WO1992019656A1 - Composition de revetement et procede d'application - Google Patents

Composition de revetement et procede d'application Download PDF

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Publication number
WO1992019656A1
WO1992019656A1 PCT/US1992/003402 US9203402W WO9219656A1 WO 1992019656 A1 WO1992019656 A1 WO 1992019656A1 US 9203402 W US9203402 W US 9203402W WO 9219656 A1 WO9219656 A1 WO 9219656A1
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WO
WIPO (PCT)
Prior art keywords
isocyanate
equivalent weight
coating
golf ball
acrylic polymer
Prior art date
Application number
PCT/US1992/003402
Other languages
English (en)
Inventor
Herbert E. Karp
Emanuel Despoteris
Russell R. Koch
Original Assignee
Technical Coatings Laboratory, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Technical Coatings Laboratory, Inc. filed Critical Technical Coatings Laboratory, Inc.
Publication of WO1992019656A1 publication Critical patent/WO1992019656A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4081—Mixtures of compounds of group C08G18/64 with other macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
    • C08G18/8029—Masked aromatic polyisocyanates
    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63B—APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT
    • A63B2102/00—Application of clubs, bats, rackets or the like to the sporting activity ; particular sports involving the use of balls and clubs, bats, rackets, or the like
    • A63B2102/32—Golf

Definitions

  • the invention relates to improved coatings, more particularly to coatings especially useful for golf balls due to their superior properties uniquely adapted for this use.
  • cut resistant golf balls particularly those having covers made of high impact natural or synthetic polymeric materials such as those ionomer resins sold under the trademark Surlyn ® , has increased the need for durable coatings to improve the appearance of the balls.
  • these balls are provided with a primer coat, e.g. an organic-solvent based epoxy or a water-based polymer, and are then over coated with a polyurethane which provides desirable properties in terms of flexibility, but achieves some desir ⁇ able properties only at the expense of others.
  • the coating composition of the invention comprises: (a) a hard acrylic polymer having a functionality reactive with an isocyanate; (b) an isocyanate; (c) a solvent for application flow and leveling; and (d) a modifying resin which is also isocyanate reactive but imparts flexibility and/or abrasion resistance to the final coating.
  • the acrylic polymer, the isocyanate, and the isocyanate-reac ⁇ tive modifiere each have equivalent weights of at least about 200.
  • the method of the invention comprises: (a) optionally applying a primer layer to a substrate, such as natural or synthetic polymer resins such as ionomeric polymers; (b) spraying onto the surface a coating composition as defined above, and (c) drying and curing the coating.
  • a primer layer such as natural or synthetic polymer resins such as ionomeric polymers
  • the coated article comprises: a substrate, such as a golf ball having a primed ionomeric layer overcoated with a dried, cured layer of an acrylic urethane coating.
  • the invention in one of its preferred aspects, pro ⁇ vides a modified acrylic urethane coating system for Surlyn ® covered golf balls.
  • the coating system comprises an acrylic resin having a functionality reactive with a polyisocyanate.
  • the functionality can be a member selected from the group consisting of hydroxyl, amine, amide, carboxyl and mixtures of any of these.
  • the acrylic typically has a functional group (e.g., hydroxyl) equivalent weight on a solid resin basis of from 200 to 2000, preferably from 500 to 700.
  • the modifiers function similarly to plasticizers and/or surface hardeners but are reactive with the isocyanate.
  • the polyisocyanate can be a suitable prepolymer, homopolymer or copolymer of diiso- cyanates such as toluene diisocyanate (TDI) , hexamethylene diisocyanate (HDI) and isophorone diisocyanate (IPDI) .
  • TDI toluene diisocyanate
  • HDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • the products e.g. ionomer-golf balls, will exhibit good hardness, flexibility, weather resistance, brightness, abrasion resis ⁇ tance and clarity.
  • Good golf ball cover materials have a balance of forming and final properties including good flowability, good old release, moderate stiffness, high abrasion resistance, high tear strength, high resilience, and the like.
  • Preferred polymeric materials are ionomer resins comprising copolymers of ethylene and unsaturated monocarboxylic acids which are available under the trademark Surlyn ® from E.I. DuPont de Nemours Company of Wilmington, Delaware. These ionic copoly ⁇ mers are sodium, lithium, or zinc salts of reaction products of olefins having from 2 to 8 carbon atoms and unsaturated monocarboxylic acids having from 3 to 8 carbon atoms. The carboxylic acid groups of the copolymer may be totally or partially neutralized.
  • thermoplastic materials and thermosetting materials including natural and synthetic polymeric materials can be employed. Balata and gutta percha, previously avail ⁇ able as natural materials are now available as synthetic polymeric materials and are suitable for use in accordance with this invention. Other materials include urethane as well as other synthetic polymers.
  • the golf ball comprises a highly resilient core having a cover stock of one of these high im ⁇ pact materials, or mixtures thereof.
  • a primer effective to promote bonding between the coating and the substrate is preferably employed.
  • the effective primers are solvent-based or water-based epoxies and water-based acrylic or urethane polymers.
  • the epoxy primers is a two component solvent-based epoxy, avail ⁇ able as TCL-3707/3631 from Technical Coatings Laboratory, Inc, Avon, Connecticut.
  • Exemplary of the water-based primers is a modified acrylic polymer coating available as TCL-5500 from the same source as above. Other primers, available from other suppliers are also effective. Primers are not always required, but do enhance results for most users.
  • the primer is applied according to specifications for the particular material, e.g. spraying to a thickness of about 1/8 to 1/2 mil.
  • Epoxy primers of the type identified above are typically cured for from 10 minutes to 24 hours, at from room temperature to 150 ⁇ F.
  • the epoxy coating has to be essen ⁇ tially solvent free before top coating.
  • the water-based poly ⁇ mers are typically cured for from 1 to 45 minutes at from room temperature to 150°F.
  • the coating composition of the invention is applied.
  • the coating composition itself com ⁇ prises an acrylic resin having an isocyanate reactive func ⁇ tionality, an isocyanate, a solvent, and a isocyanate-reactive modifier. It can also have, as desired, various catalysts, promoters, driers, hardeners, brighteners and the like.
  • the acrylic resin can be a homo or copolymer of acrylic monomers having the isocyanate-reactive functionalities, e.g. selected from the group consisting of hydroxyl, amine, amide, carboxyl, and mixtures of any of these.
  • One embodiment employs predominantly hydroxyl group isocyanate reactive functionalities.
  • the monomers can be any of those effective for producing the desired acrylic resins, and can, for example, be selected from the group consisting of acrylic acid, methacrylic acid, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, acryloni- trile, acrylamide, and the like monomers and mixtures of these.
  • Preferred blends comprise any of the above and the like, and preferred embodiments are hard polymers having a minimum of 10% styrene in the monomer composition. Some embodiments have at least about 20% styrene.
  • Some coatings of this invention contain acrylic polymers having less than about 1% of alpha-beta ethylenically unsaturated carboxylic acid monomers.
  • the acrylic resins will be prepared in conventional fashion to have isocyanate-functional equivalent weights typically above 200 and below 2000. Typically this involves solution vinyl polymerization where the monomers are added to a catalyst-containing solvent gradually over the course of the reaction and in amounts effective to give the desired equi ⁇ valent weight. Preferred equivalent weights will be in the range of from 400 to about 600 on a resin solid basis.
  • One preferred acrylic resin is based on methyl methacrylate and hydroxypropyl methacrylate monomers and has an equivalent weight of between 500 and 600, on a solids basis. Typical available resins of this type are Rohm and Haas's AU 608, AT-400, AT-410 and Henkel's G-Cure 867 and 868.
  • the isocyanate component of the coating system can be any suitable isocyanate, including prepolymers, homopolymers or copolymers of diisocyanates such as toluene diisocyanate (TDI) , hexamethylene diisocyanate (HDI) , isophorone diiso ⁇ cyanate (IPDI) , and the like.
  • TDI toluene diisocyanate
  • HDI hexamethylene diisocyanate
  • IPDI isophorone diiso ⁇ cyanate
  • iso- cyanates The various families of iso- cyanates that have been investigated have been hexamethylene diisocyanate biuret, hexamethylene/toluene diisocyanate copolymers, toluene diisocyante bicyanurate trimer, toluene diisocyante/trimethyol propane adduct, isophorone diisocyanate (IPDI) based prepolymer toluene diisocyanate multi-functional prepolymer, and hexamethylene diisocyanate trimer.
  • IPDI isophorone diisocyanate
  • the isocyanates are prepared in known manner and typically have equivalent weights to the hydroxyl or other acrylic isocyanate reactive group of at least about 100, and preferably from 200 to 800, e.g. 300 to 500 on a solids basis.
  • the isocyanates are preferably employed as prepolymer solutions with suitable solids, concentrations and viscosities for effective mixing application, drying and curing.
  • a one package polyurethane system may also be used.
  • This system uses a blocked isocyanate such as Miles's Des- modurTM BL-1185. Limitations of use may be related to the thermo-plastic characteristics of the substrate.
  • the modifiers are typically added to the final reaction mixture as a preblend with the acrylic resin.
  • the modifiers employed in the coating composition will be those which are effective to impart flexibility and abrasion resistance to the final coating.
  • Organic plasticizers can also be used in this acrylic coating composition. Monomeric and polymeric plastici ⁇ zers allow the coating to increase its workability and its flexibility. Phthalic anhydride esters such as dioctyl phtha- late, dibutyl phthalate and dicyclohexyl phthalate may be used. Epoxidized soya oils, oil free and oil modified alkyds can also be incorporated.
  • Alkylene glycol esters of benzoic and adipate acid such as ethylene glycol adipate benzoate, neopentyl adipate benzoate and ethylene glycol adipate ben ⁇ zoate phthalate can also be used in the coating compostion.
  • the preferred modifier is sufficiently reactive to prevent migration to the surface of the coating.
  • the modifiers preferably have isocyanate reactive functional groups at an equivalent weight effective for this purpose, e.g. under 10,000 and preferably from 200 to 2000 on a solids basis.
  • suitable modifiers are the members selected from the group consisting of cellulosic esters; silicones; silanes; caprolactones; vinyl polymers; acrylic polymers with carboxyl, amino or hydroxyl functionality such as Henkel's G-Cure ® 105P70 and G-Cure ® 806; polyesters; polyester- modified, hydroxylfunctional polydimethylsiloxane; and mixtures of these.
  • caprolactones such as Tone ® polyols, available from Union Carbide Cor ⁇ poration, Danbury, Connecticut and characterized by a hydroxyl equivalent weight of about 1000.
  • Suitable modifiers include the following: caprolactone polyols di and trifunctional, with equivalent weights 200 to 1800, preferably 800 to 1200; polyesters having equivalent weights of 300 to 1500; cellulosic modifiers including cellulose acetate butyrate or cellulose acetate proprionate; and solution vinyls, including the medium to low viscosity types.
  • the solvents employed for the acrylic and the iso ⁇ cyanate components will be chosen for their primary role as well as their compatibility with the overall composition, the mixing of the various components, the compatibility with the intended substrate and the ease of application, drying and curing of the coating composition.
  • the solvents are n-butyl acetate, xylene, toluene, propylene, glycol monomethyl ether acetate, ethyl acetate, Cellosolve ® acetate, and the like. All solvents are essentially water-free, i.e., urethane grade.
  • Isocyanates are the crosslinkers used in the acrylic urethane coating. These are polymeric in nature, when mixed stoichiometrically with the acrylic urethane polyol produces a tough flexible coating.
  • the mix ratio for the polyol-iso- cyanate combination are measured as the amount of NCO iso ⁇ cyanate needed to react with an equivalent amount of hydroxyl groups. Stoichiometrically the amount of NCO/OH ratio needed would be 1.0/1.0; however excess isocyanate is generally used since the isocyanate is moisture sensitive and its effective ⁇ ness would diminish upon exposure to air.
  • the range of NCO/OH can be from 1.0/1 up to 1.8/1. Changing the mix ratios will effect the physical properties of the coating; hardness, dur ⁇ ability and pot life are very common variables when this ratio is changed.
  • the preferred range for the NCO/OH is about 1.1/l to 1.5/1.
  • the coating composition can include other additives in amounts effective for their in ⁇ tended purposes.
  • catalysts such as dibutyltin dilaurate, metal driers, or tertiary amines can be employed at effective levels, e.g., of 0.01 to 0.05% based on vehicle solids. The type and level may be adjusted as needed to achieve desired pot life and cure times.
  • various color additives such as titanium dioxide, driers such as cobalt salts, managanese salts or calcium salts, and optical bright- eners and ultraviolet absorbers such as Ciba-Geigy Uvitex OB ® , Tinuvin ® 328 and Tinuvin ® 770, or equivalents, can be employed in amounts desired.
  • the coating composition is formed for application by blending an acrylic resin solution and an isocyanate solution prior to application.
  • the proportions of isocyanate and acrylic resins will be as noted above.
  • the acrylic resin premix will typically contain: from 50% to 100%, e.g. from 60 to 98% acrylic resin solids, up to 50% modifier solids; e.g. 2 to 40%; and from 20 to 90% solvent based on the weight of the solids.
  • an isocyanate premix is formed containing from 20 to 80, preferably from 68 to 72% isocyanate solids and from 20 to 80, preferably from 32 to 38%. These amounts can be varied widely as processing needs and capabilities dictate.
  • Various spray techniques can be used to apply these coatings.
  • Binks No. 18 suction spray gun equipped with a 62 fluid nozzle, a 62 fluid cap and a 66 PG air cap can very effectively be used.
  • the application tech ⁇ nique should ensure a uniform coating on the ball or other substitutes. In a production application, two to four fixed guns may be required to give a uniform coating. The coating is applied in any desired thickness, typically to give a final thickness of from 1/2 to 1 mil.
  • the applied urethane coating will cure as typical urethanes.
  • the rate of cure will depend upon temperature and humidity.
  • the preferred curing cycle is 24 hours at 105 ⁇ F and 50% relative humidity.
  • Faster cures can be achieved by in ⁇ creasing the cure temperature.
  • the balls can cure in 2 hours at 140 ⁇ F and 50% relative humidity.
  • Various catalysts or catalyst combinations can be used to help ac ⁇ celerate the cure.
  • This example describes the preparation of a coating composition according to the invention, and the application of that composition to a Surlyn ® ionomer covered golf ball to produce an improved golf ball of the invention.
  • An acrylic premix is prepared by blending an acrylic resin prepared from 2-hydroxyethyl acrylate, having a hydroxyl equivalent weight of 600 (solids basis) , with the following other components in the indicated amounts.
  • an isocyanate premix is prepared from a hexamethylene diisocyanate biuret prepolymer having an equivalent weight of about 190, based on solids, by mixing the following components in the amounts indicated.
  • a sprayable coating composition is then prepared by mixing 100 parts of the acrylic resin premix with 51 parts by weight of the isocyanate premix.
  • a Surlyn ® ionomer covered golf ball is prepared for coating with the above coating composition by first priming the surface by spray coating with a solution of a commercial solvent-based epoxy primer (TCL-3707/3631) to provide a primer coating thickness of 1/8 to 1/4 mil. The primer coating is dried for 45 minutes at 145 ⁇ F.
  • a commercial solvent-based epoxy primer TCL-3707/3631
  • the sprayable coating composition is then applied by spraying by means of a Binks no. 18 suction spray gun equipped with a 62 fluid nozzle, a 62 fluid cap, and a 66 PG air cap.
  • the coating is sufficient to provide a film thickness of 1/2 to 3/4 mil.
  • the coating is flashed at 75"F for 20 minutes and then cured for 24 hours at 145 ⁇ F.
  • Example 2 The procedure of Example 1 is repeated but this time the premixes and their proportions meet the following cri ⁇ teria:
  • the ratio of acrylic resin premix to isocyanate premix for preparing a coating composition is 100:37.5.
  • the ratio of acrylic resin premix to isocyanate premix for preparing a composition was 100:38. To these, two components are added 73.0 parts of a blended thinner com ⁇ prising aromatic hydrocarbons and esters. Flash conditions are modified to account for the high level of solvent in the coating composition.
  • the two premixes are mixed at a ratio of acrylic resin premix to isocyanate premix of 100:36.5.
  • the ratio of acrylic resin premix to isocyanate premix for preparing a composition was 100:36.5.
  • the two premix solutions are mixed at a ratio of acrylic resin solution to isocyanate solution of 100:36.5.
  • Example l The procedure of Example l is again repeated but this time the isocyanate premix and the proportions of the two premixes are modified as follows:
  • the ratio of acrylic resin premix to isocyanate premix for preparing a composition was 100:40.3.
  • the ratio of acrylic resin premix to isocyanate premix for preparing a composition was 100:38.2.
  • the ratio of acrylic resin premix to isocyanate premix for preparing a composition was 100:40.
  • the ratio of acrylic resin premix to isocyanate premix for preparing a composition was 100:41.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

Revêtements améliorés plus particulièrement utiles pour des balles de golf, lesquels sont préparées à base d'uréthanes acryliques modifiés. Ces revêtements possèdent d'importantes caractéristiques de transparence, de brillance, de durabilité, de souplesse et de résistance qui les protègent de la désagrégation par les intempéries et de l'usure par frottement. On applique la composition de revêtement en la pulvérisant de manière classique de préférence après avoir appliqué une première couche appropriée. Ladite composition de revêtement est constituée d'un mélange comprenant un polymère acrylique dur dont la fonctionnalité réagit avec un isocyanate, qu'on fait réagir ensemble dans un solvant avec un isocyanate tel que du polyisocyanate. Les balles de golf recouvertes avec ce revêtement possèdent une souplesse et une dureté améliorées.
PCT/US1992/003402 1991-04-25 1992-04-24 Composition de revetement et procede d'application WO1992019656A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US69155291A 1991-04-25 1991-04-25
US691,552 1991-04-25

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WO1992019656A1 true WO1992019656A1 (fr) 1992-11-12

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CA (1) CA2086109A1 (fr)
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999043721A1 (fr) * 1998-02-24 1999-09-02 Ppg Industries Ohio, Inc. Compositions filmogenes a base aqueuse durcissables a temperature ambiante
US6103787A (en) * 1998-03-03 2000-08-15 Acushnet Company Golf ball cover compositions
US6458462B1 (en) 2000-12-13 2002-10-01 3M Innovative Properties Company Sporting goods having a ceramer coating
US6458307B2 (en) * 1996-12-24 2002-10-01 Bridgestone Sports Co., Ltd. Method of manufacturing a golf ball
US6596837B2 (en) 2001-03-27 2003-07-22 Acushnet Company Abrasion resistant coated golf equipment
US7935421B2 (en) 2004-07-12 2011-05-03 Acushnet Company Polyurea coatings for golf equipment

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US3264272A (en) * 1961-08-31 1966-08-02 Du Pont Ionic hydrocarbon polymers
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