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Acrylamide monomer

目录号 : GC25035

Acrylamide is a neurotoxic monomer with extensive industrial applications. It could be used as a precursor to polyacrylamides.

Acrylamide monomer Chemical Structure

Cas No.:79-06-1

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25mg
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产品描述

Acrylamide is a neurotoxic monomer with extensive industrial applications. It could be used as a precursor to polyacrylamides.

Chemical Properties

Cas No. 79-06-1 SDF Download SDF
分子式 C3H5NO 分子量 71.08
溶解度 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 14.0687 mL 70.3433 mL 140.6866 mL
5 mM 2.8137 mL 14.0687 mL 28.1373 mL
10 mM 1.4069 mL 7.0343 mL 14.0687 mL
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Research Update

Acrylamide monomers in universal adhesives

Dent Mater 2023 Mar;39(3):246-259.PMID:36710097DOI:10.1016/j.dental.2023.01.003.

Objectives: The mono-functional monomer 2-hydroxyethyl methacrylate (HEMA) is often added to universal adhesives (UAs) to improve surface wetting and prevent phase separation. Nevertheless, HEMA promotes water sorption and hydrolysis at adhesive interfaces, hereby affecting long-term bonding to dentin. This study investigated if two acrylamide monomers could replace HEMA in an UA formulation applied in etch-and-rinse (2E&R) and self-etch (1SE) bonding mode. Methods: Four experimental UAs were bonded to bur-cut dentin. In addition to 12 wt% 10-MDP, 25 wt% Bis-GMA and 10 wt% TEGDMA as common monomer composition, 20 %wt ethanol and 15 %wt water as solvent, and 3 wt% polymerization-related additives, the four formulations solely differed for either the acrylamide cross-linker monomer 'FAM-201' as TEGDMA alternative and HEMA replacement, the hydroxyethyl Acrylamide monomer 'HEAA' as HEMA alternative, HEMA ('HEMA+'), or extra TEGDMA in a HEMA-free control ('HEMA-'), all added in a 15 wt% concentration. The split-tooth study design involved application in 2E&R mode on one tooth half versus 1SE mode on the corresponding half. Micro-tensile bond strength of half of the micro-specimens was measured upon 1-week distilled water storage ('immediate' 1w μTBS), with the other half measured after additional 6-month storage ('aged' 6 m μTBS). Statistics involved linear mixed-effects (LME) modelling (p < .05). Additionally, interfacial TEM characterization, thin-film (TF) XRD surface analysis, LogP determination, and a cytotoxicity assay were carried out. Results: FAM-201 revealed significantly higher μTBS than HEMA+ at 1w and 6 m when applied both in E&R and SE bonding modes. HEAA's μTBS was significantly lower than that of HEMA+ at 1w when applied in SE mode. TF-XRD and TEM revealed similar chemical and ultrastructural interfacial characterization, including stable 10-MDP_Ca salt nano-layering. FAM-201 was least cytotoxic and presented with an intermediary LogP, while HEAA presented with the highest LogP, indicating high hydrophilicity and water-sorption sensitivity. Significance: The acrylamide co-monomer FAM-201 could replace HEMA in an UA formulation, while HEAA not.

Microbial degradation of Acrylamide monomer

Arch Microbiol 1990;154(2):192-8.PMID:2403264DOI:10.1007/BF00423332.

Acrylamide, a neurotoxic monomer with extensive industrial applications was found to be degraded by the microorganisms present in a tropical garden soil. A bacterium capable of degrading acrylamide was isolated from this soil by enrichment. It was found to be aerobic, gram-negative, motile, short rod and identified as Pseudomonas sp. The bacterium degraded high concentrations of acrylamide (4 g/l) to acrylic acid and ammonia which were utilized as sole carbon and nitrogen source for growth. An amidase was involved in the hydrolysis of acrylamide, which could act on other short chain amides like formamide and acetamide but not on acrylamide analogues: methacrylamide and N,N-methylene bisacrylamide. The enzyme was sensitive to catabolite repression by succinate both in presence as well as absence of nitrogen source.

Preliminary study of Acrylamide monomer decomposition during methane fermentation of dairy waste sludge

J Environ Sci (China) 2016 Jul;45:108-14.PMID:27372124DOI:10.1016/j.jes.2015.12.016.

Polyacrylamide (PAM) used in sludge dewatering exists widely in high-solid anaerobic digestion. Acrylamide is registered in the list of chemicals demonstrating toxic, carcinogenic and mutagenic properties. Therefore, it is reasonable to ask about the mobility of such residual substances in the environment. The study was carried out to assess the impact of the mesophilic (39±1°C) and thermophilic (54±1°C) fermentation process on the level of Acrylamide monomer (AMD) content in the dairy sludge. The material was analysed using high-performance liquid chromatography (HPLC) for quantification of AMD. The results indicate that the process of methane fermentation continues regardless of the temperature effects on the degradation of AMD in dairy sludge. The degree of reduction of Acrylamide monomer for thermophilic fermentation is 100%, while for mesophilic fermentation it is 91%. In practice, this means that biogas technology eliminates the risk of AMD migration to plant tissue. Moreover, it should be stressed that 90% of cumulative biogas and methane production was reached one week earlier under thermophilic conditions - the dynamics of the methanisation process were over 20% faster.

Nervous system degeneration produced by Acrylamide monomer

Environ Health Perspect 1975 Jun;11:129-33.PMID:170076DOI:10.1289/ehp.7511129.

Acrylamide, widely employed as a vinyl monomer in the polymer industry, is a potent neurotoxin to man and to animals. The cumulative effect of prolonged, low-level exposure to Acrylamide monomer is the insidious development of a progressive peripheral neuropathy. Sensory symptoms begin in the hands and feet (numbness, pins and needles), certain reflexes are lost and, with severe exposure, muscle weakness and atrophy occur in the extremities. The peripheral neuropathy may be supplemented by symptoms indicative of central nervous system damage (ataxia, tremor, somnolence and mental changes). The neuropathologic basis for this clinical picture has been determined in cats. Here, chronic acrylamide intoxication produces selective peripheral and central nerve fiber degeneration. Degeneration first occurs in the extremities of long and large nerve fibers which later undergo a progressive, seriate proximal axonal degeneration known as dying-back. Especially vulnerable are sensory axons supplying Pacinian corpuscles and muscle spindles in the hindfoot toepads, while adjacent motor nerve axons die back later. Distal central nerve fiber degeneration is seen in the medulla and the cerebellum. The neurotoxic property of acrylamide is of practical concern in two areas. One major problem is the protection of factory workers engaged in the manufacture of acrylamide. A sensitive test of neurologic function in these individuals, i.e., touch sensation, based on the experimental observation of the exquisite vulnerability of Pacinian corpuscles in acrylamide intoxicated cats, is presently under consideration. The second area for concern is the exposure of the populace to minute amounts of neurotoxic Acrylamide monomer which contaminate acrylamide polymers currently deployed in the environment. Federal restrictions on the maximum permitted exposure to acrylamide, based on a largely clinical study of acrylamide neurotoxicity conducted ten years ago, may require a re-evaluation in the light of recent advances which have pinpointed the initial sites of nerve fiber degeneration.

Acrylamide monomer and peripheral neuropathy in chemical workers

Am J Ind Med 1992;21(2):217-22.PMID:1311148DOI:10.1002/ajim.4700210211.

The relationship between exposure to Acrylamide monomer and neurological outcomes was investigated in 82 chemical industry workers. Vibrotactile thresholds were determined quantitatively with a Vibratron II device, using forced choice and method of limits procedures. Symptoms of numbness, limb pain, peeling skin, and sweating hands had significantly higher prevalences in the exposed than in the unexposed group. Signs of peeling skin and sweating hands were significantly more common in the exposed group. Vibration thresholds were not associated with exposure.