IP Library Granted Patent US 8,207,287
Granted Patent B1
US 8,207,287 · App. 13/155,065 · Granted Jun 26, 2012

Polycarbonate polymers containing bisphenol compounds

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Quick Facts
Patent No.
US 8,207,287
App. No.
13/155,065
Granted
Jun 26, 2012
Kind
B1
Abstract

Disclosed are polymers derived from units of bisphenol compounds, such as tetramethylcyclobutane diol-bisphenol, and processes for making and using them.

Claims (53)

1. A polymer comprising units derived from a compound of Formula I

wherein m and p may be the same or different and are each an integer from 0-4; each R 1 and R 2 are the same or different and are each independently selected from one or more of halogen, C 1 -C 12 alkyl, C 1 -C 6 aliphatic, C 3 -C 6 cycloaliphatic, C 1 -C 12 alkoxy, and C 1 -C 12 alkyl ester; and

R 3 , R 4 , R 5 , and R 6 are the same or different and are each independently selected from one or more of hydrogen, and C 1 -C 2 aliphatic.

2. The polymer of claim 1 , wherein the compound of Formula I comprises tetramethylcyclobutane diol-2,5-bis(4-hydroxybenzoate) of Formula Ia

3. The polymer of claim 1 , wherein the polymer is a homopolymer or copolymer and is selected from one or more of polycarbonate, polyurethane, polyurea, polyarylate, polyester, polyether, polyetheramide, polyformyl, and polyphenylene ether.

4. The polymer of claim 1 , further comprising units derived from Formula V:

wherein Z is an aromatic moiety or an aliphatic moiety.

5. A polymer comprising units of Formula II

wherein m and p may be the same or different and are each an integer from 0-4; each R 1 and R 2 are the same or different and are each independently selected from one or more of halogen, C 1 -C 12 alkyl, C 1 -C 6 aliphatic, C 3 -C 6 cycloaliphatic, C 1 -C 12 alkoxy, and C 1 -C 12 alkyl ester; and

R 3 , R 4 , R 5 , and R 6 are the same or different and are each independently selected from one or more of hydrogen, and C 1 -C 2 aliphatic; and

n is an integer from 1 to 500.

6. The polymer of claim 5 , wherein the polymer is a copolymer and further comprises units of Formula VI

wherein Z is an aromatic moiety or an aliphatic moiety or —O—Z—O— is a fragment of Formula IV

wherein R is selected from one or more of alkyl, aryl, and alkylaryl hydrocarbons of 1 to 20 carbon atoms, disubstituted oxygen, sulfone, and spirobiindane.

7. The polymer of claim 6 comprising units of Formula III

wherein m and p may be the same or different and are each an integer from 0-4; each R 1 and R 2 are the same or different and are each independently selected from one or more of halogen, C 1 -C 12 alkyl, C 1 -C 6 aliphatic, C 3 -C 6 cycloaliphatic, C 1 -C 12 alkoxy, and C 1 -C 12 alkyl ester; and

R 3 , R 4 , R 5 , and R 6 are the same or different and are each independently selected from one or more of hydrogen, and C 1 -C 2 aliphatic;

n is an integer from 1 to 500; and

Z is an aromatic moiety or an aliphatic moiety or O—Z—O comprises a structure of Formula IV

wherein R is selected from one or more of alkyl, aryl, and alkylaryl hydrocarbons of 1 to 20 carbon atoms, disubstituted oxygen, sulfone, and spirobiindane.

8. The polymer of claim 7 , wherein R is selected from one or more of alkyl groups having from 1-8 carbon atoms, isopropylidene, 1-phenylethyl, spirobiindane and mixtures thereof.

9. A polymer comprising units of the Formula IIa

wherein n is an integer from 1 to 500.

10. A polymer comprising units of Formula IIIa

wherein n is an integer from 1 to 500; and

Z is an aromatic moiety or an aliphatic moiety.

11. The polymer of claim 10 , wherein Z is from bisphenol A and the polymer includes units of Formula IIIb

12. A polymer prepared from a compound of Formula I.

13. A process for preparing a polymer comprising polymerizing a compound of Formula I.

14. The process of claim 13 , the compound of Formula I is added to a formulation comprising phosgene, water and an organic solvent.

15. The process of claim 13 , wherein the polymer is a homopolymer.

16. The process of claim 13 , wherein the polymer is a copolymer.

17. The process of claim 16 , wherein the compound of Formula I is copolymerized with a compound of Formula VII,

wherein R is selected from one or more of alkyl, aryl, and alkylaryl hydrocarbons of 1 to 20 carbon atoms, disubstituted oxygen, sulfone, and spirobiindane.

18. The process of claim 17 , wherein the compound of Formula VII comprises a compound of Formula VIII

wherein q is an integer from 4-9, and each of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 is independently selected from one or more of hydrogen or C 1 -C 6 alkyl.

19. The process of claim 17 , wherein the compound of Formula VII is bisphenol A.

20. The process of claim 17 , the compound of Formula I and Formula VII are added to a formulation of phosgene, water and organic solvent.

21. The process of claim 13 , wherein the polymerizing comprises an interfacial polymerization reaction.

22. The process of claim 13 , wherein the polymerizing comprises melt polymerization reaction.

23. A process for preparing a polymer having units of the Formula IIa,

wherein n is an integer from 1 to 500, comprising adding a compound of Formula Ia

to a formulation comprising phosgene, water and organic solvent and polymerizing the compound of Formula Ia.

24. A process for preparing a polymer having units of the Formula IIIa,

wherein n is an integer from 1 to 500 and Z is bisphenol A, comprising combining a compound of Formula I with bisphenol A, adding the combination to a formulation comprising phosgene, water and organic solvent and copolymerizing the compound of Formula I and bisphenol A.

25. An article of manufacture comprising a polymer prepared from a composition containing the polymer of claim 1 .

26. The article of claim 25 , wherein said article is an electronic device.

27. An article of manufacture comprising a polymer prepared from a composition containing the polymer of claim 5 .

28. The article of claim 27 , wherein said article is an electronic device.

29. An article of manufacture comprising a polymer prepared from a composition containing the polymer of claim 10 .

30. The article of claim 29 , wherein said article is an electronic device.

31. The article of claim 25 , wherein said polymer is a polycarbonate.

32. The polymer of claim 1 , wherein said polymer has a thermal degradation temperature of between about 350° C. to about 450° C. as determined by thermal gravimetry analysis.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE REMOVE THE APPLICATION NUMBER 15039474 PREVIOUSLY RECORDED AT REEL: 054528 FRAME: 0467. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 23, 2021
From: SABIC GLOBAL TECHNOLOGIES B.V.
To: SHPP GLOBAL TECHNOLOGIES B.V.
Reel/Frame 057453/0680 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2020
From: SABIC GLOBAL TECHNOLOGIES B.V.
To: SHPP GLOBAL TECHNOLOGIES B.V.
Reel/Frame 054528/0467 →
CHANGE OF NAME Recorded Jun 12, 2017
From: SABIC INNOVATIVE PLASTICS IP B.V
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 042768/0323 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2011
From: MORIZUR, JEAN-FRANCOIS
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 026686/0507 →