IP Library Granted Patent US 9,018,295
Granted Patent B2
US 9,018,295 · App. 12/333,964 · 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
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,018,295
App. No.
12/333,964
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 (35)

1. A golf ball comprising a core and a cover, wherein the cover comprises a castable reactive liquid material comprising:

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 glycerol-α-bromohydrin ternarized with dimethyl sulfide, and wherein the isocyanate-containing component comprises at least one ═S;

a curative comprising an amine-terminated curing agent comprising between about 1 percent to about 50 percent ═S by weight of the amine-terminated curing agent;

at least one quaternizing agent comprising dialkyl sulfate present in an amount sufficient to react with at least about 70 percent of ═S; and

a flow modifier comprising zinc stearate, wherein the flow modifier is present in an amount of about 15 pph to about 75 pph.

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

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

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

5. The golf ball of claim 1 , wherein the amine-terminated curing agent comprises between about 5 percent to about 25 percent ═S by weight of the amine terminated curing agent.

6. A golf ball comprising at least one layer comprising a composition comprising:

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, glycerol-α-bromohydrin ternarized with dimethyl sulfide, and wherein the isocyanate-containing component comprises at least one ═S;

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

H 2 N—R 1 —NH 2 ;

R 2 HN—R 1 —NHR 2 ;

R 3 R 2 N—R 1 —NR 2 R 3 ;

H 2 N—R 1 —NHR 2 ;

R 3 R 2 N—R 1 —NH 2 ; or

R 3 R 2 N—R 1 —NHR 2

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, and wherein the amine-terminated curing agent further comprises about 1 percent to about 50 percent ═S by weight of the amine-terminated curing agent;

a neutralizing agent comprising dialkyl sulfate, wherein the neutralizing agent is present in an amount sufficient to react with at least about 0 percent ═S; and

a flow modifier comprising zinc stearate, wherein the flow modifier is present in an amount of about 15 pph to about 75 pph.

7. The golf ball of claim 6 , 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 composition.

8. The golf ball of claim 7 , wherein the intermediate layer is formed from a thermoplastic material.

9. The golf ball of claim 6 , 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 composition.

10. The golf ball of claim 6 , wherein the composition is thermoplastic.

11. The golf ball of claim 6 , wherein the amine-terminated curing agent comprises between about 5 percent and 25 percent ═S by weight of the amine-terminated curing agent.

12. A golf ball comprising a core, an intermediate layer disposed about the core, and a cover disposed about the intermediate layer, wherein at least one of the intermediate layer and cover is formed of a composition comprising:

a polyurea prepolymer formed from the reaction product of an isocyanate-containing component and an amine-terminated component, wherein the polyurea prepolymer further comprises a neutralizing agent comprising diallyl sulfate,

wherein the isocyanate-containing component consists of the reaction product of a diisocyanate and glycerol-α-bromohydrin ternarized with dimethyl sulfide, and

wherein the isocyanate-containing component comprises at least one ═S;

an amine-terminated curing agent comprising between about 5 percent to about 25 percent ═S by weight of the amine-terminated curing agent; and

a flow modifier comprising zinc stearate, wherein the flow modifier is present in an amount of about 15 pph to about 75 pph, and wherein the percent conversion of ═S to ═S ⊕ —is at least about 75 percent.

13. The golf ball of claim 12 , wherein the intermediate layer comprises a thermoplastic material.

14. The golf ball of claim 12 , wherein the composition is thermoset.

15. The golf ball of claim 12 , wherein the composition is thermoplastic.

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 021984/0059 →
Continuity (2)
Continuation 12333803 · Dec 12, 2008
Related Publication 20100151967A1 · Jun 17, 2010