Abstract

With the intention to produce dichroic filters for use in photoluminescent systems that rely on polarized UV light, we synthesized a number of linear, dichroic dyes, which absorb mainly in the near-UV range of the electromagnetic spectrum. These dyes were designed for compatibility with common thermoplastic polymers such as linear low-density poly(ethylene), poly(ethylene terephthalate), and polyamide-12. Films of these host polymers that consisted of 0.2% by weight of various dichroic UV dyes were produced by common melt-processing schemes. Uniaxial drawing of these films yielded highly dichroic UV filters with dichroic ratios in absorption that in some cases exceeded 100. The fact that these free-standing films display little or no coloration and are environmentally stable makes them useful for various applications that involve generation of polarized UV light.

© 2003 Optical Society of America

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References

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  2. J. Michl, E. W. Thulstrup, Spectroscopy with Polarized Light (VCH Publishers, New York, 1986).
  3. W. G. Driscoll, W. Vaughan, Handbook of Optics (McGraw-Hill, New York, 1987).
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    [CrossRef] [PubMed]
  6. W. A. Crossland, I. D. Springle, A. B. Davey, “Photoluminescent LCDs (PL-LCDs) using phosphors,” Proc. SID 28, 837–840 (1997).
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    [CrossRef]
  8. C. Weder, P. Smith, “Antifalsification paper and other antifalsification items,” international patent applicationWO 0 019 016 (6April2000).
  9. T. Bremi, J. Grob, K. Franken, A. Seyffert, C. Kocher, “Sicherheitsmerkmal für Wertdokumente,” international patent applicationPCT/CH03/00146 (19July2002).
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    [CrossRef]
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    [CrossRef]
  12. E. H. Land, H. G. Rogers, “Light polarizer,” U.S. patent2,173,304 (19September1939).
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    [CrossRef]
  14. A. R. A. Palmans, M. Eglin, A. Montali, C. Weder, “Tensile orientation behavior of alkoxy-substituted bis(phenylethynyl)benzene derivatives in polyolefin blend films,” Chem. Mater. 12, 472–480 (2000).
    [CrossRef]
  15. H. Zollinger, Azo and Diazo Chemistry (Interscience, New York, 1961).
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    [CrossRef]
  18. A. V. Ivashchenko, Dichroic Dyes for Liquid Crystal Displays (CRC Press, Boca Raton, Fla., 1994).
  19. Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers. 2. Ultimate properties,” Macromolecules 30, 2175–2177 (1997).
    [CrossRef]
  20. W. C. Yip, H. S. Kwok, V. M. Kozenkov, V. G. Chigrinov, “Photo-patterned e-wave polarizer,” Displays 22, 27–32 (2001).
    [CrossRef]
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  25. M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
    [CrossRef]
  26. P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
    [CrossRef]
  27. L. R. Whitlock, S. Siggia, J. E. Smola, “Spectrometric analysis of phenols and of sulfonates by formation of an azo dye,” Anal. Chem. 44, 532–536 (1972).
    [CrossRef]
  28. C. Kocher, P. Smith, C. Weder, “Aromatic 2-(2′-hydroxyphenyl)benzoxazole esters: a novel class of caged photoluminescent dyes,” J. Mater. Chem. 12, 2620–2626 (2002).
    [CrossRef]
  29. R. Willstätter, M. Benz, “Azophenols,” Justus Liebigs Ann. Chem. 39, 3492–3503 (1907).
  30. W. Wei, T. Tomohiro, M. Kodaka, H. Okuno, “Selective synthesis and kinetic measurement of 1:1 and 2:2 cyclic compounds containing 1,4,7,10-tetraazacyclododecane and azobenzene units,” J. Org. Chem. 65, 8979–8987 (2000).
    [CrossRef]
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2002 (2)

E. Beekman, C. Kocher, A. Kokil, S. Zimmermann, C. Weder, “UV polarizers based on oriented poly(vinylalcohol)-Chrysophenine-Congo Red blend films,” J. Appl. Polym. Sci. 86, 1235–1239 (2002).
[CrossRef]

C. Kocher, P. Smith, C. Weder, “Aromatic 2-(2′-hydroxyphenyl)benzoxazole esters: a novel class of caged photoluminescent dyes,” J. Mater. Chem. 12, 2620–2626 (2002).
[CrossRef]

2001 (1)

W. C. Yip, H. S. Kwok, V. M. Kozenkov, V. G. Chigrinov, “Photo-patterned e-wave polarizer,” Displays 22, 27–32 (2001).
[CrossRef]

2000 (2)

A. R. A. Palmans, M. Eglin, A. Montali, C. Weder, “Tensile orientation behavior of alkoxy-substituted bis(phenylethynyl)benzene derivatives in polyolefin blend films,” Chem. Mater. 12, 472–480 (2000).
[CrossRef]

W. Wei, T. Tomohiro, M. Kodaka, H. Okuno, “Selective synthesis and kinetic measurement of 1:1 and 2:2 cyclic compounds containing 1,4,7,10-tetraazacyclododecane and azobenzene units,” J. Org. Chem. 65, 8979–8987 (2000).
[CrossRef]

1999 (2)

M. Grell, D. C. D. Bradley, “Polarized luminescence from oriented molecular materials,” Adv. Mater. 11, 895–905 (1999).
[CrossRef]

M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
[CrossRef]

1998 (1)

C. Weder, C. Sarwa, A. Montali, C. Bastiaansen, P. Smith, “Incorporation of photoluminescent polarizers into liquid crystal displays,” Science 279, 835–837 (1998).
[CrossRef] [PubMed]

1997 (3)

W. A. Crossland, I. D. Springle, A. B. Davey, “Photoluminescent LCDs (PL-LCDs) using phosphors,” Proc. SID 28, 837–840 (1997).

P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
[CrossRef]

Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers. 2. Ultimate properties,” Macromolecules 30, 2175–2177 (1997).
[CrossRef]

1995 (1)

Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers,” Macromolecules 28, 486–491 (1995).
[CrossRef]

1993 (1)

S. Xie, A. Natansohn, P. Rochon, “Recent developments in aromatic azo polymer research,” Chem. Mater. 5, 403–411 (1993).
[CrossRef]

1991 (1)

P. Uznanski, M. Kryszewsky, E. W. Thulstrup, “Linear dichroism and trans-cis photoisomerization studies of azobenzene molecules in oriented polyethylene matrix,” Eur. Polym. J. 27, 41–43 (1991).
[CrossRef]

1972 (2)

J. Griffiths, “Photochemistry of azobenzenes and its derivatives,” Chem. Soc. Rev. 1, 481–493 (1972).
[CrossRef]

L. R. Whitlock, S. Siggia, J. E. Smola, “Spectrometric analysis of phenols and of sulfonates by formation of an azo dye,” Anal. Chem. 44, 532–536 (1972).
[CrossRef]

1962 (1)

1907 (1)

R. Willstätter, M. Benz, “Azophenols,” Justus Liebigs Ann. Chem. 39, 3492–3503 (1907).

Bastiaansen, C.

C. Weder, C. Sarwa, A. Montali, C. Bastiaansen, P. Smith, “Incorporation of photoluminescent polarizers into liquid crystal displays,” Science 279, 835–837 (1998).
[CrossRef] [PubMed]

Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers. 2. Ultimate properties,” Macromolecules 30, 2175–2177 (1997).
[CrossRef]

Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers,” Macromolecules 28, 486–491 (1995).
[CrossRef]

Beekman, E.

E. Beekman, C. Kocher, A. Kokil, S. Zimmermann, C. Weder, “UV polarizers based on oriented poly(vinylalcohol)-Chrysophenine-Congo Red blend films,” J. Appl. Polym. Sci. 86, 1235–1239 (2002).
[CrossRef]

Beltrame, P. L.

P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
[CrossRef]

Benz, M.

R. Willstätter, M. Benz, “Azophenols,” Justus Liebigs Ann. Chem. 39, 3492–3503 (1907).

Bergamasco, L.

P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
[CrossRef]

Bradley, D. C. D.

M. Grell, D. C. D. Bradley, “Polarized luminescence from oriented molecular materials,” Adv. Mater. 11, 895–905 (1999).
[CrossRef]

Bremi, T.

T. Bremi, J. Grob, K. Franken, A. Seyffert, C. Kocher, “Sicherheitsmerkmal für Wertdokumente,” international patent applicationPCT/CH03/00146 (19July2002).

Castelli, A.

P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
[CrossRef]

Chigrinov, V. G.

W. C. Yip, H. S. Kwok, V. M. Kozenkov, V. G. Chigrinov, “Photo-patterned e-wave polarizer,” Displays 22, 27–32 (2001).
[CrossRef]

Christie, R. M.

R. M. Christie, Colour Chemistry (Royal Society of Chemistry, Cambridge, 2001).

Crossland, W. A.

W. A. Crossland, I. D. Springle, A. B. Davey, “Photoluminescent LCDs (PL-LCDs) using phosphors,” Proc. SID 28, 837–840 (1997).

Davey, A. B.

W. A. Crossland, I. D. Springle, A. B. Davey, “Photoluminescent LCDs (PL-LCDs) using phosphors,” Proc. SID 28, 837–840 (1997).

Dirix, Y.

Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers. 2. Ultimate properties,” Macromolecules 30, 2175–2177 (1997).
[CrossRef]

Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers,” Macromolecules 28, 486–491 (1995).
[CrossRef]

Driscoll, W. G.

W. G. Driscoll, W. Vaughan, Handbook of Optics (McGraw-Hill, New York, 1987).

Dubini-Paglia, E.

P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
[CrossRef]

Eglin, M.

A. R. A. Palmans, M. Eglin, A. Montali, C. Weder, “Tensile orientation behavior of alkoxy-substituted bis(phenylethynyl)benzene derivatives in polyolefin blend films,” Chem. Mater. 12, 472–480 (2000).
[CrossRef]

M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
[CrossRef]

Franken, K.

T. Bremi, J. Grob, K. Franken, A. Seyffert, C. Kocher, “Sicherheitsmerkmal für Wertdokumente,” international patent applicationPCT/CH03/00146 (19July2002).

Green, F. J.

F. J. Green, The Sigma-Aldrich Handbook of Stains, Dyes and Indicators (Aldrich Chemical Company, Milwaukee, Wisc., 1990).

Grell, M.

M. Grell, D. C. D. Bradley, “Polarized luminescence from oriented molecular materials,” Adv. Mater. 11, 895–905 (1999).
[CrossRef]

Griffiths, J.

J. Griffiths, “Photochemistry of azobenzenes and its derivatives,” Chem. Soc. Rev. 1, 481–493 (1972).
[CrossRef]

Grob, J.

T. Bremi, J. Grob, K. Franken, A. Seyffert, C. Kocher, “Sicherheitsmerkmal für Wertdokumente,” international patent applicationPCT/CH03/00146 (19July2002).

Ivashchenko, A. V.

A. V. Ivashchenko, Dichroic Dyes for Liquid Crystal Displays (CRC Press, Boca Raton, Fla., 1994).

Kliger, D. S.

D. S. Kliger, J. W. Lewis, C. E. Randall, Polarized Light in Optics and Spectroscopy (Academic, San Diego, Calif., 1990).

Kocher, C.

E. Beekman, C. Kocher, A. Kokil, S. Zimmermann, C. Weder, “UV polarizers based on oriented poly(vinylalcohol)-Chrysophenine-Congo Red blend films,” J. Appl. Polym. Sci. 86, 1235–1239 (2002).
[CrossRef]

C. Kocher, P. Smith, C. Weder, “Aromatic 2-(2′-hydroxyphenyl)benzoxazole esters: a novel class of caged photoluminescent dyes,” J. Mater. Chem. 12, 2620–2626 (2002).
[CrossRef]

T. Bremi, J. Grob, K. Franken, A. Seyffert, C. Kocher, “Sicherheitsmerkmal für Wertdokumente,” international patent applicationPCT/CH03/00146 (19July2002).

C. Kocher, “Patterned optical polymer systems,” Ph.D. dissertation 15043 (ETH, Zürich, 2003), pp. 117–140.

Kodaka, M.

W. Wei, T. Tomohiro, M. Kodaka, H. Okuno, “Selective synthesis and kinetic measurement of 1:1 and 2:2 cyclic compounds containing 1,4,7,10-tetraazacyclododecane and azobenzene units,” J. Org. Chem. 65, 8979–8987 (2000).
[CrossRef]

Kokil, A.

E. Beekman, C. Kocher, A. Kokil, S. Zimmermann, C. Weder, “UV polarizers based on oriented poly(vinylalcohol)-Chrysophenine-Congo Red blend films,” J. Appl. Polym. Sci. 86, 1235–1239 (2002).
[CrossRef]

Kozenkov, V. M.

W. C. Yip, H. S. Kwok, V. M. Kozenkov, V. G. Chigrinov, “Photo-patterned e-wave polarizer,” Displays 22, 27–32 (2001).
[CrossRef]

Kryszewsky, M.

P. Uznanski, M. Kryszewsky, E. W. Thulstrup, “Linear dichroism and trans-cis photoisomerization studies of azobenzene molecules in oriented polyethylene matrix,” Eur. Polym. J. 27, 41–43 (1991).
[CrossRef]

Kwok, H. S.

W. C. Yip, H. S. Kwok, V. M. Kozenkov, V. G. Chigrinov, “Photo-patterned e-wave polarizer,” Displays 22, 27–32 (2001).
[CrossRef]

Land, E. H.

E. H. Land, H. G. Rogers, “Light polarizer,” U.S. patent2,173,304 (19September1939).

E. H. Land, “Light polarizer and process of manufacturing the same,” U.S. patent2,237,567 (8April1941).

Lewis, J. W.

D. S. Kliger, J. W. Lewis, C. E. Randall, Polarized Light in Optics and Spectroscopy (Academic, San Diego, Calif., 1990).

Makas, A. S.

Marcandalli, B.

P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
[CrossRef]

Michl, J.

J. Michl, E. W. Thulstrup, Spectroscopy with Polarized Light (VCH Publishers, New York, 1986).

Montali, A.

A. R. A. Palmans, M. Eglin, A. Montali, C. Weder, “Tensile orientation behavior of alkoxy-substituted bis(phenylethynyl)benzene derivatives in polyolefin blend films,” Chem. Mater. 12, 472–480 (2000).
[CrossRef]

M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
[CrossRef]

C. Weder, C. Sarwa, A. Montali, C. Bastiaansen, P. Smith, “Incorporation of photoluminescent polarizers into liquid crystal displays,” Science 279, 835–837 (1998).
[CrossRef] [PubMed]

Natansohn, A.

S. Xie, A. Natansohn, P. Rochon, “Recent developments in aromatic azo polymer research,” Chem. Mater. 5, 403–411 (1993).
[CrossRef]

Okuno, H.

W. Wei, T. Tomohiro, M. Kodaka, H. Okuno, “Selective synthesis and kinetic measurement of 1:1 and 2:2 cyclic compounds containing 1,4,7,10-tetraazacyclododecane and azobenzene units,” J. Org. Chem. 65, 8979–8987 (2000).
[CrossRef]

Palmans, A. R. A.

A. R. A. Palmans, M. Eglin, A. Montali, C. Weder, “Tensile orientation behavior of alkoxy-substituted bis(phenylethynyl)benzene derivatives in polyolefin blend films,” Chem. Mater. 12, 472–480 (2000).
[CrossRef]

M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
[CrossRef]

Randall, C. E.

D. S. Kliger, J. W. Lewis, C. E. Randall, Polarized Light in Optics and Spectroscopy (Academic, San Diego, Calif., 1990).

Rochon, P.

S. Xie, A. Natansohn, P. Rochon, “Recent developments in aromatic azo polymer research,” Chem. Mater. 5, 403–411 (1993).
[CrossRef]

Rogers, H. G.

E. H. Land, H. G. Rogers, “Light polarizer,” U.S. patent2,173,304 (19September1939).

Sarwa, C.

C. Weder, C. Sarwa, A. Montali, C. Bastiaansen, P. Smith, “Incorporation of photoluminescent polarizers into liquid crystal displays,” Science 279, 835–837 (1998).
[CrossRef] [PubMed]

Seves, A.

P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
[CrossRef]

Seyffert, A.

T. Bremi, J. Grob, K. Franken, A. Seyffert, C. Kocher, “Sicherheitsmerkmal für Wertdokumente,” international patent applicationPCT/CH03/00146 (19July2002).

Siggia, S.

L. R. Whitlock, S. Siggia, J. E. Smola, “Spectrometric analysis of phenols and of sulfonates by formation of an azo dye,” Anal. Chem. 44, 532–536 (1972).
[CrossRef]

Smith, P.

C. Kocher, P. Smith, C. Weder, “Aromatic 2-(2′-hydroxyphenyl)benzoxazole esters: a novel class of caged photoluminescent dyes,” J. Mater. Chem. 12, 2620–2626 (2002).
[CrossRef]

M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
[CrossRef]

C. Weder, C. Sarwa, A. Montali, C. Bastiaansen, P. Smith, “Incorporation of photoluminescent polarizers into liquid crystal displays,” Science 279, 835–837 (1998).
[CrossRef] [PubMed]

C. Weder, P. Smith, “Antifalsification paper and other antifalsification items,” international patent applicationWO 0 019 016 (6April2000).

Smola, J. E.

L. R. Whitlock, S. Siggia, J. E. Smola, “Spectrometric analysis of phenols and of sulfonates by formation of an azo dye,” Anal. Chem. 44, 532–536 (1972).
[CrossRef]

Springle, I. D.

W. A. Crossland, I. D. Springle, A. B. Davey, “Photoluminescent LCDs (PL-LCDs) using phosphors,” Proc. SID 28, 837–840 (1997).

Tervoort, T.

M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
[CrossRef]

Tervoort, T. A.

Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers. 2. Ultimate properties,” Macromolecules 30, 2175–2177 (1997).
[CrossRef]

Y. Dirix, T. A. Tervoort, C. Bastiaansen, “Optical properties of oriented polymer/dye polarizers,” Macromolecules 28, 486–491 (1995).
[CrossRef]

Thulstrup, E. W.

P. Uznanski, M. Kryszewsky, E. W. Thulstrup, “Linear dichroism and trans-cis photoisomerization studies of azobenzene molecules in oriented polyethylene matrix,” Eur. Polym. J. 27, 41–43 (1991).
[CrossRef]

J. Michl, E. W. Thulstrup, Spectroscopy with Polarized Light (VCH Publishers, New York, 1986).

Tomohiro, T.

W. Wei, T. Tomohiro, M. Kodaka, H. Okuno, “Selective synthesis and kinetic measurement of 1:1 and 2:2 cyclic compounds containing 1,4,7,10-tetraazacyclododecane and azobenzene units,” J. Org. Chem. 65, 8979–8987 (2000).
[CrossRef]

Uznanski, P.

P. Uznanski, M. Kryszewsky, E. W. Thulstrup, “Linear dichroism and trans-cis photoisomerization studies of azobenzene molecules in oriented polyethylene matrix,” Eur. Polym. J. 27, 41–43 (1991).
[CrossRef]

Vaughan, W.

W. G. Driscoll, W. Vaughan, Handbook of Optics (McGraw-Hill, New York, 1987).

Weder, C.

E. Beekman, C. Kocher, A. Kokil, S. Zimmermann, C. Weder, “UV polarizers based on oriented poly(vinylalcohol)-Chrysophenine-Congo Red blend films,” J. Appl. Polym. Sci. 86, 1235–1239 (2002).
[CrossRef]

C. Kocher, P. Smith, C. Weder, “Aromatic 2-(2′-hydroxyphenyl)benzoxazole esters: a novel class of caged photoluminescent dyes,” J. Mater. Chem. 12, 2620–2626 (2002).
[CrossRef]

A. R. A. Palmans, M. Eglin, A. Montali, C. Weder, “Tensile orientation behavior of alkoxy-substituted bis(phenylethynyl)benzene derivatives in polyolefin blend films,” Chem. Mater. 12, 472–480 (2000).
[CrossRef]

M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
[CrossRef]

C. Weder, C. Sarwa, A. Montali, C. Bastiaansen, P. Smith, “Incorporation of photoluminescent polarizers into liquid crystal displays,” Science 279, 835–837 (1998).
[CrossRef] [PubMed]

C. Weder, P. Smith, “Antifalsification paper and other antifalsification items,” international patent applicationWO 0 019 016 (6April2000).

Wei, W.

W. Wei, T. Tomohiro, M. Kodaka, H. Okuno, “Selective synthesis and kinetic measurement of 1:1 and 2:2 cyclic compounds containing 1,4,7,10-tetraazacyclododecane and azobenzene units,” J. Org. Chem. 65, 8979–8987 (2000).
[CrossRef]

Whitlock, L. R.

L. R. Whitlock, S. Siggia, J. E. Smola, “Spectrometric analysis of phenols and of sulfonates by formation of an azo dye,” Anal. Chem. 44, 532–536 (1972).
[CrossRef]

Willstätter, R.

R. Willstätter, M. Benz, “Azophenols,” Justus Liebigs Ann. Chem. 39, 3492–3503 (1907).

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S. Xie, A. Natansohn, P. Rochon, “Recent developments in aromatic azo polymer research,” Chem. Mater. 5, 403–411 (1993).
[CrossRef]

Yip, W. C.

W. C. Yip, H. S. Kwok, V. M. Kozenkov, V. G. Chigrinov, “Photo-patterned e-wave polarizer,” Displays 22, 27–32 (2001).
[CrossRef]

Zimmermann, S.

E. Beekman, C. Kocher, A. Kokil, S. Zimmermann, C. Weder, “UV polarizers based on oriented poly(vinylalcohol)-Chrysophenine-Congo Red blend films,” J. Appl. Polym. Sci. 86, 1235–1239 (2002).
[CrossRef]

Zollinger, H.

H. Zollinger, Azo and Diazo Chemistry (Interscience, New York, 1961).

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Adv. Mater. (1)

M. Grell, D. C. D. Bradley, “Polarized luminescence from oriented molecular materials,” Adv. Mater. 11, 895–905 (1999).
[CrossRef]

Anal. Chem. (1)

L. R. Whitlock, S. Siggia, J. E. Smola, “Spectrometric analysis of phenols and of sulfonates by formation of an azo dye,” Anal. Chem. 44, 532–536 (1972).
[CrossRef]

Chem. Mater. (2)

S. Xie, A. Natansohn, P. Rochon, “Recent developments in aromatic azo polymer research,” Chem. Mater. 5, 403–411 (1993).
[CrossRef]

A. R. A. Palmans, M. Eglin, A. Montali, C. Weder, “Tensile orientation behavior of alkoxy-substituted bis(phenylethynyl)benzene derivatives in polyolefin blend films,” Chem. Mater. 12, 472–480 (2000).
[CrossRef]

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W. C. Yip, H. S. Kwok, V. M. Kozenkov, V. G. Chigrinov, “Photo-patterned e-wave polarizer,” Displays 22, 27–32 (2001).
[CrossRef]

Dyes Pigments (1)

P. L. Beltrame, L. Bergamasco, A. Castelli, E. Dubini-Paglia, B. Marcandalli, A. Seves, “The cis-trans isomerization and lightfastness of azo dyes dispersed in thermoplastic fibers with different structural features,” Dyes Pigments 35, 239–247 (1997).
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[CrossRef]

J. Appl. Polym. Sci. (1)

E. Beekman, C. Kocher, A. Kokil, S. Zimmermann, C. Weder, “UV polarizers based on oriented poly(vinylalcohol)-Chrysophenine-Congo Red blend films,” J. Appl. Polym. Sci. 86, 1235–1239 (2002).
[CrossRef]

J. Mater. Chem. (2)

M. Eglin, A. Montali, A. R. A. Palmans, T. Tervoort, P. Smith, C. Weder, “Ultra-high performance photoluminescent polarizers based on melt-processed polymer blends,” J. Mater. Chem. 9, 2221–2226 (1999).
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C. Kocher, P. Smith, C. Weder, “Aromatic 2-(2′-hydroxyphenyl)benzoxazole esters: a novel class of caged photoluminescent dyes,” J. Mater. Chem. 12, 2620–2626 (2002).
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J. Opt. Soc. Am. (1)

J. Org. Chem. (1)

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R. Willstätter, M. Benz, “Azophenols,” Justus Liebigs Ann. Chem. 39, 3492–3503 (1907).

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Proc. SID (1)

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Science (1)

C. Weder, C. Sarwa, A. Montali, C. Bastiaansen, P. Smith, “Incorporation of photoluminescent polarizers into liquid crystal displays,” Science 279, 835–837 (1998).
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Figures (6)

Fig. 1
Fig. 1

Chemical structures and melting temperatures T m of dichroic UV dyes 1–6.

Fig. 2
Fig. 2

Absorption spectra of dichroic UV filters based on dyes 1–4 (0.2% w/w in LLDPE, A //) and emission spectrum of a conventional UV lamp (hatched area).

Fig. 3
Fig. 3

Absorption spectra (A //) of the dichroic UV filters based on dye 5 (0.2% w/w in LLDPE, PET, and PA12) and of dye 6 (0.2% w/w in PET and PA12) and emission spectrum of a conventional UV lamp (hatched area).

Fig. 4
Fig. 4

Polarized absorption spectra of a dichroic UV filter based on dye 3 (0.2% w/w in LLDPE; l/ l 0 = 8) before exposure and after several times of exposure to UV light from a conventional UV lamp. The absorption spectrum perpendicular to the stretching direction is not notably affected during UV exposure and therefore is shown only for the pristine sample (dotted curve).

Fig. 5
Fig. 5

Change in principal absorption A // (expressed relative to the initial absorption of the unexposed film) of a dichroic UV filter based on dye 3 in a stretched LLDPE film (0.2% w/w dye 3; l/ l 0 = 8) on UV exposure and subsequent recovery. The decrease of A // can be attributed to trans-to-cis conversion of the dye molecules and is subsequently recovered when the sample has been kept at room temperature in the dark. Curves are drawn for guidance only.

Fig. 6
Fig. 6

Effect of a dichroic UV filter consisting of a LLDPE film stretched to l/ l 0 = 8 and containing 0.2% w/w dye 3 applied as security tape to a train ticket. (a) Ticket with UV filter as seen in daylight. The position of the tape is indicated by a red arrow. (b) Under exposure to polarized UV light, the security markings appear if the polarization axis of the UV light (marked by the black arrow) is perpendicular to the stretching direction of the security tape where virtually no absorption occurs. (c) By contrast, if the polarization axis of the UV light is parallel to the stretching direction of the security tape, the polarized UV light is almost completely absorbed and the area underneath it appears dark.

Tables (2)

Tables Icon

Table 1 Optical Properties of Dichroic UV Filtersa

Tables Icon

Table 2 Performance of Dichroic UV Filtersa

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