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436909

Sigma-Aldrich

Diurethane dimethacrylate, mixture of isomers

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

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Synonym(s):
Di-HEMA trimethylhexyl dicarbamate, Diurethane dimethacrylate, Urethane dimethacrylate, methacrylate adduct
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
PubChem Substance ID:
24867310
NACRES:
NA.23

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

Signal Word

Warning

Hazard Statements

H317 - H412

Hazard Classifications

Aquatic Chronic 3 - Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

212.0 °F

Flash Point(C)

> 100 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Mehwish Pasha et al.
Materials science & engineering. C, Materials for biological applications, 114, 111040-111040 (2020-10-01)
Secondary caries is one of the most major cause for re-placement of dental composite restorations. Targeting the survival of cariogenic bacteria residing on the restoration surface may reduce this problem. The present study aims to evaluate the antibacterial potential as
Gaute Floer Johnsen et al.
Journal of dentistry, 56, 84-98 (2016-11-12)
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
Kyungsun Kim et al.
Materials (Basel, Switzerland), 14(4) (2021-03-07)
Concerns regarding unbound monomers in dental composites have increased with the increased usage of these materials. This study assessed the biological effects of urethane dimethacrylate (UDMA), a common monomer component of dental composite resins, on the cariogenic properties of Streptococcus
Saeed Hesaraki et al.
Materials science & engineering. C, Materials for biological applications, 109, 110592-110592 (2020-04-02)
Resin-based pit-and-fissure sealants (flowable resin composites) were formulated using bisphenol-A-glycerolatedimethacrylate (Bis-GMA)-triethylene glycol dimethacrylate-(TEGDMA)-diurethanedimethacrylate (UDMA) mixed monomers and multiple fillers, including synthetic strontium fluoride (SrF2) nanoparticles as a fluoride-releasing and antibacterial agent, yttria-stabilized zirconia (YSZ) nanoparticles as an auxiliary filler, and

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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