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274135

Sigma-Aldrich

N,N-Dimethylacrylamide

99%, contains 500 ppm monomethyl ether hydroquinone as inhibitor

Synonyme(s) :

2-Propenamide

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About This Item

Formule linéaire :
CH2=CHCON(CH3)2
Numéro CAS:
2680-03-7
Poids moléculaire :
99.13
Numéro Beilstein :
1742219
Numéro CE :
220-237-5
Numéro MDL:
MFCD00008626
Code UNSPSC :
12162002
ID de substance PubChem :
24856566
Nomenclature NACRES :
NA.23

Niveau de qualité

200

Pureté

99%

Forme

liquid

Contient

500 ppm monomethyl ether hydroquinone as inhibitor

Indice de réfraction

n20/D 1.473 (lit.)

Point d'ébullition

80-81 °C/20 mmHg (lit.)

Densité

0.962 g/mL at 25 °C (lit.)

Chaîne SMILES 

CN(C)C(=O)C=C

InChI

1S/C5H9NO/c1-4-5(7)6(2)3/h4H,1H2,2-3H3

Clé InChI

YLGYACDQVQQZSW-UHFFFAOYSA-N

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Description générale

N,N-Dimethylacrylamide (DMAA) is a non-ionic monomer with high reactivity and low initiation temperature. It is commonly used as a monomer in the production of polymers and copolymers for various applications such as hydrogels, polymeric flocculants, biomedical and drug delivery applications, polymer coatings, smart coatings, adhesives, sensors, self-healing materials, and water treatment agents. The unique structure of DMMA can form a three-dimensional network with other hydrogels and enhance their water retention capacity. It is also used as a crosslinking agent in polymerization reactions.

Application

N, N-Dimethylacrylamide(DMAA) can be used in the following applications:
  • Synthesis of poly(N,N-dimethylacrylamide) (PDMAA) nanoparticles which are used in biomedical and drug delivery applications.
  • Use as a co-monomer in the synthesis of thermoresponsive polymers used in smart coatings, adhesives, and sensors.
  • As a reactive diluent in the manufacture of UV-cured coatings and inks.
  • Use as a co-monomer with polyethylene glycol dimethacrylate (PEGDMA) and a chitosan derivative to develop an injectable hydrogel that can be used as a bone tissue engineering matrix.
  • A series of DMMA-based hydrogels for the removal of heavy metals and organic dyes from polluted water. These hydrogels are highly efficient in removing cationic dyes due to electrostatic interaction and hydrogen bonding in the DMMA backbone.
  • Non-toxic luminescent carbon dot/poly(DMMA) nanocomposite via surface-initiated reversible addition-fragmentation chain transfer polymerization.
  • Polymer coating for quartz crystal microbalance(QCM) sensor. The poly(DMMA) gel acts as a sensing material to adsorb Au(III) ions from HCl aqueous solution and it is inactive to most other metal ions and organic compounds.

Caractéristiques et avantages

  • It is an appropriate precursor for copolymerization due to its low initiation temperature and high reactivity.
  • Its unique structure forms a 3D network and improves the water retention capacity of hydrogels.
  • It is highly soluble in water.
  • It can easily bind to colloidal particles to enhance the bridging effect which plays a key role in flocculation.

Pictogrammes

Skull and crossbonesCorrosion
GHS06,GHS05

Mention d'avertissement

Danger

Mentions de danger

H301 + H311,H318

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Eye Dam. 1

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

158.0 °F

Point d'éclair (°C)

70 °C

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificats d'analyse (COA)

Lot/Batch Number
WXBD6858V
MKCF3531
WXBC5593V
MKCD6496
MKCD3362

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Consulter la Bibliothèque de documents

Graft copolymerization of N, N-Dimethylacrylamide to cellulose in homogeneous media using atom transfer radical polymerization for hemocompatibility
Yan L and Wei T
Journal of Biomedical Science and Engineering, 10(1), 37-37 (2008)
Yuriko Matsumura et al.
Polymers, 11(7) (2019-07-20)
In order to clarify the local environment during interpolymer complex formation between poly(carboxylic acids) and poly(acrylamide derivatives) with different N-substitutions, a fluorescence label technique was used. 3-(2-propenyl)-9-(4-N,N-dimethylaminophenyl) phenanthrene (VDP) was used as an intramolecular fluorescence probe. All polymers were synthesized
Copolymerization of N, N-dimethylacrylamide with styrene and butadiene: The first example of polar growing chain end/nonpolar monomer cross-initiation.
Nakhmanovich BI, et al.
Macromolecular Rapid Communications, 22(15), 1243-1248 (2001)
Syed Ragib Safi et al.
Scientific reports, 9(1), 11909-11909 (2019-08-17)
Arsenic contamination of groundwater is a serious concern worldwide. The research gaps in removing arsenic are selectivity, regeneration and effective removal rate at neutral pH levels. In this study, we discussed the reasons of the high arsenic adsorption from groundwater
Koki Sano et al.
Nature communications, 7, 12559-12559 (2016-08-31)
Fluids that contain ordered nanostructures with periodic distances in the visible-wavelength range, anomalously exhibit structural colours that can be rapidly modulated by external stimuli. Indeed, some fish can dynamically change colour by modulating the periodic distance of crystalline guanine sheets
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