IP Library Granted Patent US 10,899,877
Granted Patent B2
US 10,899,877 · App. 16/095,755 · Granted Jan 26, 2021

Poly(ester-carbonate)s, articles formed therefrom, and methods of manufacture

Inventors: Paul Dean Sybert (Evansville, IN); Tony Farrell (Bergen op Zoom, NL); Rob Boonman (Oosterhout, NL); Robert Dirk Van De Grampel (Tholen, NL); Mark Adrianus Johannes Van Der Mee (Breda, NL)
Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
C08G63/64C08L69/005C08L2201/08C08L2205/025C08L2207/04
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Quick Facts
Patent No.
US 10,899,877
App. No.
16/095,755
Granted
Jan 26, 2021
Kind
B2
Abstract

A poly(carbonate-ester) copolymer including carbonate units of the formula (I); and ester units of the formula (II) wherein: T is a C 2-20 alkylene, a C 6-20 cycloalkylene, or a C 6-20 arylene; and R 1 and J are each independently a bisphenol A divalent group, or a phthalimidine divalent group or a third divalent group of the formula (III), (IV), (V), (VI) or (VII) wherein X a is a C 6-12 polycyclic aryl, C 3-18 mono- or polycycloalkylene, C 3-18 mono- or polycycloalkylidene, -(Q 1 )x-G-(Q 2 ) y - group wherein Q 1 and Q 2 are each independently a C 1-3 alkylene, G is a C 3-10 cycloalkylene, x is 0 or 1, and y is 1, provided that the at least one bisphenol A divalent group, at least one phthalimidine divalent group, and at least one third divalent group are present in the poly(carbonate-ester) copolymer.

Claims (57)

1. A poly(carbonate-ester) copolymer comprising

carbonate units of the formula

and

ester units of the formula

wherein:

T is a C 2-20 alkylene, a C 6-20 cycloalkylene, or a C 6-20 arylene; and

R 1 and J are each independently a bisphenol A divalent group of the formula

or a phthalimidine divalent group of the formula

wherein

R a and R b are each independently a C 1-12 alkyl, C 2-12 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy,

each R 3 is independently a C 1-6 alkyl,

R 4 is hydrogen, C 1-6 alkyl or phenyl optionally substituted with 1 to 5 C 1-6 alkyl groups,

p, q, and j are each independently 0 to 4,

or a third divalent group of the formula

wherein R c and R d are each independently a C 1-12 alkyl, C 2-12 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy,

each R 6 is independently C 1-3 alkyl or phenyl,

and

m and n are each independently 0 to 4,

provided that the at least one bisphenol A divalent group, at least one phthalimidine divalent group, and at least one third divalent group are present in the poly(carbonate-ester) copolymer.

2. The poly(carbonate-ester) copolymer of claim 1 , wherein T is a C 6-20 divalent aromatic radical.

3. The poly(carbonate-ester) copolymer of claim 1 , wherein T is a divalent isophthaloyl radical, a divalent terephthaloyl radical, or a combination thereof.

4. The poly(carbonate-ester) copolymer of claim 1 , wherein the molar ratio of the carbonate units relative to the ester units is 2:1 to 1:2.

5. The poly(carbonate-ester) copolymer of claim 1 , wherein p, q, and j are zero, and R 4 is hydrogen, methyl, or phenyl.

6. The A poly(carbonate-ester) copolymer comprising:

carbonate units of the formula

and

ester units of the formula

wherein:

T is a C 2-20 alkylene, a C 6-20 cycloalkylene, or a C 6-20 arylene; and

R 1 and J are each independently a bisphenol A divalent group of the formula

or a phthalimidine divalent group of the formula

wherein

R a and R b are each independently a C 1-12 alkyl, C 2-12 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy,

each R 3 is independently a C 1-6 alkyl,

R 4 is hydrogen, C 1-6 alkyl or phenyl optionally substituted with 1 to 5 C 1-6 alkyl groups,

p, q, and j are each independently 0 to 4, or

a third divalent group has the structural formula

wherein

each R 1 is independently hydrogen or C 1-4 alkyl,

each R 2 is independently C 1-4 alkyl or hydrogen, and

g is 0 to 10,

provided that the at least one bisphenol A divalent group, at least one phthalimidine divalent group, and at least one third divalent group are present in the poly(carbonate-ester) copolymer.

7. The poly(carbonate-ester) copolymer of claim 6 , wherein R 1 is methyl or hydrogen, R 2 is methyl or ethyl, and g is 0 to 3.

8. The poly(carbonate-ester) copolymer of claim 1 , wherein the third divalent group is derived from 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethyl-cyclohexane.

9. The poly(carbonate-ester) copolymer of claim 1 , wherein the phthalimidine divalent group is present in an amount of 5 mol % to 30 mol % based on the sum of the moles of the bisphenol A divalent group, the phthalimidine divalent group, and the third divalent group.

10. The poly(carbonate-ester) copolymer of claim 1 , wherein third divalent group is present in an amount of 2 mol % to 50 mol % based on the sum of the moles of the bisphenol A divalent group, the phthalimidine divalent group, and the third divalent group.

11. The poly(carbonate-ester) copolymer of claim 1 , wherein the bisphenol A divalent group is present in an amount of 45 mol % to 70 mol % based on the sum of the moles of the bisphenol A divalent group, the phthalimidine divalent, and the third divalent group.

12. A thermoplastic composition comprising a poly(carbonate-ester) copolymer of claim 1 .

13. The thermoplastic composition of claim 12 further comprising a polycarbonate homopolymer, an additional poly(ester-carbonate), or a combination comprising at least one of the foregoing.

14. The poly(ester-carbonate) or the composition of claim 1 , wherein a metalized sample of the poly(ester-carbonate) or the composition has a defect onset temperature that is within 10 degrees Celsius of the heat deflection temperature of the poly(ester-carbonate) or composition measured flat on a 80×10×4 mm bar with a 64 mm span at 0.45 MPa according to ISO 75/Bf.

15. The poly(ester-carbonate) or the composition of claim 1 , wherein a metalized sample of the poly(ester-carbonate) or the composition has a defect onset temperature of 200 to 220° C.

16. The poly(ester-carbonate) or the composition of claim 1 , wherein the composition at a given temperature has a melt viscosity of less than 900 Pa·s at 644.5 sec −1 and has a shift in melt viscosity of less than 25% at the given temperature over 30 min under a nitrogen atmosphere as measured in a small amplitude oscillatory time sweep rheology at a fixed angular frequency of 10 radians/sec.

17. An article, wherein the article is a molded article, a thermoformed article, an extruded film, an extruded sheet, one or more layers of a multi-layer article, a substrate for a coated article, and a substrate for a metallized article made from the poly(ester-carbonate) or composition of claim 1 .

18. A metallized article comprising the poly(ester-carbonate) or composition of claim 1 wherein the defect onset temperature of the metallized article is within 10 degrees Celsius of the heat deflection temperature of the poly(ester-carbonate) or the composition measured in accordance with measured flat on a 80×10×4 mm bar with a 64 mm span at 0.45 MPa according to ISO 75/Bf.

19. A metallized article, comprising

a substrate comprising the poly(ester-carbonate) or composition of claim 1 ; and

a metal layer disposed on at least one side of the substrate.

Assignments (3)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2018
From: SYBERT, PAUL DEAN; FARRELL, TONY; BOONMAN, ROB; VAN DE GRAMPEL, ROBERT DIRK; VAN DER MEE, MARK ADRIANUS JOHANNES
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 047275/0927 →