Granted Patent B2

US 8,759,428 · App. 11/843,076 · Granted Jun 24, 2014

Abstract

Claims (57)

1. A polycarbonate composition, comprising:

a polycarbonate resin;

an ultraviolet absorber selected from the group consisting of 1,3-bis-[(2′-cyano-3′,3′-diphenylacryloyl)oxy]-2,2-bis-{[(2′-cyano-3′,3′-diphenylacryloyl)oxy]methyl}-propane and tetraethyl-2,2′-(1,4-phenylene-dimethylidene)-bismalonate; and

a dye of Formula (I):

wherein R 4 and R 5 are either:

(i) independently selected from the group consisting of an aliphatic radical having 1 to 12 carbon atoms, an aromatic radical having 3 to 20 carbon atoms, a cycloaliphatic radical having 3 to 12 carbon atoms, a cyano group, a nitro group, a halo group, and a —OR 7 group, wherein R 7 is selected from the group consisting of hydrogen, an aliphatic radical having 1 to 12 carbon atoms, an aromatic radical having 3 to 20 carbon atoms, and a cycloaliphatic radical having 3 to 12 carbon atoms; or

(ii) together represent an aromatic radical having 3 to 12 carbon atoms, a heteroaromatic radical having 3 to 12 carbon atoms, or a pyranone radical of the formula

R 1 and R 8 are independently selected from —O— or —NR 6 —;

R 2 and R 9 are independently selected from the group consisting of an aromatic radical having 3 to 30 carbon atoms, and a cycloaliphatic radical having 3 to 12 carbon atoms;

R 3 and R 10 are independently selected from hydrogen or a labile group with the proviso that R 3 is not a group selected from the group consisting of —CH 2 —(CH 2 ) n —CH 3 and —CH 2 —C 6 H 5 wherein n has a value 0, 1, or 2; and

R 6 is selected from the group consisting of hydrogen, an aliphatic radical having 1 to 12 carbon atoms, an aromatic radical having 3 to 20 carbon atoms, and a cycloaliphatic radical having 3 to 12 carbon atoms.

2. The composition of claim 1 , wherein the dye is selected from the group consisting of BP-3-HF, having the formula:

and

D-3-HF, having the formula:

3. The composition of claim 1 , wherein the dye is D-3-HF, having the formula:

4. The composition of claim 1 , wherein the dye is BP-3-HF, having the formula:

5. The composition of claim 1 , wherein the ultraviolet absorber is present in the amount of from about 0.1 phr to about 5.0 phr and the dye is present in the amount of from about 0.001 phr to about 0.05 phr.

6. The composition of claim 4 , wherein the ultraviolet absorber is 1,3-bis-[(2′-cyano-3′,3′-diphenylacryloyl)oxy]-2,2-bis-{[(2′-cyano-3′,3′-diphenylacryloyl)oxy]methyl}-propane.

7. The composition of claim 2 , wherein the ultraviolet absorber is present in the amount of from about 0.1 phr to about 5.0 phr and the dye is present in the amount of from about 0.001 phr to about 0.05 phr.

8. The composition of claim 1 , wherein a 0.125 inch plaque of the composition has an initial fluorescence emission intensity of 10 6 or greater.

9. The composition of claim 1 , wherein the composition has a total color shift dE* of about 1.2 or less after 100 hours exposure, according to a modified ASTM D4459.

10. The composition of claim 1 , wherein the composition has a total color shift dE* of about 1.2 or less after 300 hours exposure, according to ASTM G26.

11. The composition of claim 1 , wherein the composition has an initial fluorescence emission intensity of 10 6 or greater, and a total color shift dE* of about 1.2 or less after 300 hours exposure according to ASTM G26.

12. The composition of claim 1 , wherein the polycarbonate resin is a homopolymer.

13. The composition of claim 1 , wherein the polycarbonate resin is a blend of polycarbonate homopolymers.

14. The composition of claim 1 , wherein the composition has a light transmittance of 10% or greater at a thickness of 3.2 mm, according to ASTM D1003.

15. The composition of claim 1 , wherein the composition has a haze of 5% or less at a thickness of 3.2 mm, according to ASTM D1003.

16. The composition of claim 8 , wherein the composition has a total color shift dE* of about 1.2 or less after 100 hours exposure, according to a modified ASTM D4459.

17. The composition of claim 8 , wherein the composition has a total color shift dE* of about 1.2 or less after 300 hours exposure, according to ASTM G26.

18. A polycarbonate composition, comprising:

a polycarbonate resin;

an ultraviolet absorber selected from the group consisting of 1,3-bis-[(2′-cyano-3′,3′-diphenylacryloyl)oxy]-2,2-bis-{[(2′-cyano-3′,3′-diphenylacryloyl)oxy]methyl}-propane and tetraethyl-2,2′-(1,4-phenylene-dimethylidene)-bismalonate; and

a dye selected from the group consisting of BP-3-HF and D-3-HF:

wherein the composition has a total color shift dE* of about 1.2 or less after 300 hours exposure, according to ASTM G26; and

wherein a 0.125 inch plaque of the composition has an initial fluorescence emission intensity greater than 10 6 .

19. The composition of claim 18 , wherein the ultraviolet absorber is 1,3-bis-[(2′-cyano-3′,3′-diphenylacryloyl)oxy]-2,2-bis-{[(2′-cyano-3′,3′-diphenylacryloyl)oxy]methyl}-propane.

20. The composition of claim 19 , wherein the ultraviolet absorber is present in the amount of from about 0.1 phr to about 5.0 phr.

21. The composition of claim 18 , wherein the dye is BP-3-HF.

22. The composition of claim 19 , wherein the due is BP-3-HF.

23. The composition of claim 22 , wherein the ultraviolet absorber is present in the amount of from about 0.1 phr to about 5.0 phr.

24. A method of causing a fluorescent light emission, comprising exposing to ultraviolet light a polycarbonate composition, comprising:

a polycarbonate resin;

an ultraviolet absorber selected from the group consisting of 1,3-bis-[(2′-cyano-3′,3′-diphenylacryloyl)oxy]-2,2-bis-{[(2′-cyano-3′,3′-diphenylacryloyl)oxy]methyl}-propane and tetraethyl-2,2′-(1,4-phenylene-dimethylidene)-bismalonate; and

a dye of Formula (I):

wherein R 4 and R 5 are either:

(i) independently selected from the group consisting of an aliphatic radical having 1 to 12 carbon atoms, an aromatic radical having 3 to 20 carbon atoms, a cycloaliphatic radical having 3 to 12 carbon atoms, a cyano group, a nitro group, a halo group, and a —OR 7 group, wherein R 7 is selected from the group consisting of hydrogen, an aliphatic radical having 1 to 12 carbon atoms, an aromatic radical having 3 to 20 carbon atoms, and a cycloaliphatic radical having 3 to 12 carbon atoms; or

(ii) together represent an aromatic radical having 3 to 12 carbon atoms, a heteroaromatic radical having 3 to 12 carbon atoms, or a pyranone radical of the formula

R 1 and R 8 are independently selected from —O— or —NR 6 —;

R 2 and R 9 are independently selected from the group consisting of an aromatic radical having 3 to 30 carbon atoms, and a cycloaliphatic radical having 3 to 12 carbon atoms;

R 3 and R 10 are independently selected from hydrogen or a labile group with the proviso that R 3 is not a group selected from the group consisting of —CH 2 —(CH 2 ) n —CH 3 and —CH 2 —C 6 H 5 wherein n has a value 0, 1,or 2; and

R 6 is selected from the group consisting of hydrogen, an aliphatic radical having 1 to 12 carbon atoms, an aromatic radical having 3 to 20 carbon atoms, and a cycloaliphatic radical having 3 to 12 carbon atoms.

25. The method of claim 24 , wherein the dye is selected from the group consisting of BP-3-HF and D-3-HF:

26. The method of claim 25 , wherein the dye is BP-3.

27. The method of claim 25 , wherein the ultraviolet absorber is 1,3-bis-[(2′-cyano-3′,3′-diphenylacryloyl)oxy]-2,2-bis-{[(2′-cyano-3′,3′-diphenylacryloyl)oxy]methyl}-propane.

28. The method of claim 26 , wherein the ultraviolet absorber is 1,3-bis-[(2′-cyano-3′,3′-diphenylacryloyl)oxy]-2,2-bis-{[(2′-cyano-3′,3′-diphenylacryloyl)oxy]methyl}-propane.

29. The method of claim 25 , wherein the ultraviolet absorber is present in the amount of from about 0.1 phr to about 5.0 phr.

30. The method of claim 25 , wherein the ultraviolet absorber is tetraethyl-2,2′-(1,4-phenylene-dimethylidene)-bismalonate.

Assignments (6)