oxazolidine synthesis
Pathways. CAS the rapid preparation of potential lead compounds with biological activity. In one embodiment, the polyurethane coating is an automotive coating. 2015, 17, 4482. Table 6 further shows the color retention of polyester coatings with and without RD-20. Facile of aryl- and alkyl-substituted alkenes with N-(fluorosulfonyl)carbamate as a bifunctional Enantioenriched Oxazolidinones as Synthesis Scaffolds and Efforts towards the Total Synthesis of Marineosin A by Feng Lang B.S., Huazhong University of Science and Technology, 2007 M.S., Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, 2010 Submitted to the Graduate Faculty of The Kenneth P. Dietrich School of Additionally, any R group substituents which improve the physical properties of a preparation are within the scope of the present invention. While the invention is susceptible to various modifications and alternative forms, specific embodiments thereof have been shown by way of example and were herein described in detail. The method of improving the rheological properties of a coating of Claim 45, wherein said coating is a clearcoat. The method of improving the rheological properties of a coating of Claim 41, wherein said polyurethane coating further includes a blocked polyisocyanate. As used herein, the term "polyurethane coating" is a generic term used to describe a polymeric coating formed from the reaction of polymeric isocyanate with water, polymeric polyol, or bis-oxazolidine as disclosed herein. 41. Oxazolidine . 2012, 77, 1812. 43. A one-pot protocol for the synthesis of oxazoles from beta-hydroxy amides is also presented. The dimethyloxazoline (DMOX) derivatives of fatty acids are amenable to analysis by gas chromatography. [6], Several oxazolidine derivatives occur naturally, Some occur as post translational modifications of proteins. In still another aspect, the bis-oxazolidine compound as disclosed herein improves the potlife of a preparation. Although several new drugs have been marketed in the last 25 years, almost one-third of patients are not protected. Example 3: Potlife. system. D. C. Miller, G. J. Choi, H. S. Orbe, R. R. Knowles, J. Oxazolidine compounds have been used as curing and crosslinking reagents, reacting with polyfunctional isocyanates in the presence of polyols or water to form polymeric coatings. Q. Guo, X. Ren, Z. Lu, Org. Salt resistance is the ability of a coating to resist corrosion by aqueous salt solutions such as found near oceans and on salted roads. Both the 1-K and the 2-K systems are widely used in commercial applications depending upon the specific needs of the coating system. In a refrigeration system, the amount of moisture that enters cannot be reliably predicted. The use of a combination of silver acetate and N,N-dimethylaminopyridine The method of inhibiting corrosion of claim 26, wherein the effective amount o said bis-oxazolidine compound is from about 1 to about 10 weight percent of th total weight of said refrigerant. National Library of Medicine 56. atom transfer and radical-polar crossover. yields with high levels of enantio- and diastereoselectivities. Metals such as copper, iron, steel, aluminum, magnesium and the like are often exposed to high temperatures, pressures and flow rates in these cooling systems. 2-Amino-2-methyl-1-propanol . However, since a perfectly efficient reaction environment cannot be guaranteed in industrial settings, it is preferable that from 0.5 to about 10 A further aspect of the present invention is directed to a method of improving rheological properties and decreasing the viscosity, improving flow and leveling of a polyurethane preparation using a bis-oxazolidine compound. Tech. J Am Chem Soc. Reactive diluents reduce the viscosity of the coating by functioning as a non-volatile solvent and also improves the rheology of the coating. The invention is further illustrated by the following specific examples. WATERPROOF COMBINATION OF POLYAMINE COMPOUND BINDERS, PROCEDURE FOR MANUFACTURING AND USE IN VARNISHES AND COATINGS. yield regardless of the substitution at nitrogen and alkyne terminus. EXAMPLES Example 1: Preparation of l-aza-3,7-dioxo-2,8-dsopropyl-5-ethyl bicvclo (3.3.0) octane. Oxazolidine is a five-membered ring heterocycle with the formula .mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}(CH2)3(NH)O.The O atom and NH groups are not mutually bonded, in contrast to isoxazolidine. This water must be removed in order to produce an acceptable product. Oxazolidine-based products were originally used for their biocide properties, but they have become more widely applied recently for scavenging H2S. The formulation may be dehydrated prior to addition of the polyisocyanate through the use of drying equipment or moisture scavengers. gives N-aryl oxazolidinones in good yields. The method of improving the potlife of claim 19, wherein said polyurethane coating further includes a blocked polyisocyanate. Chem. Med. 2015, The method of reducing the volatile organic content of a coating of Claim 30, wherein the effective amount, in weight, of said bis-oxazolidine compound is from about 1 to about 50 weight percent of the total weight of said coating. 7. A microwave assisted method for the synthesis of some typical 4-substituted oxazolidinone chiral auxiliaries used in asymmetric synthesis is reported in this work. Example 4 describes how potlife is determined. Avalos M, Babiano R, Cintas P, Jimnez JL, Light ME, Palacios JC, Prez EM. Reactive diluents are used to lower the volatile content of the coatings by reducing the loss of organic solvents into the atmosphere. The bis-oxazolidines are useful in improving the physical properties of a coating. Thionyl chloride is commonly used to generate the acid chloride in situ, care being taken to maintain anhydrous conditions, as oxazolines can be ring-opened by chloride if the imine becomes protonated. Preferably, the effective amount of a moisture scavenging bis-oxazolidine is from about 1 to about 30 weight percent of the total weight of the refrigerant. Unlike the solvents it replaces, the bis-oxazolidine compound is not released into the atmosphere because it is incorporated into the polyurethane coating. Numerous studies have been concerned with the synthesis, structure, physicochemical properties, and practical application of 1,3-oxazacycloalkanes which exhibit high reactivity [1-3].However, prior to our studies [], almost no data were available on 3-(organyloxymethyl)-1,3-oxazacycloalkanes, except for 3-(isobutyloxymethyl)oxazolidine and 3-(isobutyloxymethyl)tetrahydro-1,3-oxazine . alcohols containing internal alkynes and phenyl isocyanate. N,N'-Bis(pyridin-2-ylmethyl)oxalamide (BPMO) is an efficient ligand TABLE 5, CONTROL RD-20 RD-20 RD-20 (NO RD-20) (10%) (20%) (30%), CONTROL RD-20 RD-20 RD-20 RD-20 RD-20 NO RD-20 10% 20% 20%* 30% 30%*, Set to Touch (minutes) 40 60 60 7-16 hrs. 194; (2020);,Oxazolidine WikipediaOxazolidine | C3H7NO PubChem. Epub 2007 Dec 20. effectively activates the CC triple bond by acting as a -Lewis acid to produce Generally, the effective amount will range from about 1 to about 80 weight percent based on the total weight of the formulation. Chip Resistance. palladium-catalyzed intramolecular aminohydroxylation to give various Protection of the substrate surfaces is particularly important in geographical areas with harsh environmental conditions. The solvents generally used in the formulation of specialty polyurethane systems are also compatible with the bis-oxazolidine compounds of the present invention. Chem., 2019, 84, An acrylic coating with 20% RD-20 showed superior chip resistance to coatings without RD-20 (Table 8). Commonly used refrigerants include fluorocarbons and other halogenated hydrocarbons. Synblock offers CAS 878385-72-9, tert-Butyl (4S)-4-hydroxy-1,2-oxazolidine-2-carboxylate, 95%, its formula is C8H15NO4 and mol weight is 189.21 g/mol, its documents regarding tert-Butyl (4S)-4-hydroxy-1,2-oxazolidine-2-carboxylate, including MSDS, NMR, HPLC, LC-MS and more. A bis-oxazolidine compound as disclosed herein inhibits corrosion by scavenging moisture that enters the refrigeration system. Reactive diluents are compounds used to lower the volatile organic content of coatings by reducing the amount of organic solvents in the coating and becoming a part of the coating through chemical reaction. In a 12-liter, 4-neck, round-bottom flask equipped with a 1-liter addition funnel and a Dean-Stark receiver, (500 ml. 11. The ingredients listed as Component I in the tables below were combined in an air-mixer (Fawcett Co. Inc., Richfield, Ohio). The nature of aryl As discussed above, in 1-K coating systems, the use of viscous or solid blocked polyisocyanates requires the use of large amounts of volatile organic compounds. Protein Biology. Alternatively, the reaction of racemic butadiene monoxide, in the presence of a chiral palladium or nickel catalyst, provides an enantioselective synthesis of 1,3-oxazolidines (up to 94% ee). The choice of linker between the two oxazolidine rings has a large impact on the performance when used to cure isocyanates. S)-4-Phenyl-2-oxazolidinone is an intermediate for the synthesis and development for cholesterol absorption inhibitor AZD4121. The method of improving the rheological properties of a coating of Claim 39, wherein said coating is an automotive coating. [5], Oxazolidines are prone to hydrolysis, the reverse of their syntheses. 16, 1434-1437. . 23. A polyol is a molecule with multiple hydroxyl groups. The synthesis of oxazolidinones has gained increasing interest due to their unique mechanism of action that assures high antibiotic efficiency and low susceptibility to resistance mechanisms. 08/156,955. A. C. Bell, A. Subsequent reaction of the water with the polyisocyanate component of the system results in an irreversible reaction which will harden the product, making it unusable before it can be applied to the surface to be coated. Peptides S1-S6 were screened against human keratinocytes (HaCaT) and RAW 264.7 cells. Huangdi Feng. Disclaimer. Exemplary blocking groups are known and include diethyl malonate, 3,5-dimethylpyrazole, MEK Oxime, e-caprolactam and 2-ethyl hexanol. The present invention provides compositions and methods of using a bis-oxazolidine compound having formula (I), wherien: R1 and R1' are, individually, a methyl group, or a branched or straight chain alkyl or alkanol group; R2, R3, R4, R2', R3' and R4' are, individually, a hydrogen atom, a methyl group, a straight chain or branched chain alkyl or alkanol group, a cyclic alkyl or an aryl group; and R5 is a methyl or methylol group, or a branched chain or straight chain alkyl or alkanol group. Synth. U.S. Patent No. Kobayashi, T.; Hasegawa, F.; Hirose, Y.; Tanaka, K.; Mori, H.; Katsumura, S. J. Org. 2011 Mar 28;47(12):3339-50. doi: 10.1039/c0cc04629a. The next class of protein synthesis inhibitors is the aminoglycosides. 14. oxygenation of unactivated carbamates to provide useful amino alcohol and diol Alternatively, in a one-component polyurethane system, the polyisocyanate component can be a blocked polyisocyanate. 38. allows the synthesis of various 5-methylene-1,3-oxazolidin-2-ones, which would ILNWLABKYUHGQY-UHFFFAOYSA-N 1,3-oxazolidine;pyridine Chemical compound C1COCN1.C1=CC=NC=C1 ILNWLABKYUHGQY-UHFFFAOYSA-N 0.000 description 3; sharing sensitive information, make sure youre on a federal hot spots. [8] The reaction is typically performed at room temperature. Federal government websites often end in .gov or .mil. of a polyurethane coating and exhibits good cure response, color stability, good potlife, low intrinsic viscosity, low film shrinkage, excellent solvating or viscosity reducing properties. The viscosity of the coating was determined every 30 minutes until a viscosity of 30 seconds was reached. dioxide under mild conditions to provide five-membered cyclic carbonates, including Furthermore, for a coating to be useful, it must have a reasonable pot life to provide a sufficient time for application of the coating and to provide for longer storage time. Figure 3: Synthesis of oxazolidine-2,4-dione from dialuric acid. 1. Application filed by Angus Chemical Company, CC1=CC=C(C)C=C1.CC1=CC=CC(C)=C1.CC1=CC=CC=C1C, 4-methyl-N-(oxomethylidene)benzenesulfonamide, [dibutyl(dodecanoyloxy)stannyl] dodecanoate, CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC, ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON, MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS, Polymeric products of isocyanates or isothiocyanates, Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen, Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen, Polyhydroxy compounds; Polyamines; Hydroxyamines, Use of inorganic or non-macromolecular organic substances as compounding ingredients, Heterocyclic compounds having nitrogen in the ring, Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring, Minnesota Mining And Manufacturing Company, AM AT AU BB BG BR BY CA CH CN CZ DE DK EE ES FI GB GE HU IS JP KE KG KP KR KZ LK LR LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TT UA UG UZ VN, KE MW SD SZ UG AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG, Sprayable coating compositions comprising oxazolidines and isocyanates, Sprayable coating compositions comprising oxazolidines, isocyanates and hydroxyl or amine functional resins, Preparation of tetrahydro-1,8-dioxa-4a-aza-naphthalenes and their use in coating applications, Cure-on-demand moisture-curable urethane-containing fuel resistant prepolymers and compositions thereof, Moisture-curable fuel-resistant sealant systems, Multilayer decorative coating composition with low discolouration, Urethane/urea-containing bis(alkenyl) ethers, prepolymers prepared using urethane/urea-containing bis(alkenyl) ethers, and uses thereof, Sprayable polythioether coatings and sealants, Delivery system for interstitial radiation therapy including substantially non-deflecting elongated member, Cartridge injector for pellet medicaments, Closed implanting instrument - accommodates sterile injection needle and implant before use, Apparatus and method for injecting a pharmaceutical preparation in solid form, Coating composition comprising an oxazolidine functional compound and an isocyanate functional compound comprising a uretdione and/or allophanate structure, Sprayable coating compositions comprising an oxazolidine functional compound, an isocyanate functional compound, and a compound selected from a mercapto and a sulfonic acid functional compound, Tetrahydro-1,8-dioxa-4a-aza-naphthalenes in coating applications, Aldimine oxazolidines and polyisocyanates, Novel coating compositions which may be ambient cured, Fluorinated polyurethanes with hydroxy functionality, process for preparing them and their use for the treatment of lithoidal material, Silane-crosslinkable coating formulations, Moisture-hardened polyurethane compositions containing compounds comprising aldimine, Orthoester-protected polyols for low VOC paints, Coating compositions having improved adhesion to aluminum substrates, Vapor permeation curable coatings for reaction injection molded parts, Methods for protecting substrates with urethane protective coatings, Low temperature curing maintenance coatings, Mixed polyalicyclic amines (MPCA) and MPCA alkylates, Iminoalcohol-oxazolidine mixtures and their use, A method of coating bare, untreated metal substrates, Vapor permeation curable coatings comprising polymercaptan resins and multi-isocyanate curing agents, Amino-functional polyurethane prepolymers and a process for their preparation.
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