Technical Bulletin

JEFFSOL ALKYLENE CARBONATES AS REACTIVE DILUENTS

JEFFSOL Alkylene Carbonates find utility in a number of applications as Reactive Diluents. The term
reactive diluent in this context refers to a solvent or diluent, which acts both as a viscosity reducer or
solvent, and as a reactive species within a chemical system.
JEFFSOL Alkylene Carbonates are used in both epoxy systems and in urethane systems.
EPOXY SYSTEMS
In an epoxy system, the carbonate reduces the viscosity of the epoxy resin which renders it much easier to
handle and acts as a scavenger for active hydrogen containing impurities such as alcohols, amines,
carboxylic acids and water. Studies have also shown that carbonates do not drastically change the room
temperature characteristics of the epoxy, but it does lower the glass transition temperature (Tg). Alkylene
carbonates also may accelerate the cure of epoxy systems resulting in shorter gel times, improved cured
resin properties and greater elongation. The reaction below illustrates the curing of an epoxy system
containing an alkylene carbonate (Ethylene Carbonate, EC) as a reactive diluent.
R1
O

+
O

O
reduced-viscosity resin / EC mixture

H2N-R2-NH2

R2

R2

NH

NH

HN

NH

HO

O
O

R1
O

OH

URETHANE SYSTEMS
JEFFSOL Alkylene Carbonates can also be used as reactive diluents in urethane systems. Alkylene
carbonates are used as a viscosity reducer in the isocyanate side. The carbonate does not react with the
isocyante and reduces the viscosity enough to enhance mold fill and make the overall system easier to
handle. References in the literature also claim smaller cell sizes and a more uniform dispersion of cell
sizes. Patent literature also discusses the use of alkylene carbonates in polyurea systems; the carbonate
is used as a reactive diluent for the isocyanate and acts as a compatibilizer between the two components,
thus resulting in a better mix between the A and B components.

OTHER APPLICATIONS
JEFFSOL Alkylene Carbonates may also be used as reactive diluents in other applications normally
considered to be purely reactive applications. These applications include, but are not limited to, the
alkoxylation or transesterification of solid or viscous materials, such as resorcinol. The reaction below
illustrates the reaction of resorcinol with JEFFSOL Ethylene Carbonate to form the bishydroxyethyl
derivative of resorcinol.
O
HO

OH

+ 2

HO

OH

2CO2

In this reaction, the JEFFSOL Ethylene Carbonate acts initially as a solvent for the resorcinol (reducing
viscosity). Then during the reaction, the JEFFSOL Ethylene Carbonate acts as a reactant combining with
resorcinol to form the bishydroxyethyl resorcinol product.
For more information regarding the use of JEFFSOL Alkylene Carbonates in alkoxylation or
transesterification please refer to Huntsmans Technical Bulletins entitled JEFFSOL Alkylene Carbonates
in Alkoxylation Chemistry and JEFFSOL Alkylene Carbonates in Transesterification Chemistry.
References to patent documents herein are provided as background information only, and should not be
construed as a suggestion to make, use or sell any invention claimed therein without authorization from
the patent owner.
References
Epoxy Resin Modification with Cyclic Carbonates; David C. Alexander, Texaco Chemical Company, SPIEpoxy Resin Formulators Division, March 24-26, 1993.
U.S. Patent 5,442,034 to Huntsman Corporation, USA, August 15, 1995.
U.S. Patent 5,175,231 to Fiber-Cote Corp., USA, December 29, 1992.
U.S. Patent 5,112,877 to Imperial Chemical Industries PLC, England, May 12, 1992.
U.S. Patent 5,028,635 to Mobay Corporation, USA, July 2, 1991.
U.S. Patent 5,149,458 to Miles Inc., USA, September 22, 1992.
EP 0900811A1 to Goldschmidt AG, Germany, July 09, 1997.
WO 99/28364 to Dow Chemical Company, USA, December 04, 1997.
U.S. Patent 5,059,723 to Indspec Chemical Corp., USA, October 22, 1991.
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