IP Library Granted Patent US 9,018,294
Granted Patent B2
US 9,018,294 · App. 12/333,803 · Granted Apr 28, 2015

Cationic polyurea cover compositions for a multi-layer golf ball

Inventors: Murali Rajagopalan (Fairhaven, MA); Shawn Ricci (Fairhaven, MA); Michael J. Sullivan (Fairhaven, MA); Kevin M. Harris (Fairhaven, MA); Pamela V. Arnold (Fairhaven, MA)
Assignee: Acushnet Company
C08G18/10C08K5/098C08G18/0809C08G18/0814A63B37/0027A63B37/0023A63B37/0038
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Quick Facts
Patent No.
US 9,018,294
App. No.
12/333,803
Granted
Apr 28, 2015
Kind
B2
Abstract

Golf balls that have at least one layer formed from a cationic polyurea material. In particular, the compositions of the invention, which include a polymer backbone including urea linkages with cationic groups, may be formed from an isocyanate-containing component and an isocyanate-reactive component, at least one of which includes precursor cationic groups, in the presence of an alkylating, quaternizing, or ternarizing agent.

Claims (45)

1. A golf ball comprising a core and a cover, wherein the cover comprises

a polymer comprising:

polyurea prepolymer comprising an isocyanate-containing component and an isocyanate-reactive component,

wherein the isocyanate-containing component consists of the reaction product of an isocyanate-containing compound and at least one compound selected from the group consisting of triethyl phosphine, glycerol-α-bromohydrin ternarized with dimethyl sulfide, and mixtures thereof,

and wherein the isocyanate-containing component comprises at least one precursor cationic group selected from the group consisting of ≡P, ═S, and mixtures thereof; and

a curative comprising:

an amine-terminated curing agent;

zinc stearate; and

a neutralizing agent having the general formula

QX

where Q comprises a benzyl group and X comprises a monovalent anion, and

wherein the neutralizing agent is present in an amount sufficient to react with between about 10 percent and about 70 percent of the precursor cationic groups.

2. The golf ball of claim 1 , wherein the cover comprises an inner cover and an outer cover.

3. The golf ball of claim 2 , wherein the outer cover comprises the polymer.

4. The golf ball of claim 2 , wherein the inner cover comprises the polymer.

5. The golf ball of claim 1 , wherein the isocyanate-reactive component comprises a primary diamine, a secondary diamine, a primary triamine, a secondary triamine, or a mixture thereof.

6. The golf ball of claim 5 , wherein the isocyanate-reactive component comprises a primary triamine or a secondary triamine.

7. A golf ball comprising a core and a cover, wherein the cover comprises

a polymer comprising:

a polyurea prepolymer comprising the reaction product of an isocyanate-containing component and an isocyanate-reactive component, wherein the isocyanate-reactive component has one of the following general structures:

where R 1 comprises unsubstituted or substituted straight chain or branched aliphatic groups, unsubstituted or substituted aromatic groups, or mixtures thereof, wherein R 2 and R 3 independently comprise an alkyl group, an aryl group, or an aralkyl group,

wherein the isocyanate-containing component consists of the reaction product of an isocyanate-containing compound and at least one compound selected from the group consisting of triethyl phosphine, glycerol-α-bromohydrin ternarized with dimethyl sulfide, and mixtures thereof, and

wherein the isocyanate-containing component comprises at least one precursor cationic group selected from the group consisting of ≡P, ═S and mixtures thereof; and

a curative comprising an amine-terminated compound, zinc stearate, and a neutralizing agent having the general formula QX, wherein Q comprises benzyl and X comprises a monovalent anion, and

wherein the neutralizing agent is present in an amount sufficient to react with between about 30 percent and about 70 percent of the precursor cationic groups.

8. The golf hall of claim 7 , wherein the monovalent anion comprises a halide.

9. The golf ball of claim 7 , wherein the cover comprises an inner cover layer and an outer cover layer.

10. The golf ball of claim 9 , wherein the inner cover layer comprises the polymer.

11. The golf ball of claim 9 , wherein the outer cover layer comprises the polymer.

12. A golf ball comprising at least one layer comprising a polymer comprising the reaction product of:

a polyurea prepolymer formed from the reaction product of an isocyanate-containing component and an amine-terminated component,

wherein the isocyanate-containing component consists of the reaction product of a diisocyanate and at least one compound selected from the group consisting of triethyl phosphine, glycerol-α-bromohydrin ternarized with dimethyl sulfide, and mixtures thereof,

and wherein the isocyanate-containing component comprises at least one precursor cationic group selected from the group consisting of ≡P, ═S, and mixtures thereof;

a curative comprising:

an amine-terminated curing agent having at least one of the following general formulas:

where R 1 comprises unsubstituted or substituted straight chain or branched aliphatic groups, unsubstituted or substituted aromatic groups, or mixtures thereof, wherein R 2 and R 3 independently comprise an alkyl group, an aryl group, or an aralkyl group;

a neutralizing agent having the general structure QX, wherein Q comprises a benzyl group and X comprises a monovalent anion, and wherein the neutralizing agent is present in an amount sufficient to react with between about 20 percent and about 60 percent of the precursor cationic groups; and

a flow modifier comprising zinc stearate.

13. The golf ball of claim 12 , wherein the monovalent anion comprises a halide.

14. The golf ball of claim 12 , wherein the monovalent anion comprises fluoride, chloride, bromide, iodide, hydroxide, carbonate, and mixtures thereof.

15. The golf ball of claim 12 , wherein the golf ball comprises a core, an intermediate layer disposed about the core to form an inner ball, and a cover disposed about the inner ball, and wherein the cover is formed from the polymer.

16. The golf ball of claim 15 , wherein the intermediate layer is formed from a thermoplastic material.

17. The golf ball of claim 12 , wherein the golf ball comprises a core, an intermediate layer disposed about the core to form an inner ball, and a cover disposed about the inner ball, and wherein the intermediate layer is formed from the polymer.

18. The golf ball of claim 12 , wherein the polymer is thermoplastic.

19. The golf ball of claim 12 , wherein the polymer is thermoset.

Assignments (6)
SECURITY INTEREST Recorded Aug 3, 2022
From: ACUSHNET COMPANY
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 061099/0236 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS (ASSIGNS 039506-0030) Recorded Aug 3, 2022
From: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS RESIGNING ADMINISTRATIVE AGENT
To: JPMORGAN CHASE BANK, N.A., AS SUCCESSOR ADMINISTRATIVE AGENT
Reel/Frame 061521/0414 →
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (027346/0222) Recorded Sep 7, 2016
From: KOREA DEVELOPMENT BANK, NEW YORK BRANCH
To: ACUSHNET COMPANY
Reel/Frame 039939/0181 →
SECURITY INTEREST Recorded Jul 28, 2016
From: ACUSHNET COMPANY
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 039506/0030 →
SECURITY AGREEMENT Recorded Dec 8, 2011
From: ACUSHNET COMPANY
To: KOREA DEVELOPMENT BANK, NEW YORK BRANCH
Reel/Frame 027346/0222 →
PATENT OWNERSHIP Recorded Dec 16, 2008
From: RAJAGOPALAN, MURALI; RICCI, SHAWN; SULLIVAN, MICHAEL J.; HARRIS, KEVIN M.; ARNOLD, PAMELA V.
To: ACUSHNET COMPANY
Reel/Frame 021983/0975 →
Continuity (1)
Related Publication 20100151970A1 · Jun 17, 2010