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Eco-friendly bio-based adhesive for plywood from natural rubber latex (NRL)-blended isocyanate cross-linked starch

Soubam T, Gupta A, Jamari SS

Environ Sci Pollut Res Int, 2023 Dec;30(60):124610-124618.
PMID: 35610450 DOI: 10.1007/s11356-022-20788-9

Synthetic adhesives used in the production of plywood are a matter of concern because of the emission of carcinogenic gas formaldehyde, increased environmental pollution, and the depletion of fossil fuels. In this study, a bioadhesive composed of natural rubber latex (NRL) and rice starch was developed. However, rice starch has low moisture resistance, resulting in low adhesion. Thus, to enhance the effectiveness of NRL-blended rice starch-based bioadhesive, rice starch was cross-linked with polymeric 4,4″-diphenylmethane diisocyanate (pMDI) resin, which is an environment-friendly, formaldehyde free, and moisture resistant that is highly compatible with starch. The chemical interaction, viscosity, solid content, and gel time of the developed NRL-isocyanate cross-linked rice starch-based bioadhesive was investigated. The efficacy of the formulated bioadhesive was demonstrated by the fabrication of plywood. The presence of isocyanate and urethane capabilities in the bioadhesive formulations was confirmed by Fourier transform infrared spectroscopy (FTIR). The bioadhesive type Iso-A was discovered to have the highest viscosity of 8270 mPa.s, whereas Iso-B has the shortest gel time of 3.46 min and the highest solid content of 44%; the higher solid content accelerates the gel time. In terms of physical and mechanical properties of plywood, Iso-B has the lowest thickness swelling (TS) value of 13%, lowest water absorption (WA) value of 52% and shear strength value of 1.92 MPa, which corresponds to the ISO 12466-2-2007 standard requirements. Based on the results, NRL-blended isocyanate starch-based bioadhesive could be a good potential raw material for eco-friendly plywood industries with adequate accuracy.

Matched MeSH terms: Isocyanates
Fulltext Comparative Study of Aromatic and Cycloaliphatic Isocyanate Effects on Physico-Chemical Properties of Bio-Based Polyurethane Acrylate Coatings

Mudri NH, Abdullah LC, Aung MM, Salleh MZ, Awang Biak DR, Rayung M

Polymers (Basel), 2020 Jul 03;12(7).
PMID: 32635384 DOI: 10.3390/polym12071494

Crude jatropha oil (JO) was modified to form jatropha oil-based polyol (JOL) via two steps in a chemical reaction known as epoxidation and hydroxylation. JOL was then reacted with isocyanates to produce JO-based polyurethane resin. In this study, two types of isocyanates, 2,4-toluene diisocyanate (2,4-TDI) and isophorone diisocyanate (IPDI) were introduced to produce JPUA-TDI and JPUA-IPDI respectively. 2,4-TDI is categorised as an aromatic isocyanate whilst IPDI is known as a cycloaliphatic isocyanate. Both JPUA-TDI and JPUA-IPDI were then end-capped by the acrylate functional group of 2-hydroxyethyl methacrylate (HEMA). The effects of that isocyanate structure were investigated for their physico, chemical and thermal properties. The changes of the functional groups during each synthesis step were monitored by FTIR analysis. The appearance of urethane peaks was observed at 1532 cm-1, 1718 cm-1 and 3369 cm-1 while acrylate peaks were detected at 815 cm-1 and 1663 cm-1 indicating that JPUA was successfully synthesised. It was found that the molar mass of JPUA-TDI was doubled compared to JPUA-IPDI. Each resin showed a similar degradation pattern analysed by thermal gravimetric analysis (TGA). For the mechanical properties, the JPUA-IPDI-based coating formulation exhibited a higher hardness value but poor adhesion compared to the JPUA-TDI-based coating formulation. Both types of jatropha-based polyurethane acrylate may potentially be used in an ultraviolet (UV) curing system specifically for clear coat surface applications to replace dependency on petroleum-based chemicals.

Matched MeSH terms: Isocyanates
Fulltext Characterization and Performance Evaluation of Cellulose Acetate-Polyurethane Film for Lead II Ion Removal

Iqhrammullah M, Marlina M, Khalil HPSA, Kurniawan KH, Suyanto H, Hedwig R, et al.

Polymers (Basel), 2020 Jun 09;12(6).
PMID: 32526903 DOI: 10.3390/polym12061317

Global pollution from toxic metal waste has resulted in increased research on toxic metal adsorption. A cellulose acetate-polyurethane (CA-PU) film adsorbent was successfully prepared in this research. The cellulose acetate-polyurethane film adsorbent was prepared with a polycondensation reaction between cellulose acetate and methylene diphenyl diisocyanate. The CA-PU bond formation was confirmed by functional group analysis obtained from Fourier transform infrared (FTIR) spectroscopy. The obtained film was characterized for improved tensile and thermal properties with the addition of methylene diphenyl diisocyanate (MDI). The adsorption ability of the obtained film was evaluated with laser-induced breakdown spectroscopy (LIBS). The best film adsorbent from the LIBS was selected and studied for adsorption isotherm. The FTIR analysis confirmed the formation of the CA-PU bond from the polycondensation between cellulose acetate and the methylene diphenyl diisocyanate. The result showed that the addition of methylene diphenyl diisocyanate (MDI) resulted in the urethane network's growth. The characterization result showed an improvement in the morphology, thermal stability, and tensile strength of the film. The LIBS studies showed improvement in the adsorption of Pb2+ with CA-PU compared with the neat CA. The isotherm studies revealed that Pb2+ adsorption by cellulose acetate-polyurethane film adsorbent was heterogeneously dependent on the Freundlich isotherm model (R2 = 0.97044). Overall, the polycondensation method proposed by this study enhanced the Pb2+ removal, and was comparable to those reported in previous studies.

Matched MeSH terms: Isocyanates
New polyurethane nanocomposites based on soya oil

Mohammed IA, Abd Khadir NK, Jaffar Al-Mulla EA

J Oleo Sci, 2014;63(2):193-200.
PMID: 24420063

New polyurethane (PU) nanocomposites were prepared from a dispersion of 0 - 5% montmorillonite (MMT) clay with isocyanate and soya oil polyol that was synthesized via transesterification of triglycerides to reduce petroleum dependence. FT-IR spectra indicate the presence of hydrogen bonding between nanoclay and the polymer matrix, whereas the exfoliated structure of clay layers was confirmed by X-ray diffraction (XRD) and transmission electron microscopy (TEM). Optical microscopy, mechanical and thermal analyses were done to investigate significant improvement of the nanocomposites. The results showed PU-3% nanoclay (NC) showed optimum results in mechanical properties such as tensile and flexural strength but the lowest in impact strength.

Matched MeSH terms: Isocyanates
Fulltext Chemical and Thermo-Mechanical Properties of Waterborne Polyurethane Dispersion Derived from Jatropha Oil

Saalah S, Abdullah LC, Aung MM, Salleh MZ, Awang Biak DR, Basri M, et al.

Polymers (Basel), 2021 Mar 05;13(5).
PMID: 33807622 DOI: 10.3390/polym13050795

Nowadays, there is a significant trend away from solvent-based polyurethane systems towards waterborne polyurethane dispersions due to government regulations requiring manufacturers to lower total volatile organic compounds, as well as consumer preference for more environmentally friendly products. In this work, a renewable vegetable oil-based polyol derived from jatropha oil was polymerized with isophorone diisocyanate and dimethylol propionic acid to produce anionic waterborne polyurethane dispersion. Free standing films with up to 62 wt.% bio-based content were successfully produced after evaporation of water from the jatropha oil-based waterborne polyurethane (JPU) dispersion, which indicated good film formation. The chemical and thermo-mechanical properties of the JPU films were characterized. By increasing the OH numbers of polyol from 161 mgKOH/g to 217 mgKOH/g, the crosslinking density of the JPU was significantly increased, which lead to a better storage modulus and improved hydrophobicity. Overall, JPU produced from polyol having OH number of 217 mgKOH/g appears to be a promising product for application as a binder for wood and decorative coatings.

Matched MeSH terms: Isocyanates
Fulltext Production of Biodegradable Palm Oil-Based Polyurethane as Potential Biomaterial for Biomedical Applications

Yeoh FH, Lee CS, Kang YB, Wong SF, Cheng SF, Ng WS

Polymers (Basel), 2020 Aug 17;12(8).
PMID: 32824514 DOI: 10.3390/polym12081842

Being biodegradable and biocompatible are crucial characteristics for biomaterial used for medical and biomedical applications. Vegetable oil-based polyols are known to contribute both the biodegradability and biocompatibility of polyurethanes; however, petrochemical-based polyols were often incorporated to improve the thermal and mechanical properties of polyurethane. In this work, palm oil-based polyester polyol (PPP) derived from epoxidized palm olein and glutaric acid was reacted with isophorone diisocyanate to produce an aliphatic polyurethane, without the incorporation of any commercial petrochemical-based polyol. The effects of water content and isocyanate index were investigated. The polyurethanes produced consisted of > 90% porosity with interconnected micropores and macropores (37-1700 µm) and PU 1.0 possessed tensile strength and compression stress of 111 kPa and 64 kPa. The polyurethanes with comparable thermal stability, yet susceptible to enzymatic degradation with 7-59% of mass loss after 4 weeks of treatment. The polyurethanes demonstrated superior water uptake (up to 450%) and did not induce significant changes in pH of the medium. The chemical changes of the polyurethanes after enzymatic degradation were evaluated by FTIR and TGA analyses. The polyurethanes showed cell viability of 53.43% and 80.37% after 1 and 10 day(s) of cytotoxicity test; and cell adhesion and proliferation in cell adhesion test. The polyurethanes produced demonstrated its potential as biomaterial for soft tissue engineering applications.

Matched MeSH terms: Isocyanates
Fulltext β-Cyclodextrin conjugated bifunctional isocyanate linker polymer for enhanced removal of 2,4-dinitrophenol from environmental waters

Anne JM, Boon YH, Saad B, Miskam M, Yusoff MM, Shahriman MS, et al.

R Soc Open Sci, 2018 Aug;5(8):180942.
PMID: 30225083 DOI: 10.1098/rsos.180942

In this work, we reported the synthesis, characterization and adsorption study of two β-cyclodextrin (βCD) cross-linked polymers using aromatic linker 2,4-toluene diisocyanate (2,4-TDI) and aliphatic linker 1,6-hexamethylene diisocyanate (1,6-HDI) to form insoluble βCD-TDI and βCD-HDI. The adsorption of 2,4-dinitrophenol (DNP) on both polymers as an adsorbent was studied in batch adsorption experiments. Both polymers were well characterized using various tools that include Fourier transform infrared spectroscopy, thermogravimetric analysis, Brunauer-Emmett-Teller analysis and scanning electron microscopy, and the results obtained were compared with the native βCD. The adsorption isotherm of 2,4-DNP onto polymers was studied. It showed that the Freundlich isotherm is a better fit for βCD-TDI, while the Langmuir isotherm is a better fit for βCD-HMDI. The pseudo-second-order kinetic model represented the adsorption process for both of the polymers. The thermodynamic study showed that βCD-TDI polymer was more favourable towards 2,4-DNP when compared with βCD-HDI polymer. Under optimized conditions, both βCD polymers were successfully applied on various environmental water samples for the removal of 2,4-DNP. βCD-TDI polymer showed enhanced sorption capacity and higher removal efficiency (greater than 80%) than βCD-HDI (greater than 70%) towards 2,4-DNP. The mechanism involved was discussed, and the effects of cross-linkers on βCD open up new perspectives for the removal of toxic contaminants from a body of water.

Matched MeSH terms: Isocyanates
Effect of experimental silane-based primers with various contents of 2-hydroxyethyl methacrylate on the bond strength of orthodontic adhesives

Mustafa AA, Matinlinna JP, Razak AA, Hussin AS

J Investig Clin Dent, 2015 Aug;6(3):161-9.
PMID: 24415731 DOI: 10.1111/jicd.12083

AIM: To evaluate in vitro the effect of different concentrations of 2-hydroxyethyl methacrylate (HEMA) in experimental silane-based primers on shear bond strength of orthodontic adhesives.
METHODS: Different volume percentages of HEMA were tested in four experimental silane-based primer solutions (additions of HEMA: 0, 5.0 vol%, 25.0 vol% and 50.0 vol%). An experimental silane blend (primer) of 1.0 vol% 3-isocyanatopropyltrimethoxysilane (ICMS) + 0.5% bis-1,2-(triethoxysilyl) ethane (BTSE) was prepared and used. The experimental primers together with the control group were applied onto acid-etched premolars for attachment of orthodontic brackets. After artificial aging by thermocycling the shear-bond strength was measured. The fractured surfaces of all specimens were examined under scanning electron microscopy (SEM) to evaluate the failure mode on the enamel surface.
RESULTS: The experimental primers showed the highest shear-bond strength of 21.15 MPa (SD ± 2.70 MPa) and with 25 vol% showed a highly significant increase (P < 0.05) in bond strength. The SEM images showed full penetration of adhesive agents when using silane-based primers. In addition, the SEM images suggested that the predominant failure type was not necessarily the same as for the failure propagation.
CONCLUSIONS: This preliminary study suggested that nonacidic silane-based primers with HEMA addition might be an alternative to for use as adhesion promoting primers.

Matched MeSH terms: Isocyanates/chemistry
Antibacterial efficacy of quaternized chitosan/poly (vinyl alcohol) nanofiber membrane crosslinked with blocked diisocyanate

Wu JY, Ooi CW, Song CP, Wang CY, Liu BL, Lin GY, et al.

Carbohydr Polym, 2021 Jun 15;262:117910.
PMID: 33838797 DOI: 10.1016/j.carbpol.2021.117910

N-[(2-hydroxyl-3-trimethylammonium) propyl] chitosan chloride (HTCC), which is a type of chitosan derivative with quaternary ammonium groups, possesses a higher antibacterial activity as compared to the pristine chitosan. The nanofiber membranes made of HTCC are attractive for applications demanding for antibacterial function. However, the hydrophilic nature of HTCC makes it unsuitable for electrospinning of nanofibers. Hence, biodegradable polyvinyl alcohol (PVA) was proposed as an additive to improve the electrospinnability of HTCC. In this work, PVA/HTCC nanofiber membrane was crosslinked with the blocked diisocyanate (BI) to enhance the stability of nanofiber membrane in water. Microbiological assessments showed that the PVA/HTCC/BI nanofiber membranes possessed a good antibacterial efficacy (∼100 %) against E. coli. Moreover, the biocompatibility of PVA/HTCC/BI nanofiber membrane was proven by the cytotoxicity test on mouse fibroblasts. These promising results indicated that the PVA/HTCC/BI nanofiber membrane can be a promising material for food packaging and as a potential wound dressing for skin regeneration.

Matched MeSH terms: Isocyanates/chemistry*
Indoor air pollution evaluation with emphasize on HDI and biological assessment of HDA in the polyurethane factories

Mirmohammadi M, Hakimi Ibrahim M, Ahmad A, Kadir MO, Mohammadyan M, Mirashrafi SB

Environ Monit Assess, 2010 Jun;165(1-4):341-7.
PMID: 19444630 DOI: 10.1007/s10661-009-0950-5

Today, many raw materials used in factories may have a dangerous effect on the physiological system of workers. One of them which is widely used in the polyurethane factories is diisocyanates. These compounds are widely used in surface coatings, polyurethane foams, adhesives, resins, elastomers, binders, and sealants. Exposure to diisocyanates causes irritation to the skin, mucous membranes, eyes, and respiratory tract. Hexamethylene diamine (HDA) is metabolite of hexamethylene diisocyanate (HDI). It is an excretory material by worker's urine who is exposed to HDI. Around 100 air samples were collected from five defined factories by midget impinger which contained dimethyl sulfoxide absorbent as a solvent and tryptamine as reagent. Samples were analyzed by high-performance liquid chromatography with EC\UV detector using NIOSH 5522 method of sampling. Also, 50 urine samples collected from workers were also analyzed using William's biological analysis method. The concentration of HDI into all air samples were more than 88 microg/m(3), and they have shown high concentration of pollutant in the workplaces in comparison with NIOSH standard, and all of the workers' urine were contaminated by HDA. The correlation and regression test were used to obtain statistical model for HDI and HDA, which is useful for the prediction of diisocyanates pollution situation in the polyurethane factories.

Matched MeSH terms: Isocyanates
The influence of experimental silane primers on dentin bond strength and morphology: a laboratory and finite element analysis study

Mustafa AA, Matinlinna JP, Saidin S, Kadir MR

J Prosthet Dent, 2014 Dec;112(6):1498-506.
PMID: 24993375 DOI: 10.1016/j.prosdent.2014.05.011

STATEMENT OF PROBLEM: The inconsistency of dentin bonding affects retention and microleakage.
PURPOSE: The purpose of this laboratory and finite element analysis study was to investigate the effects on the formation of a hybrid layer of an experimental silane coupling agent containing primer solutions composed of different percentages of hydroxyethyl methacrylate.
MATERIAL AND METHODS: A total of 125 sound human premolars were restored in vitro. Simple class I cavities were formed on each tooth, followed by the application of different compositions of experimental silane primers (0%, 5%, 25%, and 50% of hydroxyethyl methacrylate), bonding agents, and dental composite resins. Bond strength tests and scanning electron microscopy analyses were performed. The laboratory experimental results were validated with finite element analysis to determine the pattern of stress distribution. Simulations were conducted by placing the restorative composite resin in a premolar tooth by imitating simple class I cavities. The laboratory and finite element analysis data were significantly different from each other, as determined by 1-way ANOVA. A post hoc analysis was conducted on the bond strength data to further clarify the effects of silane primers.
RESULTS: The strongest bond of hybrid layer (16.96 MPa) was found in the primer with 25% hydroxyethyl methacrylate, suggesting a barely visible hybrid layer barrier. The control specimens without the application of the primer and the primer specimens with no hydroxyethyl methacrylate exhibited the lowest strength values (8.30 MPa and 11.78 MPa) with intermittent and low visibility of the hybrid layer. These results were supported by finite element analysis that suggested an evenly distributed stress on the model with 25% hydroxyethyl methacrylate.
CONCLUSIONS: Different compositions of experimental silane primers affected the formation of the hybrid layer and its resulting bond strength.

Matched MeSH terms: Isocyanates/chemistry

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