Diethylene Glycol Monobutyl Ether Research Articles

Synthesis and characterization of diethylene glycol monobutyl ether—Blocked diisocyanate crosslinkers

Typically blocked isocyanate systems are used to obtain the performance of two component polyurethane (PU) system in a one-component mixture. In this study four types of isocyanates namely, hexamethylene diisocyanate (HDI), diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI) and toluene diisocyanate (TDI) were blocked with diethylene glycol monobutyl ether (DEGMBE). Elimination of the isocyanate groups and the formation of urethane bonds were studied by FTIR spectroscopy and titration methods. Thermal dissociation of blocked diisocyanates was analyzed by DSC and TGA techniques.Deblocking temperature obtained by DSC and TGA techniques was compared. Based on DSC data, it was found that deblocking of blocked MDI and TDI starts at lower temperatures compared to that of the aliphatic one (HDI). Reactivity of the blocked IPDI is between blocked MDI and blocked TDI.In general, TGA results show the same trend as DSC except for IPDI which shows the lowest deblocking temperature. Deblocking temperature values obtained by TGA technique were lower than DSC values.

Density, Speed of Sound, and Refractive Index of Aqueous Binary Mixtures of Some Glycol Ethers at T = 298.15 K

The experimental data of densities (ρ), speeds of sound (u), and refractive indices (nD) of aqueous solutions of different glycol ethers, namely, ethylene glycol iso-propyl ether (EGIPE), ethylene glycol monobutyl ether (EGMBE), diethylene glycol dimethyl ether (DEGDME), diethylene glycol monobutyl ether (DEGMBE), propylene glycol monomethyl ether (PGMME), and dipropylene glycol monomethyl ether (DPGMME), over the entire composition range, at temperature T = 298.15 K, and at one atmospheric pressure have been obtained. The derived parameters such as the apparent molar volume (ϕV) of solute, isentropic compressibility of solution (βS), apparent molar isentropic compressibility (ϕKS) of solute, excess molar volume (VE) of solution, molar refraction ([R]1,2), deviation in refractive index (ΔnD) of solutions, deviation in molar refraction (Δ[R]1,2), and the deviation in isentropic compressibility (ΔβS) have been computed. The limiting apparent molar volumes of solutes (ϕV0), limiting apparent molar isentropic...

Structural and thermosensitive properties of novel octopus shape cyclotriphosphazenes

Three novel compounds ( 3– 5) were synthesized from the reactions of non-geminal cis-2,4,6 diethylene glycol monobutyl ether substituted cyclotriphosphazene ( 2a) with ethylamine, hexylamine and dodecylamine. Compounds 3– 5 were characterized by 31P NMR, MS and elemental analysis. The thermosensitive properties of compounds 3– 5 were investigated. Compound 3 showed thermosensitive properties which might enable it to be used as a biomedical material.

The investigation of structural and thermosensitive properties of new phosphazene derivative bearing glycol and aminoalcohol

Three isomers (nongeminal cis-2,4,6 ( 2); nongeminal trans-2,4,6 ( 3); geminal 2,2,4 ( 4)) were isolated from the reaction of hexachlorocyclotriphosphazatriene (trimer) ( 1) with diethylene glycol monobutyl ether (DEGBE). The substitution reactions of cis-tris isomer ( 2) with 3-amino-1-propanol were investigated under different solutions conditions to provide amphiphilic phosphazene ( 5). All of compounds were characterized by using elemental analysis, 31P NMR and mass spectroscopies. Thermosensitive properties of compound 5 were studied. The compound 5 is soluble in both water and organic media. This indicates that compound 5 is an amphiphilic molecule. Concentration-dependent LCST (Lower Critical Solution Temperature) behavior of 5 was measured in water. Compound 5 exhibited a reversible and thermosensitive phase transition in aqueous medium, from soluble to insoluble states. Compound 5 showed LCST at 37 °C (for 7 wt.% concentration) which is near to body temperature.

The investigation of structural and thermosensitive properties of new phosphazene derivatives bearing glycol and amino acid

In this study, hexachlorocyclotriphosphazene, N(3)P(3)Cl(6) (cylotriphosphazene), was reacted with hydrophilic and hydrophobic groups to synthesize amphiphilic phosphazene derivatives (4-12). Cylotriphosphazene was reacted triethylene glycol monomethyl ether (TEGME), dipropylene glycol monomethyl ether (DPGME), diethylene glycol monobutyl ether (DEGBE), (1 : 3 mole proportion) in the presence of sodium hydride and using tetrahydrofuran (THF) as solvent at -60 °C. Three isomers (nongeminal cis-2,4,6 (1a-3a); nongeminal trans-2,4,6 (1b-3b); geminal 2,2,4 (1c-3c)) were isolated from the reaction of hexachlorocyclotriphosphazatriene (trimer) (1) with TEGME, DPGME and DEGBE. The substitution reactions of cis-tris isomers (1a-3a) with 4-amino butyric acid, 5-amino valeric acid and 6-amino hexanoic acid were separately done to provide amphiphilic phosphazenes (4-12). All compounds were characterized by using elemental analysis, (31)P NMR and mass spectroscopy. Thermosensitive properties of compounds were studied. The compounds (4-12) were soluble in both water and organic media that shows they are amphiphilic molecules. Concentration-dependent LCST (Lower Critical Solution Temperature) behaviours of new compounds (4-12) were measured in water. Compounds 7, 9, 11 and 12 exhibited a reversible and thermosensitive phase transition in aqueous medium, from soluble to insoluble states.

Density and Viscosity of the Binary Mixture of Triethylene Glycol Monobutyl Ether + Water from (293.15 to 333.15) K at Atmospheric Pressure

This work reports new measurements of densities and viscosities for the binary liquid mixture of triethylene glycol monobutyl ether (CH3(CH2)3(OCH2CH2)3OH) + water as a function of composition in the temperature range from (293.15 to 333.15) K at atmospheric pressure. Densities were determined using a capillary pycnometer. Viscosities were measured with an Ubbelohde capillary viscometer. From the experimental data, the excess molar volumes, VE, and viscosity deviations, δη, were calculated. Both excess molar volumes and viscosity deviations were correlated by the Redlich−Kister-type equations. The results suggest that the molecular interaction between triethylene glycol monobutyl ether and water is stronger than that of diethylene glycol monobutyl ether and water.

Excess molar volumes and excess molar enthalpies of the binary mixtures of 1,2-dichloropropane with di- and triethylene glycol mono-alkyl ethers at T = 298.15 K

The excess molar volumes V m E and excess molar enthalpies H m E at T = 298.15 K and atmospheric pressure for the binary systems of 1,2-dichloropropane (1,2-DCP) with di- and triethylene glycol mono-alkyl ethers have been determined by measuring density and heat flux, respectively. The density has been measured by using a digital vibrating-tube densimeter, whereas heat flux measurements have been carried out by using an isothermal calorimeter with a flow-mixing cell. The diethylene glycol mono-alkyl ethers are 2-(2-alkoxyethoxy)ethanols: diethylene glycol mono-propyl ether (DEGMPE), diethylene glycol mono-butyl ether (DEGMBE), and the triethylene glycol mono-alkyl ethers are 2-(2-(2-alkoxyethoxy)ethoxy)ethanols: triethylene glycol mono-methyl ether (TEGMME), triethylene glycol mono-ethyl ether (TEGMEE), and triethylene glycol mono-butyl ether(TEGMBE). It was found that both V m E and H m E values of the binary mixtures are negative over the whole composition range except for the mixture with very high mole fraction of 1,2-DCP( x 1) in both DEGMPE and DEGMBE. In the case of 2-(2-(2-alkoxyethoxy)ethoxy)ethanols, the negative values of V m E and H m E continue to increase with an increase of the alkyl chain length of these alkoxyethanols. The minimum values of V m E shift from −0.1939 cm 3 mol −1 for the mixture with DEGMPE to −0.40 cm 3 mol −1 for the mixture with TEGMBE at x 1 = 0.40–0.50. Also, the minimum negative values of H m E have been shown ranging from −472.9 J mol −1 (DEGMBE) to −800.5 J mol −1 (TEGMBE) at x 1 = 0.40–0.50. The experimental results of both H m E and V m E were fitted to the Redlich–Kister equation. The experimental H m E data were also fitted to three local-composition models (Wilson, NRTL, and UNIQUAC). It was found that among these three models, the NRTL equation provides the most appropriate correlating result.

Excess Molar Volume and Viscosity Deviation for the Binary Mixture of Diethylene Glycol Monobutyl Ether + Water from (293.15 to 333.15) K at Atmospheric Pressure

Densities and viscosities have been measured as a function of composition for the binary liquid mixture of diethylene glycol monobutyl ether CH3(CH2)3O(CH2)2O(CH2)2OH + water in the temperature range from (293.15 to 333.15) K at atmospheric pressure. Densities were determined using a capillary pycnometer. Viscosities were measured with Ubbelohde capillary viscometer. From the experimental data, the excess molar volumes VE and viscosity deviations δη were calculated. This binary system shows negative deviations in excess molar volumes from the ideal behavior. Excess molar volumes and viscosity deviations were correlated by the Redlich−Kister type equations to obtain their coefficients and standard deviations.

Isothermal Vapor−Liquid Equilibria of Binary Mixtures of Nitrogen with Dimethyl Sulfoxide, N-Methyl-2-pyrrolidone, and Diethylene Glycol Monobutyl Ether at Elevated Pressures

High-pressure vapor−liquid phase equilibrium (P, x, y) were measured for the binary systems of nitrogen + dimethyl sulfoxide, nitrogen + N-methyl-2-pyrrolidone, and nitrogen + diethylene glycol monobutyl ether over a temperature rage between (323.15 and 393.15) K. In addition to the new data, the Soave−Redlich−Kwong, Peng−Robinson, and Patel−Teja equations of state accompanied by several types of mixing rule were also used to correlate these vapor−liquid phase behaviors. In general, the Patel−Teja equation incorporated with mixing rule-C (linear temperature-dependent combining rule for aij) yielded the best representation.

Wicking process of penetrants and inkjet inks on printing media

In this study, the dynamics of liquid capillary wicking (known as absorption, penetration, or imbibition) is discussed for a penetrant of an inkjet ink and commercial magenta inks. Different concentrations of penetrants on various printing media were tested, as well as magenta inks from HP and Canon. Penetrants are very efficient to wick inks on printing media and to reach maximum wicking area fast. The wicking areas of the penetrant solutions on test substrates are much lager than DI water. Since commercial ink contains 2 - 5% of penetrants, maximum areas of inks are larger than water and smaller than penetrant solutions. Alkylene glycol type penetrants such as Diethylene glycol monobutyl ether (DEGMBE), Diethylene glycol diethyl ether (DEGDEE) are to show large maximum wicking area and fast wicking rate. Alcohol type penetrants including Ethyl alcohol (EtOH) and Isopropyl alcohol (IPA) indicate fast drying rate at 100 and 50% concentration; however, drying rate of both alcohol type and alkylene glycol type penetrants at low concentrations are close to drying rate of water. Alkylene glycol type penetrants show less effects of concentration on wicking ratio, while concentrations of alcohol type penetrants greatly affects to absorption.

Volatile Organic Compound (VOC) Analysis and Anti-VOC Measures in Water-based Paints

We developed an analytical method for volatile organi cc ompounds (VOCs) used as film-forming agents or anti-freeze agents in water-based paints by flame ionization detection (FID-GC) and gas chromatography mass spectrometry (GC/MS). Twelve VOC components were separated using 2 types of column that differ in polarity. In addition, a pretreatment method by ethyl acetate-water partition was evaluated, and a survey of the use of VOCs in commercially available water-based paints was performed. For indoor paints, the anti-VOC measures included changes from VOC solvents to semi-VOC (SVOC) solvents such as those from 2,2,4-trimethyl-1,3-pentanediolmonoisobutyrate (TMPMIB) to 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and from ethylene glycol (EG) to triethylene glycol. However, in multipurpose paints for both indoor and outdoor use, VOCs such as EG, TMPMIB, diethyleneglycol dibutyl ether, and diethyleneglycol monobutyl ether were detected .S incethese products may be also used for indoor painting, indications of VOC components and caution for use on products are necessary.

Acute Effects of Some Volatile Organic Compounds Emitted From Water-Based Paints

Acute effects during controlled exposure to some of the volatile organic compounds emitted from water-based paints were evaluated. Healthy volunteers (10 atopics, 10 nonatopics, and 10 painters) were exposed to a mixture of propyleneglycol, texanol, diethyleneglycol monoethylether, diethyleneglycol monobutyl ether, and dipropyleneglycol monomethyl ether at a total concentration of 35 mg/m3 (G), a mixture of G and ammonia (15 mg/m3) (GA), and clean air (C). Subjective ratings of irritation in eyes, nose, throat, and dyspnea were significantly higher during the G and GA conditions, when compared with during the C condition. Nasal mucosal swelling was observed after G but not after GA exposure. No effects of the exposure on the pulmonary function, markers of inflammation in nasal lavages, and renal function in urine were seen. Exposure to G and GA caused mild irritation in eyes, nose, and airways.

Investigation of Volumetric Properties of Some Glycol Ethers Using a Simple Equation of State

In this work, a simple equation of state (EoS) has been used to predict the density and other thermodynamic properties such as the isobaric expansion coefficient, αP, the isothermal compressibility, κT, and the internal pressure, Pi, of six glycol ethers including diethylene glycol monobutyl ether (DEGBE), propylene glycol propyl ether (PGPE), diethylene glycol monomethyl ether (DEGME), diethylene glycol monoethyl ether (DEGEE), triethylene glycol dimethyl ether (TriEGDME), and tetraethylene glycol dimethyl ether (TEGDME) at different temperatures and pressures. A comparison with literature experimental data has been made. Additionally, statistical parameters between experimental and calculated densities for the GMA EoS and four other EoSs (Soave–Redlich–Kwong, Peng–Robinson, Soave–Redlich–Kwong with volume translation, and Patel–Teja) indicate the superiority of the GMA EoS.

Studies on Equation-of-State Parameters and Linear Polymer Dimensions of Poly(p-chlorostyrene) in Diethylene Glycol Monobutyl Ether by Intrinsic Viscosity Measurements

Intrinsic viscosities, [η], of poly(p-chlorostyrene) (PPCS) in diethylene glycol monobutyl ether (DGMBE) which exhibits an exothermic solubility behavior with the polymer were measured using an Ubbelohde type capillary viscometer between 25 and 85°C. Polymer solvent interaction parameters at infinite dilution (χ1), exchange energy parameter \((\bar{X}_{12})\), exchange enthalpy (X12), and entropy parameters (Q12), of the PPCS/DGMBE pair were found at studied temperature range according to equation-of-state theory.

Excess Volumetric and Spectroscopic Properties of Mixtures of Some n-Alkoxyethanols and of Some Polyethers with 2-Pyrrolidinone and N-Methyl-2-Pyrrolidinone at 298.15 K

Excess molar volumes VmE for binary liquid mixtures of n-alkoxyethanols or polyethers + 2-pyrrolidinone or N-methyl-2-pyrrolidinone have been measured with a continuous dilution dilatometer at 298.15 K and atmospheric pressure as a function of composition. The alkoxyethanols are diethylene glycol monomethylether, 2-(2-methoxyethoxy) ethanol, CH3(OC2H4)2OH; diethylene glycol monoethylether, 2-(2-ethoxyethoxy) ethanol, C2H5(OC2H4)2OH; and diethylene glycol monobutylether, 2-(2-butoxyethoxy) ethanol, C4H9(OC2H4)2OH; whereas the polyethers are diethylene glycol dimethylether, bis(2-methoxyethyl)ether, CH3(OC2H4)2OCH3; diethylene glycol diethylether, bis(2-ethoxyethyl)ether, C2H5(OC2H4)2OC2H5; and diethylene glycol dibutylether, bis(2-butoxyethyl)ether, C4H9(OC2H4)2OC4H9. In all mixtures the excess molar volumes are negative and symmetric across the entire composition range. The excess volumes are fitted to the Redlich–Kister polynomial equation to obtain the binary coefficients and the standard errors. The experimental results have also been discussed on the basis of IR measurements.

Three-Liquid-Phases Equilibria for the Quaternary System Water + Formamide + Cyclohexane + Diethylene Glycol Monobutyl Ether near the Tricritical Point

The three-liquid-phases equilibria data of the quaternary system water (1) + formamide (2) + cyclohexane (3) + diethylene glycol monobutyl ether (4) in the tricritical region are reported. It has been found that the mass fraction of formamide in (formamide + water) controls the size of the three-phase region and the approach to the tricritical point. The experimental data have been analyzed to obtain the tricritical temperature and the tricritical composition.

Diethylene glycol monobutyl ether (DGBE): two- and thirteen-week oral toxicity studies in Fischer 344 rats

Standard toxicologic endpoints, supplemented by additional examinations, were studied for groups of 10 Fischer 344 rats/sex given drinking water formulated to supply 0, 50, 250, or 1000 mg diethylene glycol monobutyl ether (DGBE)/kg/day for 13 weeks. These dose levels were based upon initial investigations using drinking water formulated to supply 0, 1000, 1500 or 2000 mg DGBE/kg/day for two weeks. All rats survived the respective treatment intervals with no adverse treatment-related in-life effects, including no alterations in a functional observational battery. In both studies, rats given ⩾1000 mg/kg/day consumed less water and feed and weighed slightly less than controls. For rats given ⩾1000 mg DGBE/kg/day, the liver and red blood cells (RBC) were the primary target organs although the effects were slight. In the 13-week study, rats given 1000 mg/kg/day had statistically significant increased relative liver weight (7–10%) and hepatic cytochrome P450s (24–39%) and UGT (∼16%) levels along with slight, statistically significant, decreases in serum total protein, cholesterol and aspartate aminotransferase. Histopathologically, very slight hepatocyte hypertrophy and increased individual hepatocyte degeneration were found in females only. At 1000 mg/kg/day, the RBC count, hemoglobin (Hgb) and hematocrit (Hct) were minimally, but statistically significantly, decreased (5.1–8.7%) but RBC morphology, RBC indices, reticuloctye count and bone marrow and spleen histopathology were unaffected. Absolute and relative kidney weights statistically significantly increased (6–13%) with an equivocal increase in minor histopathologic changes typical of early spontaneous nephropathy. There were no adverse effects on urinalysis, clinical chemistry, sperm parameters or testis histopathology. At 250 mg/kg/day, there were equivocal decreases (∼2–3%) in RBC count, Hgb and Hct that were statistically significant for the RBC count and Hgb, but these changes were within the historical control range. This dose level was considered the no adverse effect level (NOAEL).

PρT Measurements and EoS Predictions of Glycol Ethers from (283.15 to 353.15) K at Pressures up to 25 MPa

New experimental densities in the compressed liquid state are reported for diethylene glycol monobutyl ether and propylene glycol propyl ether over the temperature range (283.15 to 353.15) K and for pressures up to 25 MPa. Density values (144 experimental data points) have been measured with a high-pressure vibrating tube densimeter. These data were used to determine isothermal compressibilities, isobaric thermal expansivities, and internal pressures for these compounds. Furthermore, the predictions for the vapor pressures and for the densities of four glycol ethers with different equations of state (EoS): Soave−Redlich−Kwong, Peng−Robinson, Soave−Redlich−Kwong with volume translation, and Patel−Teja have been analyzed to test the reliability of these EoS.

Adsorption of Synthetic Water‐Soluble Polymers from Thermodynamically Good Solvents onto Microporous Column Packings

The elution behavior of polyethylene glycols, polyethylene oxide, polypropylene glycols, and sodium poly(methacrylic acid) in several mobile phases (water, methanol, acetone, dimethylacetamide, diethylene glycol monobutyl ether) was studied. The elution behavior of polyvinyl alcohol in water was also measured. ZSM‐5 and Y‐type zeolites were used as column packings. Full retention of the polymers was found in several chromatographic systems. Polyethylene oxide with average molar masses up to 545 kg/mol, polyvinyl alcohol up to 128 kg/mol, and sodium poly(methacrylic acid) up to 1027 kg/mol were fully retained within specific column packings. Additionally, to the full adsorption, a decreased recovery of polymers was observed in some sorbent–solvent systems. According to the hydrodynamic radius of macromolecules in solution, the polymer should be sterically fully excluded from all pores of the zeolites. It is assumed that polymer chains are adsorbed in flower‐like conformation, i.e., a part of polymer chain could penetrate into pores after a change in the conformation of chains. The results indicate that microporous sorbents possess high adsorption potential towards polymers.

Identification of diethylene glycol monobutyl ether as a source of contamination in an ion trap mass spectrometer

Tandem liquid chromatography-mass spectrometry coupled to online radioactive material detection (LC/RAM/MS/MS) is a technique that is used routinely for in vivo and in vitro drug metabolism studies and allows for a simultaneous correlation between radiochemical peaks and mass spectral data. The compound diethylene glycol monobutyl ether (DGBE), a component of a commercially available scintillation cocktail for RAM analysis, was identified as a source of overwhelming chemical noise in a mass spectrometer which was used in an LC/RAM/MS/MS configuration. In this report, we describe the identification of DGBE as the source of the chemical noise and the methods that were used to minimize the exposure of the mass spectrometer to volatile components of the scintillation cocktail.