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256439

Sigma-Aldrich

4,4′-Methylenebis(phenyl isocyanate)

98%

Synonyme(s) :

4,4′-MDI, Bis(4-isocyanatophenyl)methane

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About This Item

Formule linéaire :
CH2(C6H4NCO)2
Numéro CAS:
101-68-8
Poids moléculaire :
250.25
Numéro Beilstein :
797662
Numéro CE :
202-966-0
Numéro MDL:
MFCD00036131
Code UNSPSC :
12162002
ID de substance PubChem :
24855527
Nomenclature NACRES :
NA.23

Niveau de qualité

200

Pureté

98%

Forme

solid

Pertinence de la réaction

reagent type: cross-linking reagent

Point d'ébullition

200 °C/5 mmHg (lit.)

Pf

42-45 °C (lit.)

Densité

1.18 g/mL at 25 °C (lit.)

Température de stockage

−20°C

Chaîne SMILES 

O=C=Nc1ccc(Cc2ccc(cc2)N=C=O)cc1

InChI

1S/C15H10N2O2/c18-10-16-14-5-1-12(2-6-14)9-13-3-7-15(8-4-13)17-11-19/h1-8H,9H2

Clé InChI

UPMLOUAZCHDJJD-UHFFFAOYSA-N

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Description générale

4,4′-Methylenebis(phenyl isocyanate) (MDI) is an aromatic diisocyanates class of monomer that is widely used in the production of polyurethane plastics, foam insulation, coatings, adhesives, and sealants. It is highly reactive due to the presence of two isocyanate functional groups. MDI is known for its excellent strength, durability, and resistance to chemical and environmental damage, which makes it useful in resin composition, lithographic printing plates, coating films, optical films, image display devices, semiconductor devices, and polyurethane foam production.

Application

4,4′-Methylenebis(phenyl isocyanate) can be used as a starting material to synthesize:
  • Polyurethane cationomers, that are applicable in medical implants.
  • A prepolymer for preparing self-healable polyurethane elastomers.
It can also be used as a cross-linking agent to synthesize PEBA (polyether-block-amide) copolymer with improved mechanical properties, which are mainly used in soles, medical tubes, aerospace parts, and chemical separation. Additionally, MDI is also used as a crosslinker to covalently modify graphene oxide (GO) and enhance the corrosion resistance of polystyrene coatings. The resultant polystyrene/GO-MDI composite coatings showed superior corrosion resistance to unmodified polystyrene coatings. This approach can potentially be used to improve the durability of materials in various industrial and biomedical applications.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 4 Inhalation - Carc. 2 - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 Inhalation - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

411.8 °F - closed cup

Point d'éclair (°C)

211 °C - closed cup

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
MKCQ8242
MKCQ7855
MKCQ8998
MKCQ8247
MKCQ2143

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Journal of Applied Physiology, 70, 6983-6983 (1991)
Malin Engfeldt et al.
Contact dermatitis, 68(3), 175-180 (2012-10-11)
A 43-year-old woman was referred by her occupational health service with suspected occupational contact dermatitis. In connection with the investigation, a workplace visit was undertaken at her company, which used an adhesive based on pre-polymeric diphenylmethane diisocyanate in one of
Joshua W Schaeffer et al.
Journal of occupational and environmental hygiene, 10(4), 213-221 (2013-02-28)
The purpose of this study was to determine if there was a significant difference between two readily available sampling methodologies for airborne methylene bisphenyl diisocyanate (MDI), which is an essential precursor in the spray-on truck bed lining industry. Seventy-two personal
Adam V Wisnewski et al.
Molecular immunology, 54(2), 233-237 (2013-01-09)
Methylene diphenyl diisocyanate (MDI), a low molecular weight chemical important for producing polyurethane foam, coatings, and elastomers is a major cause of occupational asthma, however, mechanisms of disease pathogenesis remain poorly understood. This study characterizes the rearranged germline and hypervariable
Hanna K Lindberg et al.
Mutation research, 723(1), 1-10 (2011-04-02)
Toluene diisocyanate (TDI) and 4,4'-methylenediphenyl diisocyanate (MDI), used in the production of polyurethane foam, are well known for their irritating and sensitizing properties. Contradictory results have been obtained on their genotoxicity. We investigated the genotoxicity and protein binding of inhaled
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