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Alpha,beta-unsaturated 4-oxo acids in heterocylic synthesis. II. Behavior of 3-(1,1-dioxadibenzothein-4-oyl)acrylic acid towards carbon nucleophiles under Michael reaction condition.

3-(1,1-Dioxadibenzothien-4-oyl)acrylic acid (1) was condensed with compounds containing active methylene groups under Michael reaction conditions to furnish the Michael adducts (lactones 2a-c, lactams 3a-c, ketones 4a,b). The behavior of these adducts toward the action of hydrazine hydrate were investigated. The compounds were tested for their biological properties.

Acrylates↗

Antimicrobial effects of esters and amides of 3-(5-nitro-2-furyl)acrylic acid.

The effect of 18 newly synthesized esters and amides of 3-(5-nitro-2-furyl)acrylic acid on bacteria (Escherichia coli, Staphylococcus aureus), yeasts (Saccharomyces cerevisiae, Candida albicans), molds (Aspergillus niger, Penicillium cyclopium, Rhizopus oryzae) and algae (Chlorella pyrenoidosa, Euglena gracilis, Scenedesmus obliquus) was investigated. The MIC values revealed antimycotic, antialgal and antibacterial activity of the studied derivatives. The antimycotic activity was found to decrease with increasing the length of the alkyl chain of esters and after introduction of amino nitrogen into the furylethylene backbone. The inhibitory effect on growth is caused by blocking bioenergetic processes, glycolysis in particular.

Acrylates↗

Water-soluble UV curable urethane methyl acrylate coating: preparation and properties.

Two kinds of water-soluble and ultraviolet (UV) curable oligomers were synthesized and characterized. The oligomers were evaluated as resins for water-based UV curable coating. The rheology of the two oligomers' aqueous solutions was investigated in terms of solid fraction, pH dependence, and temperature dependence. The solutions were found to be Newtonian fluid showing rather low viscosity even at high solid fraction of 0.55. The drying process of the coatings and the properties of the cured coatings were studied by comparing them with water-dispersed UV-curable polyurethane methyl acrylate. It was evident that the water-soluble coating dried more slowly; and that the overall properties were inferior to those of the water-dispersed coating.

Acrylic Resins↗

Preparation of mucoadhesive chitosan-poly(acrylic acid) microspheres by interpolymer complexation and solvent evaporation method II.

A mucoadhesive microsphere was prepared by an interpolymer complexation and solvent evaporation method, using chitosan and poly(acrylic acid) (PAA), to prolong the gastric residence time of the delivery system. The Fourier transform infrared results showed that microspheres were formed by an electrostatic interaction between the carboxyl groups of the PAA and the amine groups of the chitosan. X-ray diffraction and differential scanning calorimetry analysis showed that the enrofloxacin in the chitosan-PAA microsphere was molecularly dispersed in an amorphous state. Scanning electron microscopy of the surface and the quantity of mucin attached to the microspheres indicated that chitosan-PAA microspheres had a higher affinity for mucin than those of chitosan alone. The swelling and dissolution of the chitosan-PAA microspheres were found to be dependent on the pH of the medium. The rate of enrofloxacin released from the chitosan-PAA microspheres was slower at higher pH; therefore, based on their mucoadhesive properties and morphology, the chitosan-PAA microspheres can be used as a mucoadhesive oral drug delivery system.

Acrylic Resins↗

Degradation of acrylic copolymers by white-rot fungi.

Various water-soluble homopolymers and copolymers of acrylamide (AAm) and acrylic acid (AA) which contained phenolic sites, such as guaiacol, lignin sulfonate (LS) and 3,4-dihydroxybenzoic acid (3,4-DHBA), were tested with regard to their degradability by white-rot fungi. Compared with Phanerochaete chrysosporium, Pleurotus ostreatus caused a significantly higher decrease in the average molecular weight ( Mw) of most of the copolymers and the homopolymer under the applied culture conditions. However, the Mw of poly(guaiacol/AAm) increased significantly during incubation with Pl ostreatus. P. chrysosporium was able to reduce only the Mw of the poly(LS/AA) to a significant degree and not that of the other polymers. The mineralization rate of AAm and AA copolymers and terpolymers of AAm, AA and phenolics (LS, 3,4-DHBA, guiacol), which were tested with P. ostreatus and Trametes versicolor, turned out to be low (0.8-3.2%). While the rates of mineralization were similar among all polymers, the decrease in radioactivity from the culture media was higher with the terpolymers bearing phenolic sites. UV spectra of the culture media revealed that the phenolic sites in the terpolymers were significantly degraded by both fungi. Obviously, the degradation of phenolics within the polymer chain caused a higher decrease in Mw but did not significantly increase the mineralization rate.

Acrylamides↗

FEMIC (Fibromes Embolisés aux MICrosphères calibrées): uterine fibroid embolization using tris-acryl microspheres. A French multicenter study.

PURPOSE: A French multicenter registry was set up to confirm the safety and efficacy of large calibrated tris-acryl gelatin microspheres for embolization of symptomatic fibroids. METHODS: Technical recommendations included embolization using large microspheres (>500 microm) with no secondary embolization agent. Postprocedural pain, clinical improvement and adverse events were prospectively evaluated during a follow-up period of at least 6 months. RESULTS: Eighty-five women complaining of fibroid-related symptoms entered the study. In seven women, a secondary embolization agent was used in addition to microspheres. Complete resolution of menorrhagia was achieved in 84% of women at 24 months and significant uterine and fibroid volume reductions were noted after 6 months (37% and 73%, respectively). Three women experienced definitive amenorrhea (4%) and two women required hysteroscopic resection of a fibroid. Eight women were treated by hysterectomy because of treatment failure. In seven of these women, treatment failure was explained by an additional cause of symptoms including diffuse adenomyosis, endometrial hyperplasia or ovarian artery supply to the fibroids. CONCLUSION: Limited uterine artery embolization using large microspheres has good clinical success rate with low postprocedural pain and complications. Women can expect excellent midterm results with a high level of symptom control and significant fibroid volume reduction. Confidence in the end-point recommended here may require the experience of several cases.

Acrylic Resins↗

Bronchial artery embolization for life-threatening hemoptysis using tris-acryl microspheres: short-term result.

A prospective study of 70 patients with life-threatening hemoptysis who had bronchial and systemic artery embolization with tris-acryl linked microspheres was performed over 15 months. The procedure was technically successful in 90% of patients and at 24 hr after the procedure (87%). Recurrent hemoptysis occurred in 13% of patients within the first week. Chest pain was experienced following embolization in 7% of patients. The mortality was 10% due to the inclusion of patients with pulmonary metastases. Bronchial artery embolization using microspheres is an effective and well-tolerated treatment for patients with life-threatening hemoptysis who are not surgical candidates.

Acrylic Resins↗

Hydrophobic acrylic versus heparin surface-modified polymethylmethacrylate intraocular lens: a biocompatibility study.

BACKGROUND: The implant of intraocular lenses (IOLs) following cataract surgery induces a foreign-body reaction to the IOL and a response on the part of the lens epithelial cells (LECs). The purpose of this study was to compare these aspects after the implantation of two different IOL materials. METHODS: Thirty-six cataract patients were randomised to receive two different foldable lens: an acrylic hydrophobic IOL (Acrysof MA30BA) and a heparin surface-modified (HSM) polymethylmethacrylate IOL (Pharmacia & Upjohn 809C) after phacoemulsification. Slit-lamp biomicroscopy with specular technique was used to assess the inflammatory cell adhesion on the anterior IOL surface, anterior capsule opacification (ACO) and membrane growth from the rhexis edge at 7, 30, 90, 180 and 360 days after surgery. RESULTS: The 809C group showed a higher percentage of patients with slight inflammatory cell adhesion on the anterior cell surface and a higher small cellular density during the whole follow-up period. The epithelioid cell response was greater in the 809C group than the Acrysof group but the difference between the two groups was not statistically significant. The ACO increased during the follow-up in both groups but was significantly higher in the 809C group. CONCLUSION: Acrysof lenses are more biocompatible than HSM IOLs, showing a lower grade of inflammatory cell adhesion and ACO. The implantation of these lenses may be particularly indicated in patients with pathologies predisposing to blood-aqueous barrier damage.

Acrylates↗

The efficacy of acrylic acid grafting and arginine-glycine-aspartic acid peptide immobilization on fibrovascular ingrowth into porous polyethylene implants in rabbits.

PURPOSE: To determine the effects of acrylic acid (AA) grafting by argon plasma treatment and of immobilization of arginine-glycine-aspartic acid (RGD) peptides on fibrovascular ingrowth rate into high-density porous polyethylene (HPPE) anophthalmic orbital implants. MATERIALS AND METHODS: Sixty rabbits were divided into three groups, with 20 rabbits in each group: (1) control group, rabbits implanted with unmodified HPPE; (2) PAA group, rabbits implanted with HPPE grafted with poly(AA) by argon plasma treatment; (3) RGD group, rabbits implanted with HPPE grafted with AA by argon plasma treatment and subsequently immobilized with RGD peptide. An HPPE spherical implant was put in the abdominal muscles of rabbit. After implantation for 4 weeks, the retrieved implants were sectioned and stained with hematoxylin and eosin (H&E). Blood vessels were counted using CD-31 immunostaining. Cross-sectional areas of fibrovascular ingrowth, blood vessel densities, and host inflammatory response scores were determined for all three groups. RESULTS: The mean cross-sectional areas of fibrovascularization at 2 and 3 weeks after implantation were the greatest in the RGD group, followed by the PAA group. While minimal fibrovascular ingrowths were noted in all implants at 1 week, all the implants showed nearly complete ingrowth at 4 weeks. Blood vessel densities were the highest in the RGD group, followed by the PAA group at 2, 3, and 4 weeks. The mean inflammation scores of the PAA and RGD groups were less than that of the control group. CONCLUSION: Fibrovascularization into HPPE implants was enhanced by surface grafting of AA and further improved by immobilizing RGD peptides onto the grafted AA surfaces. The inflammatory reactions were mild by either technique of surface modification.

Abdominal Muscles↗

The effect of temperature on PAHs emission from incineration of acrylic waste.

Incineration of acrylic waste solution in a lab scale quartz tube vertical incinerator showed the presence of 12-15 polycyclic aromatic hydrocarbons (PAHs) from a list of 16 priority pollutants at 700-1100 degrees C after an interval of 50 degrees C. The amount of total 16 PAHs at 900 and 1100 degrees C was about 8.5 and 1.25 times higher than those at 700 degrees C (739.48 microg g(-1)) respectively. The amount of total probable (2A) and possible (2B) human carcinogenic PAHs was minimum at 700 degrees C.

Acrylates↗

Preparation of a reticulated polyurethane foam grafted with poly(acrylic acid) through atmospheric pressure plasma treatment and its lysozyme immobilization.

We successfully introduced peroxide groups onto the surface of PU(Polyurethane) foam(10 PPI) through one atmospheric pressure plasma treatment and sequentially grafted PAAc(poly(acrylic acid)) on the surface of PU through radical copolymerization. The plasma treatment can generate large amount of peroxides on the surface of PU foam and the peroxide groups act as initiators for further grafting of PAAc in the monomer solution. To introduce large amount of peroxides on the surface of PU foam, we studied the effect of plasma rf-power and treatment time on the maximum grafting of PAAc. Through this study, we found that the optimum plasma treatment condition was the rf-power of 100 W and the treatment time of 100 s. On the other hand, we also studied the effect of graft reaction conditions such as temperature, monomer concentration and reaction time on the change of grafting degree (GD). The GD increased with increasing temperature and increased with reaction time before it leveled off at 3 h after reaction started. At low concentration of AAc, the GD was very low but it showed a maximum at the monomer concentration between 60 and 70%. The surface of the modified PU foam was qualitatively and quantitatively analyzed through the use of FT-IR and weight measurement, respectively. We also observed the surface change before and after plasma induced graft co-polymerization through photo and SEM analysis. Finally, we confirmed that the PU foams grafted with PAAc successfully immobilized lysozyme and other proteins from hen egg white.

Acrylic Resins↗

Effect of gamma-irradiation on the structure of poly(ethyl acrylate-co-hydroxyethyl methacrylate) copolymer networks for biomedical applications.

The effect of the sterilization process by gamma-irradiation on the structure of poly(ethyl acrylate-co-hydroxyethyl methacrylate) copolymer networks, P(EA-co-HEMA) is studied for a broad dose range (7, 15, 25 and 50 kGy) and copolymer composition interval (0, 0.3, 0.5, 0.7 and 1 weight fraction of HEMA in the copolymer). gamma-irradiation promotes chain scission in PHEMA homopolymer but induces new crosslinking points in PEA homopolymer. Both effects are present in the copolymers, with a net result that depends on composition. For copolymers with high HEMA fractions chain scission predominates, while, as the amount of EA in the copolymer increases, the situation changes and the net effect turns out to be an increase in the number of elastically active chains. Further, gamma-irradiation strengthens the gamma relaxation in PHEMA homopolymer, what suggest that the number of interchain hydrogen bonds decreases. FTIR spectroscopy reveals no oxidation as a consequence of the sterilization process.

Acrylic Resins↗

Residual acrylic adhesive after removal of plastic orthodontic brackets: a scanning electron microscopic study.

After etching for one minute with 35 per cent phosphoric acid, thirty-eight permanent teeth were furnished with plastic brackets. An additional twelve teeth were used as references and were etched but were not furnished with brackets. Four teeth served as untreated controls. Eight brackets had fallen off one week later. The remaining brackets were removed with various instruments. All the teeth were extracted and examined by scanning electron microscopy (SEM). On all of the teeth originally furnished with brackets, residual acrylic was found on the tooth surface. The SEM examination was supplemented with energy-dispersive x-ray analysis (ED) which confirmed that the observed residues differed in their chemical composition from the dental substance.

Acid Etching, Dental↗

One-year follow up for the use of collagen for biological anchoring of acrylic dental roots in the dog.

Second premolars in both upper and lower jaws of 6 dogs were extracted and acrylic resin replicas were made of the roots. Horizontal channels were drilled across the root replica perpendicular to the long axis. Before implantation, the prepared root replicas were immersed in a solution of native collagen. One year after implantation, proliferation of connective tissue and newly-formed viable bone were observed within the channel as well as surrounding the treated implants. All control implants without collagen treatment were rejected leaving chronically inflamed implantation sites.

Acrylic Resins↗

Receptor-mediated endocytosis of poly(acrylic acid)-conjugated liposomes by macrophages.

The uptake characteristics of negatively-charged liposomes made by conjugation of poly(acrylic acid) (PAA) were studied with respect to cultured RAW macrophages. The PAA-conjugated liposomes were internalized and digested in an acidic compartment at a much faster rate than the unmodified phosphatidylcholine (PC) liposomes. After incubation for 18 h, an over 5-fold increase in the uptake of PC liposomes was obtained by PAA conjugation. Subsequently, part of the aqueous phase of the internalized liposomes was exocytosed. Recognition of PAA by the macrophages seems to be responsible for the enhanced uptake of PAA-conjugated liposomes. Cross-competition experiments showed that PAA-conjugated liposomes inhibited the uptake of acetylated-low density lipoprotein (acetyl-LDL) by the macrophages and vice versa. The uptake of PAA-conjugated liposomes was also inhibited by dextran sulfate and maleylated-bovine serum albumin (maleyl-BSA), which are also known to bind to scavenger receptors. Poly(C) and BSA, which are not ligands for the scavenger receptor, competed poorly with the uptake of PAA-conjugated liposomes. Enhanced uptake of PAA-conjugated liposomes by CHO cells with low scavenger receptor expression was not observed. Unexpectedly, LDL, which is not a ligand for scavenger receptor, also partially inhibited the uptake of PAA-conjugated liposomes. The interaction of PAA-conjugated liposomes with macrophages is complex, and the endocytosis of PAA-conjugated liposomes most likely involves multiple receptors and/or pathways. The data obtained suggest that the high affinity binding of PAA-conjugated liposomes to macrophages may be due to recognition of the negative charges of PAA by cell surface receptors, including the scavenger receptor.

Acrylic Resins↗

Reflectance spectra of natural and acrylic resin teeth.

A method has been described for determining the reflectance spectra of teeth at various parts of the tooth surface. The shape and size of the teeth were accounted for by appropriate experimental and mathematical techniques. In all instances where a subtle difference in tooth color was discernible, this difference was also apparent on the corresponding spectra. The spectra of acrylic resin teeth showed characteristic absorption shoulders caused by pigmentation. These shoulders did not appear in the spectra of natural teeth where the reflectivity gradually increased with increasing wavelength. Differences were observed in the colors as well as the spectra of teeth from different shade guides which were marked with the same shade number by the manufacturer. The method may be applied for control of the color quality of artificial teeth as well as the selection of pigments in order to obtain an appropriate shade range and to reduce effects of metamerism.

Acrylic Resins↗

A temporary space maintainer using acrylic resin teeth and a composite resin.

A one-session technique for preparing a temporary space maintainer has been described. The technique consists of attaching an acrylic resin pontic to etched surfaces of natural adjacent teeth by means of a composite resin. The main advantages of this technique are elimination of premature tooth preparation, good esthetics, fair strength, low cost, and rapid completion of the restoration without the need of a dental laboratory.

Acid Etching, Dental↗