Controlled glass transition polymeric material and method

Patent metadata

Field	Value
Publication number	US-11155673-B2
Application number	US-201615773804-A
Country	US
Kind code	B2
Filing date	Nov 11, 2016
Priority date	Nov 12, 2015
Publication date	Oct 26, 2021
Grant date	Oct 26, 2021

Abstract

The present teachings contemplate relatively high glass transition temperature (Tg) polymers and/or other reaction products. A method may include reacting a diepoxide with a bisphenol in amounts and under conditions to produce a material that has a Tg as measured by differential scanning calorimetry according to ASTM E1358-08(2014) of at least about 90° C. at least about 100° C. (at least about 110° C., or at least about 120° C.

First claim

What is claimed is:

1. A polymeric material comprising a reaction product of at least one diepoxide and at least one bisphenol selected from 4,4′-(1-phenylethylidene) bisphenol, 4,4′-sulfonylbisphenol, or a combination thereof, in the presence of a catalyst; wherein the catalyst is triphenylphosphine; wherein the reaction product is a reaction product of a substantially non-equimolar reaction mixture of the at least one diepoxide and the at least one bisphenol; wherein the reaction product has a T g as measured by differential scanning calorimetry, according to ASTM E1356-08(2014), of at least about 120° C. and below about 170° C.; wherein the polymeric material is a thermoplastic; and wherein one or any combination of the following conditions are met:
(a) the reaction product is a catalyzed reaction product of a reaction mixture consisting essentially of the at least one diepoxide and the at least one bisphenol that is free of any sulfur, any ketone, or both any sulfur and any ketone moiety;
(b) the reaction product is of a reaction mixture of the at least one diepoxide and the at least one bisphenol in substantial or complete absence of any solvent; or
(c) the reaction product is of a reaction mixture of the at least one diepoxide and the at least one bisphenol in substantial absence of any ketone.

2. The polymeric material of claim 1 , wherein the reaction product exhibits one or any combination of the following characteristics: a tensile strength at yield, according to ASTM D638-14, of at least about 15 MPa; a tensile elongation strength at break, according to ASTM D638-14, of at least about 45 MPa; an elongation at break, according to ASTM D638-14, of at least about 15%; and/or a tensile modulus of elasticity, according to ASTM D638-14, of at least about 0.5 GPa.

3. The polymeric material of claim 1 , wherein the at least one diepoxide and the at least one bisphenol are reacted, in molar amounts, in a ratio of the at least one diepoxide to the at least one bisphenol of about 4:1 to about 1:4, excluding 1:1.

4. The polymeric material of claim 1 , wherein the at least one diepoxide has a molecular weight ranging from about 130 g/mol to about 460 g/mol.

5. The polymeric material of claim 1 , wherein the at least one diepoxide is a diglycidyl ether.

6. The polymeric material of claim 5 , wherein the at least one diepoxide is a diglycidyl ether having at least one phenyl group.

7. The polymeric material of claim 5 , wherein the at least one bisphenol has a molecular weight of about 200 g/mol to about 360 g/mol.

8. The polymeric material of claim 6 , wherein the at least one diepoxide is selected from resorcinol diglycidyl ether, diglycidyl ether of bisphenol A, bisphenol F diglycidyl ether, bisphenol A propoxylate diglycidyl ether, or any combination thereof.

9. The polymeric material of claim 1 , wherein the reaction product is of a reaction mixture of the at least one diepoxide and the at least one bisphenol in substantial or complete absence of any solvent.

10. A polymeric material consisting essentially of a reaction product of at least one diepoxide and at least one bisphenol selected from bisphenol S, 4,4′-(1- phenylethylidene) bisphenol, or both, in the presence of a catalyst; wherein the catalyst is triphenylphosphine; wherein the reaction product is of a substantially non-equimolar reaction mixture of the at least one diepoxide and the at least one bisphenol; wherein the reaction product has a T g as measured by differential scanning calorimetry, according to ASTM E1356-08(2014), of at least about 120° C. and below about 170° C.; and wherein the polymeric material is a thermoplastic.

11. The polymeric material of claim 10 , wherein the reaction product is of a reaction mixture of the at least one diepoxide and the at least one bisphenol in substantial or complete absence of any solvent.

Assignees

• Zephyros Inc

Inventors

• Mazich Kenneth A
• Meistermann Laurent
• Chiemelewski Craig

Classifications

• C08G59/28

  containing acyclic nitrogen atoms · CPC title

• C08G59/64

  Amino alcohols · CPC title

• C08G59/62

  Alcohols or phenols · CPC title

• C08G59/68

  characterised by the catalysts used · CPC title

• C08G59/50

  Amines · CPC title