EP1549709A1 - Polycarbonate ou polyestercarbonate contenant des azurants optiques - Google Patents

Polycarbonate ou polyestercarbonate contenant des azurants optiques

Info

Publication number
EP1549709A1
EP1549709A1 EP03757858A EP03757858A EP1549709A1 EP 1549709 A1 EP1549709 A1 EP 1549709A1 EP 03757858 A EP03757858 A EP 03757858A EP 03757858 A EP03757858 A EP 03757858A EP 1549709 A1 EP1549709 A1 EP 1549709A1
Authority
EP
European Patent Office
Prior art keywords
composition
alkyl
polycarbonate
compound
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03757858A
Other languages
German (de)
English (en)
Inventor
Rüdiger Gorny
Siegfried Anders
Wolfgang Nising
Marco Roelofs
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of EP1549709A1 publication Critical patent/EP1549709A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C08K5/3417—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings

Definitions

  • the present invention relates to compositions containing a polymer selected from the group consisting of polycarbonate and polyester carbonate and containing at least one compound which acts as an optical brightener.
  • Optical brighteners in polymers are known. The effectiveness of a particular optical brightener depends on the polymer in which it is used. The combination of a certain polymer and a certain optical brightener must therefore be well coordinated.
  • the present invention provides new optical brighteners for polycarbonates and polyester carbonates.
  • WO 98/19862 discloses two-layer plates made of polymers which contain optical brighteners and UV absorbers in one of the two layers.
  • Hostalux ® KCB is an optical brightener.
  • Hostalux ® KCB is 1,4-bis (2-benzoxazolyl) naphthalene. It is available from Clariant GmbH, Frankfurt am Main, Germany. The use of Hostalux ® KCB in powder coatings containing TiO2 is described in WO 01/18130.
  • Hostalux ® KCB in printing paper containing white pigment is described in XP-A 2001-010210 and in JP-A 03-065948.
  • Hostalux KCB ® in a mixture with other optical brighteners in PVC or EVA is described in EP-A 0,791,680.
  • Hostalux KCB ® in a mixture with other optical brighteners in Polyester ⁇ is described in EP-A 0,240,461 and in Helvetica Chimica Acta (1978), 61, pages 488-500.
  • Hostalux ® KCB in a mixture with other optical brighteners in PVC is described in DE-A 33 13 332.
  • Hostalux ® KCB in laminated PVC films is described in DE-A 21 33 16.0.
  • Leukopur ® EGM is an optical brightener.
  • Leukopur ® EGM is 7- (2H-naphtho [1,2-d] triazol-2-yl) -3-phenyl-2H-l-benzopyran-2-one. It is available from Clariant GmbH, Frankfurt am Main, Germany. The use of Leukopur ® EGM in "UV-detecting compositions" is described in JP-A 01-169327.
  • Leukopur ® EGM together with other optical brighteners in polyolefins is described in WO 02/31035.
  • Leukopur ® EGM together with other optical brighteners in PVC is described in DE-A 33 13 332.
  • Leukopur ® EGM used in PVC is described in JP-A 040 46 348.
  • Leukopur ® EGM used in greenhouse films is described in
  • Leukopur ® EGM used in polystyrene is described in US-A 4404 300th
  • Brochures from the manufacturer of Hostalux ® KCB and Leukopur ® EGM mention a number of applications.
  • Polycarbonate is not mentioned.
  • PNC, PS are mentioned , PE, PP, cellulose acetate, EVA.
  • Hostalux ® KSB is an optical brightener known for polycarbonate.
  • Hostalux ® KSB is 2- [4- [2- [4- (2-benzoxazolyl) phenyl] ethenyl] phenyl] -5-methyl-benzoxazole. It is available from Clariant GmbH, Frankfurt am Main, Germany. The use of Hostalux ® KSB in polycarbonate is described in JP-A
  • Uvitex ® OB is an optical brightener known for polycarbonate.
  • Uvitex ® OB is 2,2 '- (2,5-thiophendiyl) bis [5- (l, l-dimethylethyl) benzoxazole. It is available from the
  • Polycarbonate and polyester carbonate are often used in products that the
  • plastics Exposed to weather. It is therefore important that plastics, the poly Contain carbonate and polyester carbonate, have good weather resistance.
  • the weather resistance of the plastics also depends on which additives (for example which optical brighteners) are used in the plastics.
  • optical brighteners known for polycarbonate and for polyester carbonate have the disadvantage of not being sufficiently weather-resistant.
  • the present invention is therefore based on the object of providing optical brighteners for polycarbonate and for polyester carbonate which have good weather resistance.
  • R, R, R and R independently of one another represent H, alkyl, aryl, heteroaryl or halogen
  • R 3 and R 4 independently of one another represent H, alkyl, aryl, heteroaryl or halogen
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 independently of one another represent H, alkyl, aryl, heteroaryl, halogen or cyano.
  • a particular embodiment of the present invention is this composition, the polymer being selected from the group consisting of
  • Bisphenol-TMC is l, l-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane and has the following formula (Me stands for a methyl group):
  • the polycarbonates mentioned can additionally contain:
  • a particular embodiment of the present invention is the composition, the polymer being bisphenol A homopolycarbonate.
  • the Nerbind Carlg OB has the Foimel 1 in which R, R, R and R independently of one another are H, Ci to C 2 o-alkyl, C 1 -C 20 -aryl, Cj . - Are to C 2 o-heteroaryl or halogen, and wherein R 3 and R 4 independently of one another are H, Ci to C 2 o-alkyl, Ci to C o-aryl, - to C 20 heteroaryl or halogen ,
  • the compound OB has the formula 1 in which R 1 , R 2 , R 3 R 4 , R 5 and R 6 are H.
  • the compound OB has the formula 2 ## STR1 ## in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are, independently of one another, H, Ci to C 2 o-alkyl, Ci to C 2 o aryl, Ci to C 2 o heteroaryl, halogen or cyano.
  • the compound OB has the formula 2 in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are H.
  • the composition additionally contains UV absorbers.
  • UV absorbers examples are:
  • R and X are identical or different H or alkyl or alkylaryl
  • R 3 and R 4 are also the same or different and are H, C 1 -C 4 -Al 1, C 5 -C 6 cycloal yl, benzyl or Cg-C ⁇ aryl,
  • n 1, 2 or 3
  • n 1, 2, 3 or 4
  • R 1 , R 2 , m and n have the meaning given for formula (TV), in which also
  • R 3 and R4 have the meaning given for formula (II);
  • R 1 , R 2 , R 3 , R4 in formula (VT), identical or different, are H or alkyl or CN or halogens and
  • R ! to R4 0 are identical or different H, alkyl, CN or halogen
  • R is C 2 alkyl to -C 0 alkyl or aryl.
  • the composition additionally contains dyes and / or pigments.
  • the pigments are
  • White pigments and light scattering pigments are preferred.
  • compositions according to the invention preferably contain 0.0001 to 0.2% by weight, particularly preferably 0.0003 to 0.1% by weight, very particularly preferably 0.0005 to 0.05% by weight of the compound OB.
  • the compositions according to the invention can contain further, other polymers, so that a mixture (a so-called blend) of the polymer mentioned and the other, other polymers is present.
  • compositions according to the invention preferably contain at least 50, particularly preferably at least 80, very particularly preferably at least 90% by weight of the polymer mentioned.
  • compositions according to the invention contain only the usual auxiliaries and additives in addition to the polymers mentioned, the compound OB and, if appropriate, UV absorbers.
  • compositions according to the invention contain no further substances apart from the polymers mentioned, the compound OB and, if appropriate, UV absorbers.
  • composition described is the subject of the present invention.
  • composition according to the invention can be processed thermoplastically by injection molding, extrusion, coextrusion or other processes. You can
  • Products such as moldings, plates, profiles and pipes are preserved. These can be one or more layers.
  • the present invention therefore also relates to a product comprising the composition according to the invention.
  • This product can in particular be multi-layered and contain the composition according to the invention in at least one layer.
  • This product can in particular be selected from the group consisting of
  • a multilayer product which contains the composition according to the invention in an outer layer is particularly preferred.
  • Multi-layer plates are preferred, which can be produced in particular by coextrusion.
  • the compounds of formula 1 can be prepared by known processes. These are disclosed, for example, in Liebigs Annalen der Chemie, 1982, pages 1423 to 1433 and in US-A 3 843 632 and in US-A 3 993 659.
  • the compounds of formula 2 can be prepared by known processes. These are disclosed, for example, in JP-A 480 37 970 and in JP-A 460 07 388 and in DE-A 19 09 182.
  • compositions of the invention have numerous advantages.
  • optical brighteners By using the compounds according to the invention as optical brighteners it is achieved that, with the same concentration as with optical brighteners of the prior art, the optical properties remain good for a long time when the compositions are weathered.
  • the optically brightening effect is also maintained at a good level for a long time.
  • the fluorescence of the optical brighteners in the compositions according to the invention remains visible even after long periods of weathering. As a result, the compositions according to the invention look optically more beautiful.
  • compositions according to the invention look optically more beautiful.
  • Linear bisphenol A polycarbonate (Makrolon ® 3108 from Bayer, Germany having a melt flow rate (MFR) according to ISO 1133 of 6.5 g / lO in at 300 ° C and 1.2 kg load AG Leverkusen) was added to an extruder melted and mixed (compounded) with 0.25% by weight of Tinuvin ® 350 and with 0.02% by weight of the optical brightener mentioned in Table 1.
  • Compounds 2 and 4 are according to the invention. Compounds 1 and 3 are comparative tests.
  • Tinuvin ® 350 is 2 (2H-benzotriazol-2-yl) -4- (l, l-dimethylethyl) -6- (2-methyl ⁇ ro ⁇ yl) - phenol; it is available from the company Ciba Spezialchemie, Lampertheim,
  • Uvitex ® OB is 2.2 l - (2,5-tmophendiyl) bis [5- (l, l-dimethylethyl) benzoxazole; it is available from the company Ciba Spezialchemie, Lampertheim, Germany.
  • Leukopur ® EGM is 7- (2H-Na ⁇ htho [1,2-d] triazol-2-yl) -3-phenyl-2H-l-Benzo ⁇ yran- 2-one; it is available from Clariant GmbH, Frankfurt am Main, Germany.
  • Hostalux ® KS-N is 2- [4- [2- [4- (2-benzoxazolyl) ⁇ henyl] ethenyl] ⁇ henyl] -5-methylbenzoxazole, it is available from Clariant GmbH, Frankfurt am Main, Germany.
  • Hostalux ® KCB is 1,4-bis (2-benzoxazolyl) naphthalene; it is available from Clariant GmbH, Frankfurt am Main, Germany.
  • Test specimens (4 mm thick plates, so-called “4 mm color sample plates”) were produced from the above-mentioned compounds by injection molding. These were artificially weathered and their weathering resistance was tested.
  • the weathering was carried out in accordance with ISO 4892-2 with a Weather-O-meter from Atlas, USA, type CI 65A with a 6.5 kW xenon burner and a borosilicate / borosilicate filter with an irradiance of 0.5 W / m 2 at 340 nm.
  • the weathering cycle was: 102 min exposure and 18 min exposure and spraying with demineralized water.
  • the maximum blackboard temperature is 60 ° C (+/- 5 ° C).
  • Table 2 shows the results of the weathering:
  • the transmission was measured according to the standards ASTM E 308 and ASTM D 1003.
  • the Pye-Unicam device was used.
  • the yellowness index YI was determined in accordance with the ASTM E 313 standard.
  • the fluorescence of the color sample plates was assessed by placing them under a
  • UV lamp were placed and the intensity of the blue fluorescent light was visually assessed.
  • the examples show that the fluorescence of the color sample plates according to the invention is still visible even after long periods of weathering. As a result, the color sample plates according to the invention look optically more beautiful.
  • the examples also show that the yellowing of the color sample plates according to the invention is less than that of the comparative experiments. As a result, the color sample plates according to the invention look optically more beautiful.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Laminated Bodies (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

La présente invention concerne des compositions contenant un polymère choisi dans le groupe composé de polycarbonate et de polyestercarbonate, contenant un composé servant d'azurant optique.
EP03757858A 2002-09-30 2003-09-17 Polycarbonate ou polyestercarbonate contenant des azurants optiques Withdrawn EP1549709A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10245705A DE10245705A1 (de) 2002-09-30 2002-09-30 Ein Polycarbonat oder Polyestercarbonat enthaltend optische Aufheller
DE10245705 2002-09-30
PCT/EP2003/010325 WO2004031285A1 (fr) 2002-09-30 2003-09-17 Polycarbonate ou polyestercarbonate contenant des azurants optiques

Publications (1)

Publication Number Publication Date
EP1549709A1 true EP1549709A1 (fr) 2005-07-06

Family

ID=31969723

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03757858A Withdrawn EP1549709A1 (fr) 2002-09-30 2003-09-17 Polycarbonate ou polyestercarbonate contenant des azurants optiques

Country Status (13)

Country Link
US (1) US7265170B2 (fr)
EP (1) EP1549709A1 (fr)
JP (1) JP2006501336A (fr)
KR (1) KR20050086418A (fr)
CN (1) CN1685002A (fr)
AU (1) AU2003273894A1 (fr)
BR (1) BR0314929A (fr)
CA (1) CA2500290A1 (fr)
DE (1) DE10245705A1 (fr)
MX (1) MXPA05003296A (fr)
RU (1) RU2005113171A (fr)
TW (1) TWI309664B (fr)
WO (1) WO2004031285A1 (fr)

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DE102005039413A1 (de) * 2005-08-20 2007-02-22 Bayer Materialscience Ag Diffuser-Sheets aus CD-Material
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Also Published As

Publication number Publication date
WO2004031285A1 (fr) 2004-04-15
MXPA05003296A (es) 2005-07-05
BR0314929A (pt) 2005-08-02
CN1685002A (zh) 2005-10-19
TWI309664B (en) 2009-05-11
AU2003273894A1 (en) 2004-04-23
TW200420642A (en) 2004-10-16
KR20050086418A (ko) 2005-08-30
RU2005113171A (ru) 2005-10-27
DE10245705A1 (de) 2004-04-01
JP2006501336A (ja) 2006-01-12
CA2500290A1 (fr) 2004-04-15
US7265170B2 (en) 2007-09-04
US20040063821A1 (en) 2004-04-01

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