Polyalkylacrylate compounds for use in golf balls

• US 6,943,213 B2
• Filed: 08/13/2003
• Issued: 09/13/2005
• Est. Priority Date: 08/13/2003
• Status: Expired due to Term

• Current Assignee: Acushnet Company (FILA Holdings Corp.)
• Original Assignee: Acushnet Company (FILA Holdings Corp.)
• Inventors: Kuntimaddi, Manjari
• Primary Examiner(s): Buttner, David J.
• Application Number:
  US10/640,532
• Publication Number:
  US 20050038190A1
• Time in Patent Office: 762 Days
• Field of Search: 525/123, 525/127, 525/131, 528/61, 528/65, 528/66, 528/75, 473/371, 473/374, 473/378
• US Class Current: 525/127
• CPC Class Codes: C08G 18/6225 Polymers of esters of acrylic or methacrylic acid

Abstract

A golf ball comprising a core and a cover, wherein the cover comprises a thermoplastic or thermoset composition comprising a polyurethane prepolymer or polyurea prepolymer formed from an isocyanate and a polyacrylate polyol or polyacrylate polyamine, respectively.

Claims

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

an isocyanate; and

a α

,ω

polyacrylate polyol comprising an acrylate segment with a structure of;

where R¹ to R⁴ are independently hydrogen, aliphatic, alicyclic, aromatic, carbocyclic, heterocyclic, halogenated, perfluoroalkyl, dialkylaminoalkyl, or substituted moieties, each having less than about 20 carbon atoms; and

n is an integer from about 2 to about 300.

2. The golf ball of claim 1, wherein:

R¹ is methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, hexyl, methylhexyl, ethylhexyl, n-amyl, isoamyl, n-octyl, stearyl, lauryl, cyclohexyl, alkyl, or cycloalkyl moieties;

R² is hydrogen or methyl moiety; and

R³ and R⁴ are independently hydrogen or saturated moieties.

3. The golf ball of claim 1, wherein the polyacrylate polyol is an α

,ω

-polyacrylate diol having a formula of;

where R¹ to R⁴ are independently hydrogen, aliphatic, alicyclic, aromatic, carbocyclic, heterocyclic, halogenated, or substituted moieties, each having less than about 20 carbon atoms;

X and Y are independently alkyl, aryl, mercaptoalkyl, ether, ester, carbonate, acrylate, halogenated, or substituted moieties; and

n is an integer from about 2 to about 300.

4. The golf ball of claim 1, wherein the polyacrylate polyol comprises α

,ω

-polymethylmethacrylate diol, α

,ω

-polybutylmethacrylate diol, or α

,ω

-polyethylhexylmethacrylate diol.

5. The golf ball of claim 1, wherein the polyacrylate polyol is a random, block, or graft copolymer further comprising a long-chain hydrocarbon or an oxyalkylene segment with a structure of:

where A¹ to A⁴ are independently hydrogen, alkyl, alkoxy, cycloalkyl, aromatic, heterocyclic, halogenated, or substituted moieties;

x, y, and z are independently zero or integers from about 1 to about 10; and

m is an integer from 2 to about 300.

6. The golf ball of claim 5, wherein at least one of A¹ to A⁴ is an alkyl or cycloalkyl moiety having 1 to about 10 carbon atoms.

7. The golf ball of claim 6, wherein the polyacrylate polyol is a telechelic diol having a copolymeric backbone comprising a polytetramethylene ether glycol segment and at least one polyalkylacrylate segment or polyalkylmethacrylate segment.

8. The golf ball of claim 1, wherein the polyacrylate polyol has a glass transition temperature of less than about −

10°

C.

9. The golf ball of claim 1, wherein the polyacrylate polyol has a glass transition temperature of less than about −

30°

C.

10. The golf ball of claim 1, wherein the polyacrylate polyol has a molecular weight of about 200 to about 20,000.

11. The golf ball of claim 1, wherein the polyacrylate polyol has a molecular weight of about 1,000 to about 5,000.

12. The golf ball of claim 1, wherein:

the isocyanate is saturated, aliphatic, alicyclic, unsaturated, araliphatic, aromatic, substituted, or unsubstituted, comprising isocyanate-containing monomers, dimers, trimers, adducts, condensates, oligomers, polymers, prepolymers, low-free-monomer prepolymers, quasi-prepolymers, diisocyanates, polyisocyanates, biurets, uretdiones, isocyanurates, or blends thereof; and

an equivalent ratio of the polyacrylate polyol to the isocyanate is about 0.01;

1 to about 1;

1.

13. 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, polyamide polyahls, poly(organo)siloxane polyahls, polyahls converted from acid functional oligomers or polymers or ionomers thereof, diols, triols, tetraols, polyols, diamines, triamines, tetramines, polyamines, aminoalcohols, 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.

14. The golf ball of claim 13, wherein the isocyanate, the polyacrylate polyol, the curing agent, and the composition are all substantially saturated.

15. The golf ball of claim 1, wherein the polyurethane prepolymer further comprises a second polyol comprising polyether polyols, polyester polyols, polycaprolactone polyols, polycarbonate polyols, polyhydrocarbon polyols, polyolefin polyols, polyamide polyols, poly(organo)siloxane polyols, polyacrylate polyols, or polyols converted from acid functional oligomers or polymers or ionomers thereof.

16. The golf ball of claim 1, wherein the cover comprises an inner cover layer and an outer cover layer, at least one of which comprises the composition.

17. The golf ball of claim 16, wherein:

the inner cover layer comprises the composition having a first material hardness of about 50 Shore D to about 100 Shore D;

the outer cover layer is formed from a polyurethane or polyurea having a second material hardness of about 30 Shore D to about 70 Shore D and a flexural modulus of about 10,000 psi to about 80,000 psi; and

the first material hardness is greater than the second material hardness.

18. The golf ball of claim 16, wherein the inner and outer cover layers each have a thickness of less than about 0.05 inches.

19. The golf ball of claim 1, wherein the core has a diameter of about 1.5 inches to about 1.65 inches.

20. The golf ball of claim 1, wherein the core comprises a center having a diameter of about 0.5 inches to about 1.5 inches, and an outer core layer having a thickness of about 0.01 inches to about 0.5 inches.

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

a polyurethane prepolymer; and

a α

,ω

polyahl curing agent having an acrylate segment with a structure of;

where R¹ to R⁴ are independently hydrogen, aliphatic, alicyclic, aromatic, carbocyclic, heterocyclic, halogenated, perfluoroalkyl, dialkylaminoalkyl, or substituted moieties, each having less than about 20 carbon atoms; and

n is an integer from about 2 to about 300.

22. The golf ball of claim 21, wherein the curing agent is an α

,ω

-polyacrylate telechelic comprising α

,ω

-polyalkylacrylate diol, α

,ω

-polyalkylacrylate diamine, α

,ω

-polyalkylmethacrylate diol, α

,ω

-polyalkylmethacrylate diamine, α

-amino-ω

-hydroxy-polyalkylacrylate, α

-amino-ω

-hydroxy-polyalkylmethacrylate, or copolymeric polyol or polyamine of polytetramethylene ether glycol and polyalkylacrylate or polyalkylmethacrylate.

23. The golf ball of claim 22, wherein the α

,ω

-polyacrylate telechelic has a molecular weight of less than about 5,000.

24. The golf ball of claim 21, wherein the polyurethane prepolymer comprises:

a polyol comprising polyether polyols, polyester polyols, polycaprolactone polyols, polycarbonate polyols, polyhydrocarbon polyols, polyolefin polyols, polyamide polyols, poly(organo)siloxane polyols, polyacrylate polyols, or polyols converted from acid functional oligomers or polymers or ionomers thereof; and

an isocyanate comprising isocyanate-containing monomers, dimers, trimers, adducts, condensates, oligomers, polymers, prepolymers, low-free-monomer prepolymers, quasi-prepolymers, diisocyanates, polyisocyanates, biurets, uretdiones, isocyanurates, or blends thereof; and

wherein

an equivalent ratio of the polyol to the isocyanate is about 0.3;

1 to about 0.6;

1.

25. A golf ball comprising a core, a cover, and at least one layer comprising a thermoplastic or thermoset composition comprising an α

,ω

-polyacrylate telechelic polyahl, an isocyanate, and an optional curing agent, wherein the at least one layer is an outer core layer, a barrier layer, an intermediate layer, an inner cover layer, or a coating layer.

26. The golf ball of claim 25, wherein the composition forms a polyurethane, and the α

,ω

-polyacrylate telechelic comprises an α

,ω

-polyacrylate diol.

27. The golf ball of claim 25, wherein the composition forms a polyurea, and the α

,ω

-polyacrylate telechelic comprises an α

,ω

-polyacrylate diamine.

28. The golf ball of claim 25, wherein the α

,ω

-polyacrylate telechelic, the isocyanate, and the curing agent are all substantially saturated.