3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate

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3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate
Names
Other names
7-Oxabicyclo[4.1.0]hept-3-ylmethyl-7-oxabicyclo[4.1.0]heptane-3-carboxylate
Identifiers
3D model (
JSmol
)
Abbreviations ECC
ChemSpider
ECHA InfoCard
 100.017.463 Edit this at Wikidata
UNII
  • InChI=1S/C14H20O4/c15-14(9-2-4-11-13(6-9)18-11)16-7-8-1-3-10-12(5-8)17-10/h8-13H,1-7H2
    Key: YXALYBMHAYZKAP-UHFFFAOYSA-N
  • C1CC2C(O2)CC1COC(=O)C3CCC4C(C3)O4
Properties
C14H20O4
Molar mass 252.310 g·mol−1
Appearance Colorless liquid[1]
Density 1.17 g·cm−3[1]
Melting point −37 °C (−35 °F; 236 K)[1]
Slightly soluble (13.85 g·l−1 (20 °C))[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate (ECC) is a

Formulations based on cycloaliphatic epoxy resins such as ECC are known to form by curing thermosets with high heat and chemical resistance and good adhesion.[2]

History

The

super acid and subsequent cationic polymerization. This was the first time realized in the 1970s.[3]

Fabrication

ECC can be prepared via

peracid.[4]

Properties

ECC has a

dynamic viscosity of 400 mPa·s at 25 °C.[2]

Reactivity

For homopolymerization of ECC 1.5 to 3 wt. % of an initiator are added. Above 3 wt% initiator no further acceleration was found, increasing proportions of initiators, however, increase the brittleness of the formed thermoset. After a photopolymerization usually still a thermal post-curing is necessary for a complete reaction.[5]

It is known that the reactivity of the monomer is lower than it could be, since the contained

ester group can react with the reactive, polymerizing chain end and stabilize it. It therefore reacts significantly slower than other molecules without ester group.[2][6] ECC polymerizes also much slower than radical monomers. It is therefore the object of research to find cationic polymerizable monomers with higher polymerization rate but same performance.[2]

Crosslinking

Cationically crosslinked ECC is used in a variety of industrial applications, due to its low viscosity, excellent electrical properties and high reliability among others as an

covalently integrated via the monomer-activated mechanism into the polymer network.[10]

References

  1. ^ a b c d Record of 3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexancarboxylat in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 1 January 2015.
  2. ^
    doi:10.1016/j.porgcoat.2006.09.030
    .
  3. doi:10.1002/pol.1978.170161004
    .
  4. doi:10.1002/pola.26595
    .
  5. doi:10.1016/0032-3861(91)90108-U
    .
  6. doi:10.1002/pola.1995.080331421
    .
  7. doi:10.1002/pola.20711
    .
  8. doi:10.1016/j.eurpolymj.2012.10.015
    .
  9. doi:10.1016/S0300-9440(01)00240-5
    .
  10. doi:10.1002/(SICI)1522-9505(19990901)270:1<38::AID-APMC38>3.0.CO;2-S
    .

Literature
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