EP2118180A1 - Schmelzverarbeitbare reaktive pillen mit fähigkeit zur formung von esterkondensaten und verfahren zur formung der schmelzverarbeitbaren reaktiven pillen - Google Patents

Schmelzverarbeitbare reaktive pillen mit fähigkeit zur formung von esterkondensaten und verfahren zur formung der schmelzverarbeitbaren reaktiven pillen

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Publication number
EP2118180A1
EP2118180A1 EP08743481A EP08743481A EP2118180A1 EP 2118180 A1 EP2118180 A1 EP 2118180A1 EP 08743481 A EP08743481 A EP 08743481A EP 08743481 A EP08743481 A EP 08743481A EP 2118180 A1 EP2118180 A1 EP 2118180A1
Authority
EP
European Patent Office
Prior art keywords
reactive
combinations
mixture
pellets
group
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.)
Withdrawn
Application number
EP08743481A
Other languages
English (en)
French (fr)
Inventor
Isao Noda
William Maxwell Allen, Jr.
James Terry Knapmeyer
Michael Matthew Satkowski
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.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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 Procter and Gamble Co filed Critical Procter and Gamble Co
Priority claimed from PCT/US2008/054053 external-priority patent/WO2008101145A1/en
Publication of EP2118180A1 publication Critical patent/EP2118180A1/de
Withdrawn legal-status Critical Current

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Definitions

  • the present invention is directed to a reactive composition
  • a reactive composition comprising either a monomer mixture or reactive prepolymer capable of making crosslinked thermoset resins, particularly alkyd resins, and solid fillers, such as clay particles, formulated to be melt processable.
  • the reactive composition is made into the form of solid pellets which are capable of being fed into melt processing equipment.
  • thermoplastic and thermoset resins are typically derived from petroleum based feedstock.
  • the rising cost of petroleum has prompted the need for alternative robust, low cost materials for producing synthetic materials and corresponding articles manufactured therefrom.
  • Alkyd is a term applied to a group of synthetic thermoset resins best described as polyester condensate resins.
  • This group of material comprises ester condensates of polyhydric alcohols and organic polyacids.
  • Glycerin is the predominant polyhydric alcohol component used in ester condensates. An increasing supply of glycerin has prompted the opportunity for developing a process for forming articles from non petroleum based materials such as alkyd resins.
  • thermoplastic resins such as polyolefins, polypropylene, polyester, etc.
  • thermoplastics Upon heating, thermoplastics become a processable, soft, viscous melt which solidifies or hardens by cooling. After solidification, materials made from thermoplastic resins are not temperature stable and may once again be made molten. They may also creep or plastically deform.
  • Thermoplastic resins can be formed into granular pellets which can be easily fed by themselves or with other additives to an extruder or other process equipment to be melted and processed to fabricate various final products. Thus, the successful preparation of resin pellets often is an important first step of the development of any useful thermoplastic materials.
  • Thermoset resins such as alkyd resins start as liquid monomer or prepolymer mixtures which must be cured by crosslinking chemical reaction.
  • thermoset resins are other typical examples of thermoset resins. Unlike thermoplastics, once cured, thermoset resins are temperature stable and do not creep or plastically deform. As a result, most thermoset resins are not melt processable, and therefore, are not capable of being formed into pellets which can later be melt processed in a manner similar to conventional thermoplastics. Instead, articles made from thermoset resins are formed from liquid oligomers or so called prepolymers poured into a mold where the crosslinking reaction is completed.
  • alkyd monomers and prepolymers can become reasonably fluid upon heating, they are viscous and sticky at room temperature making them difficult to handle.
  • articles made from alkyd resins are capable of being reprocessed to a prepolymer state and formed into new articles; however, such reprocessing requires additional processing steps, energy and cost. Therefore, producing articles from alkyd resins that are typically made from thermoplastic resins could not be performed on the same equipment used in processing thermoplastics.
  • the present invention provides reactive compositions formed into melt processable reactive pellets.
  • the reactive compositions comprise a filler and a reactive mixture capable of making alkyd thermoset resins.
  • the filler can include talc, clay, pulp, ⁇ O 2 , thermoplastic starch, raw starch, wood flour, diatomaceous earth, carbon black, silica, inorganic glass, inorganic salts, pulverized plasticizer, pulverized rubber and combinations thereof.
  • the reactive mixture includes a monomer mixture comprising at least one polyhydric alcohol and a reactant selected from the group consisting of at least one organic polyacid; at least one organic anhydride; and combinations thereof.
  • the reactive mixture comprises a prepolymer formed from the monomer mixture; a combination of the prepolymer and the monomer mixture; or a combination of the prepolymer and reactants such as polyhydric alcohol, organic polyacid, organic anhydride, and combinations thereof.
  • the invention is also directed to a process for making melt processable reactive pellets by combining the aforementioned reactive mixtures and fillers to form a homogeneous mixture.
  • the homogeneous mixture is extruded into strands and cut into pellets.
  • the invention is further directed to articles such as molded objects, sheets, films, fibers, foams and combinations thereof made from the melt processable reactive pellets. 10685/DW
  • Copolymer as used herein is meant to encompass copolymers, terpolymers, and other multiple-monomer polymers.
  • Reactant refers to a chemical substance that is present at the start of a chemical reaction and reacts with one or more other substances or catalysts in or exposed as part of a chemical reaction.
  • Matture refers to a mixture of two or more of any of a defined group of components, unless otherwise specified. Lists of alternative ingredients include mixtures of such ingredients unless otherwise specified.
  • Biodegradable refers to the ability of a compound to ultimately be degraded completely into CH 4 , CO 2 and water or biomass by microorganisms and/or natural environmental factors.
  • Compostable refers to a material that meets the following three requirements: (1) the material is capable of being processed in a composting facility for solid waste; (2) if so processed, the material will end up in the final compost; and (3) if the compost is used in the soil, the material will ultimately biodegrade in the soil.
  • compositions as used herein means that various components, ingredients or steps can be conjointly employed in practicing the present invention. Accordingly, the term “comprising” encompasses the more restrictive terms “consisting essentially of and “consisting of.
  • the present reactive compositions can comprise, consist essentially of, or consist of any of the required and optional elements disclosed herein.
  • the present reactive compositions, processes and articles employ composites comprising particulate fillers and a reactive mixture capable of making crosslinked thermoset resins, particularly alkyd resins, from an ester condensation reaction.
  • the reactive mixture comprises a monomer mixture including polyhydric alcohol and a polyfunctional organic polyacid or anhydride.
  • the reactive mixture can also include a prepolymer made by reacting the monomer mixture to a precros slinking stage, or a combination of the prepolymer and the monomer.
  • the reactive mixture is mixed with fillers forming a reactive composition.
  • the reactive composition is made into small reactive pellets which are capable of storage and free flowing in granular form without conglomerating.
  • the reactive pellets can be readily fed into conventional melt processing equipment similar to those commonly used in the plastics industry for processing thermoplastics. During melt processing, the reactive pellets are heated to an elevated temperature sufficient to induce an ester condensation reaction of the reactive mixture which polymerize and crosslink the mixture by liberating water as a reaction byproduct to open atmosphere.
  • the reactive mixture used in forming the reactive pellets includes polyhydric alcohol.
  • Polyhydric alcohol refers to an alcohol having two or more alcohol (i.e., hydroxyl) functional groups. Any suitable polyhydric alcohol or combination of polyhydric alcohols is of use; however, monomers, oligomers, or short chain polymer polyhydric alcohols having a molecular weight of less than 2000 g/mol are preferred.
  • suitable polyhydric alcohols include: glycerol (also known in the art as glycerin), glycol, sugar, sugar alcohol, and combinations thereof.
  • Non-limiting examples of glycols of use include: ethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, hexane triol, and the like, oligomers thereof, and combinations thereof.
  • Non-limiting examples of sugars of use include: glucose, sucrose, fructose, raffinose, maltodextrose, galactose, xylose, maltose, lactose, mannose, erythrose, pentaerythritol, and mixtures thereof.
  • the polyhydric alcohol comprises glycerol, mannitol, sorbitol, and combinations thereof.
  • the polyhydric alcohol can be present in reactive mixtures of the present invention in an amount of from about 5% to about 80%, from about 10% to about 75%, from about 25% to about 70%, or from about 35% to about 65%.
  • the reactive mixture used in forming the reactive pellets includes organic polyacids and anhydrides.
  • the organic polyacid means an organic acid having two or more acid functionalities and can include, but is not limited to, diacids, triacids (having at least three acid groups), other acids with four or more acid functionalities, acid polymers or copolymers, or mixtures thereof.
  • Such acids include, but are not limited to adipic acid, sebatic acid, citric acid, oxalic acid, malonic acid, succinic acid, glutaric acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, terphthalic acid, and mixtures of two or more thereof.
  • Anhydrides of such acids may also be employed and within the context of the present specification, reference to organic polyacid includes such anhydrides.
  • Monoacids such as lauric acid, stearic acid, myristic acid, palmitic acid, oleic acid, linoleic acid, sebacic acid, acrylic acid, methacrylic acid, itaconic acid, and glycidyl methacrylate may optionally be included in addition to polyacids at any stage.
  • monoacids may be added as processing aids or to modify properties of the final product, e.g. flexibility, strength, etc.
  • organic polyacids and anhydrides can be used including adipic acid, citric acid, maleic acid, maleic anhydride, polyacrylic acid, phthalic anhydride, and the like, as well as their mixtures.
  • Monobasic acids especially fatty acids like stearic acid, lauric acid, oleic acid, and linoleic acid, can also be incorporated into the reaction mixture.
  • Other functional compounds with reactive acid or alcohol functionality, such as oligomeric silicone or polyethylene glycol, may also be incorporated.
  • the organic polyacid or anhydride is employed in the reactive mixtures of the present invention in an amount of from about 5% to about 80%, from about 10% to about 75%, from about 25% to about 70%, or from about 35% to about 65%.
  • triglycerides which are also known in the art as triacylglycerols, may also be included in the reactive mixture.
  • triglycerides of use include: tristearin, triolein, tripalmitin, 1 ,2-dipalmitoolein, 1,3-dipalmitoolein, l-palmito-3-stearo-2-olein, 10685/DW
  • Suitable triglycerides may be added to the present reactive compositions in neat form. Additionally, or alternatively, oils and/or processed oils containing suitable triglycerides may be added to the reactive compositions.
  • oils include coconut oil, corn germ oil, olive oil, palm seed oil, cottonseed oil, palm oil, rapeseed oil, sunflower oil, whale oil, soybean oil, peanut oil, linseed oil, tall oil, and combinations thereof.
  • triglycerides are employed in the reactive mixture in an amount up to about 75%, or from about 2% to about 50%, or from about 5% to about 25%.
  • combinations of acid and triglyceride are employed in the reactive mixture.
  • the total amounts of acid and triglyceride is from about 20% to about 80%, from about 30% to about 70%, or from about 40% to about 60%.
  • the molar ratio of the alcohol functional groups to the total of ester and acid functional groups is at least about 1: 1, or at least about 4: 1. In some embodiments, the molar ratio is from about 1:1 to about 200:1, or from about 1:1 to about 50:1.
  • the reactive mixture of the present invention may also include monobasic acid, and appropriate amounts of monoglyceride, or diglyceride as alternatives to triglyceride. Additional components
  • the reactive mixtures used in forming the reactive pellets may further include one or more additional components as desired for the processing and/or end use of the composition. Additional components may be present in any suitable amount. In some embodiments, additional components may be present in an amount of from about 0.01% to about 35% or from about 2% to about 20% by weight of the reactive mixture. Non-limiting examples of additional components include, but are not limited to, additional polymers, processing aids and the like.
  • Non-limiting examples of additional polymers of use include: polyhydroxyalkanoates, polyethylene, polypropylene, polyethylene terephthalate, maleated polyethylene, maleated polypropylene, polylactic acid, modified polypropylene, nylon, caprolactone, and combinations thereof. Additional polymers also include polyvinyl alcohol and polyhydric alcohols having molecular weights of greater than 2000 g/mol.
  • polyesters containing aliphatic components are suitable 10685/DW
  • ester polycondensates containing aliphatic constituents and poly(hydroxycarboxylic acid) are preferred.
  • the ester polycondensates include, but are not limited to: diacids/diol aliphatic polyesters such as polybutylene succinate, and polybutylene succinate co-adipate; aliphatic/aromatic polyesters such as terpolymers made of butylenes diol, adipic acid, and terephthalic acid.
  • the poly(hydroxycarboxylic acids) include, but are not limited to: lactic acid based homopolymers and copolymers; polyhydroxybutyrate; and other polyhydroxyalkanoate homopolymers and copolymers. In some embodiments, a homopolymer or copolymer of poly lactic acid is preferred. Modified polylactic acid and different stereo configurations thereof may also be used. Suitable polylactic acids typically have a molecular weight range of from about 4,000 g/mol to about 400,000 g/mol . Examples of suitable commercially available poly lactic acids include NATUREWORKSTM from Cargill Dow and LACEATM from Mitsui Chemical.
  • polystyrene resin sold as BIONOLLETM 1000 and BIONOLLETM 3000 from the Showa Highpolmer Company, Ltd. Located in Tokyo, Japan.
  • An example of a suitable commercially available aliphatic/aromatic copolyester is the poly(tetramethylene adipate-co- terephthalate) sold as EASTAR BIOTM Copolyester from Eastman Chemical or ECOFLEXTM from BASF.
  • the biodegradable polymer or combination of polymers may comprise polyvinyl alcohol.
  • biodegradable polymers and combinations thereof may be present in an amount of from about 0.1% to about 70%, from about 1% to about 50%, or from about 2% to about 25%, by weight of the reactive mixture.
  • Processing aids are generally present in the reactive mixture in amounts of from about 0.1% to about 3% or from about 0.2% to about 2% by weight of the reactive mixture.
  • processing aids include: lubricants, anti-tack, polymers, surfactants, oils, slip agents, and combinations thereof.
  • processing aids include: Magnesium stearate; fatty acid amides; metal salts of fatty acids; wax acid esters and their soaps; montan wax acids, esters and their soaps; polyolefin waxes; non polar polyolefin waxes; natural and synthetic paraffin waxes; fluoro polymers; and silicon.
  • CrodamideTM CrodamideTM (Croda, North Humberside, UK), AtmerTM (Uniqema, Everberg, Belgium,) and EpostanTM (Nippon Shokobai, Tokyo, JP).
  • additives can be present in the reactive mixture to impart additional physical properties to the final product or material formed therefrom.
  • additives include compounds 10685/DW
  • Such compounds include oligomeric silicone, polyethylene glycol and combinations thereof
  • the fillers mixed with the reactive mixture providing the reactive composition which is formed into reactive pellets comprise solid particulates having an equivalent diameter of less than 300 microns, less than 100 microns or less than 50 microns.
  • Non-limiting examples of fillers present in the reactive composition of the present invention include: talc, clay, pulp, wood, flour, walnut shells, cellulose, cotton, jute, raffia, rice chaff, animal bristles, chitin, Ti ⁇ 2 , thermoplastic starch, raw starch, granular starch, diatomaceous earth, nanoparticles, carbon fibers, kenaf, silica, inorganic glass, inorganic salts, pulverized plasticizer, pulverized rubber, polymeric resins and combinations thereof.
  • inorganic fillers such as the oxides of magnesium, aluminum, silicon, and titanium may also be added as inexpensive fillers or processing aides.
  • inorganic materials include hydrous magnesium silicate, titanium dioxide, calcium carbonate, boron nitride, limestone, mica glass quartz, and ceramics.
  • inorganic salts including alkali metal salts, alkaline earth metal salts, phosphate salts, may be used as processing aides.
  • Another material that can be added is a chemical composition formulated to further accelerate the environmental degradation process such as cobalt stearate, citric acid, calcium oxide, and other chemical compositions found in U.S. patent 5,854,304 to Garcia et al.
  • the aforementioned fillers and combinations thereof may be present in the reactive composition forming the reactive pellets in an amount of from about 25% to about 80%, from about 30% to about 70%, or from about 50% to about 65%, by weight of the reactive composition.
  • alkyd resins are made from the condensation reaction of a reactive mixture comprising monomers, such as polyhydric alcohol and a polyfunctional organic polyacid, or from an oligomer which is prepolymer made by reacting the monomer mixture to a precros slinking stage where condensation reaction has already at least partially, but not completely taken place between the polyhydric alcohol and the acid.
  • a reactive mixture comprising monomers, such as polyhydric alcohol and a polyfunctional organic polyacid, or from an oligomer which is prepolymer made by reacting the monomer mixture to a precros slinking stage where condensation reaction has already at least partially, but not completely taken place between the polyhydric alcohol and the acid.
  • the composition which is formed will convert to a water stable alkyd resin composition.
  • the reactive mixture can be 10685/DW
  • the resulting extrudate comprises a reactive mixture, which may be further processed, if desired, and which is convertible to water stable compositions by further heating.
  • the reactive mixture can therefore be provided in this embodiment in a form which facilitates handling, further processing, or the like.
  • the reactive mixture can be combined with filler forming a reactive composition in accordance with the present invention that can be extruded into a solid form.
  • the reactive composition extrudate is formed into reactive pellets which are suitable for melt processing.
  • the further melt processing of the reactive pellets to form films, sheets, coatings, and molded articles, or other desired product forms may be conducted under sufficient conditions of temperature and time to effect the conversion of the reactive composition to a water stable composition or product.
  • the melt processing is not conducted under sufficient conditions of temperature and time to effect the conversion of the reactive composition to a water stable composition, the resulting reactive composition can be subsequently heated and converted to a water stable product.
  • the reactive monomer mixture or prepolymer is mixed with a substantial amount of particulate fillers previously described, such that the rheological consistency of the mixture is suited for producing melt processable reactive pellets.
  • the monomer mixture or prepolymer can be heated to make it sufficiently fluid for easy mixing with particulate fillers.
  • the temperature of the reactive mixture ranges from about 80 0 C to about 130 0 C and the viscosity of the reactant mixture can be less than about 1000 poise, less than about 500 poise, less than about 200 poise, and less than about 100 poise.
  • a sufficient amount of particulate fillers are added to achieve the consistency of pliable dough or molten plastic which can be extruded into strands and cut into small pellets. Upon cooling, the pellets become sufficiently hard and non sticky maintaining a granular form without conglomerating to facilitate handling.
  • melt processing equipment such as an extruder coupled with an injection mold, in a manner similar to the processing of conventional thermoplastic resins.
  • the ester condensation reaction resulting in crosslinking is below the gel point for the alkyd condensation reaction.
  • the gel point is defined as the state at which enough polymer chains formed by the products of the reactants are bonded together such that at least one very large molecule is coextensive with the polymer phase and flow is no longer possible such that the material behaves more like a solid. It is desirable for the reactant mixture to be below the gel point before final processing so as to retain sufficient flow behavior to enable shaping of the mixture into articles.
  • the condensation reaction of the reactive mixture may proceed to a point where prepolymers such as oligomers or even larger molecules are formed, yet the mixture retains the ability to flow and be shaped into useful articles.
  • the reactive pellets according to the present invention can be formed by melt mixing and/or extruding a reactive composition including a reactive mixture comprising reactive monomer mixture or prepolymer and filler using conventional mixing and/or extrusion techniques.
  • the components are typically mixed using conventional compounding techniques.
  • the objective of the compounding step is to produce a visually homogeneous melt composition.
  • a suitable mixing device is a multiple mixing zone twin screw extruder with multiple injection points.
  • the multiple injection points can be used to add the reactive mixture and filler.
  • a twin screw batch mixer or a single screw extrusion system can also be used. As long as sufficient mixing and heating occurs, the particular equipment used is not critical.
  • An alternative method for compounding the materials comprises adding reactive mixtures to an extrusion system where they are mixed in progressively increasing temperatures. For example, a twin screw extruder with six heating zones may be employed. However, it may not be necessary to extrude a melt mixture in order to form the pellets, and, in general, any method known in the art or suitable for the purposes hereof can be used to combine the ingredients of the components to 10685/DW
  • the crosslinking reaction can be completed either during the melt processing of the reactive pellets or by an additional post curing step following the melt processing.
  • the ester condensation reaction of the reactive mixture is induced, and/or driven towards completion through the application of heat during melt processing. Water produced as a reaction byproduct is effectively removed to promote the reaction.
  • the reaction mixture temperature may be between about 100 0 C and about 300 0 C, between about 120 0 C and about 280 0 C, or between about 150 0 C and about 260 0 C to drive the crosslinking reaction to completion during melt processing.
  • a catalyst may be used to initiate and/or accelerate the ester condensation and/or transesterification reactions.
  • Any suitable catalyst is of use.
  • Non-limiting examples of useful catalysts include Lewis acids.
  • Non-limiting examples of catalysts include para-toluenesulfonic acid, methanesulfonic acid, and linear alkylbenzenesulfonic acid.
  • Completing the crosslinking reaction via post curing can be accomplished in a conventional convective or radiant oven or microwave oven, as well as other means to heat the product during the post curing step to complete the ester condensation reaction and corresponding final removal of water from the article.
  • a conventional convective or radiant oven or microwave oven as well as other means to heat the product during the post curing step to complete the ester condensation reaction and corresponding final removal of water from the article.
  • article is meant to encompass articles made solely from, or having at least one portion made from melt processable reactive pellets according to the present invention.
  • Articles include, but are not limited to extruded articles such as: films, sheets, laminates, coatings, and foams; molded articles; and combinations thereof.
  • Personal hygiene articles and absorbent articles may be articles or comprise articles made from reactive compositions of the present invention. 10685/DW
  • the article is a film.
  • film means a thin continuous material or substrate having a high length to thickness ratio and a high width to thickness ratio, "high” meaning a ratio of over about 10:1. While there is no requirement for a precise upper limit of thickness, an upper limit would be about 0.254 mm, about 0.01 mm, or about 0.005 mm.
  • the films of the present invention can be employed in a variety of disposable products including, but not limited to, disposable personal hygiene articles (e.g., diapers, catamenials and the like), wrapping (e.g., food wraps, consumer product wraps, pallet and/or crate wraps, and the like), or bags (grocery bags, food storage bags, sandwich bags, resealable bags, garbage bags, and the like).
  • disposable personal hygiene articles e.g., diapers, catamenials and the like
  • wrapping e.g., food wraps, consumer product wraps, pallet and/or crate wraps, and the like
  • bags grocery bags, food storage bags, sandwich bags, resealable bags, garbage bags, and the like.
  • the protective value of the present films may depend on its being continuous, i.e., without holes or cracks, such that it may serve as an efficient barrier to molecules such as atmospheric water vapor, and/or oxygen.
  • the films are liquid impervious and suitable for use in
  • Films of the present invention may have a number of physical characteristics, such as biodegradability and compostability, for example. Films that perform well as compostable backsheets in personal hygiene articles including, but not limited to, diapers and feminine hygiene pads, may have characteristics such as those described in U.S. Patent Number 5,498,692.
  • the films of the present invention may be made using any suitable process that is used for producing single or multilayer films. Non-limiting examples of methods of use include cast film blowing, cast film extrusion and blown film extrusion. These methods as well as other suitable methods are described in U.S. Patent Number 5,498,692.
  • strands, pellets, or powders made from the presently disclosed reactive compositions, as well as combinations thereof are dry blended and melt mixed in a film extruder.
  • the strands, pellets, powders and combinations thereof can be first dry blended and then melt mixed in a pre- compounding extruder followed by re-pelletization prior to film extrusion. Foams
  • the article is foam.
  • foam refers to the reactive compositions of the present invention wherein the apparent density has been substantially decreased by the presence of numerous cells distributed throughout its 10685/DW
  • Such two-phase gas/solid systems in which the solid is continuous and composed of a synthetic polymer or rubber include cellular polymers (or copolymers), expanded plastics and foamed plastics (ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY, Vol. 11, John Wiley & Sons, New York (1980)).
  • the gas phase may be distributed into pockets or voids called "cells" which are classified into two types, open and closed.
  • Open-celled materials are foams the cells of which are interconnected such that gases may pass freely through the cells.
  • Closed-cell materials have cells that are discrete and isolated from each other.
  • Foams are further categorized into flexible and rigid foams. This classification is based on a particular ASTM test procedure (see ASTM D, Vol. 37, pp. 1566-1578, American Society of Testing and Materials, Philadelphia, Pa., (1978)). Flexible foam is foam which does not rupture when a 20 x 2.5 x 2.5 cm piece is wrapped around a 2.5 cm mandrel at a uniform rate of 1 lap/5s at 15-25°C. Foams that do rupture under this test are referred to as rigid foams.
  • Foams according to the present invention may find any suitable use including, but not limited to, packaging, comfort cushioning, insulation, structural components and the like.
  • a foamed material having increased biodegradability and/or compostability would offer superior benefits to packaging that is currently used, such as polystyrene, paper and starch foams for example.
  • polystyrene offers significantly higher thermal insulation over the only currently degradable alternative, paper wraps.
  • Foamed articles comprising the reactive compositions of the present invention have the thermal insulating properties of polystyrene, yet are biodegradable and/or compostable. These materials are ideal for hot food take-out and cold food packaging.
  • Foamed polystyrene chips are used as cushioned packing materials for consumer and industrial goods. Many of these chips are disposed of in landfills. Foamed chips comprising a reactive composition of the present invention can perform like polystyrene yet have increased biodegradability and/or compostability. Moreover, foamed chips according to the present invention may be water stable.
  • foams of the present invention may be made using any suitable process. Non- limiting examples of methods are described in U.S. Patent Number 5,498,692. Molded Articles
  • the article is a molded article.
  • molded articles refer to objects that are formed from the reactive composition.
  • melt processable reactive pellets formed from the reactive composition of the present invention may be melt processed and subsequently, for example, injected, compressed, or blown by means of a gas into shape defined by a female mold.
  • objects can be solid objects like toys, or hollow like bottles and containers. Methods of making molded articles are described in further detail in U.S. Patent Number 5,498,692. Disposable Personal Care Products
  • the present invention further relates to disposable personal care products comprising reactive compositions of the present invention.
  • disposable personal care absorbent articles comprise a liquid pervious topsheet, a liquid impervious backsheet comprising a film of the present invention, and an absorbent core positioned between the topsheet and backsheet.
  • the personal care absorbent articles are compostable. Non- limiting examples of such absorbent articles include infant diapers, adult incontinent briefs and pads, and feminine hygiene pads and liners.
  • Additional personal care products comprising a reactive composition of the present invention include, but are not limited to: personal cleansing wipes; disposable health care products such as bandages, wound dressings, wound cleansing pads, surgical gowns, surgical covers, surgical pads; other institutional and health care disposables such as gowns, wipes, pads, bedding items such as sheets and pillowcases, foam mattress pads.
  • the absorbent articles according to the present invention may be biodegradable and/or compostable to a greater extent than conventional absorbent articles which employ materials such as a polyolefin (e.g., a polyethylene backsheet).
  • a polyolefin e.g., a polyethylene backsheet
  • Example 1 1,000 g of the mixture of glycerol, maleic anhydride, and HLAS in Example 1 is heated to 140 0 C to carry out the condensation reaction between maleic anhydride and glycerol to produce oligomeric reactive prepolymer. The reaction is stopped and cooled below 100 0 C within 40 minutes to keep the mixture from gelling. Other reactive prepolymers are also made in a similar manner by using the other reactive monomer mixtures of Example 1.
  • Example 2 450 g of the warm reactive glycerol maleate prepolymer Example 2 is mixed with 550 g of kaolin clay (Unimin Corporation, Snobrite) using a laboratory mixer to produce a soft dough.
  • the dough is further mixed by passing it through an electric meat grinder (Kitchen Aid, St. Joseph, MI).
  • the dough mixture is fed to a co-rotating extruder (Berstorff Ultraglide), with the zone temperature setting of 106 0 F, 160 0 F, 200 0 F, 271°F, 300 0 F, 325°F, and 350 0 F, which is operated with the screw speed at 150 rpm.
  • a strand of the hot extrudate is cooled on an air table and then pelletized with a Berlyn pelletizer (Worcester, MA).
  • a similar procedure is used for making pellets with other reactive prepolymers of Example 2.
  • Example 1 400 g of 140 0 C mixture of glycerol and maleic anhydride of Example 1 is mixed with 600 g of kaolin clay (Unimin Corporation, Snobrite) using a laboratory mixer to produce a soft dough. The dough is further mixed by passing it through a meat grinder (Kitchen Aid, St. Joseph, MI). The dough mixture is fed to a co-rotating extruder (Berstorff Ultraglide), with the zone temperature setting of 106 0 F, 160 0 F, 200 0 F, 271°F, 300 0 F, 325°F, and 350 0 F, which is operated with the screw speed at 150 rpm. A strand of the hot extrudate is cooled on an air table and then pelletized with a Berlyn pelletizer (Worcester, MA). A similar procedure is used for making pellets with other monomer mixtures of Example 1.
  • a meat grinder Karlin Aid, St. Joseph, MI
  • the dough mixture is fed to a co-rotating extruder (Ber
  • Example 3 The melt processable reactive pellets of Example 3 are fed to an extruder (Berstorff Ultraglide) coupled with an injection molder (Arburg GmbH), and molded articles are produced in a manner similar to ordinary plastic articles. Some of the molded articles are baked in an oven at 90 0 C for 16 hours to further complete the curing of the reactive component. 10685/DW

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  • Compositions Of Macromolecular Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)
EP08743481A 2007-02-15 2008-02-15 Schmelzverarbeitbare reaktive pillen mit fähigkeit zur formung von esterkondensaten und verfahren zur formung der schmelzverarbeitbaren reaktiven pillen Withdrawn EP2118180A1 (de)

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US90148607P 2007-02-15 2007-02-15
PCT/US2008/054053 WO2008101145A1 (en) 2007-02-15 2008-02-15 Melt processable reactive pellets capable of forming ester condensates and process for forming melt processable reactive pellets

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EP (1) EP2118180A1 (de)
JP (1) JP2010519352A (de)
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US20110196108A1 (en) * 2010-02-05 2011-08-11 Isao Noda Gel Point Modification In Alkyd Resin Manufacture
WO2012028496A1 (de) * 2010-08-31 2012-03-08 Basf Se Verzweigte polyester auf basis von zitronensäure sowie deren herstellung und verwendung

Family Cites Families (5)

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US3825517A (en) * 1972-05-25 1974-07-23 Reichhold Chemicals Inc Thermosetting polyester molding compositions and method of preparation
EP0021690B1 (de) * 1979-06-11 1984-12-19 Premix, Inc. Verfahren zur Herstellung von festem härtbarem Polyester in Form von Pellets
JPS63261610A (ja) * 1987-04-17 1988-10-28 日立化成工業株式会社 電気絶縁用樹脂組成物および電気絶縁処理方法
JP2756825B2 (ja) * 1989-05-15 1998-05-25 昭和電工株式会社 アリル系熱硬化性樹脂組成物
JPH1143519A (ja) * 1997-07-30 1999-02-16 Dainippon Ink & Chem Inc 活性エネルギー線硬化樹脂組成物

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Title
See references of WO2008101145A1 *

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JP2010519352A (ja) 2010-06-03
CN101616966A (zh) 2009-12-30

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