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Search results for: non-isocyanate polyurethanes
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Non-isocyanate Polyurethanes
PublicationThe main aim of this chapter is to present a general overview of the NIPU synthesis method (i.e., polycondensation and polyaddition), and to describe structure and properties of selected intermediates and final polymeric products. The focus is on five-membered ring cyclic carbonate intermediates, which were obtained by cycloaddition of carbon dioxide to selected glycidyl ethers and thiol-ene coupling of unsaturated cyclic carbonates...
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Non-Isocyanate-Based Waterborne Polyurethanes
PublicationNon-isocyanate polyurethanes (NIPUs) are a greener alternative for the conventional polyurethanes synthesized using toxic and moisture-sensitive di- or polyisocyanates. The most often described method of NIPU synthesis involves the reaction of five-membered cyclic carbonates with amines, and resulting polymers containing primary and secondary hydroxyl groups (so they are also known as polyhydroxyurethanes), which can be further...
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Renewable natural resources as green alternative substrates to obtain bio-based non-isocyanate polyurethanes-review
PublicationCommercially available polyurethanes are synthesized by the polyaddition of diisocyanates with polyols and low molecular weight chain extenders. A new approach to polyurethanes synthesis is realized via non-isocyanate routes. Negative impacts of petroleum-based chemicals on the environment and human health as well as gradual reduction of fuel-based resources, which leads to an increase in their prices, are an incentive to looking...
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Synthesis and structural characterization of bio-based bis(cyclic carbonate)s for the preparation of non-isocyanate polyurethanes
PublicationBio-based cyclic carbonates are of significant research interest as monomers for non-isocyanate polyurethane (NIPU) synthesis. This research describes the synthesis of a series of five-membered bis(cyclic carbonate)s using bio-based polyether polyols (PO3G) with different molecular weights (250, 650 and 1000 g mol−1) and carbon dioxide as green feedstocks. The utilization of CO2 as a source of carbon in the chemical reaction is...
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Isocyanate-Free Polyurethanes
PublicationIsocyanate-free polyurethanes (also called non-isocyanate polyurethanes, or NIPUs) are alternatives to the conventional (commercially used) polyurethanes synthesized using di- or polyisocyanates, polyols, and chain extenders with low molecular weight. The major routes of NIPUs’ synthesis involve polyaddition of cyclic carbonates and di- or polyamines, polycondensation of carbamates, and diols. The most important intermediates are...
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Diamine derivatives of dimerized fatty acids and bio-based polyether polyol as sustainable platforms for the synthesis of non-isocyanate polyurethanes
PublicationA series of environmentally friendly non-isocyanate polyurethanes (NIPUs) were successfully prepared via the polyaddition reaction of bio-based polyether polyol-based cyclic carbonate with diamine derivative of dimerized fatty acids. The syntheses of NIPUs were realized by the three-step method in the absence of toxic solvents and, importantly, the process of carbonation did not require the use of elevated pressure. The effect...
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Progress in non-isocyanate polyurethanes synthesized from cyclic carbonate intermediates and di- or polyamines in the context of structure–properties relationship and from an environmental point of view
PublicationCommercially, polyurethanes are produced by the reaction of diisocyanates, polyols (polyester or polyether) and low molecular weight chain extender. Toxicity, moisture sensitivity and phosgene-based synthesis of diisocyanates resulted in investigations focused on obtaining the non-isocyanate polyurethanes (NIPUs). This work presents the review of synthesis and structure–properties relationship of non-isocyanate polyurethanes obtained...
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Bio‑derived polyurethanes obtained by non‑isocyanate route using polyol‑based bis(cyclic carbonate)s—studies on thermal decomposition behavior
PublicationNon-isocyanate polyurethanes (NIPUs) constitute one of the most prospective groups of eco-friendly materials based on their phosgene-free synthesis pathway. Moreover, one of the steps of their obtaining includes the use of carbon dioxide (CO 2 ), which allows for the promotion of the development of carbon dioxide capture and storage technologies. In this work, non- isocyanate polyurethanes were obtained via three-step synthesis...
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The influence of 4,4'-bis(6-hydroxyhexoxy)biphenyl moieties on properties of polyurethanes based on 4,4'-methylenebis(cyclohexyl isocyanate)
PublicationZsyntetyzowano dwie serie poliuretanów z 4,4'-bis(6-hydroksyheksyloksy)bifenylu (BH6), poliadypinianu 1,6-heksylenu i diizocyjanianu 4,4'-dicykloheksylometanu o udziałach izomeru trans, wynoszącym odpowiednio 16 i 46%. Badano wpływ udziału wagowego (u) małocząsteczkowego diolu(BH6)w odniesieniu do sumy mas komonomerów diolowych, na właściwości uzyskanych poliuretanów metodami DSC, DTA, TGA, mikroskopii polaryzacyjnej, WAXS, DMTA...
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Synthesis, structure and properties of novel poly(hydroxyurethane)s obtained by non-isocyanate route
PublicationNon-isocyanate polyurethanes (NIPUs) can be synthesized by polyaddition of five-membered bis(cyclic carbonate)s and primary diamines. NIPUs are an alternative for the commonly used (in the form of foams, elastomers, coatings or fibers) in the industry polyurethanes obtained using toxic and moisture sensitive diisocyanates, polyols and low-molecular weight chain extenders. The main aim of this work was to synthesize non-isocyanate...
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Challenges and recent advances in bio-based isocyanate production.
PublicationPolyurethanes (PUs) are key players in the plastics industry. According to the Global Polyurethane Market (2019–2023), their value in the global market reached $95.13 billion in 2019 and is expected to grow at a compound annual growth rate of 12%. This is in line with the increase in the number of research papers and patents on the synthesis and application of petroleum-based PUs (P-PUs) and biomass or green PUs (G-PUs) (from 67 657...
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Novel bio-based thermoplastic poly(ether-urethane)s. Correlations between the structure, processing and properties
PublicationThe main purpose of this work was to analyze the effect of the number of unreacted isocyanate groups and the [NCO]/[OH] molar ratio during the chain extension of a prepolymer during the polymerization process on the structure, processing and selected properties of thermoplastic poly(ether-urethane)s. Three series of novel thermoplastic polyurethanes were obtained via a prepolymer route. Three prepolymers were synthesized from diisocyanate...
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Synteza, struktura chemiczna i właściwości bezizocyjanianowych poliuretanów otrzymywanych z wykorzystaniem CO2 oraz surowców pochodzenia naturalnego.
PublicationZ uwagi na wciąż rosnącą świadomość proekologiczną, politykę zrównoważonego rozwoju, a także nurt zielonej chemii wiodącym trendem w przemyśle tworzyw sztucznych jest poszukiwanie alternatywnych metod otrzymywania materiałów polimerowych. Komercyjnie poliuretany otrzymywane są w wyniku reakcji poliaddycji di- lub poliizocyjanianów z poliolami i małocząsteczkowymi przedłużaczami łańcucha. Z uwagi na niekorzystne właściwości diizocyjanianów,...
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Microwave radiation in the synthesis of urethane prepolymers
PublicationThis paper describes the use of microwave radiation in the synthesis of urethane prepolymers in bulk (without solvent). The prepolymers were synthesized using 1,6-hexamethylene diisocyanate (HDI) and poly (ε-caprolactone) diol (PCL) at a molar ratio of 4:1. The reaction was carried out without a catalyst in the reactor with a conventional heating system (oil bath) or in the microwave reactor (MW Reactor NOVA 09) at temperatures...
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DETERMINATION OF THE HYDROXYL NUMBER OF GROUND TIRE RUBBER PARTICLES VIA MODIFIED TEST METHOD FOR ISOCYANATE GROUPS
PublicationNowadays, considering the environmental trends and law regulations associated with the circular economy, it is very important to seek for the methods of by-products and waste utilization. The example of such material, which requires the attention and recycling method is ground tire rubber generated during recycling of post-consumer car tires. It can be introduced into various polymer matrices as a filler, but to enhance its effectivity...
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Novel Biomass-Based Polymers: Synthesis, Characterization, and Application
PublicationA wide range of polymers were prepared from biomass-derivatives, using different polymerization mechanisms. Well-defined, fully hydroxy-functional polyesters based on aliphatic diols were synthesized, using either conventional metal-based catalysts or the organic superbase 1,5,7-triazabicyclododecene (TBD). Unsaturated polyesters were also made, offering additional functionality to these biobased resins. Metal-catalyzed or enzymatic...
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The influence of amorphous macrodiol, diisocyanate type and l-ascorbic acid modifier on chemical structure, morphology and degradation behavior of polyurethanes for tissue scaffolds fabrication
PublicationStudies described in this work were related to the bulk synthesis and characterization of polyurethanes (PURs) obtained with the use of cyclic 4,4′-methylene bis(cyclohexyl isocyanate) (HMDI) or linear 1,6-hexamethylene diisocyanate (HDI), amorphous α,ω-dihydroxy(ethylene-butylene adipate) macrodiol (PEBA), 1,4-butandiol (BDO) chain extender and dibutyltin dilaurate (DBTDL) catalyst. Obtained PURs were modified with l-ascorbic...
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Synthesis, structure and properties of poly(ester-urethane)s obtained using bio-based and petrochemical1,3-propanediol and 1,4-butanediol
PublicationIn this paper, the poly(ester-urethane)s obtained using petrochemical and bio-based chain extenders were prepared and characterized. The influence of glycols’ origin on the chemical structure, mechanical and thermal properties of the prepared polyurethanes was studied. The materials were synthesised by prepolymer method. The first step involved the reaction of α,ω-dihydroxy(ethylene-butylene adipate (POLIOS 55/20) with 4,4’-diphenylmethane...
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Insights into Stoichiometry Adjustments Governing the Performance of Flexible Foamed Polyurethane/Ground Tire Rubber Composites
PublicationPolyurethanes (PU) are widely applied in the industry due to their tunable performance adjusted by changes in the isocyanate index—stoichiometric balance between isocyanate and hydroxyl groups. This balance is affected by the incorporation of modifiers of fillers into the PU matrix and is especially crucial for PU foams due to the additional role of isocyanates—foaming of the material. Despite the awareness of the issue underlined...
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Medical-Grade PCL Based Polyurethane System for FDM 3D Printing—Characterization and Fabrication
PublicationThe widespread use of three-dimensional (3D) printing technologies in medicine has contributed to the increased demand for 3D printing materials. In addition, new printing materials that are appearing in the industry do not provide a detailed material characterization. In this paper, we present the synthesis and characterization of polycaprolactone (PCL) based medical-grade thermoplastic polyurethanes, which are suitable for forming...
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Synthesis and characterization of cycloaliphatic hydrophilic polyurethanes, modified with l-ascorbic acid, as materials for soft tissue regeneration
PublicationIn this paper we described synthesis and characteristic of obtained hydrophilic polyurethanes (PURs) modified with ascorbic acid (commonly known as vitamin C). Such materials may find an application in the biomedical field, for example in the regenerative medicine of soft tissues, according to ascorbic acid wide influence on tissue regeneration Flora (2009), Szymańska-Pasternak et al. (2011), Taikarimi and Ibrahim (2011), Myrvik...
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Polyurethanes
PublicationThe chapter content is devoted to Polyurethanes and consists of the following items: general characteristics of polyurethanes, raw materials used in the synthesis of crosslinked polyurethanes, synthesis and crosslinking reactions of polyurethanes, morphology of liniear and branched PU, manufacturing methods and functional properties.
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Recycling of Polyurethanes
PublicationPolyurethane waste can be recycled by mechanical methods (i.e., grinding and applying as a filler or pressing with a bonding agent) and chemical methods (mainly by e.g., glycolysis, hydrolysis, or aminolysis). There is also possibility to the recover energy from polyurethanes waste (by incineration, gasification, and pyrolysis).
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THERMOMECHANICAL PERFORMANCE OF FLEXIBLE POLYURETHANE FOAMS AS A FUNCTION OF THE ISOCYANATE INDEX
PublicationPolyurethane foams are very versatile materials applied in different branches of industry. Their popularity is attributed, among others, to the flexibility in engineering their mechanical performance by the adjustment of their formulations. One of the most crucial factors is the isocyanate index, determining the ratio between the free hydroxyl and isocyanate groups present in the polyurethane system. By the change of this ratio,...
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Development of polyurethanes for bone repair
PublicationThe purpose of this paper is to review recent developments on polyurethanes aimed at the design, synthesis, modifications, and biological properties in the field of bone tissue engineering. Different polyurethane systems are presented and discussed in terms of biodegradation, biocompatibility and bioactivity. A comprehensive discussion is provided of the influence of hard to soft segments ratio, catalysts, stiffness and hydrophilicity...
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Polyurethanes as a carrier of drugs for gentamicin
PublicationGentamicin is one of the most popular drug and is widely used due to its antibiotic properties. 3% of world production of polyurethanes (PU) is dedicated to biomedical applications, where they can serve are parts of orthopedic prosthesis or artificial organs, disposable medical devices, wound and burn dressing, contact lenses among others. In the study, to obtain drug carriers, a combination of these two materials were prepared...
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A mathematical model of rheological behavior of novel bio-based isocyanate-terminated polyurethane prepolymers
PublicationIn this paper, the results of rheological study on isocyanate-terminated polyurethane prepolymers, containing modified soybean oil residues incorporated into the chemical structure are described. Isocyanate-terminated prepolymers were synthesized from 4,4′-diphenylmethane diisocyanate and the mixture of hydroxylated soybean oil and commercial polyether. The measurements were performed by using rotary rheometer R/S-CPS+ (Brookfield,...
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Bioactive polyurethanes applied as a surgical implants
PublicationSynthetic materials are applied in many branches of the industry, i.a. in medicine as a casing of apparatus, elements of artificial organs (hearts, blood vessels), catheters, wound healings, intra aortic balloons, mammary implants to mention but a few. Polymeric material used in such applications must be distinguished by a good biocompatybility. Since many years extensive research are employed to develop a new polymers that can...
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Renewable Resources for Polyurethanes and Polyurethane Composites: A Review
PublicationEach year, more than two million tons of polyurethane is produced in the EU by reacting isocyanates with polyols made from fossil fuel. In addition, there are appreciable quantities of petroleum based functional additives applied in the industry nowadays for both polyols and polyurethane materials. It is therefore of key importance to develop sustainable economically viable polyols with enhanced functionalities, and thereby reducing...
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Performance properties of rigid polyurethane-polyisocyanurate/brewers’ spent grain foamed composites as function of isocyanate index
PublicationIn the presented work, rigid polyurethane-polyisocyanurate (PUR-PIR) foams filled with brewers’ spent grain (BSG) were prepared. The influence of the isocyanate index (II) on its performance was investigated. Foams obtained with higher isocyanate index required a higher amount of hydrofluorocarbon physical blowing agent to provide the same apparent density of material. An increase of isocyanate index resulted in a slight decrease...
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Recycling of Polyurethanes Containing Flame-Retardants and Polymer Waste Transformed into Flame-Retarded Polyurethanes
PublicationThe growing number of polyurethanes (PUs) produced every year has developed methods for their mechanical and chemical recycling which yield valuable products like substitutes for commercial polyols or flame-retardants. PUs can be produced in different shapes and forms (i.e., elastomers, flexible or rigid foams, coatings, etc.) using several different components (i.e., di- or polyisocyanates, ester- or ether-based polyols, low-molecular...
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Polyurethanes modified with natural polymers for medical application. I. Polyurethanes/ Chitosan and polyurethane/collagen.
PublicationFor over three decades polyurethanes (PUR or PU) have been reported for application in a variety of medical devices. These polymers consist of hard and soft segments, which allow for more subtle control of their structure and properties. By varying the composition of the different segments, properties of PURcan be tuned up for use in many areas of medicine. Recently there is a great interest in modification of biomedical PUR with...
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Polyurethanes
PublicationHandbook of Thermoset Plastics, Fourth Edition provides complete coverage of the chemical processes, manufacturing techniques and design properties of each polymer, along with its applications. This new edition has been expanded to include the latest developments in the field, with new chapters on radiation curing, biological adhesives, vitrimers, and 3D printing. This detailed handbook considers the practical implications of using...
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Cross-linked epoxy-isocyanate blends containing Epidian-6 modified by glycols
PublicationPolymeric films of cross-linked structure may be formed using epoxy-isocyanate blends composed of Epidian-5 epoxy resin, 4,4’-diphenylmethanediisocyanate (MDI), Z-1 polyamine hardener and Epidian-6 epoxy resin modified by glycols. The effect of the component natures and ratio, process temperature and time on the gel-fraction content, as well as film hardness, was examined. The chemistry of the film forming process was determined...
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Degradation of polyurethanes in Compost Under Natural Conditions
PublicationThe estimation of degradibility of different polyurethanes under natural weather depending conditions in compost pile was the subject of the studies. The incubation of polymer samples took place for a period up to 24 months. The characteristic parameters of the compost: temperature, pH, moisture content, and activity of dehydrogenasis were monitored and their influence on degradation of polyuiretahnes was discussed. The compostability...
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The Impact of Isocyanate Index and Filler Functionalities on the Performance of Flexible Foamed Polyurethane/Ground Tire Rubber Composites
PublicationThe structure and performance of polyurethane (PU) foams are strongly driven by the stoichiometry of the polyaddition reaction, quantitatively described by the isocyanate index. It determines the balance between isocyanate and hydroxyl groups in the reacting system and is affected by the introduction of additional functionalities originated, e.g., from applied fillers. Nevertheless, this issue is hardly taken into account in research...
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Novel Research on Biomedical Polyurethanes
PublicationThe variety of mechanical properties characterizes properly designed PURs. They may be biocompatible and reveal compatibility with blood, making them attractive materials for the fabrication of tissue scaffolds; however, like all synthetic materials, PURs don’t reveal sufficient biocompatibility. PURs may undergo certain chemical modifications (e.g., 1,4:3,6-dianhydro-D-sorbitol, ascorbic acid (AA), growth factors, covering with...
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Thermoplastic polyurethanes with glycolysate intermediates from polyurethane waste recycling
PublicationThe polyol is a major component in polyurethane formulations and therefore introducing to the formulation recycled polyol (obtained during decomposition process) allows decreasing the usage of pure petrochemical components. In this work, thermoplastic polyurethanes were prepared using various mixtures of a petrochemical macrodiol poly(ethylene-butylene adipate)diol (PEBA) and a recycled glycolysate intermediate, called glycolysate...
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Thermal and mechanical properties of polyurethanes modified with L-ascorbic acid
PublicationIn this study we report the thermal and mechanical properties of polyurethanes modified with ascorbic acid (AA). Ascorbic acid was used as a modifier at concentration of 1 or 2 mass%. The antioxidative properties of AA may improve the biocompatibility of the obtained materials, which were designed for biomedical applications. In this paper we describe characterization of obtained unmodified and ascorbic acid modified polyurethanes...
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Environmental impact and industrial development of biorenewable resources for polyurethanes
PublicationPolyurethanes are among the most developed types of polymers. They are produced from the three primary components, i.e., polyols, low-molecular-weight glycols used as chain extenders, and diisocyanates. Until recently, all these substrates have been obtained via petrochemical processes. A decrease in petroleum-based resources and new ecological trends in chemistry, chemical technology, and materials engineering have generated increasing...
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The structure of novel polyurethanes containing synthetic poly[(R,S)-3-hydroxybutyrate]
PublicationThe aim of this study was to estimate the structure of new polyurethanes with the potential to be used in medicine. Atactic poly[(R,S)-3-hydroxybutyrate], obtained via a ring-opening polymerization, and polycaprolactonediol or polyoxytetramethylenediol were used to built the soft segments. 4,4'-methylene dicyclohexyl diisocyanate and 1,4-butanediol were the components to form hard segments. Polyurethanes with low-molecular weight...
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Gelatin-Modified Polyurethanes for Soft Tissue Scaffold
PublicationRecently, in the field of biomaterials, which are being designed for soft tissue scaffolding, is growing the interest of their modification with natural polymers. Synthetic polymers are often hard, not easy to process and they do not possess fine biodegradable profile. From the other hand natural polymers are biocompatible, but weak when used alone. The combination of natural and synthetic polymers gives the suitable properties...
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A New Approach to Chemical Recycling of Polyamide 6.6 and Synthesis of Polyurethanes with Recovered Intermediates
PublicationA new efficient method for the chemical decomposition of polyamide 6.6 by the glycolysis and amino-glycolysis processes was proposed. The glycolysis was conducted using the mass excess of ethylene glycol (EG) as a decomposing agent in the presence of a catalyst. Also, a mixture of EG and triethylenetetramine was used as another decomposing agent in the amino- glycolysis process. The described process of decomposition did not...
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Degradibility in vitro of polyurethanes based on synthetic atactic poly[)R,S)-3-hydroxybutyrate
PublicationThe aim of the paper was to determine the degradibility of aliphatic polyurethanes in hydrolytic and oxidative solutions. DSC, GPC, density, polymer surface morphology were studied.
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Polyurethanes as a Potential Medical-Grade Filament for Use in Fused Deposition Modeling 3D Printers – a Brief Review
PublicationThe possibility of using 3D printing technology (3DP) in medical field is a kind of revolution in health care. This has contributed to a rapid growth in demand for 3D printers, whose systems and materials are adapted to strict medical requirements. In this paper, we report a brief review of polyurethanes as a potential medical-grade filament for use in Fused Deposition Modeling (FDM) 3D printer technology. The advantages of polyurethanes...
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Effect of hydroxylated soybean oil and bio-based propanediol on the structure and thermal properties of synthesized bio-polyurethanes
PublicationThe aim of this work was to obtain bio-polyurethanes using synthetic compounds and bio-components, i.e. bio-glycols. Bio-polyurethanes were prepared by means of the prepolymer method. Prepolymers were synthesized from 4,4′-diphenylmethane diisocyanate (MDI) and a polyol mixture containing 75% by weight of commercial polyether and 25% by weight of hydroxylated soybean oils (H2 or H3), the latter being obtained in the reaction with...
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Thermal and Mechanical Properties of Microporous Polyurethanes Modified with Reduced Graphene Oxide
PublicationMicroporous polyurethanes (MPU) were modified by adding 0.25%–1.25 wt% of reduced graphene oxide (RGO). The materials were prepared without solvent via in situ polymerization. From a technological point of view, it is very important to obtain functional materials by using reacting compounds only. The thermal characteristics of obtained MPU were investigated using TGA, DSC, and DMA techniques. In comparison to nonmodified microporous...
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Comparison of disk and tube methods for estimation of biostatic properties of polyurethanes based on synthetic poly[(R,S)-3-hydroxybutyrate
PublicationThe influence of novel aliphatic polyurethanes on growth of Staphyloccocus aureus (SA)in the around of polymer samples has been estimated by disk method. It was staed that the growth of SA was inhibited.The influence of polyurethanes on planctonic Staphyloccocus aureus was also pefrormed by tube method. In this test the slight decrease of bacteria concentration was noticed.
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Cast polyurethanes obtained from reactive recovered polyol intermediates via crude glycerine decomposition process
PublicationIn this work, the possibility of applying intermediates from polyurethane waste recycling in polyurethane synthesis was presented. Polyurethanes were synthesised in a two-step method using a mixture of petrochemical polyol and glycerolysate, used as a reactive component, 4,4-diphenylmethane diisocyanate (MDI) and 1,4-buthanediol (BD). Glycerolysates were produced during decomposition of polyurethane elastomer by crude glycerine...
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Investigation of Thermoplastic Polyurethanes Synthesized via Two Different Prepolymers
PublicationThe man aim of this work was to investigate the effect of the molecular weight of polyols, mixture of prepolymers, and [NCO]/[OH] molar ratio used during the prepolymer chain extending step on the chemical structure, thermomechanical and mechanical properties, and thermal stability of thermoplastic poly(ether-urethane)s In this work thermoplastic poly(ether-urethane)s were synthesized by using polyols with a various molecular weight,...