Golf ball compositions comprising a novel acid functional polyurethane, polyurea, or copolymer thereof

• US 6,610,812 B1
• Filed: 02/05/2002
• Issued: 08/26/2003
• Est. Priority Date: 02/05/2002
• Status: Expired due to Term

• Current Assignee: Acushnet Company (FILA Holdings Corp.)
• Original Assignee: Acushnet Company (FILA Holdings Corp.)
• Inventors: Ricci, Shawn, Wu, Shenshen, Sullivan, Michael J., Rajagopalan, Murali
• Primary Examiner(s): GORR, RACHEL F
• Application Number:
  US10/072,395
• Publication Number:
  US 20030153716A1
• Time in Patent Office: 567 Days
• Field of Search: 528/60, 528/85, 528/71, 473/357, 473/365, 473/372, 473/373, 473/385
• US Class Current: 528/60
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• 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 18/32 Polyhydroxy compounds; Polyamines; Hydroxyamines
• CPC Class Codes: C08G 18/4263 containing carboxylic acid groups

Abstract

A golf ball comprising a core and a cover, wherein the core or the cover is formed from a composition comprising at least one acid functional polyurethane, polyurea, or copolymer thereof.

Claims

1. A golf ball comprising a core and a cover, wherein at least one of the core or the cover is formed from a composition comprising at least one acid functional polyurethane, polyurea, or copolymer thereof formed from a prepolymer having a formula of:

where

A is a straight chain or branched aliphatic or alicyclic group, a substituted straight chain or branched aliphatic or alicyclic group, or an aromatic or substituted aromatic group; and

B=R—

Y, R being a straight chain or branched aliphatic or alicyclic group, a substituted straight chain or branched aliphatic or alicyclic group, or an aromatic or substituted aromatic group, and Y being HSO₃, HCO₂, or H₂PO₃.

2. The golf ball of claim 1, wherein the core comprises at least one outer core layer comprising at least one acid functional polyurethane, polyurea, or copolymer thereof.

3. The golf ball of claim 1, wherein the cover comprises an inner cover layer and an outer cover layer comprising at least one acid functional polyurethane, polyurea, or copolymer thereof.

4. The golf ball of claim 1, wherein the prepolymer comprises at least one acid functional isocyanate.

5. The golf ball of claim 1, wherein the prepolymer comprises an acid functional polyol or oligomer comprising polyester polyol, polyether polyol;

polylactone polyol;

polytetramethylene ether glycol;

poly(oxypropylene)glycol;

polybutadiene glycol;

polyethylene adipate glycol;

polyethylene propylene adipate glycol;

polybutylene adipate glycol;

diethylene glycol initiated polycaprolactone;

1,4butanediol initiated polycaprolactone;

trimethylol propane initiated polycaprolactone;

neopentyl glycol initiated polycaprolactone;

oligomers of dimethylol proprionic acid;

oligomers of isopthalic sulfonic acid;

poly(ethylene oxide capped oxypropylene)glycol;

propylene glycol inibated polyeaprolactone;

1,5-pentanediol initiated polycaprolactone;

1,6-hexanediol initiated polycaprolactone;

polytetramethylene ether glycol initiated polycaprolactone;

ortho-phthalate-1,6-hexanediol polyester polyol;

polyethylene terephthalate polyester polyol;

poly(hexamethylene adipate)glycol;

poly(phthalate carbonate) glycol;

poly(hexamethylene carbonate)glycol;

polycarbonate glycols containing bisphenol A;

hydroxy-terminated liquid isoprene rubber;

acrylic polyol;

or mixtures thereof.

6. The golf ball of claim 5, wherein the acid functional polyol or oligomer has an acid number of at least about 10.

7. The golf ball of claim 5, wherein the acid functional polyol or oligomer has an acid number of from about 25 to about 150.

8. The golf ball of claim 5, wherein the acid functional polyol or oligomer has a hydroxyl number of at least about 10.

9. The golf ball of claim 5, wherein the acid functional polyol or oligomer has a hydroxyl number of from about 20 to about 175.

10. The golf ball of claim 5, wherein the acid functional polyol or oligomer has a hydroxyl functionality of at least about 1.8.

11. The golf ball of claim 1, wherein the prepolymer comprises an isocyanate and has an isocyanate content of from about 2% to about 32%.

12. The golf ball of claim 1, wherein the composition further comprises a curing agent comprising an amine curing agent, a glycol curing agent, an epoxy curing agent, or a mixture thereof, and wherein an equivalent ratio of the prepolymer to the curing agent is less than about 1:

0.75.

13. The golf ball of claim 11, wherein the isocyanate comprises 4,4′

-diphenylmethane diisocyanate;

3,3′

-dimethyl-4,4′

-biphenylene diisocyanate;

toluene diisocyanate;

polymeric diphenylmethane diisocyanate;

modified liquid 4,4′

-diphenylmethane diisocyanate;

hexamethylene-diisocyanate;

4,4′

-dicyclohexylmethane diisocyanate;

isophorone diisocyanate;

meta-tetramethylxylene diisocyanate;

para-tetramethylxylene diisocyanate;

para-phenylene diisocyanate;

meta-phenylene diisocyanate;

2,2′

- or 2,4′

-diphenylmethane diisocyanates;

tetramethylene diisocyanate;

dodecane diisocyanate;

octamethylene diisocyanate;

decamethylene diisocyanates;

cyclobutane-1,3-diisocyanate;

1,2-, 1,3-, or 1,4-cyclohexane diisocyanates;

2,4 or 2,6-methylcyclohexane diisocyanates;

2,4′

- or 4,4′

-dicyclohexyldiisocyanates;

1,3,5-cyclohexane triisocyanates;

isocyanatomethylcyclohexane isocyanates;

isocyanatocthylcyclohexane isocyanates;

bis(isocyanatomethyl)-cyclohexane diisocyanates;

2,4′

- or 4,4′

-bis(isocyanatomethyl)-dicyclohexane;

1,2-phenylene diisocyanate;

triphenyl methane-4,4′

,4″

-triisocyanate;

naphthylene-1,5-diisocyanate;

2,2′

-, 2,4′

-, or 4,4′

-biphenyl diisocyanates;

polyphenyl polymethylene polyisocyanates;

diphenylether4,4′

-diisocyanate;

perhydrodiphenylmethane-2,4′

-diisocyanante;

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

1,2-, 1,3-, or 1,4-xylylene diisocyanates;

low free isocyanate of said isocyanates;

or a mixture thereof.

14. The golf ball of claim 12, wherein the amine curing agent comprises 4,4′

-bis-(sec-butylamino)cyclohexylmethane;

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

3,5-dimethylthio-2,4 (2,6)-toluenediamine;

3,5-diethyl-2,4 (2,6)-toluenediamine;

N,N′

-dialkyldiamine diphenyl methane;

trimethylene-glycol-di-p-anobenzoate;

polytetramethyleneoxide-di-p-aminobenzoate with molecular weight ranging from about 250 to about 1000;

polymethylene-di-p-aminobenzoates;

polyethyleneglycol-bis(4-aminobenzoates);

polydimethylsiloxane-bis(4-aminobenzoates);

polypropyleneglycol-di-p-aminobcnzoates;

or a mixture thereof.

15. The golf ball of claim 12, wherein the glycol curing agent comprises ethylene glycol;

diethylene glycol;

propylene glycol;

1,3-propane glycol;

1,4butanediol;

1,5-pentanediol;

1,6-hexanediol;

polytetraethylene ether glycol with molecular weight ranging from about 250 to about 1000;

or a mixture thereof.

16. The golf ball of claim 4, wherein the at least one acid functional isocyanate comprises carboxylated, sulfonated or phosphonated derivatives of diphenylmethane-2,4′

-diisocyanate;

diphenylmethane-4,4′

-diisocyanate;

3,3′

-dimethyl-4,4′

-biphenylene diisocyanate;

2,4-toluene diisocyanate;

methylenebis-(4cyclohexyl diisocyanate);

phenylene-1,4-diisocyanate;

diphenyl ether 4,4′

-diisocyanate;

naphthylene-1,4-diisocyanate;

p-phenylene diisocyanate;

p,p′

-diphenyl diisocyanate;

hexahydrophenylene-1,3-diisocyanate;

hexahydrophenylene-1,4isocyanate;

triphenylmethane4,4′

,4′

-triisocyanate;

perhydrodiphenylmethane-2,4′

-diisocyanate;

perhydrodiphenylmethane-4,4′

-diisocyanate;

ethylene diisocyanate;

propylene-1,2-diisocyanate;

tetramethylene-1,4-diisocyanate;

hexamethylene-1,6-diisocyanate;

dodecane-1,12-diisocyanate;

dicyclohexylmethane diisocyauate;

cyclobutane-1,3-diisocyanate;

cyclohexane-1,3-diisocyanate;

cyclohexane-1,4-diisocyanate;

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

1,3-xylene diisocyanate;

or a mixture thereof.

17. The golf ball of claim 1, wherein the acid functional prepolymer comprises at least one acid functional organic amine comprising carboxylated, sulfonated or phosphonated derivatives of polyamines;

polymethylene-di-p-aminobenzoates;

polyethyleneglycol-bis(4-aminobenzoates);

polydimethylsiloxane-bis(4-aminobenzoates);

polytetramethylencetherglycol-di-p-aminobenzoates;

polypropyleneglycol-di-p-aminobenzoates;

N,N,N′

,N′

-tetramethyl-ethylenediamine;

1,4-diazobicyclo(2,2,2)-octane;

N-methyl-N′

-dimethylaminoethylpiperazine;

N,N-dimethylbenzylamine;

bis-(N,N,-diethylaminoethyl)-adipate;

N,N-diethylbenzylamine;

pentamethyldiethylenetriamine;

N,N-dimethylcyclohexylamine;

N,N,N′

,N′

-tetramethyl-1,3-butanediamine;

N,N-dimethyl-β

-phenylethylamine;

1,2-dimethylimidazole;

2-methylimidazole;

or a mixture thereof.

18. The golf ball of claim 1, wherein the prepolymer further comprises a copolymer polyol comprising polytetramethylene ether glycol;

poly(oxypropylene) glycol;

poly(ethylene oxide capped oxypropylene)glycol;

diethylene glycol initiated polycaprolactone;

propylene glycol initiated polycaprolactone;

1,4-butanediol initiated polycaprolactone;

trimethylol propane initiated polycaprolactone;

neopentyl glycol initiated polyeaprolactone;

1,5-pentanediol initiated polycaprolactone;

1,6-hexanediol initiated polycaprolactone;

polytetramethylene ether glycol initiated polycaprolactone;

polyethylene adipate glycol;

polyethylene propylene adipate glycol;

polybutylene adipate glycol;

ortho-phthalate-1,6-hexanediol polyester polyol;

polyethylene terephthalate polyester polyol;

poly(hexamethylene adipate)glycol;

poly(phthalate carbonate)glycol;

poly(hexamethylene carbonate)glycol;

polycarbonate glycols containing bisphenol A;

hydroxy-terminated polybutadiene glycol;

hydroxy-terminated liquid isoprene rubber;

acrylic polyol;

dimer alcohols converted from dimerized fatty acids, or mixtures thereof.

19. The golf ball of claim 1, wherein the composition further comprises at least one additional thermoplastic or thermoset component selected from the group comprising non-anionic polyurethanes, epoxy resins, polyethylenes, polyamides, polyesters, acid copolymers or their ionomer derivatives, non-polyurethane/polyurea ionomers, polystyrenes, polycarbonates, polyacrylics, thermoplastic or thermoset ionomers, non-ionomeric thermoplastic or thermoset resins, or mixtures thereof.

20. The golf ball of claim 1, wherein the composition further comprises catalysts;

surfactants;

blowing agents for foams;

stabilizers;

metals;

colorants including pigments and dyes;

density fillers;

viscosity modifiers;

release agents;

plasticizers;

processing aids;

antioxidants;

compatibility agents;

dispersing agents;

UV absorbers;

hindered amine light stabilizers;

or a mixture thereof.

22. The golf ball of claim 12, wherein at least one of the prepolymer or the curing agent composes an acid functional oligomer.

23. The golf ball of claim 22, wherein the acid functional oligomer comprises oligomers of dimethylol proprionic acid, oligomers of isophthalic sulfonic acid, or a mixture thereof.

24. The golf ball of claim 1, wherein the core has a compression of at least about 55.

25. The golf ball of claim 24, wherein the core compression is about 70 to about 110.

26. The golf ball of claim 3, wherein the outer cover layer has a thickness of about 0.02 inches to about 0.1 inches, a hardness of about 25 Shore D to about 70 Shore D, and a surface dimple coverage of at least about 70%.

27. The golf ball of claim 1, further comprising an intermediate layer disposed between the core and the cover, wherein the intermediate layer has a thickness of at least about 0.02 inches, a flexural modulus of about 1,000 psi to about 100,000 psi, and a hardness of at least about 15 Shore D.

21. A golf ball comprising a core and a cover, wherein at least one of the core or the cover comprises an acid functional polyurethane or polyurea prepolymer having a formula of:

where

B is a straight chain or branched aliphatic or alicyclic group, a substituted straight chain or branched aliphatic or alicyclic group, or an aromatic or substituted aromatic group; and

A=R—

Y, R being a straight chain or branched aliphatic or alicyclic group, a substituted straight chain or branched aliphatic or alicyclic group, or an aromatic or substituted aromatic group, and Y being HSO₃, HCO₂, or H₂PO₃.