Polyarylene ether sulfone (PAES) polymers

Patent metadata

Field	Value
Publication number	US-9868825-B2
Application number	US-201414889635-A
Country	US
Kind code	B2
Filing date	Apr 30, 2014
Priority date	May 8, 2013
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

A poly(arylether sulfone) polymer [(t-PAES) polymer, herein after], wherein more than 70% moles of the recurring units are recurring units (R t ) of formula (St): -E-Ar 1 —S0 2 -[Ar 2 -(T-Ar 3 ) n —SO 2 ]m-Ar 4 — (formula S t ) wherein: n and m, equal to or different from each other, are independently zero or an integer of 1 to 5, each of Ar 1 , Ar 2 , Ar 3 and Ar 4 equal to or different from each other and at each occurrence, is an aromatic moiety, T is a bond or a divalent group optionally comprising one or more than one heteroatom; -E is of formula (E t ), wherein each of R′, equal to or different from each other, is selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium; j′ is zero or is an integer from 1 to 4, and said (t-PAES) polymer having a number average molecular weight (M n ) ranging from 41 000 to 90 000.

First claim

The invention claimed is:

1. A poly(arylether sulfone) polymer, (t-PAES) polymer, wherein more than 70% moles of the recurring units are recurring units (R t ) of formula (S t ):
-E-Ar 1 —SO 2 —[Ar 2 -(T-Ar 3 ) n —SO 2 ] m —Ar 4 —  (formula S t )

wherein:
n and m, equal to or different from each other, are independently zero or an integer of 1 to 5;
each of Ar 1 , Ar 2 , Ar 3 and Ar 4 equal to or different from each other and at each occurrence, is an aromatic moiety;
T is a bond or a divalent group optionally comprising one or more than one heteroatom;
E is of formula (E t ):

wherein:
each of R′, equal to or different from each other, is selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium;
j′ is zero or is an integer from 1 to 4; and

said (t-PAES) polymer having a number average molecular weight (M n ) ranging from 41,000 to 90,000 and a polydispersity index of less than 4.0.

2. The (t-PAES) polymer of claim 1 , wherein said (t-PAES) polymer has a solubility in an aqueous sulphuric acid solution having a density of 1.84 g/cm 3 of less than 1.00 g/I.

3. The (t-PAES) polymer according to claim 1 , wherein said recurring units (R t ) are selected from the group consisting of formula (S t -1) to (S t -4):

wherein
each of R′, equal to or different from each other, is selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium;
j′ is zero or is an integer from 1 to 4; and
T is a bond or a divalent group optionally comprising one or more than one heteroatom.

4. The (t-PAES) polymer according to claim 1 , additionally comprising recurring units (R a ) of formula (K a ):
-E-Ar 5 —CO—[Ar 6 -(T-Ar 7 ) n —CO] m —Ar 8 —  (formula K a )

wherein:
n and m, equal to or different from each other, are independently zero or an integer of 1 to 5;
each of Ar 5 , Ar 6 , Ar 7 and Ar 8 equal to or different from each other and at each occurrence, is an aromatic moiety;
T is a bond or a divalent group optionally comprising one or more than one heteroatom;
E is of formula (E t ):

wherein:
each of R′, equal to or different from each other, is selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium.

5. The (t-PAES) polymer according to claim 1 , additionally comprising recurring units (R b ) comprising a Ar—SO 2 —Ar′ group, with Ar and Ar′, equal to or different from each other, being aromatic groups, said recurring units (R b ) complying with formulae (S1):
—Ar 9 -(T′-Ar 10 ) n —O—Ar 11 —SO 2 —[Ar 12 -(T-Ar 13 ) n —SO 2 ] m —Ar 14 —O—  (S1):

wherein:
Ar 9 , Ar 10 , Ar 11 , Ar 12 , Ar 13 and Ar 14 , equal to or different from each other and at each occurrence, are independently an aromatic mono- or polynuclear group;
T and T′, equal to or different from each other and at each occurrence, is independently a bond or a divalent group optionally comprising one or more than one heteroatom; and
n and m, equal to or different from each other, are independently zero or an integer of 1 to 5.

6. The (t-PAES) polymer according to claim 1 , additionally comprising recurring units (R c ) comprising a Ar—C(O)—Ar′ group, with Ar and Ar′, equal to or different from each other, being aromatic groups, said recurring units (R c ) are selected from the group consisting of formulae (J-A) to (J-L):

wherein:
each of R′, equal to or different from each other, is selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium; and
j′ is zero or is an integer from 0 to 4.

7. The (t-PAES) polymer according to claim 1 , wherein the (t-PAES) polymer has a tensile yield elongation, as measured according to ASTM D638, equal to or above 2%.

8. The (t-PAES) polymer according to claim 1 , wherein the (t-PAES) polymer has a tensile elongation at break, as measured according to ASTM D638, equal to or above 9%.

9. The (t-PAES) polymer of claim 1 , wherein molded parts of the (t-PAES) polymer have a degree of crystallinity below 30% and wherein said molded parts are 102 mm×102 mm×1.6 mm plaques made by compression molding of said (t-PAES) polymer and wherein said plaques were annealed at 350° C. for 3 hours under air.

10. A gel-permeation chromatography (GPC) method for determining the number average molecular weight (M n ) of a poly(arylether sulfone) polymer, (t-PAES) polymer, wherein more than 70% moles of the recurring units are recurring units (R t ) of formula (S t ):
-E-Ar 1 —SO 2 —[Ar 2 -(T-Ar 3 ) n —SO 2 ] m —Ar 4 —  (formula S t )

wherein:
n and m, equal to or different from each other, are independently zero or an integer of 1 to 5;

each of Ar 1 , Ar 2 , Ar 3 and Ar 4 equal to or different from each other and at each occurrence, is an aromatic moiety;
T is a bond or a divalent group optionally comprising one or more than one heteroatom;
E is of formula (E t ):

wherein:
each of R′, equal to or different from each other, is selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium;
j′ is zero or is an integer from 1 to 4, said (t-PAES) polymer having a number average molecular weight (M n ) ranging from 41,000 to 90,000 and a polydispersity index of less than 4.0, wherein said GPC method comprises (i) dissolving said (t-PAES) polymer at a temperature from 100 to 250° C. in a solvent suitable for GPC providing a polymer solution wherein the concentration of said (t-PAES) polymer in said polymer solution is between 1.0 to 10.0 mg/ml, and (ii) eluting a specimen of said polymer solution in a GPC column using N-methyl-2-pyrrolidone (NMP) containing at least one salt as eluent, at a temperature from 20 to 50° C.

11. A process for manufacturing the (t-PAES) polymer according to claim 1 , having a number average molecular weight (M n ) of at ranging from 41,000 to 90,000 and a polydispersity index of less than 4.0, comprising reacting in a solvent mixture comprising a polar aprotic solvent and in the presence of an alkali metal carbonate, a monomer mixture comprising:
at least one dihydroxyaryl compound, diol (AA), of fo

Assignees

• Solvay Specialty Polymers Usa

Inventors

• Louis Chantal
• El-Hibri Mohammad Jamal
• Thomas David B
• Patel Hemantkumar

Classifications

• C08G75/23 Primary

  Polyethersulfones · CPC title

• G01N30/02

  Column chromatography · CPC title

• B29C45/0001

  characterised by the choice of material · CPC title

• B29C48/022

  characterised by the choice of material · CPC title

• B05D1/12

  Applying particulate materials (B05D1/06, B05D1/10 take precedence) · CPC title