Condensation Product Of Formaldehyde Research Articles

The development of dual-function solid-phase method as extraction and a decomposition reaction media for the determination of a formaldehyde releaser, imidazolidinyl urea, in cosmetics

In this study, we present a simple method to determine imidazolidinyl urea (IU) in cosmetics using a solid phase as both a decomposition field and an extraction phase. IU is difficult to quantify because it is a mixture of allantoin–formaldehyde condensation products that are easily decomposed to release formaldehyde. In our method, IU is decomposed to allantoin and 1-[4-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea (4-HU) on an aminopropyl-bonded silica solid phase. Subsequent high-performance liquid chromatography enables quantification of the resulting allantoin and 4-HU. The quantified value was converted to the total allantoin amount on the basis of molecular weight, and the calculated value was compared with that of an IU reference standard to determine the contents. The calibration curves of the decomposed IU as allantoin and 4-HU were both linear over an IU solution concentration range from 0.05 to 0.65% (w/v). The recoveries from lotion, body soap, and conditioners, which contained 0.1%, 0.3%, and 0.6% (w/w) of IU, respectively, ranged from 88.2 to 107.5%. The relative standard deviation values for the recovery tests of six replicates ranged from 1.03 to 6.97%. The intra-laboratory precisions for the lotion and conditioner A containing 0.3% IU were 3.02 and 4.94%, respectively. This method was well validated and would be helpful in determining IU in cosmetic samples.

Study of the Suspension Stability of Titanium Dioxide of Anatase Modification for Self-Purifying Fine Concrete

The suspension stability of the titanium dioxide of anatase modification, obtained by ultrasonic dispersion (USD) at the ultrasound frequency of 35 kHz in the aqueous medium of the stabilizer for self-purifying fine concrete as a finishing material for building envelope, is studied. The extreme dependence of the zeta potential on the ultrasonic dispersion parameters of titanium dioxide in the aqueous medium of the surfactant on the basis of sodium salts of naphthalene sulfonic acid and formaldehyde condensation products is established. Various variants of the sequence of the surfactant introduction into the titanium dioxide suspension are analysed. The ratio between TiO2 and the stabilizer, at which the zeta potential exceeds the threshold value of 30 mV and the suspension stability is maintained during 15 days, is determined. The optimal sequence of the suspension components introduction and the ultrasonic dispersion time are established. The influence mechanism of intermittent surfactant introduction on stabilization of the suspension of titanium dioxide of anatase modification is offered. The dependences of the fine concrete strength on zeta potential of the studied suspensions are obtained.

Urea-formaldehyde resins: production, application, and testing

Urea-formaldehyde (UF) resin, one of the most important formaldehyde resin adhesives, is a polymeric condensation product of formaldehyde with urea, and being widely used for the manufacture of wood-based composite panels, such as plywood, particleboard, and fiberboard. In spite of its benefits such as fast curing, good performance in the panels (colorless), and lower cost; formaldehyde emission (FE) originated from either UF resin itself or composite products bonded by UF resins is considered a critical drawback as it affects human health particularly in indoor environment. In order to reduce the FE, lowering formaldehyde/urea (F/U) mole ratio in the synthesis of the UF resin was done. In this study, synthesis of UF resins was carried out following the conventional alkaline-acid two-step reaction with a second addition of urea, resulting in F/U mole ratio around 1.0, namely 0.95; 1.05, and 1.15. The UF resins produced were used as binder for particleboard making. The board was manufactured in the laboratory using shaving type particle of Gmelina wood, 8% UF resin based on oven dry particle, and 1% NH4Cl (20%wt) as hardener for the resin. The target of the thickness was 10 mm and the dimension was 25 cm x 25 cm. The resulted particleboard then was evaluated the physical and the mechanical properties by Japanese Industrial Standard (JIS) A 5908 (2003). Further, the resulted particleboard also was used for the mice cage’s wall in order to mimic the real living environment. After four weeks exposure in the cages, the mice then were evaluated their mucous organs as well as their blood. The experiment results were as follows: 1) It was possible to synthesis UF resins with low F/U mole ratio; 2) However, the particleboard bonded UF resins with low F/U mole ratio showed poor properties, particularly on the thickness swelling and modulus of elasticity; 3) There was no significant differences among the mucous organs of the mice after a month exposure FE originated from cages wall using histopathology assessment.

Rac-aqua(4-methyl-oxazolidine-4-carboxylato)(nitrato)(1,10-phenanthroline)copper(II), the aldol condensation product of formaldehyde with the d- and l-(alaninato)aqua(1,10-phenanthroline)copper(II) nitrate

The d- and l-enantiomers of the ternary complex [Cu(phen)(ala)(H2O)]NO3 [phen = 1,10-phenanthroline; ala = alanine; l-enantiomer (1a); d-enantiomer (1b)] both undergo an aldol-type condensation with formaldehyde under mild acidic conditions to yield racemic rac-[Cu(phen)(4MeOCA)(H2O)(NO3)] (2) (4MeOCA = 4-methyl-oxazolidine-4-carboxylate). The precursors and the products were characterized by circular dichroism, FTIR, UV–Vis, fluorescence spectroscopy, molar conductivity and electrospray ionization mass spectrometry. The racemic nature of the product was established by X-ray crystallography . In the crystal structure, the copper atom has a tetragonally elongated octahedral geometry in which the water and an oxygen atom of a nitrate group are mutually trans. A possible mechanism for the racemization of the ligand is proposed.

Partial conversion of methanol to formaldehyde in the gas chromatography injection port and reactivity with amines

The partial conversion of methanol (MeOH) to formaldehyde (HCHO) in the gas chromatograph (GC) injection port was studied. The presence of formaldehyde in the injection port can result in reaction with injected analytes, especially primary and secondary amines. A systematic study of this problem was undertaken using norephedrine and ephedrine as probe analytes, and experiments involving varying inlet temperature, comparisons among solvents and solvent mixtures, isotopic labeling, and formaldehyde spiking. These experiments showed a direct correlation between inlet temperature and formation of the amine–formaldehyde condensation products. The mass spectra of the norephedrine and ephedrine condensation products were consistent with addition of the methylene group derived from formaldehyde across the amine and alcohol moieties to form the corresponding oxazolidine-ring compounds. Results for the imine condensation product of didesmethylsibutramine formed in the injection port are also presented.

Reaction network and mechanism of the synthesis of methylenedianiline over dealuminated Y-type zeolites

The reaction network and mechanism of the synthesis of methylenedianiline (MDA) from the condensation product of aniline and formaldehyde (aminal) on microporous acidic materials has been elucidated. The first step of the reaction, the decomposition of the aminal to N-benzylanilines, is limited by film diffusion, and the second and significantly slower step, the acid catalyzed rearrangement of these intermediates to MDA, is controlled by microkinetics on mesoporous dealuminated Y-type zeolites. This second step of the reaction network is limited by pore diffusion on zeolite BEA as an example for non-mesoporous materials. Based on time-concentration profiles, we were able to determine the reaction orders of the initial decomposition of the aminal to one and two for the following rearrangement of para-aminobenylaniline to 4,4′-MDA. From the kinetic data we deduced an SN2-type reaction mechanism and a complex reaction network, which is able to simulate the observed concentration profiles. The aniline to formaldehyde ratio in the starting mixture had a negligible influence on the final product distribution.

Unusually Large Bite Angle of a Distally Diphosphanylated Calix[4]arene Chelator (Eur. J. Inorg. Chem. 31/2010)

The cover picture shows the structure of a calix[4]arene-based ligand with an unusually large bite angle. Calix[4]arenes constitute versatile macrocyclic compounds, which can be obtained by condensation of phenols with formaldehyde. The so-called CALDIPs, which are diphosphanes built upon such a skeleton, have recently found applications in a variety of C–C bond-forming reactions, including polymerisation reactions. In the presence of group 8–10 transition metals, CALDIP ligands form straightforwardly dynamic chelate complexes, in which the ligand bite angle undergoes periodic variation. In the article by C. Jeunesse, D. Matt et al. on p. 4917 ff, a new chelate complex is described in which a CALDIP ligand adopts an unexpectedly large bite angle of 139°, which thus illustrates the great flexibility of the calix[4]arene core. The key ligand is depicted as superimposed over the sky of Strasbourg city (photo courtesy of Dr. R. Ruppert, UdS). Phenol–formaldehyde condensation products were already synthesised in Strasbourg by A. Baeyer in 1872.

ChemInform Abstract: Identification of Histrionicotoxins by GC-MS and GC-FTIR: Photo- and Chemical-Artefacts and Revised 13C NMR Assignments.

Abstract GC-mass and CG-FTIR spectral data together permit the rapid identification of the histrionicotoxin (HTX) alkaloids. 13C-NMR chemical shifts (δc) are reported for HTX 235A and revised δc are tabulated for nine HTXs and a perhydro-derivative. A butylboronic acid HTX derivative offers GC-MS and GC-FTIR advantages. Artefactural trans diene photoisomers of the HTX class are described as are formaldehyde condensation products. Two new HTX alkaloids 261 and 265E, are characterized by mass and FTIR spectra.

Effect of Composition on Adhesive Blends Consisting of Neoprene and Phenol-Cardanol-Formaldehyde Copolymer

This study is concerned with the adhesive properties of blends consisting of a copolymer phenolic resin and neoprene rubber. The phenolic resin is the condensation product of formaldehyde and a mixture of phenol and cardanol, a substituted phenol. Cardanol is the main ingredient of cashew nut shell liquid, a renewable resource and a cheap agro-by-product. The specific objective of the study is to arrive at optimum stoichiometric ratios between total phenol and formaldehyde (P/F ratio) so that the best peel and shear properties are obtained for aluminum-aluminum (Al–Al), styrene butadiene rubber-styrene butadiene rubber (SBR–SBR), and Al–SBR specimens. In general, the composition of the resin (represented by the P/F ratio) has only limited influence over the shear properties. Peel strength, on the other hand, is influenced by the P/F ratio. It is found to be a maximum for a P/F ratio of 1:1.5–1:1.7 for all cases. The results also prove that cardanol, a cheap renewable resource, can be a useful starting material for adhesive formulations.

Structures of interpolymer complexes based on carboxymethylcellulose and urea-formaldehyde resin

Interaction of carboxymethylcellulose with polymeric condensation products of urea and formaldehyde was studied. The structure of the final product was found to depend on the nature and structure of the components involved in the interaction.

Effect of management history and temperature on the mineralization of methylene urea in soil

A soil incubation and a greenhouse study on processing tomato were used to test the effects of soil temperature and the size and activity of the soil microbial biomass (SMB) on the degradation (mineralization) rate of a slow-release N fertilizer, methylene urea (MU), a condensation product of urea and formaldehyde. The mineralization rates of three MUs: Short (S), Medium (M), and Long (L) with different water solubilities were measured at two temperatures in a soil with low (fallow, F) and high (cover crop, CC) microbial activity. In the greenhouse study, the fate of fertilizer N was followed using 15N-urea and 15N-MU. The fertilizer N efficiency calculated for urea using the 15N mass balance approach was 93 and 85% compared with 65 and 67% for MU-S in F and CC soils, respectively. During six months of incubation, 52 and 63% of MU-S N was mineralized at 20 and 30 °C, respectively. The accumulated N data suggested that the degradation of all three MU types followed first-order reaction kinetics. The reaction rates were similar for all three MUs and increased with increasing temperature. However, fitting discrete, non-accumulated data revealed that MU mineralization is more complex and cannot be modeled with simple exponential decay equations. The size and activity of SMB did not affect the mineralization rate of MU-N under laboratory or greenhouse conditions. Interestingly, Activity Index (AI), defined as the slowly available pool of MU-N, was not a reliable indicator for the mineralization rate and plant availability of MU-N.

Mechanism of Microbial Degradation of Slow-Release Fertilizers

Methyleneureas are condensation products of urea and formaldehyde of different molecular mass and solubility; they are used in large amounts both as resins, binders, and insulating materials for industrial applications, as well as a slow-release nitrogen fertilizer for greens, lawns, or in bioremediation processes. In the present study, the microbial breakdown of these products was investigated. The nitrogen was released as ammonia and urea, and the formaldehyde released immediately oxidized via formiate to carbon dioxide. The enzymatic mechanism of metabolization of methyleneureas was studied in microorganisms isolated from soil, which were able to use these compounds as the sole source of nitrogen for growth. A strain of the Gram-negative bacterium Ralstonia paucula (formerly Alcaligenes sp. CDC group IVc-2) completely degraded methylenediurea and dimethylenetriurea to urea, ammonia, formaldehyde, and carbon dioxide. The enzyme initiating this degradation (methylenediurease) was purified and turned out to be different from the previously described enzyme from Ochrobactrum anthropi with regard to its regulation of expression and physicobiochemical properties. Fungal degradation of methyleneureas may occur via the formation of organic acids, thus leading to a nonenzymatic degradation of methyleneureas, which are unstable under acidic conditions.

Development of wood adhesives using flavonoid‐glycosides from orange mesocarp

Condensation products of orange mesocarp extract (flavonoid‐glycosides) and formaldehyde were modified with phenol, cashewnut shell liquid and resorcinol respectively. The copolymer resins formed were used in the formulation of wood adhesives. The glued veneers were evaluated for their shear strength and percentage wood failure assessed. The results showed that the adhesives cured to give gluelines of considerable strength and durability.

Mucosal disruption due to use of a widely-distributed commercial vaginal product: potential to facilitate HIV transmission.

Policresulen vaginal suppositories are a condensation product of metacresolsulfonic acid and formaldehyde. We investigated their use by female commercial sex workers (CSW) and whether such use could facilitate HIV transmission. We interviewed female CSW in Thailand about use of the product, and we directly observed the effects of self-administration of a single suppository by each of six women. Of 200 CSW interviewed, 32% had used policresulen vaginal suppositories in the preceding year and 46% had used them at some time. Many used them for reasons not listed on the package insert, such as improving their male partners' sexual pleasure, and most did not abstain from vaginal sex following use. Among 36 brothel-based and 67 non-brothel-based CSW with known HIV infection, the use of the product was not associated with HIV-1 infection (adjusted relative risk 1.0, 95% confidence interval, 0.5-2.0). Exfoliation of the vaginal and cervical mucosa was observed in all six CSW 1 day after product use, and, although it could have been the result of repeated examinations, an increase in genital HIV-1 RNA shedding was also detected in all three HIV-seropositive women. Although there was no epidemiological association with HIV infection, policresulen vaginal suppository use did disrupt the genital mucosa and therefore may have the potential to facilitate HIV transmission. Drug licensing authorities may wish to reassess the safety of this product. If the product continues to be distributed, steps should be taken to limit its use to the specific conditions for which it is indicated and to ensure that women abstain from vaginal sex following its use.

Inhibitory effect of Anaphylactic Reaction of Sosiho-Tang

Mast cells synthesize and secrete chemical mediators which play an central role in anaphylactic reactions. Compound 48/80 is a condensation product of formaldehyde with paramethoxyphenylethylamine that reliably induces the release of chemical mediators in the mast cell granules. Aggregation of the high-affinity Fc receptor also stimulates the mast cells. The objective of the current study was to determine the effect of Sosiho-Tang (SS-Tang) on mast cell-mediated anaphylactic reaction. SS-Tang completely inhibited systemic anaphylaxis induced by compound 48/80 in mice. SS-Tang inhibited local anaphylaxis induced by anti-dinitrophenyl (DNP) IgE. In addition SS-Tang concentration-dependently inhibited histamine release in mast cells induced by compound 48/80 or anti-DNP IgE. These results indicate that SS-Tang may contain compounds with actions that inhibit mast cell degranulation.

Purification and characterization of an enzyme from a strain ofOchrobactrum anthropithat degrades condensation products of urea and formaldehyde (ureaform)

An enzyme hydrolyzing the condensation products of urea and formaldehyde (ureaform) was purified and characterized from a bacterium isolated from soil and described as Ochrobactrum anthropi UF4. The enzyme designated as methylenediurea amidinohydrolase (methylenediurea deiminase) hydrolyzed ureaform condensation products of different length (methylenediurea, dimethylenetriurea, trimethylenetetraurea) to ammonium, formaldehyde, and urea at molar ratios of 2:1:1 (methylenediurea), 4:2:1 (dimethylenetriurea), and 6:3:1 (trimethylenetetraurea). Two other substrates, ureidoglycolate and allantoate, were also hydrolyzed, yielding glyoxylate and urea (ureidoglycolate) and glyoxylate, urea, and ammonium (allantoate), respectively. The molecular mass of the enzyme was determined by size exclusion chromatography to be 140 ± 25 kDa; the enzyme was composed of identical subunits of 38 ± 5 kDa, indicating that the native enzyme has a tetrameric structure. Growth of the bacterium in the presence of ureaform specifically induced the methylenediurea deiminase and no complete repression of enzyme synthesis by ammonium was observed.Key words: ureaformaldehyde, methylenediurea deiminase, fertilizer, Ochrobactrum anthropi.

5585496 Catalytic preparation of condensation products of formaldehyde: Teles Joaquim H; Melder Johann-Peter; Gehrer Eugen; Harder Wolfgang; Ebel Klaus; Groening Carsten; Meyer Regina Ludwigshafen, Germany assigned to Basf Aktiengesellschaft

5585496 Catalytic preparation of condensation products of formaldehyde: Teles Joaquim H; Melder Johann-Peter; Gehrer Eugen; Harder Wolfgang; Ebel Klaus; Groening Carsten; Meyer Regina Ludwigshafen, Germany assigned to Basf Aktiengesellschaft

2,8-Dimethyl-5,11-dipropyl-1,4,5,6,7,10,11,12-octahydroimidazo[4,5-h]imidazo[4,5-c][1,6]diazecine Hexahydrate

Crystals of the title compound, C18H30N6.6H2O, are composed of molecules of pronmeim (the condensation product of 2-methylimidazole, n-propylamine and formaldehyde) and water linked together by hydrogen bonds to form a two-dimensional network. The diazecine ring is in a chair conformation. Bonds lengths and angles are within the normal ranges.

Study of the membrane morphology and investigation of sensitivity to ions for sensors based on calixarenes

Many investigations on dielectric, electronic and spectroscopic characterisation have been achieved on molecular materials for their eventual application as sensors or electronic devices. Calixarenes exhibit an interesting supramolecular structure on account of their receptor properties; they represent receptor molecules of widely varying size for metal cations and organic molecules. They are comparatively new cyclic condensation products of para-substituted phenols and formaldehyde; they form a series of well-defined cyclic oligomers. Therefore, the variation of cavity size according to the requirements (i.e. ion sensitivities) of different guests is possible. The macro cycles are characterised by the phenolic unit number (4,6,8,…). p-tert-Butyl calix[ n]arene ( n = 4 and 8), used as a sensitive membrane incorporating the receptor molecule on the top of the gate oxide, was characterised. The calixarene was thermally evaporated on the oxide to form a semiconductor-oxide-film capacitance structure. It is shown, by means of structural and spectroscopic studies, that films have good adherence to the oxide and are chemically very stable allowing the use of such a structure as a chemical sensor in liquid media. The studies of ISFET structure using calix[ n]arene membranes are in progress, showing an interesting selectivity and stability.

Proof of the Bis(oxazolidine)methane Structure for the Norephedrine—Formaldehyde Condensation Product

AbstractThe norephedrine—formaldehyde condensation product, a potential prodrug, was shown to have a bis(oxazolidine)methane structure by an X‐ray crystallography study.