Reaction Of Isophorone Diisocyanate Research Articles

Development of biocompatible aqueous polyurethane dispersions using chitosan and curcumin to improve physicochemical properties of textile surfaces

The present research work aims to synthesize a blend of chitosan (CSN) and curcumin (CRN) based aqueous polyurethane dispersions (CSN-CRN APUDs) for the modification of textile surfaces. A series of anionic CSN-CRN APUDs were prepared by the reaction of isophorone diisocyanate (IPDI) with polyethylene glycol (PEG) and extended with chain extenders (CSN and CRN). Structural characterizations of prepared materials were examined through a fourier transformed infrared (FTIR) spectrophotometer. The performances of coated CSN-CRN APUDs on the colorfastness properties (washing, rubbing and perspiration) and the mechanical properties like tensile strength and tearing strength of plain weaved poly/cellulosic textiles (dyed, printed and white) were examined before and after the application of CSN-CRN APUDs. The findings showed that the mechanical and colorfastness properties of all the CSN-CRN APUDs treated poly/cellulosic textile samples were improved significantly as compared with untreated poly/cellulosic textile samples. The newly synthesized CSN-CRN APUD coating materials are sustainable and greener products, particularly derivatized from bio-resources. These coating materials can be utilized as outstanding eco-friendly substitutes for poly/cellulosic textile coatings for surface modifications.

Development of amylopectin based polyurethanes for sustained drug release studies

In this research work, the crosslinked structure of polyurethane has been exploited for sustained drug delivery. Polyurethane composites have been prepared by the reaction of isophorone diisocyanate (IPDI) and polycaprolactone diol (PCL), which were further extended by varying the mole ratios of amylopectin (AMP) and 1,4-butane diol (1,4-BDO) chain extenders. The progress and completion of the reaction of polyurethane (PU) were confirmed using Fourier Transform infrared (FTIR) and nuclear magnetic resonance (1H NMR) spectroscopic techniques. Gel permeation chromatography (GPC) analysis showed that the molecular weights of prepared polymers were increased with the addition of amylopectin into the PU matrix. The molecular weight of AS-4 (Mw ≈ 99,367) was found threefold as compared to amylopectin-free PU (Mw ≈ 37,968). Thermal degradation analysis was done using thermal gravimetric analysis (TGA) and inferred that AS-5 showed stability up to 600 °C which was the maximum among all PUs because AMP has a large number of –OH units for linking with prepolymer resulting in a more cross-linked structure which improved the thermal stability of the AS-5 sample. The samples prepared with AMP showed less drug release (<53 %) as compared to the PU sample prepared without AMP (AS-1).

Preparation of microcapsules with IPDI monomer and isocyanate prepolymer as self-healing agent and their application in self-healing materials

Microcapsules were synthesized with the hybrid of Isophorone diisocyanate (IPDI) and terminal isocyanate prepolymer (CPU) as active healing agent, then the microcapsules were mixed with epoxy resin in order to form a metal anti-corrosion coating with excellent self-healing properties. Through process optimization and molecular design, the core material which was isocyanate hybrid (CPU-IPDI) with 17% Isocyanate group (-NCO) was synthesized by the reaction of IPDI and castor oil, and then the CPU-IPDI was encapsulated in the microcapsule with Diphenylmethane diisocyanate (MDI) as the shell by interface polymerization. Fourier transform infrared spectroscopy (FT-IR) and thermogravimetric spectroscopy (TGA) confirmed the successful encapsulation of CPU-IPDI. The effect of the content of sodium lignosulfonate (NaLS) on the size and morphology of microcapsules were investigated. Optical microscopy (OM) and laser particle size analyzer show that the size of microcapsules decreases with the increase of the content of stabilizing agent. The microcapsules were prepared with 1% NaLS with a core content of 51.3%, an average particle size of 26.3 μm and a shell thickness of 1.44 ± 0.9 μm. In addition, the microcapsules loaded with CPU-IPDI were added to the epoxy coating, and the healing process of blank coating and self-healing coating was detected by SEM. The results show that the coating wound of containing 10% microcapsules has obvious healing. With saline infiltration and electrochemical impedance spectroscopy (EIS) test coating corrosion process, the results prove that after soaking in 3.5% NaCl solution for 7 days, the |Z| f = 0.01Hz value of the coating with 10 wt % microcapsules is about 1.9 × 106 Ω cm2, nearly three order higher than that of pure epoxy coating (3.1 × 103 Ω cm2), demonstrating the enhancement of protection ability.

Preparation and photochemical properties of PEG based alpha-hydroxyalkylphenone photoinitiator

A novel emulsified photoinitiator (named as OP10-IPDI-2959) was prepared by the reaction of isophorone diisocyanate (IPDI) with 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Ir-2959) and nonylphenol polyoxyethylene ether (OP-10). The structure of OP10-IPDI-2959 was characterized by FT-IR, 1H NMR, UV–vis and high-resolution mass spectrometry. The photochemical behavior of OP10-IPDI-2959 was investigated through the photolysis and polymerization of neopentyl glycol diacrylate (NPGDA), mixture of epoxy acrylate resin and 1,6-hexanediol diacrylate (HDDA). Under irradiation of UV light, the OP10-IPDI-2959 has similar photochemical properties with the Ir-2959. Combined with benzophenone, the photoinitiated rate of OP10-IPDI-2959 is higher than that of Ir-2959. The polyoxyethylene fragment of OP10-IPDI-2959 is not only an alternative to toxic amine as hydrogen donor, but also a hydrophilic unit for interface between oil and water. The OP10-IPDI-2959 can effectively emulsify the epoxy acrylate resin and 1,6-hexanediol diacrylate mixture to form low viscosity emulsion. Compared with Ir-2959, OP10-IPDI-2959 has good photoinitiation activity, lower migration and good water emulsification performance.

A novel thioxanthone-hydroxyalkylphenone bifunctional photoinitiator: Synthesis, characterization and mechanism of photopolymerization

A novel bifunctional photoinitiator (named as TX-EG-IPDI-2959) with thioxanthone and hydroxyalkylphenone moieties was synthesized by the reaction of isophorone diisocyanate with Irgacure 2959 and 2-(2-hydroxyethoxy) thioxanthone. The molecular structure of TX-EG-IPDI-2959 was characterized by 1H NMR, high-resolution mass spectroscopy, UV–vis and FT-IR. The photochemical behavior of TX-EG-IPDI-2959 was investigated through the photolysis and polymerization of butyl acrylate by UV–vis and HRMS. Compared with the combination of Irgacure 2959 and 2-(2-hydroxyethoxy) thioxanthone, the CC bond cleavage of hydroxyalkylphenone to produce free radical fragments was effectively done under the irradiation of visible LED light. The obvious intramolecular synergistic effect between the hydroxyalkylphenone and thioxanthone moieties has been confirmed based on HRMS analysis of photobleach and photopolymerization. In addition, the photopolymerization kinetic of an UV gel and trimethylolpropane triacrylate initiated by TX-EG-IPDI-2959 were also investigated. The plausible photochemical reaction mechanism of TX-EG-IPDI-2959 was proposed.

Synthesis and characterization of hydroxyethyl cellulose (HEC)-TiO2-based polyurethane bionanocomposites

A novel green series of hydroxyethyl cellulose (HEC) based polyurethane (PUs) prepolymersblended with TiO2 nanoparticles were synthesized by reaction of Isophorone diisocyanate (IPDI), hydroxyl-terminated polybutadiene (HTPB), and hydroxyethyl cellulose (HEC). The chain was further extended with 1,4-butanediol (BDO) to get final HEC based polyurethane bio nanocomposites (FPUNC). A mixture of HEC based polymer and TiO2 nanoparticles was formed in solution polymerization, in which the TiO2 nanoparticles dispersed depending on interaction of TiO2 nanoparticles with polymer chains. The molecular structure of the synthesized PU bionanocomposites was confirmed by FTIR. A series of FPUNCs was prepared by varying the percent composition of the TiO2 nanoparticles into the PU matrix. The morphology of the bionanocomposites was carried out by X-ray diffraction (XRD) studies and scanning electron microscopy (SEM). SEM images verified the good dispersion of TiO2 nanoparticles into PU matrix. The thermal stability of the synthesized FPUNCs was done by thermal gravimetric analysis (TGA), and the FPUNC12 with 5% contents of TiO2 nanoparticles showed better thermal stability. The resultant HEC-TiO2 based FPUNCs material have promising bio-degradable and bio functional materials with good thermal properties and have potential applications in the field of biomaterials.

Tailoring the morphology and properties of waterborne polyurethanes by incorporation of acrylic monomers

A series of waterborne polyurethane-acrylate (WPUA) hybrid emulsions in the presence of organic silicon were synthesized by the reaction of isophorone diisocyanate, polytetramethylene ether glycol, double hydroxyl terminated polydimethylsiloxane, methyl methacrylate, and butyl acrylate as mainly raw materials. Three WPUA dispersions with differently internal structures (core-shell, inverse core-shell and semi-interpenetrating network (semi-IPN)) were designed in this study. The morphological analysis was carried out by transmission electron microscopy (TEM) and showed that the designed structures were obtained by changing synthesis method. The mobility of silicon, which affects the water resistance of the films, is determined by the structure of the WPUA and was evaluated by X-ray photoelectron spectroscopy (XPS) and contact angle (CA) measurements. The degree of silicon migration and water resistance were the highest for the WPUA with the semi-IPN structure. The WPUA with the core-shell structure had the highest tensile strength and the best thermal stability. The WPUA with the inverse core-shell structure had the worst mechanical property. Scanning electron microscopy (SEM) results showed that the WPUA with semi-IPN structure had the highest degree of phase separation.

UV-curable urethane acrylate zirconium oxide nanocomposites: Synthesis, study on viscoelastic properties and thermal behavior

In the present study, UV-curable urethane acrylate was synthesized by the reaction of isophorone diisocyanate with1,4-butanediol and 2-hydroxyethyl methacrylate in the presence of dibutyltin dilaurate as a catalyst and acetone as a solvent. The structure of urethane acrylate oligomer was characterized by nuclear magnetic resonance and Fourier transform infrared spectroscopy. In order to examine the influence of inorganic phase of zirconium oxide nanoparticles on characteristics of synthesized resin, organic–inorganic nanocomposites were prepared by urethane acrylate resin and nano zirconium oxide with 1, 3, and 5 wt%. In order to improve nanoparticles dispersion, the surface of zirconium oxide nanoparticles was modified by vinyltrimethoxysilane coupling agent. The analysis of nanoparticle surface modification by Fourier transform infrared spectroscopy and scanning electron microscopy suggested a good reaction of vinyltrimethoxysilane with the surface of zirconium oxide nanoparticles. The characteristics of the prepared nanocomposites were evaluated through thermogravimetric analysis and dynamic mechanical thermal analysis. All of conducted tests represented improved thermal stability properties, storage modulus, and viscoelastic properties of urethane acrylate–zirconium oxide nanocomposites in comparison with polymeric coatings without nanoparticles.

Synthesis and characterization of novel renewable castor oil-based UV-curable polyfunctional polyurethane acrylate

In recent years, a lot of interest has been given to renewable resources for their environmental friendliness and potential biodegradability in the synthesis of urethane-derived polymers. In this work, UV-curable castor oil-based polyfunctional polyurethane acrylate (COPUA) was prepared by the reaction of isophorone diisocyanate (IPDI) with castor oil and pentaerythritol triacrylate (PETA). The structures and molecular weights of the targeted IPDI–PETA and COPUA were characterized by FTIR, 1H NMR, and GPC, respectively. In addition, the effect of reactive diluent content on damping properties, thermal stabilities, and mechanical properties of COPUA was characterized by dynamic mechanical analysis (DMA), thermogravimetric analysis (TGA), and universal test machine. DMA revealed the copolymers had a glass transition temperature (T g) from 31.81 to 48.09°C. TGA showed that thermal initial decomposition temperatures were above 344.5°C, indicating the copolymers had certain thermal stability. Finally, some physical properties of curing films were studied by the contact angle and water absorption, and the results showed that the coatings exhibited good hydrophobicity. The COPUA obtained from castor oil can be used as eco-friendly materials and other applications alternative to the use of other petrochemicals in coatings.

Novel polymerizable HMPP-type photoinitiator with carbamate: Synthesis and photoinitiating behaviors

Abstract A novel polymerizable photoinitiator (HEMA-IPDI-2959) was synthesized through the reaction of Isophorone diisocyanate with 2-hydroxyethyl methacrylate and Irgacure 2959. The molecular structure of HEMA-IPDI-2959 was characterized through 1 H NMR, FT-IR, UV–vis and a high-resolution mass spectrum. The UV–vis spectrum and 1 H NMR of the photolysis product of HEMA-IPDI-2959 suggest HEMA-IPDI-2959 to be a type I photoinitiator. Furthermore, HEMA-IPDI-2959 and Irgacure 2959 were also used to initiate the polymerization of 1,6-hexanediol diacrylate and Trimethylolpropane triacrylate. Results suggest that HEMA-IPDI-2959 has a higher reactivity with a lower migration rate relative to Irgacure 2959.

Method for improving the mechanical performance and thermal stability of unsaturated polyester resin/waste‐printed circuit board nonmetals composites via isocyanate chemistry

ABSTRACTTo strengthen the interfacial interactions between waste‐printed circuit board (WPCB) nonmetals and unsaturated polyester resin (UPE) and achieve a high performance in UPE composites, a novel type of polyurethane prepolymer (pre‐PU) with dual functions was prepared by the reaction of isophorone diisocyanate with poly(ethylene glycol). We found that pre‐PU was chemically bonded to the surface of the WPCB nonmetals, and a stronger interaction between the WPCB nonmetals and UPE matrix was formed. The mechanical properties and thermal stability of the UPE/pre‐PU–WPCB nonmetal composites showed remarkable improvements compared with those of the UPE/WPCB nonmetals composites, in particular, the impact toughness, which increased threefold. We envision that this promising modification method will not only open up new opportunities for the preparation of high‐performance plastic composites but also provide a guarantee for the practical industrial application of WPCB nonmetals. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45129.

Silica를 함유하는 Polyurethane dispersion 투습방수 Film의 제조

Silica-polyurethane hybrid breathable films were prepared and their breathabilities were assessed. Appropriately aggregated silica was prepared through sol-gel reaction of water glass and its particle size ranged 360∼500nm. The polyurethane dispersion was prepared by the reaction of isophorone diisocyanate(IPDI) as diisocyanate and polytetramethylene glycol(PTMG) and dimethylol propionic acid(DMPA) as polyol, particle size ranging 30∼120nm. The reaction between isocyanate and hydroxyl group to form urethane bonding was checked by the intensity of the stretch peak of isocyanate at 2270cm -1 in the FT-IR. The silica was incorporated into polyurethane dispersion and casted into film. It was shown that the incorporated silica(1∼5wt.%) increased water vapour permeability of the films by 30∼100%, and decreased the hydrostatic pressure by 10∼40%. From the results, it could be concluded that the appropriate hybridization of silica can increase the breathability of polyurethane dispersion film, while minimizing the loss of hydrostatic pressure.

Toward UV-curable urethane acrylate/silica hybrid coatings: Introducing urethane methacrylate trimethoxysilane (UAMS) as organic–inorganic coupling agent

Urethane methacrylate trimethoxysilane (UAMS) organic–inorganic material was synthesized by the reaction of isophorone diisocyanate with hydroxyethyl methacrylate and aminopropyltrimethoxysilane. This precursor was then added to urethane trimethacrylate (UTMA); consequently, silica domains were appeared within the resulting ultraviolet (UV)-irradiated hybrid coatings. The sol–gel precursors having different amounts of UAMS as well as the UV-irradiated nanocomposite specimens were thoroughly characterized by FTIR, 1H NMR, 13C NMR, SEM, and TGA. The results provided support for the fact that thermo-mechanical properties of hybrid coatings were enhanced markedly by the incorporation of UAMS. This can be explained by the generation of Si–O–Si hard segments throughout the UV-cured films. Study on hardness and thermal stability behavior provided further evidences for the action of UAMS as coupling agent. Noticeably, thermal stability of hybrid coatings experienced an upward trend with the UAMS content, which can be inferred on the basis of strict restrictions on the mobility of polymer chains imposed by the crosslinked network.

Preparation, characterization and swelling behaviors of polyurethane-grafted calcium alginate hydrogels

Polyurethane was synthesized by the reaction of isophorone diisocyanate, 2-hydroxyethyl methacrylate and diethylene glycol. Then polyurethane grafted calcium alginate gel material was prepared via free-radical grafting polymerization with azobisisobutyronitrile as an initiator. Modified calcium alginate hydrogel was improved in thermal property, crystallinity and anti-swelling properties. The reason is that polyurethane side chains affect the arrangement of calcium alginate by forming highly ordered crystal region.

Synthesis and evaluation of thermoplastic polyurethanes as thermo-optic waveguide materials

The refractive index and thermo-optic coefficient (dn/dT) of linear polyurethanes and UV-cured polyacrylates were determined over a range of near infrared (NIR )wavelengths. Three different linear polyurethanes were prepared from the polycondensation of isophorone diisocyanate (IPDI) and novel diols containing cyclic substituents, such as 1,3-dithiane, cyclic O,S-acetal and 1,3-dithiolane. The polymers exhibited a glass transition at 71–131 °C and were stable up to ∼250 °C. Urethane-diacrylate was prepared via a reaction of IPDI and 2-hydroxyethyl methacrylate, and a urethane-acrylate polymer film was produced under UV-irradiation. The urethane content of the UV-polymers was adjusted using composite films from a diacrylate-derived from 1,3-dithiane-attached diol. The linear polyurethane provided a high thermo-optic coefficient (dn/dT) of −3.63 × 10−4 °C−1 (1550 nm). The coefficient was dependent on the urethane content of the UV-composite films, which exhibited a larger thermo-optic effect than the pure UV-acrylate films because of the urethane group. All the urethane-polymer films exhibited a very low birefringence (<0.0004). The presence of N-H in the urethane backbones rarely resulted in additional absorption loss as waveguide materials at specific wavelengths of 1100, 1310 and 1550 nm. A urethane-acrylate composite film exhibited propagation losses of 0.09 (1100 nm), 0.244 (1310 nm) and 0.288 dB cm−1 (1550 nm). The losses (1310 and 1550 nm) were reduced to <0.09 dB cm−1 in the deuterium-exchanged film. UV-cured polyurethanes and linear polyurethanes are investigated for the potential use of thermo-optic waveguide materials. The thermo-optic effects of these polymer films are improved with higher contents of urethane backbones. The urethane polymers exhibit high light transmission in NIR region after deuterium-exchange reaction.

Ink Binder용 UV 경화형 조성물의 제조 및 특성

본 연구에서는 ink binder용으로 isophorone diisocyanate (IPDI)/polyether polyol/2-hydroxyethyl acrylate (HEA)계 UV 경화형 우레탄 아크릴레이트를 중합하였다. HEA/PETA 혼합 비율을 달리한 조성물의 UV 조사 시간에 따른 광경화거동을 FT-IR spectrophotometer, probe tack tester 및 Photo-DSC로 확인하였다. UV 조사 시간이 증가함에 따라 전환률 및 gel content는 증가하였으며 probe tack은 감소하였다. 반응성 희석제로 사용한 PETA 함량이 증가함에 따라 저장탄성률, 인장강도 및 초기분해 온도가 증가하였다. HEA/PETA 비율이 30/70인 경우 UV 경화 후 PMMA sheet에 대한 부착특성이 가장 우수하였다. In this study, Ultraviolet (UV) curable urethane acrylates for ink binder was prepared by reaction of IPDI, polyether polyol and HEA. The UV curing behavior of compositions with HEA/PETA ratio on UV irradiation time was investigated by FT-IR spectrophotometer, probe tack tester and Photo-DSC. Conversion % and gel content were increased with increasing UV irradiation time, but probe tack was decreased. Storage modulus, tensile strength and decomposition temperature were increased as PETA content increased. In case of HEA/PETA ratio was 30/70, adhesion property of UV-cured composition on PMMA sheet was excellent.

Synthesis and Properties of IPDI-TMP Waterborne Curing Agent

The waterborne curing agent was prepared by reaction of isophorone diisocyanate (IPDI), polyethylene glycol single methyl ether(MPEG) and trimethylol propane (TMP). The synthesis process of curing agent were monitored by Fourier transform infrared (FTIR) spectroscopy, and initial tack, peel strength, heat aging resistance, shear strength, creep resistance of all samples with different curing agent content were measured. The results showed that the curing agent dispersed well as an incorporated state in the waterborne polyurethane. The water and ethanol absorption decreased with increasing curing agent content, the peel strength was significantly increased up to 6.7 N/mm.

Microporous Bio-Membrane Materials Based on High Molecular Weight Polylactide and Low Molecular Weight Poly(ethylene glycol)

In this work, microporous membrane biomaterials based on high weight molecular polylactide (PLA) and low molecular weight poly(ethylene glycol) (PEG) using rapid solvent evaporation method were prepared and investigated. The effect of PEG segments added on the thermal and degradation behaviors was studied. According to the results, produced PLA/PEG biomaterial has lower glass transition temperature (Tg)in comparison with neat PLA. It was also found that the degradation rates of the PLA/PEG biomaterials were significantly increased with adding of PEG, which explained by increasing hydrophilic groups. For better porous fixation, CL-blocked polyisocyanate (CL-bp), which was synthesized from reaction of isophorone diisocyanate (IPDI) with dimethylol propionic acid (DMPA) and Trimethylolpropane (TMP) followed by addition of caprolactam (CL), were introduced. The microporous forms were observed by the scanning electron microscope (SEM), which showed the mean diameters of prepared PLA/PEG microporous were around 10μm.

Influence of blocked polyisocyanate on the mechanical, thermal and interfacial properties of bamboo/hydroxyl-terminated polyurethane composites

In this study, chemical modification of bamboo powder (BP)/hydroxyl-terminated polyurethane (HPU) composites obtained by hot press was investigated using blocked polyisocyanate synthesized from reaction of isophorone diisocyanate with 1,1,1-trimethylolpropane (TMP) followed by addition of methyl ethyl ketoxime (MEKO). The modified surface of MEKO-blocked polyisocyanate (M-bp)-treated BP/HPU composites was identified by Fourier transform infrared spectroscopy from the appearance of CO bands absorbance and the reduction in relative intensity of OH, with respect to bamboo. The effects of M-bp as a cross-linker on the properties of the products were studied. Mechanical testing results showed that the tensile and flexural properties of the composites were improved by addition of such a cross-linker. The morphology analysis revealed that the M-bp-modified composites exhibited better compatibility and homogeneous morphologies in comparison with the unmodified composites. Moreover, the thermogravimetric analysis demonstrated that thermal resistance of the composites was enhanced by addition of M-bp. The moisture absorption characteristics of the products were also studied and discussed, because it is a major influencing factor for natural fibre composites. The results showed that better water resistance of modified composites was obtained due to stronger interfacial adhesion. Based on the findings in this work, they all indicated that the chemical modification occurred by the cross-linking effect of M-bp, which induced the strong bonds among the composite components.

Preparation and properties of waterborne cationic fluorinated polyurethane

Waterborne cationic fluorinated polyurethane (WCFPU) micro-emulsion was prepared by the reaction of isophorone diisocyanate (IPDI), polytetramethyleneether glycol (PTMG1000), 1,4-butanediol (BDO), N-methyldiethanolamine (MDEA), trimethylolpropane (TMP) and perfluoroalkylethyl octanol (FEOH), and then the films of the WCFPU were prepared. The influence on the mechanical properties and water absorption of the films, such as the molar ratio of NCO to OH, the dosage of MDEA, TMP and FEOH, was investigated. Their structure, morphology and heat performance were characterized by fourier transform infared spectrometer (FT-IR), dynamic light scattering (DLS), transmission electron microscope (TEM), X-ray diffraction (XRD), differential scanning calorimeter (DSC) and thermogravimetry (TG). The results revealed that the best mechanical properties and water resistance could be obtained under the condition that NCO/OH molar ratio was 1.25, w(TMP) was 1.1%, w(MDEA) was 7.29% and w(FEOH) was 22.3%. In addition, WCFPU was endowed with low surface energy of its film and the membrane surfaces had excellent water and oil repellency. Furthermore, the thermal stability of the waterborne cationic fluorinated polyurethane increased with the incorporation of perfluoroalkyl chain. And XRD, DSC and TG showed that micro-crystallinity of polyurethane increased with the increase of FEOH, which was benefit to the micro-phase seperation.