WO2004071281A2 - Materiaux pour chaussures produits a partir de polyurethannes a base d'huile vegetale - Google Patents

Materiaux pour chaussures produits a partir de polyurethannes a base d'huile vegetale Download PDF

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Publication number
WO2004071281A2
WO2004071281A2 PCT/US2004/003874 US2004003874W WO2004071281A2 WO 2004071281 A2 WO2004071281 A2 WO 2004071281A2 US 2004003874 W US2004003874 W US 2004003874W WO 2004071281 A2 WO2004071281 A2 WO 2004071281A2
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WO
WIPO (PCT)
Prior art keywords
parts
sockliner
shoe insert
poiyurethane
article
Prior art date
Application number
PCT/US2004/003874
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English (en)
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WO2004071281A3 (fr
Inventor
Larry E. Mashburn
Edward T. Patterson
William H. Harrison
Original Assignee
Universal Textile Technologies
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.)
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Publication date
Application filed by Universal Textile Technologies filed Critical Universal Textile Technologies
Publication of WO2004071281A2 publication Critical patent/WO2004071281A2/fr
Publication of WO2004071281A3 publication Critical patent/WO2004071281A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A43—FOOTWEAR
    • A43B—CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
    • A43B17/00—Insoles for insertion, e.g. footbeds or inlays, for attachment to the shoe after the upper has been joined
    • A43B17/14—Insoles for insertion, e.g. footbeds or inlays, for attachment to the shoe after the upper has been joined made of sponge, rubber, or plastic materials
    • A—HUMAN NECESSITIES
    • A43—FOOTWEAR
    • A43B—CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
    • A43B13/00—Soles; Sole-and-heel integral units
    • A43B13/02—Soles; Sole-and-heel integral units characterised by the material
    • A43B13/12—Soles with several layers of different materials
    • A—HUMAN NECESSITIES
    • A43—FOOTWEAR
    • A43B—CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
    • A43B17/00—Insoles for insertion, e.g. footbeds or inlays, for attachment to the shoe after the upper has been joined
    • A43B17/10—Insoles for insertion, e.g. footbeds or inlays, for attachment to the shoe after the upper has been joined specially adapted for sweaty feet; waterproof
    • A43B17/102—Moisture absorbing socks; Moisture dissipating socks
    • A—HUMAN NECESSITIES
    • A43—FOOTWEAR
    • A43B—CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
    • A43B7/00—Footwear with health or hygienic arrangements
    • A43B7/14—Footwear with health or hygienic arrangements with foot-supporting parts
    • A43B7/1405—Footwear with health or hygienic arrangements with foot-supporting parts with pads or holes on one or more locations, or having an anatomical or curved form
    • A43B7/1415—Footwear with health or hygienic arrangements with foot-supporting parts with pads or holes on one or more locations, or having an anatomical or curved form characterised by the location under the foot
    • A43B7/142—Footwear with health or hygienic arrangements with foot-supporting parts with pads or holes on one or more locations, or having an anatomical or curved form characterised by the location under the foot situated under the medial arch, i.e. under the navicular or cuneiform bones

Definitions

  • the present invention relates generally to a shoe insert or sockliner and more particularly to a shoe insert or sockliner which cushions a foot.
  • Foam sockliners or shoeliners frequently are used in shoes to attenuate the impact forces applied to the feet by the ground during walking and running.
  • these articles frequently were made of closed cell poiyurethane foam which offered excellent shock attenuation properties and durability. Typical of such articles are those disclosed in U. S. patents nos. 6,321,465; 6,199,304; 6,038,793; 5,827,596; 4,823,483 and 4,782,605
  • a blowing agent is added to cause gas or vapor to be evolved during the reaction.
  • the blowing agent creates the void cells in the final foam, and may be a relatively low boiling solvent or water.
  • a low boiling solvent evaporates as heat is produced during the isocyanate/polyol reaction to form vapor bubbles.
  • water is used as a blowing agent, a reaction occurs between the water and the isocyanate group to form an amine and CO 2 gas in the form of bubbles. In either case, as the reaction proceeds and the material solidifies, the vapor or gas bubbles are locked into place to form void cells.
  • Final urethane foam density and rigidity may be controlled by varying the amount or type of blowing agent used.
  • a cross-linking agent is often used to promote chemical cross-linking to result in a structured final urethane product.
  • the particular type and amount of cross-linking agent used will determine such final urethane properties such as elongation, tensile strength, tightness of cell structure, tear resistance and hardness.
  • the degree of cross-linking that occurs correlates to the flexibility of the final foam product.
  • Relatively low molecular weight compounds with greater than single functionality are found to be useful as cross-linking agents.
  • Catalysts may also be added to control reaction times and to effect final product qualities.
  • the effects of catalysts generally include the speed of the reaction. In this respect, the catalyst interplays with the blowing agent to affect the final product density.
  • the reaction should proceed at a rate such that maximum gas or vapor evolution coincides with the hardening of the reaction mass.
  • the effect of a catalyst may include a faster curing time, so that urethane foam may be produced in a matter of minutes instead of hours.
  • Polyols used in the production of urethanes are petrochemicals, being generally derived from ethylene glycol with polyester polyols and polyether polyols being the most common polyols used in urethane production.
  • polyester or polyether polyols with molecular weights of from 3,000 to 6,000 are generally used, while for flexible foams shorter chain polyols with molecular weight of from 600 to 4,000 are generally used.
  • polyester and polyether polyols available for use, with a particular polyol being used to engineer and produce a particular urethane elastomer or foam having desired particular final toughness, durability, density, flexibility, compression set ratio, and modulus and hardness quality.
  • petrochemicals such as polyester or polyether polyols
  • petrochemicals are ultimately derived from petroleum, they are a non-renewable resource.
  • the production of a polyol requires a great deal of energy, as oil must be drilled, extracted from the ground, transported to refineries, refined and otherwise processed to yield the polyol.
  • These required efforts add to the cost of polyols, and to the disadvantageous environmental effects of its production.
  • the price of polyols tends to be somewhat unpredictable as it tends to fluctuate based on the fluctuating price of petroleum.
  • polyester or polyether polyols as used in the production of urethane elastomers and foams with a more versatile, renewable, less costly, and more environmentally friendly component.
  • Plastics and foams made using fatty acid triglycerides derived from vegetables have been developed, including soybean derivatives. Because soybeans are renewable, relatively inexpensive, versatile, and environmentally friendly, they are desirable as ingredients for plastics manufacture. Soybeans may be processed to yield fatty acid triglyceride rich soy oil and a protein rich soy flour.
  • soy protein based formulations have been developed.
  • U.S. Pat. No. 5,710,190 discloses the use of soy protein in the preparation of a thermoplastic foam.
  • Such plastics are not suitable for use in applications that call for the particular properties of urethanes. Since urethanes don't utilize proteins in their formulations, soy proteins are not relevant for urethane manufacture.
  • Epoxidized soy oils in combination with polyols have also been used to formulate plastics and plastic foams, including urethanes.
  • U.S. Pat. No. 5,482,980 teaches use of an epoxidized soy oil in combination with a polyol to produce a urethane foam.
  • a polyester or polyether polyol remains in the formulation, however.
  • use of an un-modified soy oil would be more advantageous.
  • U.S. Pat. Nos. 2,787,601 and 2,833,730 disclose a rigid cellular plastic material that may be prepared using any of several vegetable oils, including soy oil.
  • the foam disclosed in these patents is made from a multistep process requiring the preparation of a pre-polymer and, in the case of U.S. Pat. No. 2,833,730, relatively low cross-linker concentrations are urged, resulting in questionable product stability.
  • use of a particular isocyanate, namely toluene diisocyanate is disclosed which is disadvantageous due to its relatively high toxicity.
  • This present invention generally is related to improvements in the art of making sockliner or insert material for the shoe industry.
  • Sockliners are shoe inserts commonly in the configuration of a foot. They are generally constructed of any type of convenient and suitable material or composite. It is common practice in the industry to construct these inserts from composites of nonwoven or woven textiles coated or laminated with foamed polyurethanes.
  • the present invention relates to the use of poiyurethane prepared from vegetable oils, in particular, soy oil. For example, a non-woven textile fabric is coated with a vegetable oil-based poiyurethane foam. A sockliner with this composite structure adds comfort and shock absorbency to the shoe.
  • FIG. 1 is a cross-sectional view of a shoe insert according to the invention in the ball area of the insert .
  • FIG. 2 is a cross-sectional view of a shoe insert according to the invention in the heel area of the insert.
  • the poiyurethane coatings are typically of various densities and gauge (height), depending in each case on the particular shoe or footwear for which it is designed.
  • the nonwoven or woven textile layer may comprise any of those typically used in the manufacture of such inserts, e.g., polyesters, nylons, acrylics and the like. They generally have a density of from about 2 to about 16 oz. per square yard.
  • foams of the invention are prepared according to the process described in U. S. patent application serial no. 10/097,439, filed March 15, 2002; the entire contents and disclosure of which are incorporated herein by reference.
  • the poiyurethane cellular material of the invention comprises the reaction product of an A-component and a B-component, wherein the A-component is comprised of an aromatic or aliphatic polyisocyanate, preferably a diisocyanate, (for example phenyl diisocyanate, 4,4'-biphenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate (TDI) ditoluene diisocyanate, naphthalene 1,4- diisocyanate, 2,4'- and/or 4,4'-diphenylmethane diisocyanate (MDI), polymethylene polyphenylene polyisocyanates (polymeric MDI), 1,6-hexamethylene diisocyanate, isophorone diisocyanate, 1,4-cyclohexyl diisocyanate, or any other modified MDI or TDI or vegetable oil based isocyanate
  • At least one an environmentally friendly vegetable oil based polyol such as from soybeans or such a vegetable oil based polyol plus in combination with a petrochemical polyol or prepolymer;
  • a cross linking agent such as a multi functional alcohol
  • the B-component may also contain:
  • fillers e.g., calcium carbonate, aluminum trihydrate and flyash
  • the B-component is typically mixed in a standard mix tank and reacted with the A-component (in a one step process) just prior to the point of use.
  • flexibility, rigidity, density and hardness can be controlled (i.e. precoats, foams and laminates acquired).
  • higher molecular weight and higher functionality isocyanates would result in a less flexible foam than the use of a lower molecular weight and lower functionality isocyanate with the same polyol.
  • lower molecular weight and lower functionality cross linkers will result in a more flexible foam than higher molecular weight and higher functionality cross linkers when used with the same polyol.
  • A-component and B-component reactants Upon the combination of A-component and B-component reactants an exothermic reaction occurs which may reach completion in several minutes or several hours depending on the reactants and the concentrations used.
  • the catalyst level is altered to accelerate or decelerate the reaction.
  • the blowing agent level is altered to affect the film structure thus forming a foam or poiyurethane elastomer.
  • the A-component comprises a polyisocyanate, and usually is based on diphenylmethane diisocyanate (“MDI”) or toluenediisocyanate (“TDI").
  • MDI diphenylmethane diisocyanate
  • TDI toluenediisocyanate
  • the particular isocyanate chosen will depend on the particular final qualities desired in the urethane.
  • the B-component material is generally a solution of a vegetable oil polyol, cross-linking agent, and blowing agent.
  • a catalyst is also generally added to the B- component to control reaction speed and effect final product qualities.
  • flexible urethane foams of a high quality can be prepared by substituting at least a portion of the petroleum-based polyol in the B-component preparation with a vegetable oil in the presence of a multi-functional alcohol cross-linking agent.
  • the molar ratio of the hydroxyl (OH) groups of the cross- linking agent hydroxyl (OH) groups to the vegetable oil is at least 0.7 to 1, and preferably between about 0.7 and 1.2 to 1.
  • the replacement is made on a substantially 1:1 weight ratio of vegetable oil for replaced petroleum-based polyol.
  • the process of producing the urethane does not change significantly with the petroleum-based polyol replaced by the vegetable oil, with all other components and general methods as are generally known in the art.
  • the qualities of the final flexible or semi-rigid urethane foam produced using the vegetable oil are consistent with those produced using a high grade, expensive polyol.
  • Vegetable oils are abundant, renewable, and easily processed commodities, as opposed to polyols, which are petroleum derivatives and which entail significant associated processing costs. As such, they may currently be acquired for a cost of approximately half that of average grade petroleum-based polyester or polyether polyols, and approximately one quarter the cost of high-grade petroleum- based polyester or polyether polyols. Also, as polyols derived from petroleum, they are not renewable and carry a certain environmental cost with them. There is a distinct marketing advantage to marketing products that are based on environmentally friendly, renewable resources such as vegetable oils.
  • the A-component isocyanate reactant of the urethane of the invention is preferably comprised of an isocyanate chosen from a number of suitable isocyanates as are generally known in the art. Different isocyanates may be selected to result in different final product properties.
  • the A-component reactant of the urethane of the invention preferably comprises 4,4 '-diphenylmethane diisocyanate, 2,4- diphenylmethane diisocyanate or modified diphenylmethane diisocyanate. It should be understood that mixtures of different isocyanates may also be used.
  • the A-side of the reaction may also be a prepolymer isocyanate.
  • the prepolymer isocyanate is the reaction product of an isocyanate, preferably a diisocyanate, and most preferably some form of diphenylmethane diisocyanate and a vegetable oil.
  • the vegetable oil can be soy oil, rapeseed oil, cottonseed oil, or palm oil, or any other oil having a suitable number of reactive hydroxyl (OH) groups.
  • the most preferred vegetable oil is soy oil.
  • the vegetable oil and isocyanate are mixed in a 1:1 ratio for 10-15 seconds every 10-15 minutes for a total of 4 hours or until the reaction has ended.
  • isocyanate (NCO) groups there will still be unreacted isocyanate (NCO) groups in the prepolymer.
  • the prepolymer reaction reduces the cost of the A-side component by decreasing the amount of isocyanate required and utilizes a greater amount of inexpensive, environmentally friendly soy oil.
  • additional isocyanate must be added to elevate the isocyanate (NCO) level to an acceptable level.
  • the B-component reactant of the urethane reaction includes at least the vegetable oil, a cross-linking agent, and a blowing agent. It is believed that the isocyanate reacts with the fatty acids of the vegetable oil to produce the polymeric . backbone of the urethane.
  • the vegetable oils that are suitable for use tend to be those that are relatively high in triglyceride concentration and that are available at a relatively low cost.
  • the preferred vegetable oil is soy oil, although it is contemplated that other vegetable oils, such as rapeseed oil (also known as canola oil) and palm oil can be used in accordance with the present invention. Except for the preliminary blowing step, where air is passed through the oil to remove impurities and to thicken it, the soy oil is otherwise unmodified. It does not require esterification as is required for some urethane products of the prior art.
  • preferred blowing agents for the invention are those that are likewise known in the art, and may be chosen from the group comprising 134A HCFC refrigerant available from Dow Chemical Co., Midland Mi., methyl isobutyl ketone (MIBK), acetone, a hydrofluorocarbon and methylene chloride. These preferred blowing agents boil to create vapor bubbles in the reacting mass. Should other blowing agents be used that react chemically, such as water, to produce a gaseous product, concentrations of other reactants may be adjusted to accommodate the reaction.
  • blowing agent also includes mechanical blowing agents such as inert gases such as air which are incorporated into the liquid phase of the reaction mixture by mechanical beating in high shear equipment, e.g., under pressure.
  • the cross-linking agents of the foam of the present invention are also those that are well known in the art. They must be at least di-functional.
  • the preferred cross-linking agents for the flexible foam of the invention are ethylene glycol, diethylene glycol, triethylene glycol and 1,4 butanediol. It has been found that mixtures of these cross-linking agents is particularly advantageous in the practice of the present invention.
  • Ethylene glycol tends to offer a shorter chain molecular structure with many "dead end" sites, tending to create a firmer final foam resistant to tearing or "unzipping," while butane diol offers a longer chain molecular structure, tending to create a softer foam. Proper mixture of the two can create engineered foams of almost any desired structural characteristics.
  • catalysts may be present.
  • Preferred catalysts for the urethanes of the present invention are those that are generally known in the art, and are most preferably tertiary amines chosen from the group comprising DABCO 33-VL (containing 33% of 1,4- diaza- bicyclco-octane and 67% dipropylene glycol) a gel catalyst available from Air Products Corporation; DABCO BL-22 blowing catalyst available from the Air Products Corporation; and POLYCAT 41 trimerization catalyst available from the Air Products Corporation.
  • the B-component reactant may further comprise a silicone surfactant which functions to influence liquid surface tension and thereby influence the size of the bubbles formed and ultimately the size of the hardened void cells in the final foam product. This can affect foam density and foam rebound (index of elasticity of foam). Also, the surfactant may function as a cell-opening agent to cause larger cells to be formed in the foam. This results in uniform foam density, increased rebound, and a softer foam.
  • a silicone surfactant which functions to influence liquid surface tension and thereby influence the size of the bubbles formed and ultimately the size of the hardened void cells in the final foam product. This can affect foam density and foam rebound (index of elasticity of foam).
  • the surfactant may function as a cell-opening agent to cause larger cells to be formed in the foam. This results in uniform foam density, increased rebound, and a softer foam.
  • a molecular sieve may further be present to absorb excess water from the reaction mixture.
  • the preferred molecular sieve of the present invention is available under the trade name L-past.
  • the preferred flexible and semi-rigid foams of the invention will have greater than approximately 60% open cells.
  • the preferred flexible foam of the invention will also have a density of from 1 to 45 lb. per cubic foot and a hardness of durometer between 20 and 70 Shore "A".
  • the urethane foam of the present invention is produced by combining the A- component reactant with the B-component reactant in the same manner as is generally known in the art.
  • use of the vegetable oil to replace the petroleum- based polyol does not require significant changes in the method of performing the reaction procedure.
  • a reaction ensues which generates heat, and which may reach completion in anywhere from several minutes to several hours depending on the particular reactants and concentrations used.
  • the reaction is carried out in a mold so that the foam expands to fill the mold, thereby creating a final foam product in the shape of the mold.
  • the preferred flexible foam of the invention B-component mixture when using the preferred components, is prepared with the following general weight ratios:
  • This preferred B-component formulation is then combined with the A- component to produce a foam.
  • the preferred A-component is comprised of MDI, and is present in an approximate ratio of about 35-85 parts to 100 parts B-component.
  • Flexible urethane foams may be produced with differing final qualities using the same vegetable oil by varying the particular other reactants chosen. For instance, it is expected that the use of relatively high molecular weight and high functionality isocyanates will result in a less flexible foam than will use of a lower molecular weight and lower functionality isocyanate when used with the same vegetable oil. Similarly, it is expected that lower molecular weight and lower functionality cross linkers will result in a more flexible foam than will higher molecular weight higher functionality cross linkers when used with the same vegetable oil. Also, an ethylene glycol cross linker will result in shorter final chains and a firmer foam, whereas the use of a butane diol cross linker results in longer chains and a softer foam. Moreover, so-called “chain extenders” may also be included in the reaction mixture. Indeed, the polyol cross-linkers of the invention may also function as "chain-extenders”.
  • the blowing agent may comprise any conventionally employed in the art and include methyl isobutyl ketone, acetone, water, mechanically frothed gas, e.g., air and the like.
  • the poiyurethane coatings may be prepared and applied to textiles by typical coating operations, including by doctor bar spraying and the like, or in the manner described in the U.S. Patents described hereinabove as well as U.S. Patent No. 6,180,686, the entire contents and disclosures of which are incorporated herein by reference.
  • FIGS. 1 and 2 illustrate the details of the shoe insert construction of the present invention.
  • the insert 10 comprises a base layer 12, a foam layer 11, and a fabric layer 14.
  • the layers 11, 12, and 14 are relatively resilient and conform in shape to the desired shoe size.
  • the foam layer 11 is constructed of the above-described , poiyurethane foam material.
  • the base layer 12 may be constructed of any suitable material such as, for example, cross-linked polyethylene.
  • the fabric layer 14 may be woven, or non-woven and mat be constructed of, for example, cotton, polyester, or a polypropylene knit.
  • a poiyurethane foam (181b. density) prepared from the following formulation is coated at 125 thousandths of an inch onto a polyester non-woven fabric.
  • soyol may be increased or decreased; different type foams (densities, e.g., from 3 lbs. to 30 lbs.), and composites of foams and different types of substrates.

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  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention a trait à une première de propreté ou à une garniture intérieure de chaussure, destinées à être utilisées conjointement avec une chaussure afin de fournir un rembourrage qui protège un pied introduit dans la chaussure. La première de propreté ou la garniture intérieure de chaussure sont constituées d'un matériau produit à partir d'une composition formant du polyuréthanne, qui contient : (A) un polyisocyanate et (B) un mélange fait d'huile végétale, d'un agent de réticulation composé d'un alcool polyvalent présent selon un rapport à l'huile végétale égal à au moins 0,7 moles de groupes OH par mole d'huile végétale en vrac, d'un catalyseur et d'un gonflant.
PCT/US2004/003874 2003-02-07 2004-02-09 Materiaux pour chaussures produits a partir de polyurethannes a base d'huile vegetale WO2004071281A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US44545103P 2003-02-07 2003-02-07
US60/445,451 2003-02-07

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WO2004071281A2 true WO2004071281A2 (fr) 2004-08-26
WO2004071281A3 WO2004071281A3 (fr) 2004-11-18

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7786239B2 (en) 2004-06-25 2010-08-31 Pittsburg State University Modified vegetable oil-based polyols
US8901187B1 (en) 2008-12-19 2014-12-02 Hickory Springs Manufacturing Company High resilience flexible polyurethane foam using MDI
US8906975B1 (en) 2009-02-09 2014-12-09 Hickory Springs Manufacturing Company Conventional flexible polyurethane foam using MDI

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8293808B2 (en) 2003-09-30 2012-10-23 Cargill, Incorporated Flexible polyurethane foams prepared using modified vegetable oil-based polyols

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020192456A1 (en) * 2001-03-15 2002-12-19 Mashburn Larry E. Carpet backings prepared from vegetable oil-based polyurethanes

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020192456A1 (en) * 2001-03-15 2002-12-19 Mashburn Larry E. Carpet backings prepared from vegetable oil-based polyurethanes

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7786239B2 (en) 2004-06-25 2010-08-31 Pittsburg State University Modified vegetable oil-based polyols
US8153746B2 (en) 2004-06-25 2012-04-10 Cargill, Incorporated Modified vegetable oil-based polyols
US8901187B1 (en) 2008-12-19 2014-12-02 Hickory Springs Manufacturing Company High resilience flexible polyurethane foam using MDI
US8906975B1 (en) 2009-02-09 2014-12-09 Hickory Springs Manufacturing Company Conventional flexible polyurethane foam using MDI

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