Color-stable thermoplastic composition
View Patent ↗A thermoplastic composition is disclosed that includes a polyaryl ester polymer or copolymer and a phthalone compound according to the formula wherein Z 1 represents the atoms necessary to complete a 9- to 13-membered single or fused aromatic ring structure, Z 2 represents the atoms necessary to complete a pyridine or quinoline ring, each R 1 and each R 2 can independently be halogen, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an aromatic or aliphatic thioether group, an aromatic or aliphatic carboxylic acid ester group, or an aromatic or aliphatic amide group, a is an integer from 0 to 6, b is an integer from 0 to 4, n is 1 or 2, and X is present only if n=2 and is a single bond or a divalent organic radical bonded to the Z 1 ring structure through an ether, ketone, or thio linkage.
1. A thermoplastic composition comprising a polyaryl ester polymer or copolymer and
a compound comprising a phthalone ring structure selected from:
a compound according to the formula:
wherein R 1.1 , R 1.2 , R 1.3 , R 1.4 , R 2.1 , R 2.2 , R 2.3 , and R 2.4 are each independently hydrogen, halogen, a C 1 -C 18 alkyl group, a C 6 -C 12 aryl group, a C 1 -C 18 alkoxy group, or a C 6 -C 12 aryloxy group, n is 2, and X is a single bond or a divalent organic radical bonded to the phthalone ring structure through an ether, ketone, or thio linkage and is present in place of one of R 1.1 , R 1.2 , R 1.3 , or R 1.4 , or
a compound according to the formula
wherein R 1.1 , R 1.2 , R 1.3 , R 1.4 , R 1.5 , R 1.6 , R 2.1 , R 2.2 , R 2.3 , and R 2.4 are each independently hydrogen, halogen, a C 1 -C 18 alkyl group, a C 6 -C 12 aryl group, a C 1 -C 18 alkoxy group, or a C 6 -C 12 aryloxy group, n is 2, and X is a single bond or a divalent organic radical bonded to the phthalone ring structure through an ether, ketone, or thio linkage and is present in place of one of R 1.1 , R 1.2 , R 1.3 , R 1.4 , R 1.5 , or R 1.6 .
2. The thermoplastic composition of claim 1 , wherein a 35 μm thick film of the thermoplastic composition exhibits a change in ΔE value of the CIE1976 L*, a*, b* color measurement system as specified by ISO 11664-4:2008(E)/CIE S 014-4/ E:2007, measured according to ASTM D2244-11, of less than or equal to 1.0 after 252 kJ/m 2 of exposure according to accelerated weathering testing protocol of ASTM G-155-05a.
3. The thermoplastic composition of claim 2 , wherein the thermoplastic composition exhibits a ΔE color difference value of less than or equal to 0.7 after 252 kJ/m 2 of exposure.
4. The thermoplastic composition of claim 2 , wherein the thermoplastic composition exhibits a change in ΔE value of less than or equal to 0.5 after 252 kJ/m 2 of exposure.
5. The thermoplastic composition of claim 1 , wherein the thermoplastic composition exhibits CIE1976 L*, a*, b* values determined according to ASTM D2244-11 of an L* value of greater than 60, an a* value of greater than or equal to −1, and a b* value of less than or equal to 1.
6. The thermoplastic composition of claim 1 , wherein the thermoplastic composition exhibits CIE1976 L*, a*, b* values determined according to ASTM D2244-11 of an L* value of greater than 65, an a* value of greater than or equal to −1, and a b* value of less than or equal to 0.5.
7. The thermoplastic composition of claim 1 , wherein the compound has a decomposition onset temperature, T d , of at least 250° C., as determined according to ASTM E2550-11.
8. The thermoplastic composition of claim 2 , wherein the compound has a decomposition onset temperature, T d , of at least 250° C., as determined according to ASTM E2550-11.
9. The thermoplastic composition of claim 1 , wherein the compound has a decomposition onset temperature, T d , of at least 270° C., as determined according to ASTM E2550-11.
10. The thermoplastic composition of claim 1 , comprising the compound according to the formula:
wherein
R 1.1 , R 1.2 , R 1.3 , R 1.4 , R 2.1 , R 2.2 , R 2.3 , and R 2.4 are each independently hydrogen, halogen, a C 1 -C 18 alkyl group, a C 6 -C 12 aryl group, a C 1 -C 18 alkoxy group, or a C 6 -C 12 aryloxy group, n is 2, and X is a single bond or a divalent organic radical bonded to the phthalone ring structure through an ether, ketone, or thio linkage and is present in place of one of R 1.1 , R 1.2 ,R 1.3 or R 1.4 .
11. The thermoplastic composition of claim 1 , comprising the compound according to the formula:
wherein
R 1.1 , R 1.2 , R 1.3 , R 1.4 , R 1.5 , R 1.6 , R 2.1 , R 2.2 , R 2.3 , and R 2.4 are each independently hydrogen, halogen, a C 1 -C 18 alkyl group, a C 6 -C 12 aryl group, a C 1 -C 18 alkoxy group, or a C 6 -C 12 aryloxy group, n is 2, and X is a single bond or a divalent organic radical bonded to the phthalone ring structure through an ether, ketone, or thio linkage and is present in place of one of R 1.1 , R 1.2 , R 1.3 , R 1.4 , R 1.5 , or R 1.6 .
12. The thermoplastic composition of claim 1 , wherein Z 2 represents the atoms necessary to complete a quinoline ring.
13. The thermoplastic composition of claim 1 , comprising at least 0.0001 wt. % and less than 0.1 wt. % of the compound, based on the total weight of the polyaryl ester polymer or copolymer.
14. The thermoplastic composition of claim 1 , comprising at least 0.01 wt. % of the compound, based on the total weight of the polyaryl ester polymer or copolymer.
15. The thermoplastic composition of claim 1 , comprising from 0.02 wt. % to 0.03 wt. % of the compound, based on the total weight of the polyaryl ester polymer or copolymer.
16. The thermoplastic composition of claim 1 , further comprising a blue colorant to balance the color of the compound.
17. The thermoplastic composition of claim 1 , wherein the polyaryl ester polymer or copolymer is a polyaryl ester-polycarbonate copolymer.
18. The thermoplastic composition of claim 1 , wherein the polyaryl ester polymer or copolymer is a copolymer of a polyaryl ester derived from resorcinol and a mixture of isophthalic acid or anhydride, terephthalic acid or anhydride, and resorcinol, and a polycarbonate derived from bisphenol A and a carbonate source.
19. The thermoplastic composition of claim 1 , wherein the polyaryl ester polymer or copolymer comprises at least 5 weight percent, based on the weight of the polyaryl ester polymer or copolymer, of repeating units of the formula:
in which at least 80 percent of the total number of T groups, and/or at least 80 percent of the total J groups contain aromatic moieties and the balance thereof are aliphatic, alicyclic, or aromatic.
20. The thermoplastic composition of claim 19 , wherein the at least 80 percent of the total number of T groups containing aromatic moieties are derived from isophthalic acid and/or terephthalic acid.
21. The thermoplastic composition of claim 19 , wherein at least 90 percent of the total number of T groups contain aromatic moieties derived from isophthalic acid and/or terephthalic acid.
22. The thermoplastic composition of claim 19 , wherein at least 80 percent of the total number of J groups contain aromatic moieties derived from resorcinol and the balance thereof are aliphatic, alicyclic, or aromatic.
23. The thermoplastic composition of claim 1 , wherein all of the repeat units of the polyaryl ester polymer or copolymer are represented by the formula:
in which at least 90 percent of the total number of T groups, and/or at least 90 percent of the total J groups contain aromatic moieties and the balance thereof are aliphatic, alicyclic, or aromatic.
24. The thermoplastic composition of claim 23 , wherein at least 90 percent of the total number of T groups contain aromatic moieties derived from isophthalic acid and/or terephthalic acid.
25. The thermoplastic composition of claim 1 , wherein the polyaryl ester polymer or copolymer comprises:
from 5 wt. % to 30 wt. % of ester repeat units represented by the formula:
in which at least 90 percent of the total number of T groups, and/or at least 90 percent of the total J groups contain aromatic moieties and the balance thereof are aliphatic, alicyclic, or aromatic; and
from 70 wt.% to 95 wt.% of carbonate repeat units represented by the formula:
in which at least 60 percent of the total number of R 1 groups contain aromatic moieties and the balance thereof are aliphatic, alicyclic, or aromatic;
wherein the weight percentages are based on the weight of the thermoplastic composition and with the proviso that the sum of wt. % of the ester repeat units and the wt. % of the carbonate repeat units is 100.
26. The thermoplastic composition of claim 25 , wherein least 90 percent of the total number of T groups contain aromatic moieties derived from isophthalic acid and/or terephthalic acid.
27. The thermoplastic composition of claim 25 , wherein all of the R 1 groups contain aromatic moieties.
28. The thermoplastic composition of claim 25 , wherein all of the R 1 groups are derived from bisphenol A and/or resorcinol.
29. The thermoplastic composition of claim 25 , wherein the T groups are derived from isophthalic acid and/or terephthalic acid, the J groups are derived from resorcinol, and the R 1 groups are derived from bisphenol A.
30. The thermoplastic composition of claim 1 , that is free of dyes with thermal stability less than 270° C. and/or UV-VIS absorption more than 450 nm that exhibit photobleachable absorbance of light in the 400-450 nm range.
31. The thermoplastic composition of claim 1 , wherein the compound exhibits photobleachable absorbance of light in the 400-450 nm range and the polyaryl ester polymer or copolymer exhibits photoyellowing in the 400-450 nm range.
32. A formed plastic article comprising the thermoplastic composition of claim 1 .
33. The plastic article of claim 32 , wherein the article is an electronic display window, an illuminant lens or cover, or an opaque automotive component.
34. A method of making a plastic article, comprising heating the composition of claim 1 to a melt temperature of at least 250° C., and extruding or molding the plastic article.
35. The method of claim 34 , wherein the melt temperature is at least 280° C.
36. The method of claim 34 , wherein the melt temperature is at least 290° C.
37. A plastic article prepared by the method of claim 34 .
38. The plastic article of claim 32 , wherein the plastic article is an LED light cover.
39. The thermoplastic composition of claim 1 , wherein the polyaryl ester copolymer is derived from resorcinol and a mixture of isophthalic acid or anhydride, terephthalic acid or anhydride, and resorcinol, and a polycarbonate derived from bisphenol A and a carbonate source polyaryl ester.
40. The plastic article of claim 32 , wherein:
the article has a thickness of 0.035-0.49 mm and thermoplastic composition comprises at least 0.001 wt. % and less than 0.1 wt. % of the compound;
the article has a thickness of 0.5-1.49 mm and thermoplastic composition comprises at least 0.0001 wt. % and less than 0.1 wt. % of the compound;
the article has a thickness of 1.5-2.49 mm and thermoplastic composition comprises at least 0.0001 wt. % and less than 0.1 wt. % of the compound; or
the article has a thickness of 2.5-3 mm and thermoplastic composition comprises at least 0.0001 wt. % and less than 0.1 wt. % of the compound.