group consisting of polyethylene propylene glycol, polytetramethylene ether glycol, poly(oxypropylene)glycol, and mixtures thereof.

3. The golf ball of claim 2, wherein the polyether polyol comprises polytetramethylene ether glycol.

4. The golf ball of claim 1, wherein the polyol is a polyester polyol selected from the group consisting of polyethylene adipate glycol, polybutylene adipate glycol, polyethylene propylene adipate glycol, ortho-phthalate-1,6-hexanediol, and mixtures thereof.

5. The golf ball of claim 1, wherein the polyol is a polycaprolactone polyol selected from the group consisting of 1,6-hexanediol-initiated polycaprolactone;

diethylene glycol initiated polycaprolactone;

trimethylol propane initiated polycaprolactone;

neopentyl glycol initiated polycaprolactone;

1,4-butanediol-initiated polycaprolactone;

polytetramethylene ether glycol-initiated polycaprolactone; and

mixtures thereof.

6. The golf ball of claim 1, wherein the polyurethane composition further comprises a density-modifying filler.

7. The golf ball of claim 1, wherein the polyol has a molecular weight from about 600 to about 4000.

8. The golf ball of claim 1, wherein the polyol comprises saturated or unsaturated bonds and substituted or unsubstituted aromatic and cyclic groups.

9. The golf ball of claim 1, wherein the polyol is present in an amount of about 70 to 98 percent by weight of the prepolymer, the para-phenylene diisocyanate is present in an amount of about 2 to 30 percent by weight of the prepolymer, and the curing agent is present in an amount of about 10 to 110 weight percent of the prepolymer.

10. The golf ball of claim 9, wherein the para-phenylene diisocyanate is present in an amount of about 2 to 12 percent by weight of the prepolymer.

11. The golf ball of claim 10, wherein the para-phenylene diisocyanate is present in an amount of about 5 to 8 percent by weight of the prepolymer.

12. The golf ball of claim 1, wherein the at least one hydroxy-terminated curing agent has a molecular weight from about 48 to 2000 and is selected from the group consisting of 1,3-bis(2-hydroxyethoxy)benzene and 1,3-bis-[2-(2-hydroxyethoxy) ethoxy]benzene, and 1,3-bis-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}benzene;

resorcinol-di-(β

-hydroxyethyl)ether;

hydroquinone-di-(β

-hydroxyethyl)ether;

ethylene glycol;

diethylene glycol;

polyethylene glycol; and

mixtures thereof.

13. The golf ball of claim 1, wherein the polytetramethylene ether glycol has an average molecular weight between about 250 to 2000.

14. The golf ball of claim 1, wherein the amine curing agent is selected from the group consisting of isomers of 3,5-diethyltoluene-2,4(2,6)-diamines, isomers of 3,5-dimethylthio-2,4(2,6)-toluenediamines, 4,4′

-bis-(sec-butylamino)-diphenylmethane, 1,4-bis-(sec-butylamino)-benzene, 4,4′

-methylene-bis-(2-chloroaniline), 4,4′

-methylene-bis-(3-chloro-2,6-diethylaniline), trimethylene glycol-di-p-aminobenzoate, polytetramethyleneoxide-di-p-aminobenzoate, and mixtures thereof.

15. The golf ball of claim 14, wherein the amine curing agent has a molecular weight of about 64 to about 2000.

16. The golf ball of claim 1, wherein the polyurethane composition comprises a reaction product of para-phenylene diisocyanate, polytetramethylene ether glycol, and mixtures of 3,5-dimethylthio-2,4-toluenediamine and 3,5-dimethylthio-2,6-toluenediamine.

17. The golf ball of claim 1, wherein the cover is comprised of the polyurethane composition.

18. The golf ball of claim 1, wherein the ball comprises at least one said intermediate layer and wherein at least one said layer is comprised of the polyurethane composition.

19. The golf ball of claim 1, wherein the center is a fluid-filled center, a solid center, a gel center, or a hollow center.

20. A polyurethane composition, suitable for forming golf equipment, comprising a reaction product of:

a prepolymer of para-phenylene diisocyanate and polytetramethylene ether glycol; and

at least one amine curing agent comprising mixtures of 3,5-dimethylthio-2,4-toluenediamine, and 3,5-dimethylthio-2,6-toluenediamine.

21. The composition of claim 20, wherein the polyol is present in an amount of about 70 to 98 percent by weight of the prepolymer, the para-phenylene diisocyanate is present in an amount of about 2 to 30 percent by weight of the prepolymer, and the curing agent is present in an amount of about 10 to 110 weight percent of the prepolymer.

22. The composition of claim 21, wherein the para-phenylene diisocyanate is present in an amount of about 2 to 12 percent by weight of the prepolymer.

23. The composition of claim 22 wherein the para-phenylene diisocyanate is present in an amount of about 5 to 8 percent by weight of the prepolymer.

24. The golf ball of claim 20, wherein the polytetramethylene ether glycol has an average molecular weight between about 250 to 2000.

25. The composition of claim 20, wherein the polyurethane composition further comprises a density-modifying filler.