Golf balls comprising chiral diols or chiral cyclic ethers

• US 6,949,617 B2
• Filed: 05/09/2003
• Issued: 09/27/2005
• Est. Priority Date: 05/09/2003
• Status: Expired due to Fees

• Current Assignee: Acushnet Company (FILA Holdings Corp.)
• Original Assignee: Acushnet Company (FILA Holdings Corp.)
• Inventors: Wu, Shenshen, Rajagopalan, Murali
• Primary Examiner(s): Gorr, Rachel
• Application Number:
  US10/434,739
• Publication Number:
  US 20040225100A1
• Time in Patent Office: 872 Days
• Field of Search: 528/76, 473/378, 473/376
• US Class Current: 528/76
• 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 cover comprises a thermoplastic or thermoset composition comprising:

a reactant A comprising an isocyanate; and

a reactant B comprising a polyether polyol comprising a repeating branched oxyalkylene monomer unit of the structure;

 

where

Y₁ is a hydrocarbon,

Y₂, Y₃, and Y₄ are independently hydrogen or hydrocarbons,

a, b, and x are independent whole numbers of 0 to about 10, and

at least one of a, b, and x is an integer of 1 to about 10, or

a polymerized polyol formed from a chiral diol of the structure;

or a chiral cyclic ether of the structure;

 

where

R₁ and R₄ are different linear or branched hydrocarbons of 1 to about 10 carbon atoms, and

R₂ and R₃ are different moieties of hydrogen or linear or branched hydrocarbons of 1 to about 10 carbon atoms.

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

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

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

5. 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.

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

7. 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.

8. 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.

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

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

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

12. 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%.

13. 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.

14. The golf ball of claim 1, wherein the reactants A and B form a prepolymer having an NCO content of 7% to 15%.

15. The golf ball of claim 1, wherein the branched oxyalkylene monomer unit comprises —

O—

CH₂—

CH(CH₃)—

CH₂—

CH₂—

, —

O—

CH₂—

CH₂—

CH(CH₃)—

CH₂—

, —

O—

CH(CH₃)—

CH₂—

CH₂—

CH₂—

, or —

O—

CH₂—

CH₂—

CH₂—

CH(CH₃)—

.

16. The golf ball of claim 15, wherein the polyether polyol further comprises a linear oxyalkylene monomer unit comprising —

O—

CH₂—

CH₂—

CH₂—

CH₂—

CH₂—

, —

O—

CH₂—

CH₂—

CH₂—

CH₂—

, —

O—

CH₂—

CH₂—

CH₂—

, or —

O—

CH₂—

CH₂—

.

17. The golf ball of claim 15, wherein the polyether polyol has a formula of:

where

—

O—

R₅—

is —

O—

CH₂—

CH₂—

CH₂—

CH₂—

;

—

O—

R₆—

is —

O—

CH₂—

CH(CH₃)—

CH₂—

CH₂—

;

m and n are independent integers of about 5 to about 50; and

z is an integer from 1 to about 50.

18. The golf ball of claim 2, wherein a molar ratio of the chiral diol or the chiral cyclic ether to the second diol or cyclic ether is about 85:

15 to about 20;

80.

19. The golf ball of claim 1, wherein the polyether polyol or the polymerized polyol has a hydroxyl number of 10 to 150.

20. The golf ball of claim 1, wherein the core has a diameter of about 1.5 inches to about 1.65 inches, a compression of about 30 to about 120, and a coefficient of restitution of about 0.75 or greater.

21. The golf ball of claim 1, wherein the cover comprises an outer cover layer and at least one intermediate layer disposed between the core and the outer cover layer, at least one of the intermediate layer and the outer cover layer comprises the composition and has a thickness of about 0.005 inches to about 0.05 inches.

22. The golf ball of claim 1, wherein the composition further comprises a curative comprising 2,3-dimethyl-2,3-butanediol, 2-methyl- 1,3-propanediol, 2-methyl-1,4-butanediol, or 1,4-butanediol.

23. The golf ball of claim 1, wherein the polyether polyol is a hydroxy-terminated poly(tetrahydrofuran-co-methyltetrahydrofuran).

26. The golf ball of claim 1, wherein the oxyalkylene unit comprises —

O—

CH₂—

CH(CH₃)—

CH₂—

CH₂—

, —

O—

CH₂—

CH₂—

CH(CH₃)—

CH₂—

, —

O—

CH(CH₃)—

CH₂—

CH₂—

CH₂—

, or —

O—

CH₂—

CH₂—

CH₂—

CH(CH₃)—

, and the polyol further comprises —

O—

CH₂—

CH₂—

CH₂—

CH₂—

.

24. A golf ball comprising a core and a cover, the cover comprising a thermoplastic or thermoset composition comprising a polyol and a hindered secondary diamine, wherein the polyol comprises a repeating oxyalkylene unit of:

where

Y₁ is a hydrocarbon,

Y₂, Y₃, and Y₄ are independently hydrogen or hydrocarbons,

a, b, and x are independent whole numbers of 0 to about 10, and

at least one of a, b, and x is an integer;

or the polyol is formed from a diol

or a cyclic ether

where

R₁ is a linear or branched hydrocarbon of 1 to about 10 carbon atoms,

R₂ is a hydrocarbon of 1 to about 10 carbon atoms, or hydrogen when R₁ is a branched hydrocarbon,

R₃ is hydrogen or a linear or branched hydrocarbon of 1 to about 10 carbon atoms, and

R₄ is a linear or branched hydrocarbon of 1 to about 10 carbon atoms.

25. The golf ball of claim 24, wherein the hindered secondary diamine comprises 4,4′

-bis-(sec-butylamino)-dicyclohexylmethane.

27. A golf ball comprising a core, an intermediate layer disposed about the core, and a cover disposed about the intermediate layer, wherein:

the core has a diameter of about 1.5 inches to about 1.65 inches and a compression of about 20 to about 120;

the intermediate layer has a water vapor transmission rate lower than that of the cover; and

the cover comprises a hydroxy-terminated poly(tetrahydrofuran-co-methyltetrahydrofuran), a saturated polyisocyanate, and a hindered secondary diamine.