28156-60-7

Usage

Uses

Used in Drug Delivery Systems:
Poly-N-(2-hydroxyethyl)acrylamide is used as a carrier for drug delivery systems for its biocompatibility and non-toxicity, which allows for the safe and effective delivery of therapeutic agents.
Used in Tissue Engineering:
Poly-N-(2-hydroxyethyl)acrylamide is used as a scaffold material in tissue engineering for its high water content and softness, which provide a suitable environment for cell growth and tissue regeneration.
Used in Medical Adhesives:
Poly-N-(2-hydroxyethyl)acrylamide is used as an adhesive in medical applications for its ability to bond with biological tissues and promote healing.
Used in Coating Materials and Surface Modification:
Poly-N-(2-hydroxyethyl)acrylamide is used as a coating material and for surface modification to improve biocompatibility and bioadhesion, enhancing the performance of medical devices and implants.

InChI:InChI=1/C5H9NO2/c1-2-5(8)6-3-4-7/h2,7H,1,3-4H2,(H,6,8)

Upstream product

• 141-43-5 ethanolamine 
• 79-10-7 acrylic acid 
• 814-68-6 acryloyl chloride 
• 75639-78-0 N-hydroxyethyl norborn-5-ene-2-carboxamide 
• 2051-76-5 acrylic acid anhydride 
• 108-24-7 acetic anhydride 
• 477572-64-8 N-{2-[(2-acryloylamino-ethoxy)-(4-methoxy-phenyl)-methoxy]-ethyl}-acrylamide 

Downstream Products

• 1415505-61-1 2-(acryloylamino)ethyl hydrogen (4-benzoylbenzyl)phosphonate 
• 1318074-12-2 C₄₈H₅₂N₂O₁₅S 

Relevant academic research and scientific papers

Novel amphiphilic diblock copolymers bearing acid-labile oxazolidine moieties: Synthesis, self-assembly and responsive behavior in aqueous solution

A novel oxazolidine based acid-labile monomer N-acryloyl-2,2-dimethyl-1,3- oxazolidine (ADMO) was synthesized and polymerized by reversible addition fragmentation chain transfer (RAFT) polymerization using poly(ethylene glycol) based chain transfer agent (PEG-CTA). The diblock copolymers PEG-b-PADMO were composed of hydrophilic PEG with fixed length and hydrophobic PADMO with different lengths, which formed core-shell micelles in water. Morphologies and sizes of micelles were obtained by transmission electron microscopy (TEM) and dynamic light scattering (DLS), which showed that the shapes of polymeric aggregates developed from small spherical micelles, worm-like micelles to larger size of vesicles, as the length of PADMO increased. The hydrolysis kinetics of the micelles was studied using 1H NMR, DLS and release of loaded Nile Red dye, whose rate strongly depended on pH and micellar structure. It led to the disruption of polymeric micelles and concomitant release of the guest molecules, due to the transformation of hydrophobic PADMO into hydrophilic poly(2-hydroxyethyl acrylamide) (PHEAM).

Transiently Thermoresponsive Acetal Polymers for Safe and Effective Administration of Amphotericin B as a Vaccine Adjuvant

The quest for new potent and safe adjuvants with which to skew and boost the immune response of vaccines against intracellular pathogens and cancer has led to the discovery of a series of small molecules that can activate Toll-like receptors (TLRs). Whereas many small molecule TLR agonists cope with a problematic safety profile, amphotericin B (AmpB), a Food and Drug Administration approved antifungal drug, has recently been discovered to possess TLR-triggering activity. However, its poor aqueous solubility and cytotoxicity at elevated concentrations currently hampers its development as a vaccine adjuvant. We present a new class of transiently thermoresponsive polymers that, in their native state, have a phase-transition temperature below room temperature but gradually transform into fully soluble polymers through acetal hydrolysis at endosomal pH values. RAFT polymerization afforded well-defined block copolymers that self-assemble into micellar nanoparticles and efficiently encapsulate AmpB. Importantly, nanoencapsulation strongly reduced the cytotoxic effect of AmpB but maintained its TLR-triggering capacity. Studies in mice showed that AmpB-loaded nanoparticles can adjuvant an RSV vaccine candidate with almost equal potency as a highly immunogenic oil-in-water benchmark adjuvant.

Method for synthesizing acrylamide derivative

The invention relates to a method for synthesizing an acrylamide derivative from alkyl primary amine and acrylamide as raw materials and belongs to the field of chemical product synthesis methods. Themethod for synthesizing the acrylamide derivative comprises the following steps: 1) under conditions of 150-160 DEG C and 0.6-1MPa, conducting a Diels-Alder reaction on acrylamide and anthracene so as to obtain an acrylamide addition intermediate of 1:1; 2) conducting backflowing on the addition intermediate, alkyl primary amine and a catalyst for 6-20 hours at 50-180 DEG C, and conducting an amino exchange reaction so as to obtain an acrylamide derivative addition intermediate; and 3) carrying out thermal cracking on the acrylamide derivative addition intermediate at 150-180 DEG C and 1-3kPa, conducting rectification so as to obtain an acrylamide derivative, conducting sublimation recycling on anthracene, and repeating the process. The method for synthesizing the acrylamide derivative, which is provided by the invention, is free of liquid solvent, is capable of effectively reducing the content of VOCs (volatile organic compounds) in the generation process, and is simple in reaction process, easy in product and recycling raw material separation, easy in reaction condition control, high in security, high in reaction yield, small in byproduct amount, simple in aftertreatment, high in product purity and easy in industrial production.

Hydrophobic Nanoparticles Reduce the β-Sheet Content of SEVI Amyloid Fibrils and Inhibit SEVI-Enhanced HIV Infectivity

Semen-derived enhancer of virus infection (SEVI) fibrils are naturally abundant amyloid aggregates found in semen that facilitate viral attachment and internalization of human immunodeficiency virus (HIV) in cells, thereby increasing the probability of infection. Mature SEVI fibrils are composed of aggregated peptides exhibiting high β-sheet secondary structural characteristics. Herein, we show that polymers containing hydrophobic side chains can interact with SEVI and reduce its β-sheet content by ～45% compared with the β-sheet content of SEVI in the presence of polymers with hydrophilic side chains, as estimated by polarization modulation-infrared reflectance absorption spectroscopy measurements. A nanoparticle (NP) formulation of this hydrophobic polymer reduced SEVI-mediated HIV infection in TMZ-bl cells by 60% compared with the control treatment. Although these NPs lacked specific amyloid-targeting groups, thus requiring high concentrations to observe biological activity, the use of hydrophobic interactions to alter the secondary structure of amyloids represents a useful approach to neutralizing the SEVI function. These results could, therefore, have general implications in the design of novel materials that can modify the activity of amyloids associated with a variety of other neurological and systemic diseases.

MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Method for preparing N-hydroxyethyl acrylamide

The invention discloses a method for preparing N-hydroxyethyl acrylamide. Acrylic anhydride and amino-ethanol perform reaction mildly at low temperature. Acrylic acid serving as a byproduct and a product are separated in distillation mode. The N-hydroxyethyl acrylamide obtained by the method has high purity and high yield, and the production process is simple and easily available.

Preparation method of acrylamide-based compounds

The present invention relates to the field of fine chemical materials, particularly to a new mild, efficient and economical preparation process technology of a class of acrylamide-type compounds, wherein a beta-amine substituted propionamide precursor is subjected to an in-situ amine elimination reaction under the action of a suitable electrophilic reagent so as to prepare the target product.

METHOD FOR PRODUCING 2-HYDROXYALKYL (METH) ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide a method for producing N-(2-hydroxyalkyl)(meth) acrylamide. SOLUTION: The reaction of a ketimine compound or an aldimine compound of 2-aminoalkyl (meth) acrylate with water makes it possible to produce N-(2-hydroxyalkyl)(meth) acrylamide with high yields. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide an industrial method for efficiently producing a high-purity N-substituted (meth)acrylamide in a short time even under mild reaction conditions, which uses (meth)acrylic acid as a starting material and generates only water as a byproduct. SOLUTION: There is provided a method for producing an N-substituted (meth)acrylamide to obtain an objective compound, N-substituted (meth)acrylamide by the step of: reacting a (meth)acrylic and an amine compound to synthesize an aminopropionic acid derivative; then adding an inorganic material composed mainly of silica as a catalyst and performing amidation with the same amine compound to obtain an aminopropionic acid derivative; and subsequently eliminating an amine by the thermal decomposition reaction. COPYRIGHT: (C)2015,JPOandINPIT

(Meth) acrylamide hydroxyakyl production (by machine translation)

PROBLEM TO BE SOLVED: To provide a method of manufacturing hydroxyalkyl (meth) acrylamide which uses dibutyl amine as a double bond protecting reagent, and thereby can stably carry out thermal decomposition of an amide adduct without an acid catalyst. SOLUTION: In the method, methyl (meth)acrylate and dialkylamine are reacted to convert into an ester adduct, the adduct is made to react with alkanolamine under the presence of a strong base nature catalyst, an amide adduct which is a synthetic intermediate is obtained after the sulfuric acid neutralizing of the ester adduct, and then thermal decomposition of the amide adduct is carried out to manufacture hydroxyalkyl (meta) acrylamide. Dibutyl amine is used for double bond protecting of methyl (meth)acrylate, and thereby thermal decomposition of the amide adduct obtained thereafter can be carried out stably without using an acid catalyst to obtain hydroxyalkyl (meth) acrylamide. COPYRIGHT: (C)2012,JPO&INPIT