Functionalized polyphenylene ether from polyphenylene ether chain terminated with phenoxy moiety containing amino and hydroxy group

• US 4,888,397 A
• Filed: 02/24/1989
• Issued: 12/19/1989
• Est. Priority Date: 07/24/1985
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: van der Meer, Roelof, Yates, John B. III
• Primary Examiner(s): ANDERSON, HAROLD
• Application Number:
  US07/314,866
• Time in Patent Office: 298 Days
• Field of Search: 525/391, 525/392, 525/397, 525/132, 525/149, 525/426
• US Class Current: 525/391
• CPC Class Codes: C08K 5/00 Use of organic ingredients
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 67/00 Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 71/12 Polyphenylene oxides
• CPC Class Codes: C08L 71/126 modified by chemical after-treatment
• CPC Class Codes: C08L 77/00 Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08; Compositions of derivatives of such polymers

Abstract

Functionalized polyphenylene ethers are prepared by mixing with various functionalized olefinic or acetylenic compounds in the melt, in the absence of free radical initiator. They are useful in the preparation of compositions comprising polyphenylene ethers and polyamides or polyesters.

Claims

1. A method for functionalizing a polyphenylene ether containing a substantial proportions of end groups of the formula ##STR7## wherein:

each Q¹ is independently halogen, primary or secondary lower alkyl, phenyl, haloalkyl, aminoalkyl, hydrocarbonoxy, or halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;

each Q² is independently hydrogen, halogen, primary or secondary lower alkyl, phenyl, haloalkyl, hydrocarbonoxy or halohydrocarbonoxy as defined for Q¹ ;

each R¹ is independently hydrogen or alkyl, the total number of carbon atoms in both R¹ radicals being 6 or less; and

each R² is independently hydrogen or C_1-6 primary alkyl;

which comprises mixing said polyphenylene ether in the melt, in the absence of free radical initiators, with at least one functionalizing compound having within its molecular structure at least one carbon-carbon double or triple bond and at least one carboxylic acid, acid anhydride, acid amide, imide, ester, amino or hydroxy group.

2. A method according to claim 1 wherein the polyphenylene ether comprises a plurality of structural units having the formula ##STR8##

3. A method according to claim 2 wherein the mixture also contains an impact modifying resin for polyphenylene ether-polyamide compositions.

4. A method according to claim 2 wherein the mixture also contains a styrene homopolymer or high impact polystyrene.

5. A method according to claim 3 wherein the functionalizing compound is maleic anhydride, a maleimide or fumaric acid.

6. A method according to claim 3 wherein the polyphenylene ether is a poly(2,6-dimethyl-1,4-phenylene ether).

7. A method according to claim 6 wherein the functionalizing compound is maleic anhydride.

8. A method according to claim 6 wherein the functionalizing compound is fumaric acid.

9. A method according to claim 6 wherein the impact modifying resin is a diblock or triblock copolymer of styrene and at least one olefin or conjugated diene, any conjugated diene block being non-hydrogenated or partially or entirely hydrogenated, and is present in an amount up to about 50 parts by weight per 100 parts of polyphenylene ether.

10. A method according to claim 6 wherein the temperature of mixing is within the range of about 230°

-390°

C.

11. A functionalized polyphenylene ether prepared by the method of claim 1.

12. A functionalized polyphenylene ether prepared by the method of claim 6.

13. A functionalized polyphenylene ether prepared by the method of claim 8.

14. A method for preparing a polyphenylene ether-polyamide composition which comprises:

(A) mixing in the melt, in the absence of free radical initiators, at least a portion of a polyphenylene ether containing a substantial proportion of end groups of the formula ##STR9## wherein;

each Q¹ is independently halogen, primary or secondary lower alkyl, phenyl, haloalkyl, aminoalkyl, hydrocarbonoxy, or halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;

each Q² is independently hydrogen, halogen, primary or secondary lower alkyl, phenyl, haloalkyl, hydrocarbonoxy or halohydrocarbonoxy as defined for Q¹ ;

each R¹ is independently hydrogen or alkyl, the total number of carbon atoms in both R¹ radicals being 6 or less; and

each R² is independently hydrogen or C_1-6 primary alkyl;

with at least one functionalizing compound having within its molecular structure at least one carbon-carbon double or triple bond and at least one carboxylic acid, acid anhydride, acid amide, imide, ester, amino or hydroxy group, thereby producing a functionalized polyphenylene ether; and

subsequently

(B) melt-blending said functionalized polyphenylene ether with any additional unfunctionalized portion of said polyphenylene ether and with at least one polyamide;

with the proviso that there is also blended into said composition at least one of styrene homopolymers, high impact polystyrenes and impact modifying resins for polyphenylene ether-polyamide compositions.

15. A method according to claim 14 wherein the polyamide is nylon-6 or nylon-66 and the polyphenylene ether comprises a plurality of structural units having the formula ##STR10## and in each of said units independently, each Q¹ is independently halogen, primary or secondary lower alkyl, phenyl, haloalkyl, aminoalkyl, hydrocarbonoxy, or halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms;

and each Q² is independently hydrogen, halogen, primary or secondary lower alkyl, phenyl, haloalkyl, hydrocarbonoxy or halohydrocarbonoxy as defined for Q¹.

16. A method according to claim 15 wherein the impact modifying resin is blended into the composition during step A.

17. A method according to claim 16 wherein the functionalizing compound is maleic anhydride, a maleimide or fumaric acid.

18. A method according to claim 16 wherein the polyphenylene ether is a poly(2,6-dimethyl-1,4-phenylene ether).

19. A method according to claim 18 wherein up to about 90% by weight of the total polyphenylene oxide blended into the composition is unfunctionalized.

20. A method according to claim 18 wherein the functionalizing compound is maleic anhydride.

21. A method according to claim 18 wherein the functionalizing compound is fumaric acid.

22. A method according to claim 18 wherein the impact modifying resin is a diblock or triblock copolymer of styrene and at least one olefin or conjugated diene, any conjugated diene block being non-hydrogenated or partially or entirely hydrogenated, and is present in an amount up to about 50 parts by weight per 100 parts of polyphenylene ether.

23. A method according to claim 18 wherein the temperature of step A is within the range of about 230°

-390°

C.

24. A method according to claim 18 wherein the polyamide is nylon-66.

25. A polyphenylene ether-polyamide composition prepared by the method of claim 14.

26. A polyphenylene ether-polyamide composition prepared by the method of claim 18.

27. A polyphenylene ether-polyamide composition prepared by the method of claim 21.