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436909

Sigma-Aldrich

Diurethane dimethacrylate, mixture of isomers

contains 225 ppm±25 ppm BHT as inhibitor, ≥97%

Synonym(s):

Di-HEMA trimethylhexyl dicarbamate, Diurethane dimethacrylate, Urethane dimethacrylate, methacrylate adduct

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About This Item

Linear Formula:
R'CH2[C(CH3)(R)CH2]2CH2R', R=H or CH3, R'=NHCO2CH2CH2O2CC(CH3)=CH2
CAS Number:
72869-86-4
Molecular Weight:
470.56
EC Number:
276-957-5
UNSPSC Code:
12162002
PubChem Substance ID:
24867310
NACRES:
NA.23

Quality Level

200

assay

≥97%

form

liquid

contains

225 ppm±25 ppm BHT as inhibitor

refractive index

n20/D 1.485 (lit.)

bp

200 °C (lit.)

density

1.11 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(CCNC(=O)OCCOC(=O)C(C)=C)CC(C)(C)CNC(=O)OCCOC(=O)C(C)=C

InChI

1S/C23H38N2O8/c1-16(2)19(26)30-10-12-32-21(28)24-9-8-18(5)14-23(6,7)15-25-22(29)33-13-11-31-20(27)17(3)4/h18H,1,3,8-15H2,2,4-7H3,(H,24,28)(H,25,29)

InChI key

UEKHZPDUBLCUHN-UHFFFAOYSA-N

Related Categories

General description

Diurethane dimethacrylate (DUDA) is a mixture of isomers that belongs to the class of methacrylate monomers. It is a bifunctional monomer, which contains two methacrylate groups and two urethane linkages. It is commonly used in the field of polymer chemistry as a crosslinking agent or a reactive diluent in adhesive materials, coatings, and composites. It has good mechanical and adhesive properties, which makes it suitable for various polymer applications.

Application

The Progress in Development of Dental Restorative Materials
Diurethane dimethacrylate can be used as:
  • A monomer in the synthesis of the shape memory polymer that is used as the matrix material for the preparation of high-strength and stiffness composites. These composites show excellent shape memory behavior and mechanical strength, making them suitable for bone fixation devices.
  • A crosslinking agent to prepare the denture biomaterials, which contain antifungal drugs incorporated into the polymer matrix for controlling drug delivery.
  • A crosslinking agent in the synthesis of anion exchange membranes (AEMs) for use in electrochemical devices.
Diurethane dimethacrylate has been used as a precursor to fabricate the multifunctional polymer nanocomposite with enhanced luminescence activity. It can also be used in digital light processing (DLP) mediated 3D printing.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 3 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

212.0 °F

flash_point_c

> 100 °C

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

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This study aims at evaluating and comparing mechanical, chemical, and cytotoxicological parameters of a commercial brand name composite material against two 'own brand label' (OBL) composites. Parameters included depth of cure, flexural strength, degree of conversion, polymerization shrinkage, filler particle
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Articles

The Progress in Development of Dental Restorative Materials

With dentists placing nearly 100 million dental fillings into patients′ teeth annually in the U.S. alone, polymeric composite restoratives account for a very large share of the biomaterials market.

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