Stabilization of polyetherimide sulfones

• US 20060281840A1
• Filed: 06/09/2005
• Published: 12/14/2006
• Est. Priority Date: 06/09/2005
• Status: Active Grant

• Current Assignee: SHPP Global Technologies BV (Government of Saudi Arabia)
• Original Assignee: Sabic Innovative Plastics IP BV (Government of Saudi Arabia)
• Inventors: Gallucci, Robert R., Malinoski, Jon M.
• Granted Patent: US 7,411,014 B2
• Time in Patent Office: Days
• US Class Current: 524/115
• CPC Class Codes: C08K 5/49 Phosphorus-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08L 81/10 Polysulfonamides; Polysulfonimides

Abstract

A composition comprising a phosphorus containing stabilizer and a polyetherimide sulfone resin having an amount of anhydride functional end groups in excess of the amount of amine functional end groups. The composition may optionally comprise a hindered phenol.

Claims

1. A composition comprising:

polyetherimide sulfone resin having anhydride end groups in an amount that is in excess of the amount of amine functional end groups; and

a phosphorus containing stabilizer.

2. The composition of claim 1 further comprising a hindered phenol stabilizer.

3. The composition of claim 2 wherein the phosphorus containing stabilizer and the hindered phenol stabilizer have a molecular weight of over 500.

4. The composition of claim 1 wherein the phosphorus containing stabilizer is selected from the group consisting of aryl phosphites, aryl phosphonites and mixtures thereof.

5. The composition of claim 1 wherein the polyetherimide sulfone has a glass transition temperature of 250°

C. to 350°

C.

6. The composition of claim 1 wherein the polyetherimide sulfone has greater than or equal to 50 mole % of units derived from oxydiphthalic anhydride.

7. The composition of claim 1 wherein greater than or equal to 50 mole % of the polyetherimide sulfone repeating units comprise at least one aryl ether linkage, at least one aryl sulfone linkage and at least two aryl imide linkages.

8. The composition of claim 1 wherein the polyetherimide sulfone resin comprises structural units derived from an aromatic dianhydride selected from the group consisting of 4,4′

-bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride;

4,4′

-bis(2,3-dicarboxyphenoxy)diphenyl sulfone dianhydride;

4-(2,3-dicarboxyphenoxy)-4′

-(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride;

2,2-bis(4-(3,4-dicarboxyphenoxy)phenyl)propane dianhydride;

4,4′

-bis(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride;

4,4′

-bis(3,4-dicarboxyphenoxy)benzophenone dianhydride;

2,2-bis([4-(2,3-dicarboxyphenoxy)phenyl]propane dianhydride;

4,4′

-bis(2,3-dicarboxyphenoxy)diphenyl ether dianhydride;

4,4′

-bis(2,3-dicarboxyphenoxy)diphenyl sulfide dianhydride;

4,4′

-bis(2,3-dicarboxyphenoxy)benzophenone dianhydride;

2-[4-(3,4-dicarboxyphenoxy)phenyl]-2-[4-(2,3-dicarboxyphenoxy)phenyl]propane dianhydride;

4-(2,3-dicarboxyphenoxy)-4′

-(3,4-dicarboxyphenoxy)diphenyl ether dianhydride;

4-(2,3-dicarboxyphenoxy)-4′

-(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride;

4-(2,3-dicarboxyphenoxy)-4′

-(3,4-dicarboxyphenoxy)benzophenone dianhydride;

1,4,5,8-naphthalenetetracarboxylic acid dianhydride;

3,4,3′

,4′

-benzophenonetetracarboxylic acid dianhydride;

2,3,3′

,4′

-benzophenonetetracarboxylic acid dianhydride;

3,3′

,4,4′

-oxydiphthalic anhydride;

2,3,3′

,4′

-oxydiphthalic anhydride;

3,3′

,4,4′

-biphenyltetracarboxylic acid dianhydride;

2,3,3′

,4′

-biphenyltetracarboxylic acid dianhydride;

2,3,2′

,3′

-biphenyltetracarboxylic acid dianhydride;

pyromellitic dianhydride;

3,4,3′

,4′

-diphenylsulfonetetracarboxylic acid dianhydride;

2,3,3′

,4′

-diphenylsulfonetetracarboxylic acid dianhydride;

1,4-bis(3,4-dicarboxyphenoxy)benzene dianhydride;

2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride; and

mixtures comprising at least two of the foregoing dianhydrides.

9. The composition of claim 1 wherein the polyetherimide sulfone resin comprises structural units derived from an aromatic diamine selected from the group consisting of meta-phenylenediamine;

para-phenylenediamine;

bis(4-aminophenyl)-2,2-propane;

4,4′

-diaminodiphenyl, 3,4′

-diaminodiphenyl, 4,4′

-diaminodiphenyl ether;

3,4′

-diaminodiphenyl ether, 3,3′

-diaminodiphenyl ether, 4,4′

-diaminodiphenyl sulfone, 3,4′

-diaminodiphenyl sulfone, 3,3′

-diaminodiphenyl sulfone, 4,4′

-diaminodiphenyl sulfide;

3,4′

-diaminodiphenyl sulfide;

4,4′

-diaminodiphenyl ketone, 3,4′

-diaminodiphenyl ketone, 4,4′

-diaminodiphenylmethane;

4,4′

-bis(4-aminophenoxy)biphenyl;

4,4′

-bis(3-aminophenoxy)biphenyl, 1,5-diaminonaphthalene;

3,3-dimethylbenzidine;

3,3-dimethoxybenzidine;

benzidine;

bis(aminophenoxy)fluorene, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, 3,3′

-diaminobenzophenone, 4,4′

-diaminobenzophenone, 2,2′

-bis(4-(4-aminophenoxy)phenyl)propane, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 4,4′

-bis(aminophenyl)hexafluoropropane, diaminobenzanilide, and mixtures of two or more of the foregoing diamines.

10. The composition of claim 1 wherein the polyetherimide sulfone comprises structural units derived from an oxydiphthalic anhydride, or chemical equivalent selected from the group consisting of oxydiphthalic carboxylic acids, oxydiphthalic carboxylic esters, oxydiphthalic carboxylic acid esters, oxydiphthalic carboxylic anhydride esters, oxydiphthalic carboxylic anhydride acids, or mixtures thereof capable of forming imide linkages by reaction with diamines.

11. The composition of claim 1 wherein greater than or equal to 50 mole % of the imide linkages are derived from diamino aryl sulfones.

12. The composition of claim 1 wherein the polyetherimide sulfone has a melt viscosity, as measured by ASTM method D3835, at 350°

C. to 425°

C. of 500 to 10,000 Pascal-seconds.

13. The composition of claim 1 wherein the structural units of the polyetherimide sulfone are essentially free of benzylic protons.

14. The composition of claim 1 wherein the polyetherimide sulfone is essentially free of halogen atoms.

15. The composition of claim 1 wherein the polyetherimide sulfone resin comprises 0.1-5.0 mole % of linkages derived from a compound selected from the group consisting of;

mono functional amines, mono functional carboxylic anhydrides, 1,2-dicarboxylic acids, 1,2-dicarboxylic esters, 1,2-dicarboxylic ester acids and mixtures thereof.

16. The composition of claim 1 wherein the polyetherimide sulfone resin has a weight average molecular weight of 10,000 to 50,000 grams/mole.

17. The composition of claim 1 wherein the polyetherimide sulfone has an anhydride end group content, in excess of the amount of amine end groups present, that is 1-50 meq/kg of polyetherimide.

18. A process to prepare a stabilized polyetherimide sulfone resin comprising

preparing polyetherimide sulfone resin having an excess of anhydride end groups compared to amine end groups;

and

combining said polyetherimide sulfone resin with a phosphorus containing stabilizer.

19. The process of claim 18 wherein the stabilized polyetherimide sulfone resin is melt processed at 350-425°

C.

20. A composition comprising a phosphorus containing stabilizer and a polyetherimide sulfone resin having greater than or equal to 50 mole % of units derived from oxydiphthalic anhydride, wherein the polyetherimide sulfone has an amount of anhydride end groups in excess of the amount of amine end groups.

21. A composition comprising a phosphorus containing stabilizer and a polyetherimide sulfone resin having greater than or equal to 50 mole % of units derived from oxydiphthalic anhydride and a diamino aryl sulfone, wherein the polyetherimide sulfone has an amount of anhydride end groups in excess of the amount of amine end groups.