DE4229192C2 - Antistatically equipped molded glass parts - Google Patents

Antistatically equipped molded glass parts

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Publication number
DE4229192C2
DE4229192C2 DE19924229192 DE4229192A DE4229192C2 DE 4229192 C2 DE4229192 C2 DE 4229192C2 DE 19924229192 DE19924229192 DE 19924229192 DE 4229192 A DE4229192 A DE 4229192A DE 4229192 C2 DE4229192 C2 DE 4229192C2
Authority
DE
Germany
Prior art keywords
residue
carbon atoms
alkyl
molded glass
coated
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.)
Expired - Lifetime
Application number
DE19924229192
Other languages
German (de)
Other versions
DE4229192A1 (en
Inventor
Friedrich Jonas
Rolf Dhein
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.)
Heraeus Deutschland GmbH and Co KG
Original Assignee
Bayer 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 AG filed Critical Bayer AG
Priority to DE19924229192 priority Critical patent/DE4229192C2/en
Publication of DE4229192A1 publication Critical patent/DE4229192A1/en
Application granted granted Critical
Publication of DE4229192C2 publication Critical patent/DE4229192C2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/32—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with synthetic or natural resins
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/34—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
    • C03C17/3405—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions with at least two coatings of organic materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/16—Anti-static materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J29/00—Details of cathode-ray tubes or of electron-beam tubes of the types covered by group H01J31/00
    • H01J29/86—Vessels; Containers; Vacuum locks
    • H01J29/867—Means associated with the outside of the vessel for shielding, e.g. magnetic shields
    • H01J29/868—Screens covering the input or output face of the vessel, e.g. transparent anti-static coatings, X-ray absorbing layers
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05F—STATIC ELECTRICITY; NATURALLY-OCCURRING ELECTRICITY
    • H05F1/00—Preventing the formation of electrostatic charges

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Laminated Bodies (AREA)
  • Paints Or Removers (AREA)
  • Surface Treatment Of Glass (AREA)

Description

Glasformteile werden durch Reibung oder durch Aufbringen von Ladungen, z. B. durch Elektronenstrahlung in Fernseh­ bildröhren, elektrostatisch aufgeladen. Diese Ladungen führen dann durch Staubanziehung zu einem schnellen Ein­ stauben der Glasformteile, das in der Praxis unerwünscht ist. Es besteht daher ein Bedarf, Glasformteile gegen elektrostatische Aufladung zu schützen.Glass moldings are made by friction or by application of charges, e.g. B. by electron radiation in television picture tubes, electrostatically charged. These charges then lead to a quick introduction through dust attraction dusting the molded glass parts, which is undesirable in practice is. There is therefore a need to counteract molded glass parts to protect electrostatic charge.

Es wurde jetzt gefunden, daß durch Beschichtung der Glasformteile mit elektrich leitfähigen Polyheterocyclen wie Polypyrrolen, Polythiophenen oder Polyanilinen ein Schutz gegen elektrostatische Aufladung erreicht wird.It has now been found that by coating the Molded glass parts with electrically conductive polyheterocycles such as polypyrroles, polythiophenes or polyanilines Protection against electrostatic charge is achieved.

Für die erfindungsgemäßen Glasformteile werden Beschichtungen aus Polythiophenen der allgemeinen Formel (I)
Coatings made of polythiophenes of the general formula (I)

in der
R1 und R2 unabhängig voneinander für Wasserstoff oder eine C1-C4-Alkylgruppe stehen oder zusammen einen gegebenenfalls substituierten C1-C4-Alkylen-Rest, vorzugsweise einen gegebenenfalls durch Alkyl­ gruppen substituierten Methylen-, einen gegebenen­ falls durch C1-C12-Alkyl- oder Phenylgruppen substituierten Ethylen-1,2-Rest, einen Propylen- 1,3-Rest oder einen Cyclohexylen-1,2-Rest bilden,
eingesetzt.in the
R 1 and R 2 independently of one another represent hydrogen or a C 1 -C 4 alkyl group or together an optionally substituted C 1 -C 4 alkylene radical, preferably a methylene group which is optionally substituted by alkyl groups, if appropriate by C 1 -C 12 alkyl or phenyl groups substituted ethylene-1,2-residue, a propylene-1,3-residue or a cyclohexylene-1,2-residue,
used.

Die Herstellung von Beschichtungen aus diesen Polythio­ phenen ist z. B. in den EP-A's 339 340 und 440 957 be­ schrieben. Bevorzugt werden die Schichten in einer Dicke von 20 nm bis 10 µm auf das Glasformteil aufgebracht, um einen ausreichenden Schutz vor elektrostatischer Auf­ ladung bei hoher Transparenz zu ermöglichen. Der Oberflächenwider­ stand der Beschichtung soll unter 1010 Ω/ liegen. Zur Verbesserung der Haftung der Polythiophenschichten der Formel (I) auf dem Glasformteil werden den Beschich­ tungen, bevorzugt den Beschichtungen gemäß EP-A 440 957, Haftvermittler auf Silanbasis der Formel (II)
The production of coatings from these polythiophenes is such. B. in EP-A's 339 340 and 440 957 be written. The layers are preferably applied to the glass molding in a thickness of 20 nm to 10 μm in order to enable adequate protection against electrostatic charging with high transparency. The surface resistance of the coating should be below 10 10 Ω /. To improve the adhesion of the polythiophene layers of the formula (I) to the molded glass part, the coatings, preferably the coatings according to EP-A 440 957, have a silane-based adhesion promoter of the formula (II)

X4-m-Si(OR3)m (II)
X 4-m -Si (OR 3 ) m (II)

worin
R3 ein Wasserstoffatom, einen aliphatischen Kohlen­ wasserstoffrest mit weniger als 10 Kohlenstoff­ atomen oder einen Acylrest mit weniger als 10 Koh­ lenstoffatomen,
wherein
R 3 represents a hydrogen atom, an aliphatic hydrocarbon residue with less than 10 carbon atoms or an acyl residue with less than 10 carbon atoms,

NH2-R-, NH2-CH2-CH2-NH-R- oder R-
R einen Kohlenwasserstoffrest mit 1 bis 20 C-Atomen, und
m 1 bis 3 bedeuten,
zugesetzt.NH 2 -R-, NH 2 -CH 2 -CH 2 -NH-R- or R-
R is a hydrocarbon radical with 1 to 20 carbon atoms, and
m is 1 to 3,
added.

Die Silane der Formel (II) werden den Beschichtungen in einer Menge von 1 bis 300 Gew.-%, bezogen auf die übri­ gen festen Bestandteile der Beschichtung, zugesetzt.The silanes of the formula (II) are used in the coatings an amount of 1 to 300 wt .-%, based on the rest gene solid components of the coating, added.

Den Beschichtungen können außerdem weiter Zusätze zur Erhöhung der Kratzfestigkeit oder zur Stabilisierung gegen Leitfähigkeitsabfall zugesetzt werden.The coatings can also further additives Increased scratch resistance or for stabilization against conductivity drop.

Das Aufbringen der Schichten erfolgt mit bekannten Techniken, z. B. durch Aufdrucken (z. B. Siebdruck), Tauchlackierung, Aufrakeln, Aufsprühen oder Spincoaten.The layers are applied using known ones Techniques, e.g. B. by printing (e.g. screen printing), Dip painting, knife coating, spraying or spin coating.

Die antistatische Beschichtung aus Polythiophenen der Formel (I) kann gegebenenfalls weiterhin mit organischen oder anorganischen Polymeren abgedeckt werden, um z. B. die antistatische Beschichtung vor mechanischen Ver­ letzungen zu schützen. Die Schutzschicht wird bevorzugt in einer Dicke von 0,1 bis 100 µm aufgebracht. Geeignete Schutzschichten sind lösliche Polymere, z. B. Polyacrylate wie Polymethylmethacrylat, vernetzende Polymere, z. B. Alkydharze, Polyurethane, oder durch ionisierende Strahlung härtende Lacke.The antistatic coating made of polythiophenes Formula (I) may optionally continue with organic or inorganic polymers to be covered, for. B.  the antistatic coating before mechanical ver to protect The protective layer is preferred applied in a thickness of 0.1 to 100 microns. suitable Protective layers are soluble polymers, e.g. B. Polyacrylates such as polymethyl methacrylate, crosslinking polymers, e.g. B. Alkyd resins, polyurethanes, or by ionizing Radiation-curing paints.

Die erfindungsgemäß beschichteten Glasformteile eignen sich bevorzugt zur Herstellung von Fernsehbildröhren. Neben dem Schutz der Glasformteile vor elektrostatischer Aufladung schirmen die Beschichtungen außerdem gegen elektromagnetische Strahlung ab.The molded glass parts coated according to the invention are suitable preferred for the production of television picture tubes. In addition to protecting the molded glass parts against electrostatic Charges also shield the coatings electromagnetic radiation.

Beispiele 1Examples 1 Herstellung der Polythiophen-StyrolsulfonatlösungPreparation of the polythiophene-styrene sulfonate solution

Eine Lösung von 20 g Polystyrolsulfonsäure (Mn (Zahlenmittel) = 40 000); 5,6 g 3,4-Ethylendioxythiophen; 13 g Kalium­ peroxydisulfat und 100 mg Eisen-III-sulfat (9 aq.) gelöst in vollentsalztem Wasser zu 1 l Gesamtlösung wird bei Raumtemperatur 24 Stunden gerührt. Man erhält eine blaugefärbte wäßrige Lösung des 3,4-Polyethylendioxy­ thiophens mit einem Feststoffgehalt von 3,8 Gew.-%.A solution of 20 g of polystyrene sulfonic acid (M n (number average) = 40,000); 5.6 g 3,4-ethylenedioxythiophene; 13 g of potassium peroxydisulfate and 100 mg of ferric sulfate (9 aq.) Dissolved in deionized water to 1 l of total solution is stirred at room temperature for 24 hours. A blue-colored aqueous solution of 3,4-polyethylenedioxy thiophene with a solids content of 3.8% by weight is obtained.

Entsalzung mittels IonenaustauscherDesalination using an ion exchanger

1000 ml der obigen PEDT/PSS-Lösung werden mit 1000 ml Wasser verdünnt. Nach Zugabe von 100 g schwach basischem Ionenaustauscher und 100 g stark saurem Ionenaustauscher wird die Lösung 6 Stunden bei Raumtemperatur gerührt. Danach wird der Ionenaustauscher abfiltriert und man erhält eine entsalzte PEDT/PSS-Lösung mit einem Fest­ stoffgehalt von 1,28 Gew.-%. Die Lösung enthält nur noch 0,4 g Kaliumionen pro Liter und ist praktisch frei von Sulfationen.1000 ml of the above PEDT / PSS solution are mixed with 1000 ml Diluted water. After adding 100 g of weakly basic Ion exchanger and 100 g strongly acidic ion exchanger the solution is stirred for 6 hours at room temperature. Then the ion exchanger is filtered off and one receives a desalted PEDT / PSS solution with a solid content of 1.28 wt .-%. The solution only contains 0.4 g of potassium ions per liter and is practically free of Sulfate ions.

100 g der entsalzten Lösung werden mit 1,28 g 3-Glycid­ oxypropyltrimethoxysilan und 10 g Isopropanol gemischt und auf eine Glasplatte aufgetragen. Die Schichtdicke der Beschichtung nach dem Abdampfen des Lösungsmittels betrug 0,6 µm. Die Schicht war transparent und hatte einen Oberflächenwiderstand von 50 kΩ/. Die Beschich­ tung zeigte eine sehr gute Haftung zum Glas und konnte auch mit Wasser und organischen Lösungsmitteln nicht abgewaschen werden.100 g of the desalted solution are mixed with 1.28 g of 3-glycid mixed oxypropyltrimethoxysilane and 10 g isopropanol and applied to a glass plate. The layer thickness the coating after the solvent has evaporated was 0.6 µm. The layer was transparent and had a surface resistance of 50 kΩ /. The Beschich tion showed very good adhesion to the glass and was able to  not even with water and organic solvents be washed off.

Beispiel 2Example 2

Eine nach Beispiel 1 beschichtete Glasplatte wird mit einem durch UV-Strahlung härtenden Lack folgender Zusammensetzung:
60 Gew.-Teile Epoxyacrylatharz gemäß DE-OS 24 29 527, Beispiel 3,
35 Gew.-Teile propoxyliertes Trimethylolpropantri­ acrylat
24 Gew.-Teile diethylaminmodifiziertes, propoxyliertes Trimethylolpropantriacrylat
60 Gew.-Teile Hexandiol-1,6-diacrylat
10 Gew.-Teile Benzophenon
mit einem Handcoater in einer Dicke von 12 µm beschich­ tet und anschließend die Deckschicht mit UV-Strahlung gehärtet. Die Deckschicht haftete gut auf der Anti­ statikschicht und die Glasplatte wies auch nach der Beschichtung antistatisches Verhalten und geringe Neigung zum Einstauben auf.A glass plate coated according to Example 1 is coated with a UV-curing lacquer of the following composition:
60 parts by weight of epoxy acrylate resin according to DE-OS 24 29 527, example 3,
35 parts by weight of propoxylated trimethylolpropane tri acrylate
24 parts by weight of diethylamine-modified, propoxylated trimethylolpropane triacrylate
60 parts by weight of hexanediol 1,6-diacrylate
10 parts by weight of benzophenone
coated with a hand coater with a thickness of 12 µm and then hardened the top layer with UV radiation. The top layer adhered well to the anti-static layer and the glass plate showed antistatic behavior and little tendency to dust even after coating.

Claims (2)

1. Antistatisch ausgerüstete Glasformteile, die mit einem Polythiophen der allgemeinen Formel (I)
in der
R1 und R2 unabhängig voneinander für Wasserstoff oder eine C1-C4-Alkylgruppe stehen oder zusammen einen gegebenenfalls substituierten C1-C4-Alkylen- Rest, vorzugsweise einen gegebenenfalls durch Alkylgruppen substituierten Methylen-, einen gegebenenfalls durch C1-C12-Alkyl- oder Phenylgruppen substituierten Ethylen-1,2-Rest, einen Propylen-1,3-Rest oder einen Cyclo­ hexylen-1,2-Rest bilden,
beschichtet sind, dadurch gekennzeichnet, dass der antistatischen Beschichtung Haftvermittler auf Silanbasis der Formel (II)
X4-m-Si(OR3)m (II),
worin
R3 ein Wasserstoffatom, einen aliphatischen Kohlenwasserstoffrest mit weniger als 10 Kohlenstoffatomen oder einen Acylrest mit weniger als 10 Kohlen­ stoffatomen,
NH2-R-, NH2-CH2-CH2-NH-R- oder R-,
R einen Kohlenwasserstoffrest mit 1 bis 20 C-Atomen und
m 1 bis 3 bedeuten,
zugesetzt werden. 1. Antistatically treated glass moldings which are coated with a polythiophene of the general formula (I)
in the
R 1 and R 2 are independently hydrogen or a C 1 -C 4 alkyl group or together form an optionally substituted C 1 -C 4 alkylene radical, preferably an optionally substituted by alkyl methylene, an optionally C 1 -C 12- alkyl or phenyl groups substituted ethylene-1,2-residue, a propylene-1,3-residue or a cyclo hexylene-1,2-residue,
are coated, characterized in that the antistatic coating adhesion promoter based on silane of the formula (II)
X 4-m -Si (OR 3 ) m (II),
wherein
R 3 is a hydrogen atom, an aliphatic hydrocarbon radical with less than 10 carbon atoms or an acyl radical with less than 10 carbon atoms,
NH 2 -R-, NH 2 -CH 2 -CH 2 -NH-R- or R-,
R is a hydrocarbon radical with 1 to 20 carbon atoms and
m is 1 to 3,
be added. 2. Antistatisch ausgerüstete Glasformteile nach An­ spruch 1, dadurch gekennzeichnet, daß die anti­ statische Beschichtung mit einer Schicht aus einem organischen oder anorganischen Polymeren abgedeckt ist.2. Antistatic glass moldings according to An saying 1, characterized in that the anti static coating with a layer of one organic or inorganic polymers covered is.
DE19924229192 1992-09-02 1992-09-02 Antistatically equipped molded glass parts Expired - Lifetime DE4229192C2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19924229192 DE4229192C2 (en) 1992-09-02 1992-09-02 Antistatically equipped molded glass parts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19924229192 DE4229192C2 (en) 1992-09-02 1992-09-02 Antistatically equipped molded glass parts

Publications (2)

Publication Number Publication Date
DE4229192A1 DE4229192A1 (en) 1994-03-03
DE4229192C2 true DE4229192C2 (en) 2003-06-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
DE19924229192 Expired - Lifetime DE4229192C2 (en) 1992-09-02 1992-09-02 Antistatically equipped molded glass parts

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Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996005606A1 (en) * 1994-08-08 1996-02-22 Philips Electronics N.V. Cathode ray tube comprising a display screen having an electroconductive coating
DE19524132A1 (en) * 1995-07-03 1997-01-09 Bayer Ag Scratch-resistant conductive coatings
IT1282387B1 (en) * 1996-04-30 1998-03-20 Videocolor Spa ANTI-STATIC, ANTI-GLARE COATING FOR A REFLECTION-TRANSMISSION SURFACE
DE19619972C1 (en) * 1996-05-17 1997-10-23 Daimler Benz Ag Conductive edge coating on phosphor at rear of cathode ray tube screen
DE19633311A1 (en) * 1996-08-19 1998-02-26 Bayer Ag Scratch-resistant conductive coatings
US6201051B1 (en) 1996-12-04 2001-03-13 Bayer Aktiengesellschaft Conducting organic-inorganic hybrid materials
DE19718859C2 (en) * 1997-05-03 1999-08-26 Technoplast Beschichtungsgesel Conductive printable plastic sheets
KR20000011267A (en) * 1998-07-24 2000-02-25 김영남 Screen display faceplate on which conductive organic polymeric transparent anti-static film is formed, its solution and its manufacturing method
AU2587200A (en) 1998-11-06 2000-05-29 Goex Corporation Transparent static dissipative coating compositions
TW430850B (en) * 1998-12-29 2001-04-21 Koninkl Philips Electronics Nv Light-transmissive substrate having a light-transmissive, low-ohmic coating
DE10024738A1 (en) * 2000-05-19 2001-11-29 Qvf Engineering Gmbh Glass components with a conductive coating, their use and the apparatus, systems and pipelines made from them
DE10032631A1 (en) * 2000-07-05 2002-01-17 Bayer Ag Conductive, highly abrasion-resistant coatings, a process for their production and their use
WO2010076314A1 (en) * 2008-12-31 2010-07-08 Essilor International (Compagnie Generale D'optique) Additives for enhancing the antistatic properties of conductive polymer-based coatings

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339340A2 (en) * 1988-04-22 1989-11-02 Bayer Ag Polythiophenes, process for their preparation and their use
EP0440957A2 (en) * 1990-02-08 1991-08-14 Bayer Ag New polythiophene dispersions, their preparation and their use
DE4129282A1 (en) * 1991-09-03 1993-03-04 Bayer Ag Sheets for transparent plastic and glass useful as heat protection windows - are coated with poly-thiophene(s) or their salts

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339340A2 (en) * 1988-04-22 1989-11-02 Bayer Ag Polythiophenes, process for their preparation and their use
EP0440957A2 (en) * 1990-02-08 1991-08-14 Bayer Ag New polythiophene dispersions, their preparation and their use
DE4129282A1 (en) * 1991-09-03 1993-03-04 Bayer Ag Sheets for transparent plastic and glass useful as heat protection windows - are coated with poly-thiophene(s) or their salts

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