Coumarone-indene Resin Research Articles

Experimental study on the effect of Coumarone resin on the performance of SBS-modified asphalt.

An inexpensive and high-performing solid Coumarone resin was added to Styrene-butadiene-styrene (SBS) copolymer-modified asphalt to enhance its storage stability and road performance. To assess the effect of Coumarone resin dosage on the SBS-modified asphalt, a series of laboratory tests were conducted. The composite modified asphalt's segregation test was used to evaluate its storage stability, Dynamic Shear Rheometer (DSR) and Multiple Stress Creep Recovery (MSCR) tests were employed to investigate its high-temperature performance and permanent deformation resistance, and the Bending Beam Rheology (BBR) test was utilized to measure its low-temperature performance. Fluorescence microscopy was used to observe the composite modified asphalt's microstructure, and Fourier Transform Infrared Spectroscopy (FTIR) was conducted to study the changes in chemical structure during the modification process. The results showed that Coumarone resin can improve the compatibility of SBS and asphalt, improve the high-temperature performance and deformation resistance of SBS-modified asphalt, and adding an appropriate amount of Coumarone resin can help enhance the low-temperature cracking resistance of modified asphalt. The optimal dosage of Coumarone resin recommended for SBS-modified asphalt performance enhancement is 2% under the test conditions, as determined by comparing the test results of samples with various dosages.

Enhancing the Performance of Soil-Cement Pavement through Modified Natural Rubber Latex with Coumarone-Indene Resin

This research focuses on the modification of Natural Rubber Latex (NRL) for its application in soil-cement pavement. The NRL was modified with Coumarone-Indene (CI) and various tests were conducted to evaluate the effects of this modification. The degree of swelling test showed that the NRL's ability to absorb and retain toluene solvent was influenced by the addition of CI. The tensile tests revealed that the inclusion of CI improved the tensile modulus and tensile strength of the NRL up to an optimal content, beyond which there was a decrease. Peel strength tests demonstrated that the incorporation of CI initially increased peel strength up to an optimal CI content, after which it decreased. The splitting tensile test and the unconfined compressive test indicated that soil-cement blends containing modified NRL with CI 8 phr exhibited higher splitting tensile strength and unconfined compressive strength compared to those with neat NRL. Overall, the modification of NRL with CI showed promise in enhancing the properties of soil-cement pavement materials. The findings contribute to the understanding of modifying NRL for pavement applications and provide insights for further research and development in this field.

Comparison on the performance of solid coumarone-indene resin and liquid coumarone-indene resin modified asphalt

Coumarone-indene resin (CIR) has great potential for use as an asphalt modifier because of the cost-effective, high viscosity, and excellent mechanical properties. CIR is classified into two types based on polymerization degree: solid coumarone-indene resin (S-CIR) and liquid coumarone-indene resin (L-CIR). In this study, solid coumarone-indene resin modified asphalt (S-CMA) and liquid coumarone-indene resin modified asphalt (L-CMA) were prepared, and the comparison of the high-temperature performance, compatibility, aging performance, low-temperature performance, microstructure and modification mechanism of S-CMA and L-CMA was researched following the SuperPave standard. The results reveal that S-CIR is a solid resin with a high molecular weight that improves the high-temperature performance, permanent deformation resistance, and viscosity of asphalt, but impact on low-temperature performance negatively. In contrast, L-CIR is a liquid resin with low molecular weight that enhances the low-temperature properties and plasticity of asphalt, but decreases high-temperature properties. Additionally, solid resins with large molecular weight are prone to agglomeration in asphalt, while liquid resins with small molecular weight have better dispersibility, especially in high-content situations. Meanwhile, CIR exhibits good compatibility with asphalt. Based on the FTIR test results, chemical compositions and structures of S-CIR and L-CIR are similar, and physical miscibility was demonstrated between CIR and asphalt. In summary, modifier with different molecular polymerization degrees have a greater impact on modified asphalt, S-CMA has better high-temperature performance and viscosity than L-CMA, L-CMA has better low-temperature performance and plasticity than S-CMA, and S-CMA and L-CMA can be used for pavement construction in hot and cold areas respectively.

Дослідження природи кумарон-інден-карбазольної смоли, що одержується з рідких продуктів коксування вугілля.

The scientific achievements in the production of coumarone-indene resin (CIR) from the point of view of its use as a modifier of road bitumen are studied in detail. Its modifying disadvantages have been identified. An effective way of their elimination has been proved, in particular, by introducing carbazole into coumarone-indene resin at the stage of its synthesis. The method of ionic co-oligomerization was used to obtain coumarone-indenecarbazole resin (CICR), which, when added to road oil bitumen, has a rather neutral effect on its thermoplastic properties, but significantly improves the ability of bitumen to adhere to the surface of mineral material (adhesion characteristics). The raw materials for the production of coumarone-indene-carbazole resin were liquid non-target coal coking products, in particular, narrow coumarone-indene fractions (boiling point 140-190 °C) isolated from "heavy benzene" fractions; carbazole was the modifying agent of coumaroneindene fractions. The nature of the CICR was investigated. It is shown that indene, coumarone and styrene do not participate in co-oligomerization processes in the production of conventional coumarone-indene resin in full amount. It has been confirmed that carbazole is chemically involved in the formation of the structure of coumarone-indene-carbazole resin, which results in a decrease in the molecular weight of the resulting oligomers (compared to conventional coumarone-indene resins) and a decrease in their softening point. Under the same synthesis conditions (except for the addition of carbazole), the amount of CICR is significantly higher than that of CIR. The addition of carbazole to the feedstock "forces" not only the complete chemical conversion of indene, coumarone and styrene, but also involves other feedstock components, such as cycloalkene hydrocarbons and substances with triple bonds, in the oligomerization process. In contrast to CIR, coumarone-indenecarbazole resin contains a pyrrole ring and relatively fewer CH2 groups, alkyl fragments, and cycloalkene rings. Keywords: coumarone, indene, carbazole, resin, preparation. Corresponding author: Yu.V. Prysiazhny, e-mail: yurii.v.prysiazhnyi@lpnu.ua

Встановлення причин згущення робочої вбирної оливи при вимірі в'язкості.

Incomplete utilization of coke oven equipment and formation of tar with an unacceptably high content of quinoline–insoluble substances lead to a shortage of absorbent oil required for the recovery of benzene hydrocarbons from coke oven gas. To reduce the consumption of absorbent oil, it is necessary to extend the service life of the oil in the plant, but this leads to its thickening, affects the corrosion resistance of the equipment and contributes to coke formation on heating surfaces. The deterioration of absorbent oil is caused by polymerization of components, oxidation, and reactions with other substances, and these processes can also affect the extraction of benzene. To find out the reasons for the thickening of working oil, it is important to study how it behaves when coal tar components are added. A comparative analysis of the rheological behavior of mixtures of "fresh oil + tar" and "fresh oil + indene–coumarone resin" with recycled working oil was carried out. The rheological characteristics of the studied oils were determined on a Brookfield DV2T rotational viscometer with a thermocouple at a fixed temperature of thermostatting and variable shear rate. Studies of rheological behavior have shown that the loss of fluidity of the working oil occurs mainly due to the polymerization of unsaturated hydrocarbons of coke oven gas and absorbent oil, rather than due to the introduction of tar’s substances. Among the individual aromatic components that contribute to the loss of oil fluidity, polar rather than high molecular weight compounds have the greatest negative impact. The practical significance of the results is that due to oil regeneration, the flow mode at low shear rates is close to ideal fluids. This means that at low fluid flow rates, for example, when oil flows freely through the packing of a benzene scrubber, the viscosity of fresh oil is higher than that of the regenerated sample. Keywords: absorbent oil, indene-coumarone resin, viscosity, aromatic components, coal tar. Corresponding author: A.L. Bannikov, e-mail: artiksmartik@gmail.com

Performance Enhancement of Polymerized, Functionalized Solution Styrene–Butadiene Rubber Composites Using Oligomeric Resin towards Extremely Safe and Energy-Saving Tires

Polymerized, functionalized solution styrene–butadiene rubber (F-SSBR) is a new type of polymerized styrene–butadiene rubber solution containing specific terminal groups, which can be used in treads for high performances. However, the wet skid resistance related to safety, the rolling resistance to energy consumption, and the wear resistance to service life are often contradictory and form the performance “magic triangle”. In this work, oligomeric resins, including Coumarone resin, C9 resin, C5/C9 resin and a styrene-α-methyl styrene copolymer (SSC), were used as tire functional additives and selected to replace treated distillate aromatic extract (TDAE) to improve the performances of silica-filled F-SSBR composites. The C9 resin, C5/C9 resin and SSC could enhance the modulus at 300% and tensile strength of the F-SSBR composite. The four resins could improve the wet skid resistance and wear resistance of the composites. However, Coumarone resin caused poor silica dispersion in the F-SSBR matrix and eventually, the lower modulus, higher loss factor at 60 °C and the higher heat buildup in the composite were comparative to the composite with TDAE. Furthermore, the synergistic effect of the C5/C9 resin and SSC was found to improve the mechanical performance of the composites and it resulted in higher tensile strength and modulus, and a lower heat buildup, compared to the case when only TDAE was used. It is noted that the properties “magic triangle” was broken by the C5/C9 resin and SSC, and the C5/C910T15 increased the wet skid resistance by 21.7%, fuel-saving rate by 2.3%, and wear resistance by 8.3%, while S20T5 increased the wet skid resistance by 30.4%, fuel-saving rate by 7%, and wear resistance by 25% compared with CG.

Preparation and Application of Coumarone-Indene-Carbazole Resin as a Modifier of Road Petroleum Bitumen. 1. Influence of Carbazole:Raw Materials Ratio

The possibility of effectively using carbazole as an improver of coumarone-indene resin for use as a modifier of petroleum bitumens is studied. All starting materials for the production of coumarone-indene-carbazole resin (CICR) were obtained from various products of the coal coking process. The influence of raw material composition (amount of carbazole added to an industrial indene-coumarone fraction) on resin yield and its modifying properties was studied. The optimal amounts of carbazole in the raw material were established, and it is recommended to use CICR as an adhesive additive to bitumen.

Preparation and characterization of polyaniline microcapsule loaded with 2,2′‐azobis(2‐methylpropionitrile) initiator and its controlled release

AbstractThe thermal curing of acrylate adhesive consisting of acrylate monomer or prepolymer and 2,2′‐azobis(2‐methylpropionitrile) (AIBN) initiator is quite common. However, the two‐component adhesive is not suitable for large areas, large gap bonding, or potting because of its fast‐curing speed and intense heat release. To solve these problems, microencapsulating the initiator AIBN in the adhesive and controlling its release is proposed. Here, a new series of polyaniline microcapsules loaded with AIBN for the preparation of delayed‐release initiator were synthesized via an emulsification‐polymerization method. The coumarone indene resins were doped in polyaniline to control the release of the encapsulated AIBN. The characterization results indicate that the coumarone indene resin had been successfully mixed into the microcapsule polyaniline shell, and the interior of the microcapsules doped with resin had a rich pore structure. When a Span 80 and Tween 80 composite emulsifying system was used and its concentration was controlled at 0.1%–1.0%, the resulting microcapsules were homogeneous with good dispersibility. The release of the microcapsule was slow, and the release rate and release time could be precisely controlled by adjusting the type and doping amount of coumarone indene resin in the microcapsule shell material as well as the external temperature. For example, when the doping amount of coumarone indene resins in the PANI shell material increased from 0.2 to 1.0 g or when the temperature ranges from 75to 85°C, the release time of AIBN from the microcapsule decreased from 9 to 2 h and 12 to 3 h, respectively. With increasing demands for high performance delayed‐release initiators, the prepared polyaniline microcapsules loaded with AIBN show great potential for practical applications in adhesive, self‐healing coating, and petroleum exploitation.

Solvent-based polychloroprene contact adhesives: effect of tackifier

Solvent-based polychloroprene (CR) adhesive was formulated using four different types of tackifiers. Wood rosin (WD), coumarone-indene resin (CI), terpene-phenolic resin (TP) and para-tert-butyl phenol-formaldehyde (TBPF) resin were incorporated with CR at various amounts say 20–50 phr (parts per hundred rubber). The effect of nature and amount of resins on adhesion strength was measured on both leather to leather and rubber to rubber joints. Results indicated that the nature of resins greatly influenced the performance of the CR adhesive. The peel strength of CR/TBPF adhesive was higher than that of CR/TP, CR/CI and CR/WD adhesives. It was found that incorporation of TBPF resin also improved the thermal ageing resistance of the bonded joints. The properties of CR/resin adhesive were studied using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The interaction between the resin and CR was studied using FTIR spectroscopy. All the four tackifiers used were compatible with CR as confirmed by the DSC analysis.

Using Coking Byproducts in Paint Production: a Comparison of Quality Standards

Standard documents regarding the quality of coke-plant products are compared with standards regarding raw materials for paint and varnish production. The requirements on six products are totally consistent: benzene, indene–coumarone resin, coal tar, coal-tar solvent, solvent naphtha, and toluene. Ammonium sulfate and sulfuric acid may be used after additional treatment.

Hydrogenation of Indene–Coumarone Resin on Palladium Catalysts for Use in Polymer Adhesives

Hydrogenation of indene–coumarone resin on commercial palladium catalysts, including crusted catalysts, was studied. The process parameters were optimized to reach the maximal hydrogenation of aromatic fragments with minimal thermal degradation of the macromolecules. The optimum conditions are as follows: temperature 230°C, pressure 3 MPa, resin concentration in the solvent 10–25 wt %. Comparative analysis of the activity of the tested catalysts shows that palladium on activated carbon exhibits the highest activity. The use of indene–coumarone resin as an adhesive component of polymer hot-melt and pressure-sensitive adhesives was considered. The rheology of the initial resins and adhesives based on them, the phase state of the formulations, and their adhesiveness were compared. The advantage of using the hydrogenated resin for preparing polymer adhesives based on styrene–isoprene–styrene triblock copolymer was demonstrated.

Massive Preparation of Coumarone-indene Resin-based Hyper-crosslinked Polymers for Gas Adsorption

Hyper-crosslinked polymers (HCPs) are promising materials for gas capture and storage because of their low cost and easy preparation. In this work, we report the massive preparation of coumarone-indene resin-based hyper-crosslinked polymers via one-step Friedel-Crafts alkylation. Low-cost coumarone-indene resin serves as the new building block and chloroform is employed as both solvent and external crosslinker. A maximum surface area of 966 m2·g−1 is achieved, which is comparable with that of previously-reported coal tar-based porous organic polymers. Most importantly, a large number of heteroatoms including inherent oxygen atoms and introduced chlorine atoms in obtianed HCPs further enhance the interaction between specific sorbate molecule and adsorbent. Therefore, optimal structural and chemical property endow the new coumarone-indene resin-based HCPs with decent gas storage capacity (14.60 wt% at 273 K and 0.1 MPa for CO2; 1.18 wt% at 77.3 K and 0.1 MPa for H2). These results demonstrate that new HCPs are potential candidates for applications in CO2 and H2 capture.

PENGARUH STEARIC ACID PADA KARET ANGKATAN SEPEDA MOTOR TERHADAP KEKERASAN DAN KEKUATAN TARIK DENGAN KOMPOSISI 3Phr, 4Phr, 6Phr

Rubber damper is a simple yet important thing for the vehicle. This component is located inside the rear wheel that is directly related to the gear. There are numerous factors that affect the damage of this component. This study aims to determine how much the influence of stearic acid to the value of hardness and tensile strength of the rubber damper compound. Materials used for making compounds are RSS and synthetic rubber mixed with sulfur, black carbon white oil, ZnO, paraffin wax, MBTS, coumarone resin and stearic acid. These materials are mixed using two roll mixing to coalesce and form compound sheets. To know the duration of rubber maturation the rheometer process is done. The next process is rubber vulcanization using pressed mold with a temperature of 1600C and with a pressure of 150 psi. The tensile testing was done using rubber testing equipment with SNI ISO 37: 2015 (IDT - 2011) standard. Hardness testing was conducted using a tool with a Shore A hardness tester scale with ISO 7619 - 1: 2010 standard. Based on the results of the tests performed, the addition of sulfur highly affected the value of hardness and tensile strength. For compound hardness 3 with sulfur composition of 6 phr had the highest hardness value that is 77 Shore A and the lowest value was in composition 1 with the hardness value of 65,6 Shore A. The highest value of tensile strength was 15,394 N / mm2 in composition 1 and the lowest value was in composition 3 with a value of 11, 44 N / mm2.

Effect of type and content of tackifier on adhesion of natural rubber and reclaimed natural rubber based sealant

Adhesion property of natural rubber (NR) and reclaimed natural rubber (RNR) based sealant with concrete was studied here. The effect of tackifier type and loading on the tensile properties of the rubber based sealant sandwished between two flat cements was evaluated. There are three different tackifiers including Coumarone-indene resin (CI), petro resin (PE) and gum rosin (GR). The result initially showed that at the 20 phr of tackifier both NR and RNR sealant mixed with CI consumed the highest force to separate the rubber based sealant from the concrete. This might be due to the highest compatiblility between CI and rubber. Regardless of the tackifier type, all NR based sealants showed the cohesive failure while all RNR based sealants only showed the adhesive failure. Moreover, the NR based sealant seemed to be stronger than the RNR based one. When considering the effect of CI loading on the adhesion, it was shown that for both NR and RNR based sealents, the highest stress was observed when the rubber based sealant loaded with the 20 phr of CI.

Oil and gas processing products to obtain polymers modified bitumen

To obtain modified bitumen with excellent adhesive properties, coumarone-indene resin (CIR) was used. However, bitumens modified by CIR have somewhat worse plastic properties. For the improvement of the plastic properties of road bitumen modified by coumarone-indene resin, the paper proposes to use plasticizers. Characterized by a high content of rings (aromatic-naphthenic oils), a range of compounds was used as plasticizers. Of all different plasticizers tested, the tar produced from West-Ukrainian oils has been found to be the most effective one. The optimal ratio between modified bitumen components was determined enabling to obtain the commercial product of polymers modified bitumen of BMP 60/90-52 brand. The complex thermogravimetry and differential-thermal analysis has been used to analyze the initial and modified bitumen. Bitumens modified by CIR have shown by far the highest thermal stability under operation conditions.

Effect of Testing Rate on Adhesion Properties of Benzoyl-Peroxide-Cured ENR 25/NBR Blend Adhesive Using Gum Rosin and Coumarone-Indene Resin as Tackifiers

Dependence of adhesion properties of benzoyl-peroxide-cured epoxidized natural rubber (ENR 25)/acrylonitrile-butadiene rubber (NBR) blend adhesive on testing rate was systematically studied. Coumarone-indene resin and gum rosin were used as tackifiers. Toluene was used as solvent throughout the study. The SHEEN hand coater was used to coat the adhesive on polyethylene terephthalate at 30 and 120 µm coating thickness. The adhesion properties were measured by a Lloyd adhesion tester operating at different rates of testing. Results showed that the loop tack, peel strength, and shear strength increased with increasing testing rate, an observation that was attributed to the viscoelastic nature of adhesive. In all cases, the adhesion properties of the adhesives also increased with increasing coating thickness.

ANALYSIS OF AUTOHESION AND PHYSICO-MECHANICAL PROPERTIES (MULTIFUNCTIONAL BEHAVIOR) OF THE COAGULUM FROM THE LATEX OF EUPHORBIA CADUCIFOLIA HAINES VIS-À-VIS COMPARISON AGAINST SYNTHETIC RESINS IN NATURAL RUBBER COMPOUNDS

ABSTRACT Soft and tacky mass recognized as whole coagulum (Cog) and its toluene soluble fraction (TE) obtained through coagulation of latex of Euphorbia caducifolia Haines has been investigated in this article as green tackifier cum multifunctional agent in natural rubber (NR) based gum compounds. It was observed that inclusion of TE and Cog in the formulations increased tack strength over the control compound (without TE and Cog). At the same loading, autohesion for natural and commercial coumarone indene resin was found comparable. However, phenol formaldehyde (non–heat reactive octyl phenol formaldehyde) resin demonstrated highest tack strength among all the NR compositions studied. Presence of various functional groups such as esters/carboxylic acid, carbon–carbon unsaturation, and so on, in natural resin activated the system and reduced the activation energy barrier for curing. The optimized composition with 5 phr TE showed nearly 5% reductions in activation energy over the control compound. However, no such cure acceleration was displayed by Cog. Unaged tensile properties of the compounds with natural resin at similar proportions to commercial resins were found comparable. Retention of tensile properties after aging for the vulcanizates with TE was better than those with the commercial resins. For Cog, however, the retention of elongation at break and tensile strength were slightly higher compared with tensile modulus.

Dehydration of the still residue from the rectification of raw benzene

The still residue from the rectification of raw benzene is a stable emulsion with a water content exceeding 60%. Until 2012, it was dehydrated in the department of coumarone–indene resins by vacuum distillation. The closing of that department entailed the development of an alternative technology, which consists of two stages: 1) addition of 20–25% of the benzene fraction to the still residue and the removal of the water that settles in the lower layer; 2) distillation of the benzene and residual water by the heat from spent steam. After dehydration, the still residue contains 0.5–3.0% water and complies with Technological Specifications TU 2415-194-00190437. This technology permits the processing of the waste from the tar-distillation department in the stills of the benzene department—in particular, light distillates from the naphthalene column (containing naphthalene and 40–60% water) and light oil of no commercial value that contains phenolic hydrocarbons, resin-forming compounds, and phenols. After adding 10–15% of such wastes to the raw still residue, the mixture is dehydrated by the proposed technology. The introduction of such wastes in the still residue prior to dehydration permits the additional production of up to 4 t phenolic hydrocarbons and 40 t of commercial products such as coal solvent naphtha and coumarone–indene resin each month.

Effect of Magnesium Oxide and the Testing Rate on the Viscosity and Adhesion Properties of Epoxidized Natural Rubber/Acrylonitrile–Butadiene Rubber Blend Based Adhesives

The effect of magnesium oxide loading on the adhesion properties of epoxidized natural rubber (ENR 50)/acrylonitrile–butadiene rubber (NBR)-based pressure-sensitive adhesives was systematically investigated using 40 parts per hundred parts of rubber (phr) of coumarone–indene resin as the tackifier. The concentration range of magnesium oxide was from 10–50 phr. Toluene and polyethylene terephthalate (PET) films were selected as the solvent and the substrate, respectively, throughout the experiment. A Sheen hand coater was used to coat the adhesive onto the PET substrate at various coating thicknesses. The viscosity of the adhesive was measured using a Brookfield viscometer, whereas the loop tack, peel strength, and shear strength were determined using an adhesion tester operating at 10–60 cm/min. The results indicate that the viscosity increases with magnesium oxide loading, an observation which is attributed to the concentration effect of the filler. However, loop tack, peel strength, and shear strength increase with magnesium oxide loading up to 30 phr before decreasing upon further addition of the filler. This observation is ascribed to the effect of a varying degree of wettability of the adhesive, which culminates at 30 phr of magnesium oxide loading. At a fixed loading of magnesium oxide, all the adhesion properties of adhesives increase upon increasing the coating thickness and rate of testing.

Effect of zinc oxide on the viscosity and adhesion property of epoxidized natural rubber/acrylonitrile‐butadiene rubber‐based pressure‐sensitive adhesives

Viscosity, loop tack, peel strength, and shear strength of epoxidized natural rubber (ENR 50)/acrylonitrile‐butadiene rubber (NBR)–based pressure‐sensitive adhesive were studied in the presence of zinc oxide. The zinc oxide concentration was varied from 10 to 50 parts by weight per hundred parts of rubber (phr). Coumarone–indene resin with loading of 40 phr was chosen as the tackifier resin. Toluene and polyethylene terephthalate were used as the solvent and coating substrate, respectively, throughout the experiment. The adhesive was coated on the substrate by using a SHEEN hand coater. Viscosity of the adhesive was determined by a Brookfield Viscometer, whereas the loop tack, peel strength, and shear strength were measured by a Lloyd Adhesion Tester operating at 30 cm/min. Results indicate that viscosity increases with zinc oxide concentration owing to the concentration effect. Loop tack and peel strength pass through a maximum value at 20 phr of zinc oxide concentration. This observation is associated with the effect of varying degrees of wettability of the adhesive on the substrate. Shear strength, however, increases steadily with increasing zinc oxide loading owing to the steady increase in cohesive strength. In all cases, the adhesion properties of adhesives increase with increasing coating thicknesses. J. VINYL ADDIT. TECHNOL., 22:410–414, 2016. © 2015 Society of Plastics Engineers