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Sigma-Aldrich

Methacrylic anhydride

contains 2,000 ppm topanol A as inhibitor, ≥94%

Sinônimo(s):

Methacrylic acid anhydride

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About This Item

Fórmula linear:
[H2C=C(CH3)CO]2O
Número CAS:
760-93-0
Peso molecular:
154.16
Beilstein:
1761982
Número MDL:
MFCD00008586
Código UNSPSC:
12162002
ID de substância PubChem:
24856712
NACRES:
NA.23

Ensaio

≥94%

forma

liquid

contém

2,000 ppm topanol A as inhibitor

índice de refração

n20/D 1.453 (lit.)

pb

87 °C/13 mmHg (lit.)

densidade

1.035 g/mL at 25 °C (lit.)

cadeia de caracteres SMILES

CC(=C)C(=O)OC(=O)C(C)=C

InChI

1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3

chave InChI

DCUFMVPCXCSVNP-UHFFFAOYSA-N

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Descrição geral

Methacrylic anhydride is an organic compound derived from methacrylic acid, which belongs to the class of acrylic acids. It is primarily employed as a monomer in the production of polymers, particularly poly(methacrylic acid) and its copolymers. These polymers find applications in a wide range of industries, including bio-renewable resins, pH-sensitive hydrogels, thermosets, coatings, adhesives, and plastics, due to their excellent chemical and thermal stability. In the polymerization of methacrylic anhydride, the most common inhibitor used is Topanol A. It is typically added in small quantities (2,000 ppm) to hinder undesirable side reactions during the polymerization, ensuring controlled and high-quality polymer formation.

Aplicação

Methacrylic anhydride can be used as a starting material to synthesize:
  • Methacrylated chondroitin sulfate pH-sensitive hydrogels by copolymerization reaction. These hydrogels can be used in drug delivery systems.
  • High-performance lignin-based thermosets.
  • Gel polymer electrolyte, which is then integrated with the cathode to form high-performance lithium-ion batteries.
Methacrylic anhydride can be also used as a precursor to synthesize bio-renewable resins for composite applications. For example, it can be used to prepare soybean oil and a eugenol-based resin system. This resin possesses high thermal stability, and good mechanical properties, which makes it a suitable matrix for the pultrusion process.

Pictogramas

CorrosionExclamation mark
GHS05,GHS07

Palavra indicadora

Danger

Classificações de perigo

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

183.2 °F - closed cup

Ponto de fulgor (°C)

84 °C - closed cup

Equipamento de proteção individual

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

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Notes-Acrylic and Methacrylic Anhydrides.
Brotherton T, et al.
The Journal of Organic Chemistry, 26(4), 1283-1284 (1961)
A I Van Den Bulcke et al.
Biomacromolecules, 1(1), 31-38 (2001-11-17)
Dynamic shear oscillation measurements at small strain were used to characterize the viscoelastic properties and related differences in the molecular structure of hydrogels based on gelatin methacrylamide. Gelatin was derivatized with methacrylamide side groups and was subsequently cross-linked by radical
G Bahcecioglu et al.
Biomaterials, 218, 119361-119361 (2019-07-25)
A PCL/hydrogel construct that would mimic the structural organization, biochemistry and anatomy of meniscus was engineered. The compressive (380 ± 40 kPa) and tensile modulus (18.2 ± 0.9 MPa) of the PCL scaffolds were increased significantly when constructs were printed with a shifted design and circumferential
Kunyu Zhang et al.
Materials science & engineering. C, Materials for biological applications, 103, 109835-109835 (2019-07-28)
Hydrogels are promising soft materials for the delivery of therapeutic cells and cargo molecules. Inspired by mussel adhesion chemistry, hydrogels based on catechol (Cat)-modified polysaccharides have been developed to enhance hydrogel-tissue interactions. However, due to the inevitable side reactions such
Avathamsa Athirasala et al.
Scientific reports, 7(1), 3323-3323 (2017-06-14)
The requirement for immediate vascularization of engineered dental pulp poses a major hurdle towards successful implementation of pulp regeneration as an effective therapeutic strategy for root canal therapy, especially in adult teeth. Here, we demonstrate a novel strategy to engineer
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