Piotr Czub

Cracow University of Technology | PK · Department of Chemistry and Technology of Polymers

Nowadays, in the era of growing ecological awareness, composites based on synthetic or bio-based polymers and fillers of natural origin find various potential applications. Plant-based materials are obtained using plant-derived materials, such as e.g., vegetable oil or wood fill-ers. Such synthesis of polymer composites allows for the selection of...

Nowadays, in the era of growing ecological awareness, composites based on synthetic or bio-based polymers and fillers of natural origin fillers find various potential applications. Plant-based materials are obtained using plant-derived materials, such as e.g., vegetable oil or wood fillers. Such synthesis of polymer composites allows for the select...

The aim of this work was to develop strategies for the synthesis of dendritic macromolecules from raw materials obtained through the chemical modification of vegetable oils. Plant oils containing unsaturated fatty acids are a potential source of the ω-esters of various fatty acids as they can be obtained via metathesis using ethylene, proceeded wit...

A series of composites based on epoxy resin filled with additives of natural origin were prepared to investigate the influence of such fillers on the properties of the epoxy compositions. For this purpose, the composites containing 5 and 10 wt.% of additive of natural origin were obtained using the dispersion of oak wood waste and peanut shells in...

The aim of the present research was the development of a management method for wood-processing waste that was obtained during the production of parquet flooring. Currently mostly useless, such waste mainly ends up in landfills. The oak waste flour was used as a reinforcement material for epoxy biocomposites based on the polyaddition product of epox...

The research undertaken in this work is one of the examples of the engineering of modern polymer materials. This manuscript presents studies on the gelation process which might occur during the synthesis of epoxy resin using the modified vegetable oil via the epoxy fusion process conducted in bulk. Based on obtained results we determined rheologica...

The presented research shows the results of the investigations on the synthesis of polymeric materials through the fusion reaction of modified palm oil derivatives. First, raw palm oil was subjected to epoxidation. In order to determine the best reaction conditions, the process was conducted under four different conditions. In the next stage, the p...

Due to the environmental and sustainability issues, the interest in biobased composite materials is rapidly growing, both in terms of their industrial applications and fundamental research. However, in addition to numerous advantages, natural composites have some serious drawbacks when compared to synthetic composites. Higher moisture absorption, i...

Epoxy resins are usually synthesized by the oxidation of unsaturated compounds and more often by reaction of epichlorohydrin with bisphenols. All raw materials currently used in these syntheses are of petrochemical origin. Intensive research has been conducted for last couple of years to find alternatives to the petrochemical raw materials for the...

Due to the thermal and fire sensitivity of polymer bio-composite materials, especially in the case of plant-based fillers applied for them, next to intensive research on the better mechanical performance of composites, it is extremely important to improve their reaction to fire. This is necessary due to the current widespread practical use of bio-b...

Presented research shows the results of a study on the synthesis and mechanical properties of materials obtained by crosslinking polyaddition bio-products with blocked isocyanate based on toluene diisocyanate (TDI) as curing agent. Bio-resins, polyaddition product of epoxidized soybean oil and bisphenol A or hydroxylated soybean oil and low molecul...

In the last couple of years growing attention is paid to environmental concerns with a special attention to bio- and renewable resources as feedstock for the chemical industry. In this article we synthesized bio-based high molecular weight epoxy resins with hydroxylated soybean oil (SMEG) and a low-molecular-weight epoxy resin (EPR 0162), using the...

In general, the epoxy materials, which were synthesized with the use of products of vegetable oil modification, are characterized by inferior properties. Despite, the introduction of sepiolite doesn't improve mechanical strength of cured epoxy materials, there are some parameters, which had unexpectedly enhanced (e.g. untypically - the elongation a...

The aim of the presented research was the synthesis of epoxy resins based on epox-idized palm oil, followed by the selection of proper isocyanate-based curing agent and final-ly testing the properties of obtain cured materials.

In the presented research we studied the possibility and a degree of biodegradation of the high molecular weight epoxy resins compositions based on modified soybean oil and bisphenol A or low-molecular-weight epoxy resin (EPR 0162) cured with isocyanates of different structure.

The presented research shows the results of matrix-assisted laser desorption/ionization mass spectrometry, which was used as a means of monitoring the synthesis of novel high-molecular weight epoxy resins. The products were obtained by the reaction of epoxidized soybean oil (ESBO) and bisphenol A (BPA), using a modern and pro-ecological modificatio...

Presented research shows the results of a study on the mechanical properties of materials obtained in the course of innovatory application of epoxidized vegetable oil in the synthesis of new bio-based epoxy resins, crosslinked with curing agents which are not typical for epoxy materials. The product was obtained via modern and pro-ecological modifi...

Oxirane rings in epoxidized soybean oil were opened in reaction with monoethylene glycol and then fused with bisphenol A, hydroxylated soybean oil and a com. low-mol.- mass epoxy resin in bulk. The polymeric products were filled with sepiolite (1 or 2% by mass) and crosslinked with a 4,4’-diphenylmethane diisocyanate. The composite materials produc...

The paper presents the results of studies on the synthesis and mechanical properties of the fusion product of epoxidized soybean oil with bisphenol A, which are a part of the current research on environmentally friendly raw materials for the preparation and modification of modern polymeric materials. It has been shown that the use of 4,4’-methylene...

Knowledge of the susceptibility of plastics on the activity of enzymes is important for two reasons. Plastic products are often exposed to destruction in the conditions of their application, resulting from an uncontrolled processes of degradation caused by the activity of microorganisms. In addition, processes of this type might be use for recyclin...

Presented research shows the influence of different catalysts onto the selectivity and efficiency of soybean oil oxidation as well as their influence onto the progress of the further reaction of synthesized epoxidized oil with bisphenol A in the epoxy fusion process. Described experiments involved modification of vegetable oils and innovatory appli...

W pracy przedstawiono wyniki badań nad chemiczną degradacją odpadowego poli(tereftalanu etylenu) na drodze hydrolizy zasadowej i kwaśnej oraz aminolizy, prowadzonej przy użyciu hek-sametylenodiaminy. Uzyskano w ten sposób kwas tereftalowy oraz mieszaninę diaminoamidów kwasu tereftalowego. Sprawdzono różne metody prowadzenia degradacji PET oraz rozd...

The paper presents the results of studies on susceptibility to enzymatic degradation of the compo-sition, consisting of equal parts of commercial low-molecular-weight bisphenol A-based epoxy resin and the epoxy resin derived from the glycolysis products of waste poly(ethylene terephthalate), sub-sequently cross-linked using isophoronediamine. The c...

W związku z coraz większą świadomością ekologiczną na całym świecie prowadzone są badania nad wykorzystaniem proekologicznych surowców w syntezie i modyfikacji materiałów polimerowych. W pracy przedstawiono wyniki badań właściwości mechanicznych produktu stapiania (ang. epoxy fusion proces) epoksydowanego oleju sojowego z bisfenolem A. Otrzymany pr...

The hydroxyl derivative of soybean oil (SDEG) was obtained as a result of the epoxidation of soybean oil followed by the opening of oxirane rings in the reaction with diethylene glycol (Scheme A). This derivative was used in the process of fusion with bisphenol A-based low-molecular-weight epoxy resin EPR 162 (Scheme B), carried out using triphenyl...

This paper presents the results of the research over the course of the reaction of epoxidized soybean oil with bisphenol A conducted using the fusion method. The progress of the carried out reaction was followed both by determination of the content of epoxy and hydroxyl groups in obtained products as well as average molecular weights and the polydi...

The possibility of using a mixture of NaHSO4 and NaH2PO4 as a flame retardant for bisphenol A-based epoxy resins was examined. The optimal composition of the mixture, ensuring the most effective flame retardants activity, has been identified. A suitable content of the mixture in the composition with the epoxy resin Epidian 5 was determined. Next, s...

The main subject for this paper is presentation of different methods of natural oils modification as well as applications of vegetable oil for polymer synthesis and modification. Numerous methods of oxidation of plant oil have been discussed. Moreover, authors pointed out advantages and disadvantages of presented methods, and their possible adaptat...

The epoxidized palm oil was synthesized and prepolymerized in a reaction with isophorone diamine. The resulting palm oil derivatives were used as modifiers (in the amount 10 wt. %) of a bisphenol A-based low molecular weight epoxy resin. The prepared compositions and the pure unmodified epoxy resin were cured with isophorone diamine, and then their...

Com. Bisphenol A-based low mol. mass epoxy resin was mixed with an epoxidized soybean oil to produce 2 compns. (viscosity 1500 and 700 mPa·s) studied for flow behaviour at 25-65°C and shear rate 2-200/s. After correction of the shear rate data by Krieger-Maron and Schümmer-Worthoff methods, the sheare rate relationship of the shear stress were detd...

Bisphenol-A (BPA) is an important raw material for the synthesis of polycarbonates, epoxy resins and other polymers as well as polymer additives. It is conventionally produced by acid-catalysed condensation of phenol with acetone. Application of various catalysts for the BPA synthesis is discussed with particular attention to the substrates convers...

Rheological behaviour of the compositions of low-molecular weight epoxy resin Ruetapox 0162 with epoxidized soybean oil was studied. The Bingham and Casson models were used to describe the flow of the resin, oil and the resin-oil mixtures of various initial viscosity. Rheological parameters for the studied compositions were determined and their non...

The compositions of low-molecular weight epoxy resin Araldite GY 783 with the epoxy compounds obtained from the waste poly(ethylene terephthalate) glycolysis products were prepared and then cured with hexahydrophthalic anhydride. Selected mechanical properties (i.e., tensile strength, flexural strength, hardness and impact strength) of cross-linked...

W trzecim wydaniu (zmienionym) tej książki omówiono mechanizmy syntezy poliestrów metodami polikondensacji lub polimeryzacji, scharakteryzowano surowce stosowane do ich syntezy, podano wpływ składu chemicznego i parametrów syntezy na właściwości żywic ciekłych i utwardzonych. Przedstawiono właściwości i rodzaje nienasyconych żywic poliestrowych pro...

The results of investigations of the structure and mechanical properties of the compositions of low-molecular-weight epoxy resin containing modified soybean oil are presented in this work. The oil was chemically modified and the product epoxidized in the main chains of triglycerides and the oil with epoxy groups placed at the end of branching of ma...

Development of a method of degradation of poly(ethylene terephthalate) (PET) wastes for the preparation of materials for the synthesis and modification of epoxy resins, development of a method of preparation of epoxy resins, characterization of epoxy resins so prepared, and optimization of the composition of epoxy resins modified with recycled mate...

A method of synthesis of liquid high-molecular-weight epoxy resins from modified vegetable oils as natural raw materials is proposed. The possibility of application of epoxidized soybean, rapeseed, linseed, and sunflower oils as well as hydroxylated soybean and rapeseed oils as raw materials in the fusion process was verified. Reactions of: (i) epo...

Application of epoxidized and hydroxylated natural oils as a new group of environmentally friendly and renewable raw materials for the synthesis of high molar mass epoxy resins is described. Selected vegetable oils were first oxidized and next reacted with mono and diethylene glycols. Obtained epoxidized soybean, rapeseed, linseed and sunflower oil...

Od lat na całym świecie prowadzone są intensywne badania nad wykorzystaniem olejów roślinnych oraz produktów recyklingu, w tym między innymi odpadowego poli(tereftalanu etylenu) do modyfikacji, a coraz częściej i syntezy różnego rodzaju polimerów. Taki kierunek badań naukowych wymuszają zarówno względy ekologiczne, związane z lokalnymi i międzynaro...

The method of receiving mixed epoxy-carbazole compositions which, for the fact of its photoluminescence ability, may be used for production of LEDs diodes, has been elaborated. Mechanical, thermal and optical properties of low-molecular-weight epoxy resin Ruetapox 0162 of different content of 5-(9-carbazolyl)methyl-1,3-oxothiolane-2-thione has been...

Linseed and sunflower oils were epoxidized and used as reactive diluents for the compositions with low-molecular weight epoxy resin Ruetapox 0162. Rheological behaviour of the compositions with assumed viscosity was determined. Curing processes of modified epoxy resins with isophorone diamine were studied using DSC method. Mechanical properties (fl...

Epoxy resins (RSMEG or RSDEG) (Table 1, Scheme A) were obtained in the reaction of epichlorohydrin with soybean oil previously hydroxylated with mono- or diethylene glycol (MEG or DEG, respectively). The values of Mn and Mw of these resins as well as Mn/Mw ratio were determined using GPC method (Fig. 1, Table 1) while chemical structures were confi...

In the review the basic problems concerning nonlinear optical properties (NLO) of the materials (classical inorganic materials, organic crystals and polymeric materials showing many advantages) were discussed. Applications of polymers make possible the preparation of thin layers (a few to a few dozen of um) of NLO materials which are necessary in c...

A new material-epoxy resin (R) with added glycydyl derivative -9-(2, 3-epoxypropyl)carbazole (EPK) was studied. R x EPK (x-wt. of EPK) emits light in the range from 330 nm to 470 nm. To obtain the best luminescence properties we analyzed the influence of various factors including different solvents used during preparation, different concentration o...

Modified natural oils - epoxidized soybean and rapeseed oils were tested as reactive diluents for viscosity regulation of Bisphenol A-based low-molecular- weight epoxy resin. Satisfactory viscosity reducing ability of epoxidized oils as well as non-Newtonian rheological behaviour of the resin diluted with modified oils were demonstrated. Co-crossli...

The results of research concerning the possibility of application of epoxidized soybean oil (EOS) as a reactive diluent to reduce the viscosity of low-molecular-weight epoxy resins were presented. Fluxing curve of the composition of the resin "Rutapox 0162" with EOS as a function of EOS content has been determined (Fig. 1). On the base of the cours...

Bisphenol A based low-molecular-weight epoxy resin was modified with epoxidized soybean oil, which exhibit viscosity reducing ability comparable to commercial grade active diluents. The studied compositions showed a non-Newtonian rheological behavior, typical for Bingham liquids. The values of the flow index (n) and the consistency index (k) for th...

Host-guest systems on the base of low-molecular-weight epoxy resins are homogenous due to the co-curing reactions of glicydyl derivatives of chromophores, epoxy groups of the resin and amine hardener. These compositions possess strong absorption in the ultraviolet spectral region and high photoluminescence efficiency, characteristic for the metal c...

W pracy przestawiono wyniki badań tworzywowego obuwia importowanego z Azji, którego dokonano w CLPO w aspekcie naruszenia kryteriów Ustawy o ogólnym bezpieczeństwie produktów. W ramach tej oceny dokonano analizy budowy i składu materiałowego wybranych wzorów obuwia oraz wykonano badania higieniczne zastosowanych materiałów. Przy pomocy metod analit...

Results of investigations on novel formulations, structure-property relationships, curing, and compositions with fillers and reinforcing fibers (1997--2004) are reviewed with about 200 references to articles and several references to patents. The following topics are considered in particular: novel dibasic acids, glycols, crosslinking monomers, and...

Review of various methods of limitation of epoxy resins (EP), used for titled purpose, flammability is presented on the basis of wide literature data (up to 2004). Halogen containing flame-retardants have been discussed in details. The mechanisms of their actions were characterized as well as the methods of their use together with selected metal (m...

The low-molecular-weight epoxy resin was modified with 9-(2,3-epoxypropyl)-carbazole and 9,9’-di(2,3-epoxypropyl)fluorene in order to obtain materials for the LED’s construction. Photoluminescence properties of synthesized polymers were examined and described in this paper.

Chemical modification of polyurethane foams with epoxide derivatives makes possible to obtain the materials with beneficial mechanical properties and thermal stability. Epoxy materials have many advantages such as: high chemical resistance, good adhesion to different materials but also are rigid and brittle. On the other hand, polyurethanes are mor...

Luminescence properties of a new material - epoxy resin with added 9-(2,3-epoxypropyl)carbazole (REPK) were studied. Absorption and photoluminescence (PL) spectra of REPK are compared with those of poly(N-vinylcarbazole) (PVK). PL in REPK is shifted to shorter wavelengths. Its intensity is higher than in PVK. REPK emits light in the range from 330...

The problems concerning electronic circuitry encapsulation with epoxy resins (EP resins) were discussed in this literature review. Types of most important components of epoxy molding compounds (Table 1) as well as their functions in the epoxy systems and requirements concerning them were presented. In the encapsulated semiconductor structure (Fig....

Epoxy resins are widely known due to their excellent mechanical properties, high thermal stability and high chemical resistivity. Recently, a new class of the materials was synthesized containing carbazole derivatives. This modification does not influence superior mechanical properties of epoxy resins, but significantly improves their luminous capa...

W pracy omówiono badania właściwości fotoluminescencyjnych (PL) żywic epoksydowych modyfikowanych 9-(2,3-epoksypropylo)karbazolem. Zastosowanie szeregu rozpuszczalników używanych w technologii żywic epoksydowych pozwala otrzymać odpowiednio cienkie warstwy, niezbędne do konstrukcji urządzeń elektronicznych. Nie obserwuje się przy tym istotnego wpły...

Compositions of low-molecular weight epoxy resin Ruetapox 0162 mixed with various amounts of 9-(2,3-epoxypropyl)carbazole (EPK) have been prepared and cured by isophorone diamine. Mechanical, thermal and photoluminescence properties of obtained materials were determined. It was found that low-molecular weight epoxy resin is an excellent dispersing...

Com. epoxy resins, Bakelite's Ruetapox 0162 and Vantico's Araldite GY 793 (containing active diluents), were modified with 5, 10, or 15 wt.% of 9-(2,3-epoxypropyl)carbazole, or 5-(9-carbazolyl)methyl-1,3-oxothiolane-2-thione, or with their 3,6-dichloro- or 3,6-dibromo-derivatives to prepare homogeneous compositions that were crosslinked with isopho...

The results of the research on the dielectric properties of epoxy resins modified by 5-(9-carbazolyl)methyl-1,3-oxothiolane-2-thione are presented. Dielectric measurements were performed by placing a sample of studied material between two conducting electrodes. The frequency varied from 100 Hz to 100 kHz. The temperature range was from 25 to 100oC....

Since Burroughes et al. first reported in 1990 [1], polymer electroluminescent devices (OLED's) they have been extensively investigated as the next generation of flat panel displays because of their high luminescence intensity, low drive voltage and broad-spectrum emission. Electroluminescent properties of these materials are closely associated wit...

This paper presents the research on commonly used epoxy resins modified by carbazole derivatives. The 9-(2,3-epoxypropyl)carbazole, 5-(9-carbazolyl)methyl-1,3-oksothiolane-2-thione and 3,6-dichlor (or 3,6-dibrom) 9-(2,3-epoxypropyl)carbazole were used as modifiers. A series of cured epoxy compositions have been characterized by thermogravimetric an...

Two kinds of low-molecular weight epoxy resins: Epidian 5 and Epidian 53 were used for modification of the semi-hydrate gypsum. It was found, that epoxy resins increase the water-resistance of gypsum materials and make difficult the water infiltration in them. They also significantly improve the flexural and compression strength under dry and wet c...

W książce omówiono budowę, właściwości i metody otrzymywania żywic epoksydowych z epichlorohydryny i ze związków nienasyconych, z uwzględnieniem stosowanych utwardzaczy, rozcieńczalników i środków uelastyczniających oraz zastosowanie żywic epoksydowych. Obszernie opisano surowce otrzymywane z żywic epoksydowych – żywice lane, kleje, materiały powło...

W niniejszej pracy przedstawiono wyniki badań nad właściwościami żywic epoksydowych, modyfikowanych pochodnymi karbazolu. Wprowadzenie do żywicy epoksydowej podstawników karbazolilowych umożliwia uzyskanie nowych materiałów o właściwościach foto- i elektroluminescencyjnych. Do otrzymania kompozycji epoksydowych użyto dwóch pochodnych karbazolilowyc...

A series of model epoxides and their sulfur-containing derivatives have been cured by hexahydrophthalic anhydride. The curing process was kinetically analysed using differential scanning calorimetry data. It has been found by means of Friedman and Ozawa–Flynn–Wall methods that the apparent activation energy (E) values of the cure process are higher...

Bis-1,3-oxothiolane-2-thione resins (Scheme 1) were prepared in the reactions of commercial low-M epoxy resins, Epidian 5 and Epidian 6, with carbon disulfide. Compositions including Epidian 5 or 6 and various amounts (5, 10, 20, 30 or 40 wt. %) of oxothiolane resins as additives were prepared and cured with piperidine. Mechanical properties such a...

Cure kinetics of model epoxides and related sulphur compounds—(1,3-oxothiolane-2-thione)s—by hexahydrophthalic anhydride have been investigated by means of dynamic differential scanning calorimetry (DSC). The apparent activation energy values (E) were determined for the whole conversion range by isoconversional methods of Friedman and Ozawa–Flynn–W...

The group of products: oxothiolanethiones, dithiolaneones and dioxolanethiones can be formed in the reactions of epoxy compounds with carbon disulphide. Practical applications have been found for 5-substituted-1,3-oxothiolane-2-thiones. The review of reactions of epoxides with CS2 occurring under different conditions and possibilities of applicatio...

A study was made on the modification of low-molecular-weight epoxy resins with carbon disulfide in various reaction systems. A simple procedure was developed involving an aqueous 50% NaOH/methylene chloride system. New derivatives were prepared with sulfur atoms incorporated into the epoxide ring, di-1,3-oxothiolano-2-thione (compound V in eqn. 1)....

A series of curing reactions of epoxides and different substituted (1,3-oxo-thiolane-2-thione)s with hexahydrophthalic anhydride in the presence of 2,4,6-tri( dimethylaminomethyl) phenol have been characterized by nonisothermal and isothermal differential scanning calorimetry (DSC). The DSC method was employed to investigate the thermal behavior of...

Quaternary ammonium salts, sulfoxides and sulfoianes were used as catalysts in the syntheses of low-molecular-weight epoxy resins from bisphenol A and epichlorohydrin. The reaction was carried out in a polar organic solvent at room temperature. The process of synthesis of epoxy resins under phase transfer catalysis (PTC) conditions was studied. Dep...

Single-stage synthesis of low-M epoxy resins from dian (4,4′-isopropylidenediphenol) and epichlorohydrin has been studied in the presence of NaOH in relation to various PTC catalysts used. The epoxy number (LE), Mn, Mw, and the degree of polydispersity (Pd) of the resulting products were studied in relation to the PTC catalyst applied. Optimum proc...

The 9-[(E)-1,2-dichloroviny1]carbazole is a starting material for synthesis of 9-ethynyl-carbazole [1], which in term is monomer for preparation of photoconductive polymers [2]. Dichlorovinylation of carbazole in a solid-liquid two phase system in the presence of crown and cryptand catalysts has been studied. Application of the Phase Transfer Catal...

Primary aliphatic amines are good nucleophilic reagents which easily react with dichloroacetylene (DCA). The reactions of DCA with primary aliphatic amines have been studied and a mechanism of these reactions has been proposed and discussed.

The method of synthesis of effective phase-transfer catalysts based on modified polystyrenes has been developed. There were obtained ammonium caralysts in which the active ammonium group was linked to PS matrix with methylene chains comprising 2, 4, 5, 6, 8 or 12 carbon atoms. The catalysts were tested in the following reactions carried out under p...