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WO1996002385A1 - Revetement antiderapant a base d'eau - Google Patents

Revetement antiderapant a base d'eau Download PDF

Info

Publication number
WO1996002385A1
WO1996002385A1 PCT/US1995/000125 US9500125W WO9602385A1 WO 1996002385 A1 WO1996002385 A1 WO 1996002385A1 US 9500125 W US9500125 W US 9500125W WO 9602385 A1 WO9602385 A1 WO 9602385A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating
article
water
polyurethane
skid
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1995/000125
Other languages
English (en)
Inventor
Michael J. Dochniak
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
HB Fuller Licensing and Financing Inc
Original Assignee
HB Fuller Licensing and Financing 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 HB Fuller Licensing and Financing Inc filed Critical HB Fuller Licensing and Financing Inc
Publication of WO1996002385A1 publication Critical patent/WO1996002385A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63B—APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT
    • A63B60/00—Details or accessories of golf clubs, bats, rackets or the like
    • A63B60/06—Handles
    • A63B60/08—Handles characterised by the material
    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63B—APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT
    • A63B60/00—Details or accessories of golf clubs, bats, rackets or the like
    • A63B60/004—Striking surfaces coated with high-friction abrasive materials
    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63B—APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT
    • A63B60/00—Details or accessories of golf clubs, bats, rackets or the like
    • A63B60/06—Handles
    • 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
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/48—Polyethers
    • C08G18/4866—Polyethers having a low unsaturation value

Definitions

  • This invention relates to a new use for water dispersed polyurethanes which are well known.
  • water dispersed polyurethanes are described in a co-pending application, serial number 08/101,430, filed August 3, 1993 entitled "An Anionic Water Dispersed Polyurethane Polymer For Improved Coatings and Adhesives", which application was filed in the name of the inventor of the subject invention.
  • the subject matter of that co-pending application is incorporated herein in its entirety by reference.
  • This invention is concerned specifically with the recognition that coatings of aqueous polyurethane dispersions when combined with gripping areas or tread areas on sporting equipment, tools, and the like, particularly when the polyurethane exhibits elastomeric characteristics, will provide an improved non-skid contact surface.
  • Figure 1 shows a hockey stick coated according to the invention.
  • Figure 2 shows a baseball bat coated according to the invention.
  • Figures 3 shows a surfboard coated according to the invention.
  • Figure 4 shows a hockey glove coated according to the invention.
  • Any polyurethane dispersible in aqueous medium may be used as a non-skid coating in accordance with this invention.
  • a dispersible polyurethane exhibiting elastomeric characteristics is preferred.
  • Aqueous dispersed polyurethanes are generally prepared by reacting a polyester or poly ether based polyol, a diisocyanate, and water loving groups (hydrophiles) which render the resulting polymer dispersible in water.
  • a polymer is typically prepared as a pre-polymer which is then chain extended in water with a soluble amine.
  • a most preferred form of the water dispersed polyurethane is one which exhibits elastomeric characteristics i.e. an aqueous polyurethane elastomer.
  • Aqueous polyurethane elastomers are high molecular weight oligomers which have been modified with water loving groups (hydrophiles) rendering them water dispersible. This technique produces high performance polymers reducing the use of volatile organic compounds to provide environmentally friendly compounds having unique "stroft" (strong but soft) characteristics lending them particularly useful as non-slip grip aides and tread aids on sporting equipment, tools, and the like.
  • An example is a polyether based polyurethane dispersion which will be described specifically in more detail below. Generally, however, elastomeric characteristics are preferred for the purposes of this invention as already stated.
  • elastomer is a generic term for all substances having the properties of natural, reclaimed, vulcanized, or synthetic rubber, q.v., in that they stretch under tension, have high tensile strength, retract rapidly, and recover their original dimensions fully.
  • Typical elastomers contain long polymer chains.
  • the preferred polyurethane dispersion elastomers i.e., water dispersible polyurethanes described for this invention are soft elastomers with excellent tensile and tear strength. These properties are best created using new polyols, from OLIN CORPORATION of Stanford, Connecticut 06904 known as POLY-LTM POLYOLS.
  • OLIN CORPORATION has developed this new line of POLY-LTM polyols containing very low levels of terminal unsaturation.
  • polyol synthesis the formation of terminally unsaturated end groups results in a substantial loss in hydroxy functionality. Chains containing terminal unsaturation are monofunctional, containing only one hydroxyl group per chain. These monofunctional chains act as stoppers in polymer formation and decrease the resultant properties of the polyurethanes.
  • organomettalic catalyst such as a double metal cyanide
  • POLY-LTM polyols may be prepared with high levels of polyol and very little monofunctionality.
  • OLIN'S POLY-LTM polyol series is the preferred polyol for improving non-skid characteristics with aqueous polyurethane elastomers in accordance with this invention.
  • organometallic catalysts used to prepare the POLY-LTM polyols, the amount of unsaturation formed increases very slowly with the equivalent weight ( Figure 1).
  • the use of organometallic catalysts allows the synthesis of ultra high molecular weight polyols with low unsaturation levels and functionality very close to the theoretical values. No residual metals are detected in the polyols at a detection limit of ⁇ 1 ppm.
  • EXAMPLE This example is an aqueous polyurethane dispersion which provides a very flexible yet strong film.
  • the flexibility of this polymer was measured using a tensiometer and determined to be around 2,200%. This defines its ability to stretch or grow in length.
  • Technical data regarding physical properties are provided in Table 2 herein below. TABLE 2
  • stroft properties make aqueous polyurethane elastomers particularly useful as grip enhancing coatings for sporting equipment and the like.
  • an application which showed very good results was coating handles on baseball bats.
  • players often tape or apply tacky-oily substances like pine tar.
  • an aqueous polyurethane elastomer may be spray applied on a wooden bat handle and dried.
  • the clear, colorless dried film renders outstanding non-slip characteristics for grip.
  • such coatings "stroft" (strong but soft) properties make it a very durable coating unlike pine tar and tape.
  • Such coatings may be used with advantageous results on hockey sticks.
  • Hockey sticks are .used in cold conditions making a fiberglass coated blade or a plastic blade very hard and brittle. A puck is difficult to control with such blades and they are likely to shatter on impact.
  • the relatively softer, non-tacky coatings of the present invention are advantageous in this connection making the puck not only easier to handle with the coating applied to the blade but also adding tremendously to its strength and improved flexibility.
  • tape is no longer needed.
  • Players usually apply tape to soften the grip and add strength to the handle of the stick. Unfortunately, tape often wears or falls off the stick making it hazardous to the players.
  • the coatings of the invention exhibit very good adhesion along with water resistance, and cold weather properties.
  • the coating of the invention may be used to advantage not only to improve gripping surfaces of the hockey stick but to include its strength as well, particularly at the blade portion thereof.
  • This prepolymer is cooled to 80 deg C and charge with 22,74 gm (.224 miles) triethylamine. After stirring 5 minutes, the prepolymer is added to 904.4 gm (50.24 moles) de-ionized water and dispersed with gentle agitation. To this is charged a premix blend containing 10.9 gm (.36 Eq) ethylenediamine chain extender in 15 gm (.83 mole) de-ionized water.
  • the resulting polymer properties can be seen in Table 2 above.
  • the invention has applicability to the following exemplary areas of sporting equipment as listed in the Table 3 herein below.
  • Figure 1 shows a hockey stick generally designated at 10 having a coating 12 covering a blade portion 14, the stick portion 16 and the grip portion 18.
  • the coating may be advantageously applied to any one of these portions of the stick, to any two of them, or to all three thus in effect, coating the entire stick.
  • Figure 2 shows a baseball bat generally designated 20 having a coating 22 on the gripping area thereof.
  • Figure 3 shows a surfboard designated 30 having a non-skid tread area 32 on a portion thereof in the form of coating according to this invention.
  • Figure 4 is a hockey glove generally designated 40 having a palm surface area 42 coated according to this invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

On utilise du polyuréthanne à base d'eau en tant que revêtement antidérapant destiné à des surfaces de prise ainsi qu'à des surfaces de contact d'outils et d'équipements sportifs, tels qu'une crosse (10) de hockey comportant une couche (12) de polyuréthanne à base d'eau recouvrant la tête (14), le corps (16) ainsi que la portion de prise (18) de la crosse.
PCT/US1995/000125 1994-07-15 1995-01-05 Revetement antiderapant a base d'eau Ceased WO1996002385A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US27559094A 1994-07-15 1994-07-15
US08/275,590 1994-07-15

Publications (1)

Publication Number Publication Date
WO1996002385A1 true WO1996002385A1 (fr) 1996-02-01

Family

ID=23053000

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/000125 Ceased WO1996002385A1 (fr) 1994-07-15 1995-01-05 Revetement antiderapant a base d'eau

Country Status (1)

Country Link
WO (1) WO1996002385A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998001189A1 (fr) * 1996-07-05 1998-01-15 Bauer Inc. Lame de baton de hockey dotee d'un revetement resistant a l'abrasion, et procede de revetement de ladite lame
US7097577B2 (en) 2000-09-15 2006-08-29 Jas. D. Easton, Inc. Hockey stick
US7144343B2 (en) 2000-01-07 2006-12-05 Jas. D. Easton, Inc. Hockey stick
US7232386B2 (en) 2003-05-15 2007-06-19 Easton Sports, Inc. Hockey stick
EP2208512A1 (fr) * 2008-12-29 2010-07-21 Eurotramp Trampoline - Kurt Hack GMBH Trampoline
US7914403B2 (en) 2008-08-06 2011-03-29 Easton Sports, Inc. Hockey stick
US7963868B2 (en) 2000-09-15 2011-06-21 Easton Sports, Inc. Hockey stick
US20110165351A1 (en) * 2010-01-05 2011-07-07 Kassouni Van M Composite handle

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4196243A (en) * 1978-09-29 1980-04-01 Gaf Corporation Non-skid floor covering
US4284275A (en) * 1979-10-11 1981-08-18 Fletcher Herbert E Polyurethane gripping material
US4801644A (en) * 1985-10-04 1989-01-31 Polyvinyl Chemicals Inc. Coating compositions
US4828898A (en) * 1985-05-03 1989-05-09 Bob Bailey Auto accessory floor mat
US5269516A (en) * 1991-12-30 1993-12-14 Gencorp Inc. Racquet handle
US5332212A (en) * 1993-01-22 1994-07-26 Dsb Industries, Inc. Coated hockey stick blade

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4196243A (en) * 1978-09-29 1980-04-01 Gaf Corporation Non-skid floor covering
US4284275A (en) * 1979-10-11 1981-08-18 Fletcher Herbert E Polyurethane gripping material
US4828898A (en) * 1985-05-03 1989-05-09 Bob Bailey Auto accessory floor mat
US4801644A (en) * 1985-10-04 1989-01-31 Polyvinyl Chemicals Inc. Coating compositions
US5269516A (en) * 1991-12-30 1993-12-14 Gencorp Inc. Racquet handle
US5332212A (en) * 1993-01-22 1994-07-26 Dsb Industries, Inc. Coated hockey stick blade

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998001189A1 (fr) * 1996-07-05 1998-01-15 Bauer Inc. Lame de baton de hockey dotee d'un revetement resistant a l'abrasion, et procede de revetement de ladite lame
US7144343B2 (en) 2000-01-07 2006-12-05 Jas. D. Easton, Inc. Hockey stick
US7422532B2 (en) 2000-01-07 2008-09-09 Easton Sports, Inc. Hockey stick
US7097577B2 (en) 2000-09-15 2006-08-29 Jas. D. Easton, Inc. Hockey stick
US7963868B2 (en) 2000-09-15 2011-06-21 Easton Sports, Inc. Hockey stick
US7232386B2 (en) 2003-05-15 2007-06-19 Easton Sports, Inc. Hockey stick
US7862456B2 (en) 2003-05-15 2011-01-04 Easton Sports, Inc. Hockey stick
US7914403B2 (en) 2008-08-06 2011-03-29 Easton Sports, Inc. Hockey stick
EP2208512A1 (fr) * 2008-12-29 2010-07-21 Eurotramp Trampoline - Kurt Hack GMBH Trampoline
US20110165351A1 (en) * 2010-01-05 2011-07-07 Kassouni Van M Composite handle
US10166711B2 (en) 2010-01-05 2019-01-01 Van M. Kassouni Method of forming composite handle

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