Troy, MI, United States
Troy, MI, United States

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Mohd Noor N.,Malaysian Palm Oil Board | Sendijarevic A.,Troy Polymers, Inc. | Sendijarevic V.,Troy Polymers, Inc. | Sendijarevic I.,Troy Polymers, Inc. | And 4 more authors.
JAOCS, Journal of the American Oil Chemists' Society | Year: 2016

In this study, novel polyester diols of 2000 molecular weight (MW) were synthesized by reacting azelaic acid (AZ) with 1,3-propanediol (1,3-PDO) and diethylene glycol (DEG) in the esterification reaction catalyzed with a small amount of butyltintris(2-ethylhexanoate). As a reference, polyester polyols of 2000 MW were synthesized from adipic acid (AA) with 1,3-PDO and DEG. The properties of polyester polyols were evaluated. The polyester polyol based on AZ and 1,3-PDO is 100 % renewable polyol; 1,3-PDO used in the syntheses is renewable product produced by fermentation process of sugar. Both 1,3-PDO-polyester polyols exhibited crystalline transition above room temperature, while DEG-polyester polyols were liquid at room temperature. The polyester polyols were chain-extended with 4,4′-diphenylmethane diisocyanate (Mondur M) and 1,4-butanediol (BDO) to form thermoplastic polyurethanes (TPU). TPU were evaluated for mechanical and water resistance properties, and their morphology were studied via differential scanning calorimetry (DSC), Fourier transform infrared (FTIR), and atomic force microscope (AFM). TPU based on azelate and adipate polyols were relatively soft elastomeric materials with high melting temperatures. AFM analyses of TPU indicated better phase separation in 1,3-PDO polyester polyols with the highest phase separation observed in TPU based on 1,3-PDO/azelaic acid polyols. Water resistance of TPU based on azelate polyols was improved as compared to TPU based on adipate polyols. © 2016, AOCS.


Grant
Agency: Department of Health and Human Services | Branch: | Program: SBIR | Phase: Phase I | Award Amount: 155.64K | Year: 2010

DESCRIPTION (provided by applicant): Polymethylmethacrylate (PMMA) has been used as a bone cement in total hip arthroplasty (THA) since the 1960's and today is still used in a significant percentage of the 1.5 million THA procedures performed worldwide each year. Despite its long clinical history the orthopaedic community acknowledges shortcomings with PMMA including among other things its exotherm, the toxicity of any unreacted monomer, its encapsulation by fibrous tissue and its cement-implant interface strength [1][2]. This proposal will focus on the later point, the cement-implant (or cement-metal) interface strength. Local debonding at this interface initiates a cascade of events; micromotion, particulate debris generation, macrophage activity, bone resorption and finally aseptic loosening of the implant. Attempts have been made to improve the interface strength of PMMA, but gains have been marginal, leading researchers to conclude that it's not an issue of if the interface should fail but when [3]. The use of polyurethane (PUR) based cement provides a completely different approach to addressing this clinical problem. PURs have a proven record of biostability and biocompatibility going back several decades [4]. More recently, in situ curing PUR adhesive formulations have been introduced to European markets and are seeing clinical use as bone void fillers and in stabilizing fractures. These PUR based cements have been shown to provide strong bond to bone and metal. As clinical experience with these materials grows, there is significant interest in development of PUR bone cement for affixation of total joint replacement devices. This research proposes development of a PUR bone cement specifically engineered for the biomechanical demands of THA. Phase 1 of the project will include formulation of new PURs using fundamental structure- property principles of polymer chemistry to provide a reactive two part system that upon mixing achieves full load bearing properties within 24 hour, strong adhesion to bone and metal implants, and long-term biostability. These formulations will then undergo mechanical testing to gain a full understanding of their capabilities. Of specific interest in Phase 1 will be their adhesion to THA devices and bone. The materials will be subjected to both static and dynamic test protocols, reproducing in vivo loads in a laboratory model. In parallel, the new materials will undergo in vitro biostability testing to characterize the risk of in situ oxidative degradation that would limit its clinical viability. Furthermore, level of extractable monomers will be evaluated for developed PURs and compared to PMMA. The overarching objective of these tests is to assess each material's potential as a replacement for PMMA in THA. Later phases of the project would include further refinement of the leading candidate material to improve load bearing capability, adhesion, and biostability, and to complete biocompatibility testing, mechanical assessment under more complex loading, and ultimately human clinical use. PUBLIC HEALTH RELEVANCE: The overall goal of this project is to develop a polyurethane adhesive bone cement for use in total hip replacement surgery. This alternative to polymethylmethacrylate will have superior bond strength between the cement and the metal device, significantly reducing the risk of failure due to loosening at this interface. The technology developed in this study has the potential to improve the lives of over 1.5 million new patients each year who undergo hip replacement surgeries.


Grant
Agency: National Science Foundation | Branch: | Program: SBIR | Phase: Phase I | Award Amount: 149.94K | Year: 2012

This Small Business Innovation Research Phase I project is proposing to produce polyols from soymeal for use in the manufacturing of rigid polyurethanes foams. The proposed process follows the ?Green Chemistry? guidelines and consists of hydrolyzing the protein to amino acids and converting them to hydroxyl terminated monomers. Polymerization of these polyols will yield poly(amide-urethane)s, which can be used as foams, coatings, adhesives, sealants and elastomers. However, the focus of this proposal will be on introducing this technology to the rigid polyurethane foams market. The structure and the presence of amide linkages in these polyols should provide better dimensional stability, higher rigidity and better chemical resistance foams then current polyurethane foams that contain esters or ethers linkages. Key elements of the current program will be to prepare and characterize the polyol monomers and then evaluate them in rigid polyurethanes foams. Model compounds derived from commonly available amino acids will also be used to optimize the process and characterize the products. The data will be used to articulate the scientific basis and develop appropriate process and products. Assessing potential commercial feasibility, preliminary economic evaluation, identifying potential market segments and customers who are interested in this technology will also be examined. The broader impact/commercial potential of this project provides an opportunity to produce a desirable bio-based alternative to environmentally un-friendly and increasingly expensive petroleum-based rigid polyurethane foams. Recently, much activity has been directed to utilize the oil from soybean to produce biodiesel, however, most of the leftover protein biomass is being used for poultry, swine and cattle feed or in aquaculture feed. Only a small portion of this biomass is refined for human consumption and even a smaller amount (only 0.5%) is currently being used for industrial applications (primarily in adhesives). The relatively low cost and stable supply of this valuable raw material makes the protein biomass an economically attractive source for value-added products such as its use in the production of polyurethanes. Furthermore, the proposed manufacturing process offers distinct advantages over the production of current polyols. It is anticipated that these polyols, and the foams derived from them, will benefit the growing ?green? market. The proposed technology is expected to reduce the US dependence on foreign oil imports and will provide alternative ?grown in America? valuable products. The results from this proposed project will be broadly disseminated to enhance the scientific and technological understanding in this field.


Grant
Agency: NSF | Branch: Standard Grant | Program: | Phase: | Award Amount: 149.94K | Year: 2012

This Small Business Innovation Research Phase I project is proposing to produce polyols from soymeal for use in the manufacturing of rigid polyurethanes foams. The proposed process follows the ?Green Chemistry? guidelines and consists of hydrolyzing the protein to amino acids and converting them to hydroxyl terminated monomers. Polymerization of these polyols will yield poly(amide-urethane)s, which can be used as foams, coatings, adhesives, sealants and elastomers. However, the focus of this proposal will be on introducing this technology to the rigid polyurethane foams market. The structure and the presence of amide linkages in these polyols should provide better dimensional stability, higher rigidity and better chemical resistance foams then current polyurethane foams that contain esters or ethers linkages. Key elements of the current program will be to prepare and characterize the polyol monomers and then evaluate them in rigid polyurethanes foams. Model compounds derived from commonly available amino acids will also be used to optimize the process and characterize the products. The data will be used to articulate the scientific basis and develop appropriate process and products. Assessing potential commercial feasibility, preliminary economic evaluation, identifying potential market segments and customers who are interested in this technology will also be examined.


The broader impact/commercial potential of this project provides an opportunity to produce a desirable bio-based alternative to environmentally un-friendly and increasingly expensive petroleum-based rigid polyurethane foams. Recently, much activity has been directed to utilize the oil from soybean to produce biodiesel, however, most of the leftover protein biomass is being used for poultry, swine and cattle feed or in aquaculture feed. Only a small portion of this biomass is refined for human consumption and even a smaller amount (only 0.5%) is currently being used for industrial applications (primarily in adhesives). The relatively low cost and stable supply of this valuable raw material makes the protein biomass an economically attractive source for value-added products such as its use in the production of polyurethanes. Furthermore, the proposed manufacturing process offers distinct advantages over the production of current polyols. It is anticipated that these polyols, and the foams derived from them, will benefit the growing ?green? market. The proposed technology is expected to reduce the US dependence on foreign oil imports and will provide alternative ?grown in America? valuable products. The results from this proposed project will be broadly disseminated to enhance the scientific and technological understanding in this field.


Troy Polymers, Inc. | Entity website

Consulting and Intellectual Property Support TPI team has extensive experience in the field of polyurethanes. TPI team can help with Technical Sales and Marketing, Market Evaluation, Technology Evaluation, and IP Evaluation


Troy Polymers, Inc. | Entity website

TPI offers a wide range of services to support innovations in polyurethanes: Polyurethane Formulation and Application Development Raw Material Development and Evaluation Technical Marketing Support Training and Development of Professional Resources Testing Services Consulting and Intellectual Property Support


Troy Polymers, Inc. | Entity website

Testing Services TPI testing capabilities range from basic testing and reporting to detailed analysis and interpretation of results. PHYSICAL PROPERTIES Instron Physical Testing (with heat chamber) Tensile Properties Compression Properties Flexural Properties Hysteresis Tear Strength Peel Resistance Lap Shear Strength Shear Strength Compression Set Resilience - Bashore and Ball Rebound Abrasion (Taber Abrader) Tumbling Friability Hardness (Shore A, Shore D) Pencil Hardness Impact Resistance of Coatings Open Cell Content in Foams (Pycnometer) Viscosity (Brookfield Viscometer and Rheometer) THERMAL PROPERTIES Retention of Stress-Strain Properties with Temperature (Instron with heat chamber) Melt Transition Temperature (DSC) Glass Transition Temperature (DSC) Coefficient of Thermal Expansions (TMA) Storage and Relaxation Modulus (DMA) Thermal Stability (TGA) Flammability CHEMICAL ANALYSIS Fourier Transform Infrared (FTIR) Hydroxyl Value of Polyols Acid Value of Polyols NCO% of Isocyanates and Pre-Polymers Water Content (Karl Fischer Titration) Molecular Weight Distribution (GPC) HPLC Analyses RHEOLOGY Determination of Visco-Elastic Properties in Steady Shear (controlled stress Rheometer) Determination of Visco-Elastic Properties in Oscillatory Mode (controlled stress Rheometer)


Troy Polymers, Inc. | Entity website

Raw Material Evaluation TPI has extensive experience in evaluation of new raw materials for polyurethanes, including polyols, isocyanates, chain extenders, and various additives. With understanding of structure-property relationships and polyurethane applications, TPI can develop a customized program for evaluation of new raw materials and can generate practical data that can be used in technical marketing


Troy Polymers, Inc. | Entity website

Training and Development of Professional Resources TPI provides hands-on laboratory training that focuses on laboratory preparation of polyurethane materials and testing of materials per industry standards. Training programs can be customized to clients' needs ...


Troy Polymers, Inc. | Entity website

TPI offers a wide range of services to support innovations in polyurethanes: Polyurethane Formulation and Application Development Raw Material Development and Evaluation Technical Marketing Support Training and Development of Professional Resources Testing Services Consulting and Intellectual Property Support

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