US 11,912,819 B2
Bifuran polyesters
Monica Lotz, Houston, TX (US); Kapil Kandel, Humble, TX (US); Michael Salciccioli, Houston, TX (US); Stephen Cohn, Spring, TX (US); Alan A. Galuska, Huffman, TX (US); Javier Guzman, Porter, TX (US); S. Richard Turner, Blacksburg, VA (US); Hans Eliot Edling, Radford, VA (US); and Edward E. Paschke, Galena, IL (US)
Assigned to ExxonMobil Chemical Patents, Inc., Baytown, TX (US); and Virginia Tech Intellectual Properties, Inc., Blacksburg, VA (US)
Appl. No. 17/284,717
Filed by ExxonMobil Chemical Patents Inc., Baytown, TX (US); and Virginia Tech Intellectual Properties, Inc., Blacksburg, VA (US)
PCT Filed Nov. 13, 2019, PCT No. PCT/US2019/061070
§ 371(c)(1), (2) Date Apr. 12, 2021,
PCT Pub. No. WO2020/106510, PCT Pub. Date May 28, 2020.
Claims priority of provisional application 62/770,064, filed on Nov. 20, 2018.
Prior Publication US 2021/0355271 A1, Nov. 18, 2021
Int. Cl. C08G 63/185 (2006.01); C08G 63/199 (2006.01); C08G 63/80 (2006.01); C08G 63/85 (2006.01)
CPC C08G 63/185 (2013.01) [C08G 63/199 (2013.01); C08G 63/80 (2013.01); C08G 63/85 (2013.01); C08G 2120/00 (2013.01); C08G 2250/00 (2013.01)] 17 Claims
 
1. A bifuran polyester comprising:
polyethylene-2,2′-bifuran-5,5′-dicarboxylate (PEBF) homopolyester or copolyester comprising up to 5 mole percent isophthalate or up to 2.7 mole percent terephthalate, based on total moles of a diacid component, or up to 2.5 mole percent 1,4-cyclohexanedimethanol (CHDM), based on total moles of a diol component; and
wherein the bifuran polyester is prepared by a method comprising: esterifying or transesterifying the diacid component and the diol component in the presence of a catalyst compound comprising metal present in an amount of from about 10 to about 550 ppm, based on the weight of the bifuran polyester; and polycondensation to form the bifuran polyester
with an intrinsic viscosity of at least 0.4 g/dL and a semicrystalline melting peak (Tm) with ΔHf equal to or greater than 5 J/g on the second heating ramp in a heat/cool/reheat differential scanning calorimetry (DSC) scan over a temperature range from 30° C. to 300° C. with heating and cooling rates of 10° C./min and holding the sample at temperature for 3 min before and after the cooling ramp, wherein:
(a) a melt-pressed specimen of the bifuran polyester has an elongation at break equal to or greater than 10% according to ASTM D638 and one or more or all of the following tensile properties measured from a melt-pressed specimen according to ASTM D638:
a yield stress equal to or greater than 80 MPa;
a tensile stress at break equal to or greater than 50 MPa; or
a Young's modulus equal to or greater than 2600 MPa; and
(b) an injection molded specimen of the bifuran polyester has one or more or all of the following tensile properties measured from an injection molded specimen according to ASTM D638:
flexural modulus equal to or greater than 2500 MPa;
a tensile modulus equal to or greater than 3000 MPa; or
a tensile stress at maximum load equal to or greater than 40 MPa.