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

1. A poly(ester-carbonate) 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) a bisphenol A divalent group of the formula

 and

(b) a C 16 or higher divalent group (b) 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,

X a is a C 6-12 polycyclic aryl, C 3-18 mono- or polycycloalkylene, C 3-18 mono- or polycycloalkylidene, a -(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, and

m and n are each independently 0 to 4;

provided that

the C 16 or higher divalent group (b) is present in an amount of 40 mol % to 50 mol % based on the total moles of the bisphenol A divalent groups and the C 16 or higher divalent groups;

the ester units are present in an amount of 40 mol % to 60 mol % based on the sum of the moles of the carbonate units and the ester units; and

wherein

the poly(ester-carbonate) copolymer has a weight average molecular weight of 18,000 Daltons to 24,000 Daltons, as measured by gel permeation chromatography, using a crosslinked styrene-divinylbenzene column and calibrated to bisphenol A homopolycarbonate references; and

a sample of the composition has

a glass transition temperature of 210° C. to 235° C. as determined by differential scanning calorimetry (DSC) as per ASTM D3418 with a 20° C./min heating rate; and

a melt viscosity of less than 1050 Pa·s at 644 sec −1 and 350° C., determined according to ISO11443.

2. The poly(ester-carbonate) copolymer of claim 1 , having one or more of the following properties:

a shift in melt viscosity of less than 25% at 350° C. 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;

a glass transition temperature of 220° C. to 235° C. as determined by differential scanning calorimetry (DSC) as per ASTM D3418 with a 20° C./min heating rate;

a Vicat B120 of 220 to 225° C., measured according to ISO 306;

a melt viscosity of less than 1000 Pa·s at 644 sec −1 and 350° C., determined according to ISO11443; or

a yellowness index of less than 18 determined in accordance with ASTM D1925.

3. The poly(ester-carbonate) copolymer of claim 1 , wherein

R 1 and J are each independently the bisphenol A divalent group or the C 16 or higher divalent group; and

at least a portion of the J groups are the C 16 or higher divalent group.

4. The poly(ester-carbonate) copolymer of claim 1 , wherein greater than 20 mol % and less than 35 mol % of the J groups are the C 16 or higher group based on the total moles of the J groups.

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

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

7. The poly(ester-carbonate) copolymer of claim 1 , wherein the C 16 or higher divalent group has the formula:

wherein

R c and R d are each independently C 1-3 alkyl or phenyl,

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

m and n are each independently 0 to 4,

each R 3 is independently C 1-4 alkyl or hydrogen, and

g is 0 to 10.

8. The poly(ester-carbonate) copolymer of claim 1 , wherein the C 16 or higher divalent group is derived from 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethyl-cyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, or a combination thereof.

9. A thermoplastic composition comprising the poly(ester-carbonate) copolymer of claim 1 .

10. The thermoplastic composition of claim 9 , further comprising a polycarbonate homopolymer, a second poly(ester-carbonate) different from the poly(ester-carbonate) copolymer, a copolycarbonate, or a combination comprising at least one of the foregoing.

11. The thermoplastic composition of claim 9 , wherein the composition has a haze of less than 15% and a transmission greater than 75%, each measured in accordance with ASTM D1003 using the color space CIE1931 (Illuminant C and a 2° observer) at a 3.2 mm thickness.

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

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

14. The poly(ester-carbonate) copolymer of claim 1 , wherein the poly(ester-carbonate) copolymer at a given temperature has a melt viscosity of less than 1050 Pa·s at 644 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.

15. The poly(ester-carbonate) copolymer of claim 1 , wherein the copolymer has a melt flow rate of 10 to 30 cm 3 /10 minutes measured at 330° C. under a load of 2.16 kg in accordance with ASTM D1238-04.

16. An article comprising the copolymer of claim 1 , 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, or a substrate for a metallized article.

17. The article of claim 16 , wherein the article is a metallized article comprising the copolymer, wherein the defect onset temperature of the metallized article is within 10° C. of the heat deflection temperature of the copolymer measured flat on a 80×10×4 mm bar with a 64 mm span at 0.45 MPa according to ISO 75/Bf.

18. The article of claim 17 , comprising

a substrate comprising the copolymer; and

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

19. The article of claim 18 , further comprising a protective layer disposed on the metal layer.

20. A method for the manufacture of the poly(ester-carbonate) copolymer of claim 1 , the method comprising:

providing a slurry comprising water, a water-immiscible organic solvent, a phase transfer catalyst, and bisphenol A;

co-feeding to the slurry a solution comprising aqueous NaOH or aqueous KOH, an aromatic dicarboxylic halide of the formula

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

a dihydroxy compound of the formula

or a combination comprising at least one of the foregoing, 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

to provide a polyester oligomer; and

reacting the polyester oligomer with a carbonate source to provide the poly(ester-carbonate).