Poly(ether sulfone)s and poly(ether amide sulfone)s and methods of their preparation

Patent metadata

Field	Value
Publication number	US-2016002431-A1
Application number	US-201414321877-A
Country	US
Kind code	A1
Filing date	Jul 2, 2014
Priority date	Jul 2, 2014
Publication date	Jan 7, 2016
Grant date	—

Abstract

Poly(ether sulfones) (PES) and poly(ether amide sulfones) (PEAS) were prepared from post-consumer polycarbonates and polyesters, respectively, using a single vessel in batch mode (all reactants present when heating was initiated). The depolymerization of the initial polymer occurs concurrently with step growth polymerization to form a product polymer having a number average molecular weight of at least 5000.

First claim

What is claimed is:

1 . A poly(ether amide sulfone) (PEAS), having a structure in accordance with formula (16):

wherein
n is a positive number having an average value greater than or equal to 1,
m is a positive number having an average value greater than or equal to 1,
each E′ is an independent monovalent radical selected from the group consisting of hydrogen and electron withdrawing groups,
each L a is an independent divalent radical comprising 2 or more carbons,
each L d is an independent divalent radical comprising 2 or more carbons,
each L′ is an independent divalent linking group comprising 1 or more carbons,
Z′ is a first polymer chain end group,
Z″ is a second polymer chain end group, and
vertical stacking of the repeat units enclosed by parentheses within the square brackets indicates a random distribution of the repeat units in the structure of the PEAS.

2 . The PEAS of claim 1 , wherein L d comprises an aromatic ring.

3 . The PEAS of claim 1 , wherein L a comprises an aromatic ring.

4 . The PEAS of claim 1 , wherein L′ comprises an aromatic ring.

5 . The PEAS of claim 1 , wherein *—O-L a -O—* is a dioxy residue of bisphenol A.

6 . The PEAS of claim 1 , wherein each E′ is hydrogen.

7 . The PEAS of claim 1 , wherein each E′ is a nitro group.

8 . A method, comprising:
forming a mixture comprising
i) a polyester having a repeat unit of formula (8):

wherein
L′ is a divalent radical comprising 1 or more carbons, and
L″ is a divalent radical comprising 2 or more carbons,

ii) an amino-alcohol of formula (10):
HO-L d -NH 2   (10),

wherein
L d is a divalent radical comprising 2 or more carbons,

iii) a bis-aryl sulfone of formula (4):

wherein
each E′ is an independent monovalent radical selected from the group consisting of hydrogen and electron withdrawing groups, and
each X′ is an independent monovalent leaving group,

iv) a diol compound of formula (1),
HO-L a -OH  (1),

wherein
L a is a divalent radical comprising 2 or more carbons,

v) a base, and
vi) a solvent; and
heating the mixture at a reaction temperature of about 150° C. to about 250° C., wherein the diol compound is substantially non-volatile at the reaction temperature, thereby forming a poly(ether amide sulfone) (PEAS).

9 . The method of claim 8 , wherein the PEAS has a structure in accordance with formula (16):

wherein
n is a positive number having an average value greater than or equal to 1,
m is a positive number having an average value greater than or equal to 1,
each E′ is an independent monovalent radical selected from the group consisting of hydrogen and electron withdrawing groups,
each L a is an independent divalent radical comprising 2 or more carbons,
each L d is an independent divalent radical comprising 2 or more carbons,
each L′ is an independent divalent linking group comprising 1 or more carbons,
Z′ is a first polymer chain end group,
Z″ is a second polymer chain end group, and
vertical stacking within the square brackets of the repeat units enclosed by parentheses indicates random distribution of the repeat units in the structure of the PEAS.

10 . The method of claim 8 , wherein the polyester is selected from the group consisting of poly(ethylene terephthalate) (PET), poly(butylene terephthalate) (PBT), and combinations thereof.

11 . The method of claim 8 , wherein the polyester is a post-consumer polyester.

12 . The method of claim 8 , wherein the amino-alcohol comprises an aromatic ring.

13 . The method of claim 8 , wherein the amino-alcohol has a structure according to formula (11):
HO-L e -CH 2 —NH 2   (11),

wherein
L e a divalent radical comprising 1 or more carbons.

14 . The method of claim 8 , wherein the amino-alcohol has a structure according to formula (12):

wherein
j′ is an integer having a value of 0 to 4,
k′ is an integer having a value of 0 or more, and
each C′ is an independent monovalent radical selected from the group consisting of halides and substituents comprising 1 or more carbons.

15 . A method, comprising:
forming a mixture comprising
i) a polycarbonate having a repeat unit of formula (2):

wherein
L b is a divalent radical comprising 2 or more carbons,

ii) a bis-aryl sulfone of formula (4):

wherein
each E′ is an independent monovalent radical selected from the group consisting of hydrogen and electron withdrawing groups, and
each X′ is an independent monovalent leaving group,

iii) a base, and
iv) a solvent; and
heating the mixture at a reaction temperature of about 150° C. to about 250° C., thereby forming a poly(ether sulfone) (PES).

16 . The method of claim 15 , wherein the polycarbonate is post-consumer poly(bisphenol A carbonate).

17 . The method of claim 15 , wherein each X′ of formula (4) is fluoride and each E′ of formula (4) is hydrogen.

18 . The method of claim 15 , wherein the PES has a structure in accordance with formula (5):

wherein
m is a positive number greater than or equal to 1,
each L b is an independent divalent linking group comprising 2 or more carbons,
each E′ is an independent monovalent radical selected from the group consisting of hydrogen and electron withdrawing groups,
Y′ is a first polymer chain end group, and
Y″ is a second polymer chain end group.

19 . The method of claim 18 , wherein L b comprises at least one aromatic ring.

20 . The method of claim 15 , wherein the PES has a structure in accordance with formula (6):

wherein
m is a positive number greater than or equal to 1,
R′ is a monovalent radical selected from the group consisting of hydrogen, halides, and groups comprising 1 or more carbons,
R″ is a monovalent radical selected from the group consisting of hydrogen, halides, and groups comprising 1 or more carbons,
each E′ is an independent monovalent radical selected from the group consisting of hydrogen and electron withdrawing groups,
Y′ is a first polymer chain end group, and
Y″ is a second polymer chain end group.

21 . The method of claim 20 , wherein R′ and R″ are methyl.

22 . A molding composition comprising the PEAS of claim 1 and one or more optional additives.

23 . A molding composition comprising the PES of claim 15 and one or more optional additives.

24 . A method, comprising:
forming a mixture comprising
i) an ester material comprisi

Assignees

• IBM

Inventors

• Bajjuri Krishna M
• Garcia Jeannette M
• Hedrick James L

Classifications

• C08G69/42

  Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen (C08G69/12, C08G69/32 take precedence) · CPC title

• C08G69/40

  Polyamides containing oxygen in the form of ether groups (C08G69/12, C08G69/32 take precedence) · CPC title

• C08J11/08 Primary

  using selective solvents for polymer components · CPC title

• C08G75/23 Primary

  Polyethersulfones · CPC title

• C08J2381/10

  Polysulfonamides; Polysulfonimides · CPC title