Golf balls comprising chiral diols or chiral cyclic ethers

• US 20040225100A1
• Filed: 05/09/2003
• Published: 11/11/2004
• Est. Priority Date: 05/09/2003
• Status: Active Grant

• Current Assignee: Acushnet Company (FILA Holdings Corp.)
• Original Assignee: Acushnet Company (FILA Holdings Corp.)
• Inventors: Wu, Shenshen, Rajagopalan, Murali
• Granted Patent: US 6,949,617 B2
• Time in Patent Office: Days
• US Class Current: 528/44
• CPC Class Codes: A63B 37/0003 Golf balls
• CPC Class Codes: A63B 37/0031 Hardness
• CPC Class Codes: A63B 37/0037 Flexural modulus; Bending stiffness
• CPC Class Codes: A63B 37/0087 Deflection or compression
• 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 18/4825 Polyethers containing two hydroxy groups C08G18/4833 - C08G18/5096 take precedence

Abstract

A golf ball comprising a core and a cover, wherein the core or the cover comprises a thermoplastic or thermoset composition comprising a polyurethane prepolymer formed from a reactant A comprising an isocyanate; and a reactant B comprising a polyether polyol having a repeating branched oxyalkylene monomer unit, or a polymerized polyol formed from a chiral diol or a chiral cyclic ether.

Claims

1. A golf ball comprising a core and a cover, wherein the core or the cover comprises a thermoplastic or thermoset composition comprising a polyurethane prepolymer formed from:

a reactant A comprising an isocyanate; and

a reactant B comprising a polyether polyol having a repeating branched oxyalkylene monomer unit, or a polymerized polyol formed from a chiral diol or a chiral cyclic ether.

2. The golf ball of claim 1, wherein reactant B is the polymerized polyol, the polymerized polyol being formed from a chiral diol having a formula of:

3. The golf ball of claim 1, wherein reactant B is the polymerized polyol, the polymerized polyol being formed from a copolymerization of a chiral diol and a second diol or cyclic ether having about 2 carbon atoms to about 20 carbon atoms.

4. The golf ball of claim 3, wherein the chiral diol comprises 2-methyl-1,4-butanediol, and the second diol or cyclic ether comprises 1,4-butanediol or tetrahydrofuran.

5. The golf ball of claim 1, wherein reactant B is the polymerized polyol, the polymerized polyol being formed from a chiral cyclic ether having a formula of:

6. The golf ball of claim 1, wherein reactant B is the polymerized polyol, the polymerized polyol being formed from a copolymerization of a chiral cyclic ether and a second diol or cyclic ether having about 2 carbon atoms to about 20 carbon atoms.

7. The golf ball of claim 6, wherein the chiral cyclic ether comprises 2-methyl-tetrahydrofuran, and the second diol or cyclic ether comprises 1,4-butanediol or tetrahydrofuran.

8. The golf ball of claim 1, wherein reactant B is the polyether polyol, the polyether polyol comprising a repeating branched oxyalkylene monomer unit having a formula of:

9. The golf ball of claim 1, wherein reactant B is the polyether polyol, the polyether polyol having a formula of:

10. The golf ball of claim 9, wherein R₅ comprises —

CH₂—

CH₂—

CH₂—

CH₂ , R₆ comprises —

CH₂—

CH(CH₃)—

CH₂—

CH₂—

or —

CH₂—

CH₂ CH(CH₃)—

CH₂—

, m and n are independently selected from about 5 to about 50, and z is from 1 to about 50.

11. The golf ball of claim 1, wherein the reactant B is a substantially non-crystalline block co-polyether polyol having a melting point of less than about 15°

C.

12. The golf ball of claim 1, wherein reactant B has a molecular weight of about 500 to about 10,000.

13. The golf ball of claim 1, wherein reactant A is an organic, modified organic, aliphatic, alicyclic, unsaturated, araliphatic, aromatic, substituted, or unsubstituted isocyanate, comprising isocyanate-containing monomers, dimers, trimers, multimeric adducts, oligomers, polymers, prepolymers, low-free-monomer prepolymers, quasi-prepolymers, diisocyanates, polyisocyanates, uretdiones, isocyanurates, or blends thereof.

14. The golf ball of claim 1, wherein an equivalent ratio of reactant B to reactant A is about 0.01:

1 to about 1;

1, and the polyurethane prepolymer has a NCO content of less than about 15 percent.

15. The golf ball of claim 1, wherein the composition further comprises a curing agent comprising saturated or unsaturated monomeric polyahls, oligomeric polyahls, polyether polyahls, polyester polyahls, polycaprolactone polyahls, polycarbonate polyahls, polyhydrocarbon polyahls, polyamide polyahls, polyolefin polyahls, polyahls converted from acid functional oligomers or polymers or ionomers thereof, diols, triols, tetraols, polyols, diamines, triamines, tetramines, polyamines, amine- and hydroxy-containing hybrid compounds, or epoxies;

and wherein an equivalent ratio of the polyurethane prepolymer to the curing agent is about 1;

0.6 to about 1;

1.5.

16. The golf ball of claim 1, wherein the composition is substantially saturated.

17. The golf ball of claim 1, wherein the composition has a material hardness of less than about 70 Shore D.

18. The golf ball of claim 1, wherein the golf ball has a compression of less than about 100.

19. The golf ball of claim 1, wherein the golf ball further comprises an intermediate layer disposed between the core and the cover, the intermediate layer comprising ionomers, elastomers, or acid copolymers or terpolymers having an acid content of about 2% to about 50% and being neutralized by about 0% to about 100%.

20. The golf ball of claim 1, wherein the cover comprises an outer cover layer and an inner cover layer, at least one of the cover layers is formed from a polyurethane or polyurea composition having a Shore D hardness of about 30 to about 70 and a flexural modulus of about 10,000 psi to about 80,000 psi.

21. A golf ball comprising a core and a cover, wherein the core or the cover comprises a thermoplastic or thermoset polyurethane formed from:

an isocyanate; and

a curing agent comprising a polyether polyahl having a repeating branched oxyalkylene monomer unit, or a polymerized polyahl formed from a chiral diol or a chiral cyclic ether.

22. The golf ball of claim 21, wherein the curing agent comprises the polymerized polyahl, the polymerized polyahl being formed from a copolymerization of the chiral diol or chiral cyclic ether and a second diol or cyclic ether.

23. The golf ball of claim 21, wherein the polyether polyahl has a formula of:

24. The golf ball of claim 21, wherein the polyether polyahl or the polymerized polyahl has a melting point of less than about 15°

C., and a molecular weight of about 200 to about 5,000.

25. The golf ball of claim 21, wherein the isocyanate is a polyurethane prepolymer.

26. The golf ball of claim 21, wherein the polyurethane composition is substantially saturated.

27. A golf ball comprising a core, a cover, and an intermediate layer disposed between the core and the cover, wherein at least one of the core, the intermediate layer, or the cover comprises a thermoplastic or thermoset composition formed from:

an isocyanate; and

a polymerized polyahl comprising a hydroxy-terminated poly(tetrahydrofuran-co-methyltetrahydrofuran).