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WO2013003591A2 - Composites polymères résistant à l'humidité - Google Patents

Composites polymères résistant à l'humidité Download PDF

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Publication number
WO2013003591A2
WO2013003591A2 PCT/US2012/044647 US2012044647W WO2013003591A2 WO 2013003591 A2 WO2013003591 A2 WO 2013003591A2 US 2012044647 W US2012044647 W US 2012044647W WO 2013003591 A2 WO2013003591 A2 WO 2013003591A2
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WO
WIPO (PCT)
Prior art keywords
composition
coupling agent
composite
desiccant
cellulosic material
Prior art date
Application number
PCT/US2012/044647
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English (en)
Other versions
WO2013003591A3 (fr
Inventor
Jeffrey Jacob Cernohous
Adam R. Pawloski
Neil R. Granlund
Original Assignee
Interfacial Solutions Ip, Llc
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Filing date
Publication date
Application filed by Interfacial Solutions Ip, Llc filed Critical Interfacial Solutions Ip, Llc
Publication of WO2013003591A2 publication Critical patent/WO2013003591A2/fr
Publication of WO2013003591A3 publication Critical patent/WO2013003591A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/045—Reinforcing macromolecular compounds with loose or coherent fibrous material with vegetable or animal fibrous material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C08L23/12—Polypropene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2323/10—Homopolymers or copolymers of propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/14—Polymer mixtures characterised by other features containing polymeric additives characterised by shape
    • C08L2205/16—Fibres; Fibrils

Definitions

  • This disclosure is directed to polymer composites containing cellulosic materials that are moisture resistant and possess desired color fastness.
  • a coupling agent e.g., a polystyrene, a polystyrene, and a polystyrene.
  • Synthetic fiber reinforced thermoplastic composite materials have become staples for automotive, construction, defense, aerospace and consumer products. Most of these composites are derived from glass or carbon fiber reinforced engineering thermoplastics. However, polyolefin based composite materials are being applied in cost sensitive applications that demand higher performance. Examples include glass reinforced polypropylene (PP) composites and natural fiber reinforced polyolefin composites. Wood polymer composite based products (WPC's) have rapidly penetrated non- structural wood applications because they offer the consumer low maintenance attributes and durability.
  • PP polypropylene
  • WPC's Wood polymer composite based products
  • WPC's have found broad application in the building and construction industry, especially for non-structural applications. These materials typically comprise a thermoplastic matrix filled with 20 to 80 wt % of a cellulosic fiber. As a result, the composite is often very sensitive to moisture. When a composite component is exposed to high humidity conditions, it is not uncommon for it to absorb as much as 10% of its mass in moisture. This absorption, and the resulting swelling, can have an extremely deleterious effect on the composite's dimensional stability, color fastness, microbial resistance and aesthetics. Additives have been utilized to improve the mechanical properties and moisture resistance of WPC's. However, conventional technologies arguably do not provide adequate protection for these applications. The WPC's often exhibit poor moisture resistance, which in turn may cause the color or aesthetics of the article to fade when exposed to wet or humid environments over time.
  • the moisture resistance, weatherability and color fastness of WPC's may be enhanced by the inclusion of a coupling agent and a multifunctional coupling agent.
  • the combination of a coupling agent with a multifunctional coupling agent at specific loading levels in WPC's enhances the moisture resistance and color fastness of the WPC.
  • WPC's containing the specific materials also demonstrated greater retention of mechanical properties after steam exposure.
  • composite formulations containing the present combination exhibited slight darkening rather than lightening in color after steam exposure.
  • the additives provided better color retention and fastness when compared to conventional composite formulations.
  • a desiccant is utilized to address the moisture content of raw material for WPC's during melt processing and allow the coupling agent to function properly.
  • color fastness means a polymeric composite material that retains at least its original color without fading after exposure to moisture over an extended or repeated period of time.
  • coupling agent means a composition that improves the compatibility and interfacial adhesion between the thermoplastic matrix and the cellulosic material and any other fillers or materials.
  • “desiccant” means a material that can effectively irreversibly react with or bind water under melt processing conditions.
  • multifunctional coupling agent means a composition having at least two distinct functional groups all capable of interaction with other materials in a melt processable composition.
  • “resistance to moisture” or “moisture resistance” means a polymeric composite material that does not absorb more than the greater of (i) 2.5% water by weight of the total composite, or (ii) 8.5% by weight of cellulosic material, when allowed to soak in a room temperature bath for over 35 days.
  • hydrophilic synergist means a water soluble or dispersible material that when combined with a desiccant improves the efficacy or kinetics of its reaction with moisture.
  • the combination of a coupling agent and a multifunctional coupling agent in a polymer and cellulose composite enhances the moisture resistance and color fastness of the resulting WPC.
  • the function of the multifunctional coupling agent in the WPC may also be addressed by a tetraalkyl orthosilicate compound.
  • the composite derived from the combination of the polymeric matrix, a cellulosic material, a coupling agent, and a multifunctional coupling agent exhibits exceptional moisture resistance and color fastness upon repeated or extended exposure to water or water vapor.
  • the optional use of a desiccant and hydrophilic synergist during melt processing can reduce moisture present in the raw materials.
  • the polymeric matrix functions as the host polymer and is a primary component of the melt processable composition.
  • a wide variety of polymers conventionally recognized in the art as suitable for melt processing are useful as the polymeric matrix.
  • the polymeric matrix includes polymers that are suitable for melt processing, especially when combined with cellulosic materials. Both hydrocarbon and non-hydrocarbon polymers are applicable.
  • useful polymeric matrices include, but are not limited to, polyamides, polyimides, polyurethanes, polyolefmes, polystyrenes, polyesters, polycarbonates, polyketones, polyureas, polyvinyl resins, polyacrylates, and polymethylacrylates.
  • the polymeric matrix may comprise from about 20% to about 90% by weight of the entire composition.
  • polymeric matrices may include high density polyethylene (HDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), polypropylene (PP), polyolefm copolymer (e.g., ethylene -butene, ethylene -octene, ethylene vinyl alcohol), polystyrene, polystyrene copolymers (e.g., high impact polystyrene, acrylonitrile butadiene styrene copolymer) polyacrylates, polymethacrylates, polyesters, polyvinylchloride (PVC), fluoropolymers, liquid crystal polymers, polyamides, polyether imides, polyphenylene sulfides, polysulfones, polyacetals, polycarbonates, polyphenylene oxides, polyurethanes, thermoplastic elastomers, epoxies, alkyds, melamines, phenolics, urethanes, thermoplastic e
  • Useful polymeric matrices include blends of various thermoplastic polymers and blends thereof containing conventional additives such as antioxidants, light stabilizers, fillers, fibers, antiblocking agents, heat stabilizers, impact modifiers, biocides, compatibilizers, flame retardants, plasticizers, tackifiers, colorants and pigments.
  • the polymeric matrix may be incorporated into the melt processable composition in the form of powders, pellets, granules, or in any other extrudable form.
  • Cellulosic materials may be utilized in melt processable compositions as fillers to impart specific physical characteristics, reduce cost of the finished composition or both.
  • Cellulosic materials generally include natural or wood based materials having various aspect ratios, chemical compositions, densities, and physical characteristics.
  • Non-limiting examples of cellulosic materials include wood flour, wood fibers, sawdust, wood shavings, newsprint, paper, flax, hemp, rice hulls, kenaf, jute, sisal, and peanut shells.
  • Combinations of cellulosic materials and a modified polymer matrix may also be used in the melt processable composition. The amount of cellulosic filler in the composite material may be adjusted to address end use processing.
  • cellulosic filler amounts may be adjusted in the composite to prevent defects in thermoforming applications, such as tearing during molding.
  • the cellulosic materials may be included in the WPC in amount from about 10% to about 90% by weight.
  • a master batch with greater than 60% by weight of cellulosic materials may be created and subsequently let down into a host polymer.
  • the melt processable composition includes coupling agents to improve the compatibility and interfacial adhesion between the thermoplastic matrix and the cellulosic material and any other fillers.
  • coupling agents include functionalized polymers, organotitanates and organozirconates.
  • Preferred functionalized polymers included functionalized polyolefms, maleated polyolefms, polyethylene-co-vinyl acetate, polyethylene-co-acrylic acid, and polyethylene-co-acrylic acid salts.
  • the coupling agents may be included in the WPC in amount from about 0.25% to about 15% by weight. In certain embodiments, the coupling agent may be included at about 0.5% to about 5% by weight.
  • a multifunctional coupling agent has at least two distinct functional groups all capable of interaction with other materials in the melt processable composition, such as for example, other coupling agents and available hydroxyl groups on fillers. With no desire to bound by theory, it is believed that the interaction between the multifunctional coupling agent make take the form of covalent bonding, ionic bonding, hydrogen bonding, dipole bonding or attraction by van der Waals forces.
  • Non- limiting examples of multifunctional coupling agents include various organosilanes.
  • 3-glycidoxypropyltrimethoxysilane is well suited to prevent moisture uptake of the WPC and exhibits a very desirable color fastness.
  • alkoxysilanes are desirable.
  • the multifunctional coupling agent may be included in the WPC in amount from about greater than 1.0% to about 5% by weight. Alternatively, the multifunctional coupling agent may be 3.5%) to 10%o by weight of the cellulosic material.
  • terra alkyl orthosilicates are used with the coupling agent in the WPC to generate a resulting product that is resistant to moisture and does not fade in color over time.
  • tetraethyl orthosilicate is well suited to for achieving moisture resistance and color fastness in WPC applications.
  • the tetra alkyl orthosilicate may be included in the WPC in amount from about 0.25% to about 5% by weight.
  • a desiccant is utilized to address the moisture content of any additive or filler during melt processing.
  • the function of the desiccant in the melt blend is to tie up the moisture present in the filler, any additives, and the polymer matrix in order to allow the coupling agent to serve its intended function.
  • the desiccant may be any conventional material capable of moisture uptake and suitable for application in melt processed polymeric matrices.
  • the desiccant is selected from calcium oxide, magnesium oxide, strontium oxide, barium oxide, aluminum oxide, or combinations thereof.
  • the amount of desiccant will vary, but may include a range of about 1 to 80 wt % of the formulation in the compatibilizer blend.
  • a hydrophilic synergist is added to improve the efficacy of the desiccant material at scavenging moisture during melt processing.
  • the hydrophilic synergist acts to help disperse the desiccant in the polymeric matrix, subsequently exposing more surface area to moisture and improving the overall kinetics and efficiency of the moisture scavenging event.
  • suitable hydrophilic synergists include polyalkylene oxide polymers and copolymers and polyvinyl alcohol copolymers, and organic polyols (e.g., glycerol, pentaerythirtol).
  • the desiccant and optional hydrophilic synergist may improve the processibility and reduce the surface defects encountered when melt processing polymeric matrices containing fillers.
  • the desiccant and optional hydrophilic synergist may be pre-compounded in a thermoplastic carrier to form a concentrate and subsequently added to a filled polymeric matrix to improve dispersion, processibility, and reduce melt defects.
  • the concentrate may be supplied separately as a pellet or masterbatch concentrate to the melt processable composition.
  • the additive may optionally include the hydrophilic synergist and/or a polymeric carrier material.
  • XP340 from Interfacial Solutions LLC (River Falls, WI).
  • the melt processable composition can be prepared by any of a variety of ways.
  • the polymeric matrix, filler, coupling agent, multifunctional coupling agent and desiccant can be combined together by any of the blending means usually employed in the plastics industry, such as with a compounding mill, or a Banbury mixer.
  • the melt processable materials may be used in the form, for example, of a powder, a pellet, or a granular product. The mixing operation is most conveniently carried out at a temperature above the melting point or softening point of the polymeric matrix.
  • the resulting melt- blended mixture can be either extruded directly into the form of the final product shape or pelletized or otherwise comminuted into a desired particulate size or size distribution and fed to an extruder, which typically will be a single-screw extruder, that melt-processes the blended mixture to form the final product shape.
  • WPC may be injection molded.
  • the resulting composite exhibits superior performance results.
  • melt-processing typically is performed at a temperature from 120° to 300° C, although optimum operating temperatures are selected depending upon the melting point, melt viscosity, and thermal stability of the composition. Different types of melt processing equipment, such as extruders, may be used to process the melt processable compositions of this invention. Those of ordinary skill in the art in polymer processing are able to select appropriate operating conditions based upon the specific materials utilized in the composite.
  • a WPC comprised of a polypropylene matrix, wood flour, maleated polypropylene and an epoxysilane, exhibit desirable tensile strength, increases in flexural modulus, and flexural strength and impact strength.
  • CIE L*a*b* CIELAB is the most complete color space specification. It is often used to describe the colors visible to the human eye and was created to serve as a reference model.
  • the three coordinates of CIELAB represent the lightness of the color (L*), its position between red/magenta and green (a*), and its position between yellow and blue (b*).
  • An L* value of zero represents black and an L* value of 100 indicates white.
  • the L* value is used to demonstrate fading or lightening of the WPC after exposure to steam over a given period of time.
  • the L* value of the resulting WPC after exposure to steam for a twenty-four hour period, does not increase.
  • An increase in the L* value would represent an undesirable lightening of the material.
  • Wood materials are hydrophilic and tend to absorb water. With the absorption of water, a conventional WPC will generally tend to fade in color. Color fastness, for the purpose of this disclosure, indicates a resistance to fade, which may be measured according to the L* value of the WPC.
  • An increase in the L* value essentially a move toward the L* limit of 100, is considered whitening or fading of the material. In certain commercial applications, it is preferred that the WPC's retain this color over continued use, particularly under exposure to continuous wet or moist environments.
  • the WPC may be applied to household applications that are subject to continued dishwashing. It is important under those circumstances that the material minimally fades over its useful life.
  • the resulting WPC may even demonstrate a negative change in its L* value after exposure to moisture. A negative change in L* is an indication of darkening. Often this may be desirable aesthetic property and comparable to the aging of wood.
  • the desired L* value having no change, or a negative change is coupled with an increase in the a* value.
  • a negative change in a* values indicate a move toward green while positive values indicate magenta.
  • the combined coupling agent and multifunctional coupling agent enable a darkening of the WPC after exposure to water or water vapor over time. The darkening is exemplified by either no change, or a negative change, in the L* value and a positive change in the a* value. Certain embodiments exhibit a negative change in L* of 5 points or more and positive change in a* of 5 or more points.
  • Some embodiments prevent the significant uptake of moisture by cellulose materials that are generally very hydrophilic.
  • certain embodiments are capable of achieving an average water uptake of (i) 2.5% water by weight of the total composite, or (ii) 8.5% by weight of cellulosic material, when allowed to soak in a room temperature bath for over 35 days.
  • the resulting pellets were injection molded into test specimens following ASTM D638 (tensile) and D790 (flexural) specification. Injection molding on composite formulations was performed using an 85 ton machine (commercially available from Engel Corporation, York, PA) having a barrel and nozzle temperature of 200 °C. The tensile and impact resistance properties were subsequently tested as specified in the ASTM methods.
  • Example A-F molded specimens were subjected to two types of tests. The first test measured water absorption by the composite. In this test, Examples A-F were allowed to soak in a room temperature water bath for 35 days. Periodically, the Examples were removed from the water bath, dried with a towel to remove surface moisture, and weighed. The second test was designed as an accelerated aging test. For this test, specimens were subjected to steam between 34.5 and 103 kPa in a closed vessel in 8 hour increments. [0031] Room Temperature Water Uptake
  • FIG. 1 is a graph of the average percent water uptake of the composite over time for Examples A-F.
  • a multifunctional coupling agent is added to polypropylene and wood, a reduction in water absorption is found. This demonstrates that when used alone, the multifunctional coupling agent imparts an improved barrier to water absorption by the wood.
  • test specimens were subjected to a low pressure steam bath for 8 hours. After 8 hours, the test specimens were allowed to condition in a 50% humidity environment for 48 hours prior to testing tensile and impact resistance properties. Table 3 lists the results from tensile tests, and Table 4 lists the results from impact resistance tests before and after steam treatment.
  • the addition of the coupling agent generally improves mechanical properties of tensile strength, modulus, and impact resistance.
  • Increasing the concentration of the coupling agent increases tensile strength and impact resistance. This trend is preserved in the Examples subjected to 8 hours of steam treatment, despite a significant drop in tensile properties after steam treatment.
  • Example E containing solely a multifunctional coupling agent (without a coupling agent) exhibits properties very close to those of the comparative formulation A, both before and after steam treatment.
  • the use of both the multifunctional coupling agent and the coupling agent for formulation F significantly improves mechanical properties over all other formulations. The improvement is substantially greater than the coupling agent alone, even when added at significantly higher concentration.
  • Formulation F demonstrates a 30% increase in tensile strength above the control formulation A and about 17% increase over formulation C that contains the same concentration of the coupling agent.
  • the results for impact resistance are even more substantial with more than a 50% increase over formulation A and more than 40% increase over formulation C.
  • the tensile and impact resistance properties for formulation F are largely unchanged.
  • FIGS. 2 (a-d) display photographs of Examples from Examples A, C, and F prior to and after steam treatment at various intervals. As seen by the photographs, the addition of the multifunctional coupling agent dramatically improved the surface appearance of the composite. Even after 32 hours of steam treatment, Example F exhibits a smooth surface finish with minimal swelling of wood fibers. Example F exhibited desired color fastness. Table 5.
  • Example G Preparation and Characterization of Example G - coupling agent
  • Example G was prepared using the following protocol. Polymer (polypropylene, Grade 5626 2mi from Exxon Mobil, Irving, TX), maleic anhydride (Alpha Aesar, Ward Hill, MA) and peroxide (2,5-Dimethyl-2,5-di(tert-butylperoxy)hexane, United Initiators, Elyria, OH) were blended in a polyethylene bag in the following percentages: 97.8% of the noted poypropylene, 2% maleic anhydride, 0.2% peroxide.
  • the resulting blend was volumetrically fed into the feed zone of a 26 mm co-rotating twin screw extruder (commercially available from Labtech Engineering Company, Praksa, Maung, Samutprakan, Thialand). Calcium oxide (Mississippi Lime, St. Louis, MO) was used as a desiccant.
  • the extruder was fitted with a side stuffer which fed the desiccant in zone 4 at a rate such that desiccant was 50% of the total formulation .
  • zone 1 150°C
  • zone 2-3 190°C
  • zone 4-5 200°C
  • zone 6-9 220°C and die 220°C.
  • the resulting strands were subsequently cooled in a water bath and pellet
  • Composite sample H was prepared and tested using the following protocol.
  • Polymer (PP), filler, coupling agent, Example G, and the multifunctional coupling agent (MFCA) were blended in a polyethylene bag.
  • zone 1 170 °C
  • zone 2-7 180°C
  • zone 8 160°C.
  • the resulting strands were subsequently cooled in a water bath and pelletized into 0.64 cm pellets to produce the composite formulation.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un composite pouvant être transformé à l'état fondu, obtenu par la combinaison d'une matrice polymère, d'une matière cellulosique, d'un agent de couplage, d'un agent de couplage multifonctionnel et éventuellement d'un déshydratant. Le composite présente une solidité de la couleur et une résistance à l'humidité.
PCT/US2012/044647 2011-06-28 2012-06-28 Composites polymères résistant à l'humidité WO2013003591A2 (fr)

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US201161501886P 2011-06-28 2011-06-28
US61/501,886 2011-06-28
US201261618929P 2012-04-02 2012-04-02
US61/618,929 2012-04-02

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WO2013003591A3 WO2013003591A3 (fr) 2013-04-11

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015193533A1 (fr) * 2014-06-18 2015-12-23 Upm-Kymmene Corporation Procédé pour fournir un composite comprenant un agent de processus de dessiccation et composites associés
WO2017165959A1 (fr) * 2016-03-31 2017-10-05 West Fraser Mills Ltd. Composites de lignine

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992007009A2 (fr) * 1990-10-23 1992-04-30 Beshay Alphons D Cires modifiees et leurs applications
WO2002083824A1 (fr) * 2001-04-16 2002-10-24 Honeywell International, Inc. Elements structurels composites
WO2007016277A1 (fr) * 2005-07-28 2007-02-08 Chemtura Corporation Composite cellulosique/thermoplastique et son procede de production
US20080011194A1 (en) * 2004-12-03 2008-01-17 Dow Global Technologies Inc. Wood Fiber Plastic Composites

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992007009A2 (fr) * 1990-10-23 1992-04-30 Beshay Alphons D Cires modifiees et leurs applications
WO2002083824A1 (fr) * 2001-04-16 2002-10-24 Honeywell International, Inc. Elements structurels composites
US20080011194A1 (en) * 2004-12-03 2008-01-17 Dow Global Technologies Inc. Wood Fiber Plastic Composites
WO2007016277A1 (fr) * 2005-07-28 2007-02-08 Chemtura Corporation Composite cellulosique/thermoplastique et son procede de production

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015193533A1 (fr) * 2014-06-18 2015-12-23 Upm-Kymmene Corporation Procédé pour fournir un composite comprenant un agent de processus de dessiccation et composites associés
WO2017165959A1 (fr) * 2016-03-31 2017-10-05 West Fraser Mills Ltd. Composites de lignine

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