WO2007139535A1 - Dossiers de moquette préparés à partir de polyuréthannes à base d'huile végétale hydroxylée - Google Patents

Dossiers de moquette préparés à partir de polyuréthannes à base d'huile végétale hydroxylée Download PDF

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Publication number
WO2007139535A1
WO2007139535A1 PCT/US2006/020437 US2006020437W WO2007139535A1 WO 2007139535 A1 WO2007139535 A1 WO 2007139535A1 US 2006020437 W US2006020437 W US 2006020437W WO 2007139535 A1 WO2007139535 A1 WO 2007139535A1
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Prior art keywords
composition
textile
parts
polyurethane
woven
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PCT/US2006/020437
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English (en)
Inventor
Larry E. Mashburn
Edward Patterson
William Harrison
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Universal Textile Technologies
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Priority to PCT/US2006/020437 priority Critical patent/WO2007139535A1/fr
Publication of WO2007139535A1 publication Critical patent/WO2007139535A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes

Definitions

  • This invention relates to, plastic elastomers and their method of preparation. Specifically, the present invention relates to flexible urethane foams and elastomers, useful as environmentally friendly carpet backings, prepared by the reaction between isocyanates and vegetable oils.
  • U.S. Pat. Nos. 3,849,156, 4,035,529, 4,657,790 and 4,853,280 The process of U.S. Pat. No. 3,849,156 comprises applying a froth directly to the back of carpeting, shaping the froth into the desired shape, and curing the shaped froth at a temperature of at least 70° C to form a polyurethane foam backing on the carpeting material.
  • This polyurethane comprises a substantially non- aqueous mixture of a polyisocyanate, an active hydrogen-containing material, an organosilicon surfactant, and a catalyst having substantial activity only at temperatures of at least 70° C.
  • An inert gas is dispersed throughout the mixture by mechanical beating of the mixture to form a heat curable froth. Carpet fibers and textile filaments may not be firmly enough locked into the carpeting by these mechanically frothed foams, i.e., the "tuft lock" strength may be too low to maintain integrity of the carpet under heavy use conditions.
  • U.S. Pat. No. 4,035,529 describes a process using two coats of polyurethane backings for floor coverings having improved fixing of textile filaments, i.e., higher "tuft lock", and increased stiffness of the carpet.
  • This process comprises applying a first coat to a textile floor covering, a precoat, which consists essentially of a polyol and a large excess of an isocyanate.
  • a foamable main coat of substantially equivalent amounts of a polyol and an isocyanate are then applied before the first coat is hardened, and both coats are subsequently hardened in a heating zone.
  • the "open time” that is, the time that elapses between application of the precoat and the foamable main coat is limited.
  • U.S. Pat. No. 4,657,790 relates to the use of general polyurethane formulation in a specific process.
  • This process comprises forming a precoat layer of a reaction mixture comprising a curable polymer-forming composition, separately forming a capcoat layer of a mixture comprising a curable polymer forming composition, contacting the precoat layer with one surface of the substrate before the precoat layer is tack free, contacting the capcoat layer with one surface of the precoat layer before either the precoat layer or the capcoat layer is tack free, completing the curing of the capcoat and precoat layers, and cooling the polymer backed substrate to less than about 35° C before mechanical distortion.
  • This process is carried out under conditions such that mechanically induced stress is minimized.
  • This process has the disadvantage that the capcoat is produced separately and then laminated to the precoat in an additional manufacturing step.
  • the multi-layered polymer backed floor covering of U.S. Pat. No. 4,853,280 is releasable. It allows the entire installed carpet or carpet padding to be easily removed from the floor surface without tearing so that portions of it do not remain on the floor surface.
  • the backing comprises a facing layer and a bottommost release backing layer both comprising a non-woven fabric, and a polymer layer bonded to the release layer on one side and directly or indirectly to the facing layer on the other side.
  • a precoat layer may be used between the facing layer and the polymer layer.
  • This backing is produced by applying a layer of an uncured polymer-forming composition to the back side of a textile, applying a layer of a non-woven fabric to the polymer backing, and curing the polymer forming composition to a tack free state.
  • the adhesion between the precoat and foamable layer has to be sufficient to avoid delamination at that interface.
  • latex-based precoats are used to assure adequate interfacial adhesion; however, these latex materials may potentially contain volatile organic compounds.
  • Polyurethane unitary layers that may be used as precoats are described, for example, in U.S. Pat. Nos. 4,269,159 and 4,696,849.
  • Polyurethane-backed carpeting is the subject of U.S. Pat. No. 4,296,159. These carpets comprise a primary backing, a yam tufted or woven through the primary backing to create a bundle on the underside of the tufted good, and a polyurethane composition is then applied to the underside to encapsulate the yarn bundles to the primary backing providing high "tuft lock".
  • This polyurethane composition comprises a high molecular weight polyether polyol, a low molecular weight polyol, and organic polyisocyanate or polyisothiocyanate, and an inorganic filler.
  • the isocyanate used in the examples are either isocyanate prepolymers based on toluene diisocyanate, or a modified diphenylmethane thioisocyanate.
  • U.S. Pat. No. 4,696,849 discloses polyurethane compositions suitable for carpet backing comprising the reaction product of a polyurethane-forming composition which comprises at least one relatively high equivalent weight polyol containing an average of about 1.4-1.95 hydroxyl groups per molecule, of which hydroxyl groups at least 30% are primary hydroxyls; a relatively low equivalent weight compound having about 2 active hydrogen containing moieties per molecule; a polyisocyanate and a catalyst.
  • Toluene diisocyanate 2,4- and 4,4-diphenyl methane diisocyanates and the isocyanate-terminated prepolymers thereof are said to be suitable isocyanates.
  • the average functionality of the reactive components i.e., all the active hydrogen containing components and isocyanates
  • the average functionality of the reactive components i.e., all the active hydrogen containing components and isocyanates
  • Urethanes are formed when NCO groups react with hydroxyl groups.
  • the most common method of urethane production is via the reaction of a polyol and an isocyanate which forms the backbone urethane group.
  • a cross-linking agent may also be added.
  • the precise formulation may be varied. Variables in the formulation include the type and amounts of each of the reactants.
  • 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, and 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.
  • 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 conventionally 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.
  • lower molecular weight polyols and lower functionality polyols tend to produce more flexible foams than do heavier polyols and higher functionality polyols.
  • 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.
  • 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 prepolymer 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.
  • a carpet backing comprising a textile having at least one adherent polyurethane backing, the backing being prepared from a polyurethane forming composition which comprises: (A) a polyisocyanate and (B) a mixture of a vegetable oil, a cross-linking agent comprised of a multi-functional alcohol present in a ratio to said vegetable oil such that there are at least 0.7 moles of OH groups per mole of bulk vegetable oil, a catalyst, and a blowing agent.
  • the present invention relates to a cellular material useful in the manufacture of carpet backings that is the reaction product of an A-component and a B-component, wherein the A-component is comprised of an aromatic or aliphatic isocyanate (for example phenyl diisocyanate, 4,4'- biphenylene diisocyanate, 2,4-toIuene diisocyanate, 2,6-toluene diisocyanate (TDI) ditoluene diisocyanate, naphthalene 1,4-diisocyanate, 2,4'- and/or 4,4'-diphenylmethane diisocyanate (MDI), polyniethylene polyphenylene polyisocyanates (polymeric MDI), 1,6-hexamethylene diisocyanate, isophorone diisocyanate, 1,4-cyclohexyl diisocyanate, or any other modified MD
  • an aromatic or aliphatic isocyanate for example pheny
  • an environmentally friendly hydroxylated vegetable oil having a functionality of 1-4 (such as from soybeans);
  • a catalyst (amine or metal, for example).
  • the B-component may also contain:
  • fillers e.g., calcium carbonate, aluminum trihydrate and flyash
  • pigment e.g., calcium carbonate, aluminum trihydrate and flyash
  • the present invention is predicated on the discovery that improved urethane foam carpet backings can be prepared by substituting hydroxylated vegetable oils having a functionality of 1-4 for the vegetable oils and cross linkers employed products, compositions and methods of Pub-910.
  • hydroxylated vegetable oils having a functionality of 1-4 for the vegetable oils and cross linkers employed products, compositions and methods of Pub-910.
  • the inclusion of the hydroxylated vegetable oils in the formulations of the invention eliminates the necessity for including petrol-polyols in the mix ion order to achieve optimal results and properties.
  • the employment of the hydroxylated vegetable oils also removes the necessity for including cross linkers in the formulation.
  • 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.
  • One embodiment of the invention relates to its utilization as a precoat layer for carpet. Traditionally a carpet can be broadloom, tile or rugs, woven or tufted into a primary substrate which is typically a woven or non woven, made of various fiber types such as polypropylene or polyester.
  • a typical construction for example, is a broadloom carpet tufted into a woven polypropylene primary. This construction is then percolated (knife over a roll, sprayed, etc.) on the back component with the biobased polyurethane composition of the invention. This is a very critical part of the process where both application and chemical formulation come together in order to accomplish:
  • the biobased precoat is finish-cured, e.g., in a heated oven.
  • Another embodiment of the invention is its use as a coating over an already precoated carpet described in the above embodiment, in order to laminate thereto a secondary t substrate.
  • This substrate can be a woven, non- woven or a composite of both, made of various fiber types such as polypropylene, polyester or combinations thereof. After the introduction of the secondary into the biobased coating layer the composite is finished cured in a heated oven.
  • This laminated construction offers additional physical stability of the carpet composite through the manufacturing process.
  • the laminated construction offers such additional attributes such as: [0041] a bondable surface for direct adhesive installation;
  • An additional embodiment of the invention is its utilization as a foam coating over the above-described precoated carpet.
  • the carpet construction in then finished cured in a heated oven.
  • the advantages of having applied foam to the carpet are:
  • a still further embodiment of the invention is its use as a foam coating over an already precoated carpet construction described above, followed by introducing a secondary into the foam structure.
  • the secondary substrates that can be employed are described hereinabove.
  • the carpet construction is then finish-cured in a heated oven.
  • Another embodiment of the invention is its employment as a precoat and laminate in a one step-application process.
  • 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 the hydroxylated vegetable oil, catalyst 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 the vegetable oils disclosed by Pub-910 with hydroxylated vegetable oils having a functionality of 1-4 and eliminating the multi-functional alcohol cross- linking agent 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 previously used vegetable oils and crosslmking agent replaced by the hydroxylated vegetable oil of the present invention; all of the other components and general methods being generally known in the art.
  • the qualities of the final flexible or semi-rigid urethane foam produced using the hydroxylated vegetable oil are consistent with those produced using conventional high grade, expensive petrol-based polyol or mixtures thereof with the vegetable oils of Pub-910.
  • urethane foams of varying and selectable final qualities including differing flexibilities, densities, and hardnesses, can be made by varying only the degree of hydrogenation. It would be difficult, if not impossible, to create such varied final foams using a single petroleum-based polyester or polyether polyol with the same variations in the remaining reactants. Instead, different petroleum-based polyols would be required to produce such varied results.
  • functionality the average number of isocyanate reactive sites per molecule. It is calculated according to the following formula:
  • Average functionality (Total moles OH) / (Total moles polyol)
  • the hydoxyl number is a measure of the amount of reactive hydroxyl groups available for reaction. This value is determined by a wet analytical method and is reported as the number of milligrams of potassium hydroxide equivalent to the hydroxyl groups found in one gram equivalent of the sample:
  • hydroxylated vegetable oil employed depends upon the desired characteristics in the resulting product (generally, the higher the functionality, the harder the compound). Hydroxylated soy oils having, but limited to, the following functionalities may be employed in the practice of the invention:
  • hydroxylated vegetable oils suitable for use in the present invention are known in the art as shown in the examples. Alternatively, they may be prepared according to the methods of synthesis disclosed in US patents nos. 4,742,112 and 6,583,302; United States Patent Application Publication nos. 2006004115, 20060041156, 20030232956; 20040010095 and 20060041155; Okieimen et al, European Journal of Lipid Science and Technology, Volume 107, Issue 5 , Pages 330 - 336; UK Patent GB2278350B;
  • Suitable oils that may be hydroxylated for use according to the present invention include, e.g., soy, corn, safflower, sunflower, palm, cottonseed and the like.
  • the A-component isocyanate reactant of the urethane of the invention is preferably comprised of a 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 diphenylmethane diisocyanate (MDI).
  • MDI diphenylmethane diisocyanate
  • the B-component reactant of the urethane reaction includes at least the hydroxylated vegetable oil 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 hydroxylated vegetable oils that are suitable for use are available from Biobased Technologies and described in US application publication no. 20060041155, the entire contents and disclosure of which is incorporated herein by reference.
  • 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 and hydroxylation to the desired functionality, the soy oil is otherwise unmodified. It does not require esterification as is required for some urethane products of the prior art.
  • the preferred B-component reactant used to produce the foam of the invention is generally known in the 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 Mich., methyl isobutyl ketone (MIBK), acetone 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.
  • 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-LV (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.
  • 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.
  • 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-Paste.
  • 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 Ib. per cubic foot and a Shore hardness of durometer from 20/70 and 20/95.
  • a carpet backing comprising a textile having at least one adherent polyurethane backing, the backing being prepared from a polyurethane forming composition which comprises: (A) a polyisocyanate and (B) a mixture of a vegetable oil, a cross-linking agent comprised of a multi-functional alcohol present in a ratio to said vegetable oil such that there are at least 0.7 moles of OH groups per mole of bulk vegetable oil, a catalyst, and a blowing agent.
  • a polyurethane forming composition which comprises: (A) a polyisocyanate and (B) a mixture of a vegetable oil, a cross-linking agent comprised of a multi-functional alcohol present in a ratio to said vegetable oil such that there are at least 0.7 moles of OH groups per mole of bulk vegetable oil, a catalyst, and a blowing agent.
  • a polyurethane forming composition which comprises: (A) a polyisocyanate and (B) a mixture of a vegetable oil, a
  • soy oils contain a significant amount of unreactables (approximately 25 percent), thereby limiting the amount that could be used in the formulation to a maximum of 50 parts.
  • Chain extenders i.e., dipropylene glycol, tripropylene glycol and ethylene glycol were required to maintain physical stability.
  • the hydroxylated oils utilized in the present invention can be formulated with higher parts of fillers. This attribute allows the formulation, for example of 100 parts Agrol, 100 to 600 pts filler loading and 40 parts ISO.
  • the combination of the stability of soy pricing, the rapid renewable aspect, and the acceptance of filler loading allows the manufacturer to address pricing with acceptable quality where such could not be accomplished with the old system or any petro polyol.
  • 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 components may be combined in differing amounts to yield differing results, as will be shown in the Examples presented in the Examples below.
  • the preferred flexible foam of the invention B-component mixture when using the preferred components, is prepared with the following general weight ratios:
  • 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.
  • the blowing agent may comprise any conventionally employed in the art and include methyl isobutyl ketone, acetone, water, mechanically frothed air and the like.
  • polyurethane coatings may be prepared and applied to textiles in the manner described in the U.S. patents described hereinabove as well as U.S. Pat. No. 6,180,686, the entire contents and disclosures of each of which are incorporated herein by reference.
  • the equipment employed to conduct the method consisted of l)a small batching system that could mix up to 600 lbs. of chemicals for trials (2) a blending head for mixing polyols, iso and side adds (3) an applicator station and (4) an oven to cure the products. It was found that by pre-heating the soy polyol to 150° F that the viscosity dropped to 80 centipoise and the filler (coal fly ash) could be charged from 200 up to 600 parts. [0092] It was also found that by maintaining temperature at 150° F, agitating and recirculating the compound that the suspension of high filler loads and stabilization of the compound could be maintained indefinitely. It was also advantageous to heat all of the piping from storage to the blending head to maintain the low viscosity of the compound while moving it from storage to process.

Landscapes

  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne un textile comprenant au moins un dossier adhérent en polyuréthanne, le dossier étant préparé à partir d'une composition formant un polyuréthanne, comprenant : (A) un polyisocyanate et (B) un mélange d'une huile végétale hydroxylée ayant une fonctionnalité comprise entre 1 et 4 et d'un agent gonflant.
PCT/US2006/020437 2006-05-26 2006-05-26 Dossiers de moquette préparés à partir de polyuréthannes à base d'huile végétale hydroxylée WO2007139535A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113087870A (zh) * 2021-03-01 2021-07-09 辽宁石油化工大学 一种基于不同结构大豆油基聚氨酯泡沫的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4688860A (en) * 1985-09-09 1987-08-25 Engineered Data Products, Inc. Truck and holder for tape cartridges

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4688860A (en) * 1985-09-09 1987-08-25 Engineered Data Products, Inc. Truck and holder for tape cartridges

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113087870A (zh) * 2021-03-01 2021-07-09 辽宁石油化工大学 一种基于不同结构大豆油基聚氨酯泡沫的制备方法

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