IP Library Granted Patent US 9,127,119
Granted Patent B2
US 9,127,119 · App. 13/740,094 · Granted Sep 8, 2015

Polycarbonate compositions having improved thermal dimensional stability and high refractive index

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Quick Facts
Patent No.
US 9,127,119
App. No.
13/740,094
Granted
Sep 8, 2015
Kind
B2
Abstract

Disclosed herein are methods and compositions of polycarbonate compositions having, among other characteristics, improved thermal dimensional stability, hydrolytic stability and high refractive index. The resulting polycarbonate copolymer composition, comprising a polycarbonate and a polysulfone, can be used in the manufacture of articles for optical applications. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Claims (80)

1. A polycarbonate copolymer composition comprising:

(a) monomeric units comprising a carbonate unit derived from a first aromatic dihydroxy compound, wherein the carbonate unit comprises the formula:

wherein Ra and Rb each represent a halogen atom or a monovalent hydrocarbon group and can be the same or different; p and q are each independently integers of 0 to 4, R3 is each independently a C1-6 alkyl group, j is 0 to 4, and R4 is a C1-6 alkyl, phenyl, or phenyl substituted with up to five C1-6 alkyl groups; and

(b) monomeric sulfone units comprising the formula

wherein m is from 4-7.

2. The composition of claim 1 , further comprising monomeric units (c) comprising a carbonate unit derived from a second aromatic dihydroxy compound.

3. The composition of claim 1 , wherein the monomeric units (a) further comprise a carbonate unit derived from a second aromatic dihydroxy compound.

4. The composition of claim 1 , wherein the carbonate unit is derived from bisphenol A, PPPBP, bisphenol acetophenone or a combination thereof.

5. The composition of claim 2 , wherein the carbonate unit of (a) comprises PPPBP, and wherein the carbonate unit of (c) comprises bisphenol A.

6. The composition of claim 5 , wherein the monomeric units (c) further comprises a ester unit derived from an aromatic diol, a C6-C44 aliphatic dicarboxylic acid, or a derivative thereof.

7. The composition of claim 6 , wherein the monomeric units (c) comprises a polyester-carbonate.

8. The composition of claim 7 , wherein the polyester unit is derived from an aliphatic dicarboxylic acid.

9. The composition of claim 7 , wherein the polyester unit is derived from an aliphatic dicarboxylic acid of the formula:

where m and m′ are independently 0 to 38, n and n′ are independently 0 to 38, and the sum m+m′+n+n′ is an integer from 8 to 38.

10. The composition of claim 6 , wherein the aliphatic dicarboxylic acid is selected from the group comprising C36 aliphatic dicarboxylic acid, C44 aliphatic dicarboxylic acid, or a combination thereof.

11. The composition of claim 9 , wherein the C36 aliphatic dicarboxylic acid comprises a mixture of hydrogenated dimer fatty acids.

12. The composition of claim 5 , wherein the wherein the bisphenol-A polycarbonate has a weight-averaged molecular weight from about 18,000 to about 32,000.

13. The composition of claim 5 , wherein the bisphenol-A polycarbonate has a weight-averaged molecular weight from about 28,000 to about 32,000.

14. The composition of claim 1 , wherein the composition exhibits a refractive index of at least about 1.59.

15. The composition of claim 1 , wherein the composition exhibits a refractive index of at least about 1.60.

16. The composition of claim 1 , wherein the composition exhibits a refractive index of at least about 1.61.

17. The composition of claim 1 , wherein the composition exhibits a refractive index of at least about 1.62.

18. The composition of claim 1 , wherein the composition exhibits a refractive index of at least about 1.63.

19. The composition of claim 1 , wherein the composition exhibits a refractive index of at least about 1.64.

20. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 130° C.

21. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 135° C.

22. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 140° C.

23. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 145° C.

24. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 150° C.

25. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 155° C.

26. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 160° C.

27. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 165° C.

28. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 170° C.

29. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 175° C.

30. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 180° C.

31. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 185° C.

32. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 133° C.; and wherein the composition exhibits a refractive index of at least about 1.59.

33. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 140° C.; and wherein the composition exhibits a refractive index of at least about 1.59.

34. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 150° C.; and wherein the composition exhibits a refractive index of at least about 1.60.

35. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 160° C.; and wherein the composition exhibits a refractive index of at least about 1.61.

36. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 170° C.; and wherein the composition exhibits a refractive index of at least about 1.62.

37. The composition of claim 1 , wherein the composition exhibits a hydrolytic stability with substantially the same weigh average molecular weight retention than that of a reference polycarbonate composition when the hydrolytic stability is determined in a hydrolytic aging chamber for 1000 hours at temperature of about 85° C. with a relative humidity of about 85%.

38. The composition of claim 1 , wherein the composition exhibits a hydrolytic stability with at least 10% greater weight average molecular weight retention than that of a reference polycarbonate composition when the hydrolytic stability is determined in a hydrolytic aging chamber for 1000 hours at temperature of about 85° C. with a relative humidity of about 85%, wherein the reference polycarbonate composition comprises a PPPBP/BPA copolycarbonate comprising 33% PPPBP.

39. The composition of claim 1 , wherein the composition exhibits a hydrolytic stability with at least 25% greater weight average molecular weight retention than that of a reference polycarbonate composition when the hydrolytic stability is determined in a hydrolytic aging chamber for 1000 hours at temperature of about 85° C. with a relative humidity of about 85%, wherein the reference polycarbonate composition comprises a PPPBP/BPA copolycarbonate comprising 33% PPPBP.

40. The composition of claim 37 , wherein the reference polycarbonate composition comprises XHT.

41. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 130° C., a refractive index of at least about 1.59, and a hydrolytic stability with substantially the same weight average molecular weight retention than that of a reference polycarbonate composition when the hydrolytic stability is determined in a hydrolytic aging chamber, wherein the reference polycarbonate composition comprises a PPPBP/BPA copolycarbonate comprising 33% PPPBP.

42. The composition of claim 1 , wherein the composition exhibits a glass transition temperature of at least about 170° C., a refractive index of at least about 1.62, and a hydrolytic stability with at least 10% greater weight average molecular weight retention than that of a reference XHT polycarbonate composition when the hydrolytic stability is determined in a hydrolytic aging chamber, wherein the reference polycarbonate composition comprises a PPPBP/BPA copolycarbonate comprising 33% PPPBP.

43. The composition of claim 1 , wherein the composition has respective molar ratios of about 10 mol % to about 75 mol % of carbonate units (a); and about 10 mol % to about 90 mol % of sulfone units (b); wherein the mol % of carbonate units (a) and sulfone units (b) combined is 100 mol %.

44. A polycarbonate copolymer composition comprising:

(a) monomeric units comprising a carbonate unit derived from a first aromatic dihydroxy compound, wherein the carbonate unit comprises the formula:

wherein Ra and Rb each represent a halogen atom or a monovalent hydrocarbon group and can be the same or different; p and q are each independently integers of 0 to 4, R3 is each independently a C1-6 alkyl group, j is 0 to 4, and R4 is a C1-6 alkyl, phenyl, or phenyl substituted with up to five C1-6 alkyl groups; and

(b) monomeric sulfone units comprising the formula

wherein m is 4-7, and

the composition further comprising monomeric units (c) comprising a carbonate unit derived from a second aromatic dihydroxy compound, and

wherein the composition has respective molar ratios of about 10 mol % to about 75 mol % of carbonate units (a); about 10 mol % to about 90 mol % of sulfone units (b); and about 10 mol % to about 75 mol % of carbonate units (c), wherein the mol % of a carbonate units (a), sulfone units (b), and carbonate units (c) combined is 100 mol %.

45. A polycarbonate copolymer composition comprising:

(a) monomeric units comprising a carbonate unit derived from a first aromatic dihydroxy compound, wherein the carbonate unit comprises the formula:

wherein Ra and Rb each represent a halogen atom or a monovalent hydrocarbon group and can be the same or different; p and q are each independently integers of 0 to 4, R3 is each independently a C1-6 alkyl group, j is 0 to 4, and R4 is a C1-6 alkyl, phenyl, or phenyl substituted with up to five C1-6 alkyl groups; and

(b) monomeric sulfone units comprising the formula

wherein m is from 4-7

the composition further comprising monomeric units (c) comprising a carbonate unit derived from a second aromatic dihydroxy compound, and

the composition further comprising monomeric units (c) comprising a carbonate unit derived from a second aromatic dihydroxy compound, and

wherein the carbonate unit of (a) comprises PPPBP, and

wherein the composition has respective molar ratios of about 10 mol % to about 75 mol % of carbonate units (a); about 10 mol % to about 90 mol % of sulfone units (b); about 10 mol % to about 75 mol % of carbonate units (c); and about 1 mol % to about 25 mol % of ester units, wherein the mol % of carbonate units (a), sulfone units (b), carbonate units (c) and ester units combined is 100 mol %.

46. The composition of claim 1 , wherein the carbonate unit (a) is present in the composition as a total amount from about 10 mol % to about 80 mol %, wherein the mol % of carbonate units (a), and sulfone units (b) combined is 100 mol %.

47. The composition of claim 1 , wherein the sulfone unit (b) is present in the composition as a total amount from about 10 mol % to about 90 mol % wherein the mol % of carbonate units (a), and sulfone units (b) combined is 100 mol %.

48. The composition of claim 2 , wherein the carbonate unit (a) is present in the composition as a total amount from about 10 mol % to about 80 mol % wherein the mol % of carbonate units (a), sulfone units (b), carbonate units (c), and ester units combined is 100 mol %.

49. The composition of claim 6 , wherein the ester unit is present in the composition as a total amount from about 1 mol % to about 25 mol % wherein the mol % of carbonate units (a), sulfone units (b), carbonate units (c), and ester units combined is 100 mol %.

50. The composition of claim 1 , wherein the composition further comprises at least one additive selected from thermal stabilizers, antioxidants, UV stabilizers, plasticizers, visual effect enhancers, extenders, antistatic agents, catalyst quenchers, mold releasing agents, fire retardants, blowing agents, impact modifiers and processing aids.

51. An article of manufacture formed from the composition of claim 1 .

52. The article of claim 51 , wherein the article is an extruded film or sheet.

53. The article of claim 51 , wherein the article is injection molded.

54. The article of claim 51 , wherein the article is a component for an electronic, imaging, or optical device.

55. The article of claim 52 , wherein the device is selected from a mobile phone, a mobile computing device, a camera, a video recorder, a projector, corrective lenses, a diffuser, or a copier.

56. A polycarbonate copolymer composition comprising:

(a) a carbonate unit comprising 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine (PPPBP);

(b) a sulfone unit comprising a compound having the formula:

wherein m is 4 to 7; and

(c) a carbonate unit comprising bisphenol A.

57. The composition of claim 56 , wherein the carbonate unit (c) further comprises a C6-C44 aliphatic dicarboxylic acid ester unit.

Assignments (6)
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 →
CORRECTIVE ASSIGNMENT TO CORRECT THE 12/116841, 12/123274, 12/345155, 13/177651, 13/234682, 13/259855, 13/355684, 13/904372, 13/956615, 14/146802, 62/011336 PREVIOUSLY RECORDED ON REEL 033591 FRAME 0673. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Aug 29, 2014
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 033663/0427 →
CORRECTIVE ASSIGNMENT TO CORRECT REMOVE 10 APPL. NUMBERS PREVIOUSLY RECORDED AT REEL: 033591 FRAME: 0673. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Aug 28, 2014
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 033649/0529 →
CHANGE OF NAME Recorded Aug 22, 2014
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 033591/0673 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2013
From: RAI, ROOPALI; HOEKS, THEO; PAL, JAYKISOR; GADGOLI, UMESH BALKRISHNA; NAIK, SHANTARAM NARAYAN; SANTHANAM, SUBRAMANYAM; HEGDE, SHWETA; RAMALINGAM, HARIHARAN
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 030813/0327 →