DE3005300A1 - METHOD FOR THE PRODUCTION OF ELECTRICALLY CONDUCTIVE POLYAROMATS AND THEIR USE IN ELECTROTECHNICS AND FOR THE ANTISTATIC EQUIPMENT OF PLASTICS - Google Patents
METHOD FOR THE PRODUCTION OF ELECTRICALLY CONDUCTIVE POLYAROMATS AND THEIR USE IN ELECTROTECHNICS AND FOR THE ANTISTATIC EQUIPMENT OF PLASTICSInfo
- Publication number
- DE3005300A1 DE3005300A1 DE19803005300 DE3005300A DE3005300A1 DE 3005300 A1 DE3005300 A1 DE 3005300A1 DE 19803005300 DE19803005300 DE 19803005300 DE 3005300 A DE3005300 A DE 3005300A DE 3005300 A1 DE3005300 A1 DE 3005300A1
- Authority
- DE
- Germany
- Prior art keywords
- production
- plastics
- electrically conductive
- polyaromats
- electrotechnics
- 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- Withdrawn
Links
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
Description
Syntheses Collectiven, Vol. 1, (1979) Seiten 109 bis 110, Verlag John Wiley & Sons und "Naturwissenschaften" 3§_ (I969) Seiten 308 bis 313 herzustellen. Außerdem ist die Herstellung von Polyphenylenen durch stufenweise PoIy-20 kondensation nach R. Gehm und W. Kern aus "Makromolekulare Chemie" ]_ (1951) Seiten 46 öl bekannt, wobei besonders einheitliche para-verkettete methylsubstituierte Derivate erhalten werden, die nicht zusätzlich durch ortho- oder meta-verknüpfte Polymere verunreinigt sind.Syntheses Collectiven, Vol. 1, (1979) pages 109 to 110, Verlag John Wiley & Sons and "Naturwissenschaften" 3§_ (1969) pages 308 to 313. In addition, the preparation of polyphenylenes by stepwise poly-20 condensation according to R. Gehm and W. Kern from "Makromolekulare Chemie" ] _ (1951) pages 46 oil is known, with particularly uniform para-chained methyl-substituted derivatives being obtained which are not additionally carried out by ortho- or meta-linked polymers are contaminated.
Der Erfindung lag die Aufgabe zugrunde, die an sich bekannten Effekte bei den Polyphenylene^ die stabellenförmig angeordnet sind entsprechend der Formel:The invention was based on the object of the known effects in the polyphenylenes ^ the bar-shaped are arranged according to the formula:
auf polycyclische Kohlenwasserstoffe, bei denen die Ringsysteme kondensiert oder anelliert sind, zu übertragen.to be transferred to polycyclic hydrocarbons, in which the ring systems are condensed or fused.
13003A/029613003A / 0296
3.0 0 5 3QQ3.0 0 5 3QQ
BASF Aktiengesellschaft - <r - O. Z. 0050/034292BASF Aktiengesellschaft - <r - O. Z. 0050/034292
-3--3-
""Diese Aufgabe wurde erfindungsgemäß dadurch gelöst, daß man den Polyaromaten unter Ausschluß von Wasserfeuchtigkeit und von Sauerstoff, 0,5 bis 5 Gew.%, bezogen auf den eingesetzten Polyaromaten, an Natrium, Kalium, Rubidium, Cäsium oder deren Aminen zugesetzt werden. Nach bevorzugter Verfahrensweise wird Na, K, Rb, Cs oder deren Amine in Tetrahydrofuran, Dirnethoxyglykol, Anthrazen, Naphthalin oder 2-Methylstyrol, jeweils im Molverhältnis 1:1 bis 1:50, vorzugsweise 1:2 bis 1:3* zugesetzt."" This object is inventively achieved in that one be added to the polyaromatics under the absence of moisture and of oxygen, 0.5 to 5 wt.%, Based on the used polyaromatics, sodium, potassium, rubidium, cesium or their amines. According to a preferred procedure, Na, K, Rb, Cs or their amines in tetrahydrofuran, dirnethoxyglycol, anthracene, naphthalene or 2-methylstyrene, each in a molar ratio of 1: 1 to 1:50, preferably 1: 2 to 1: 3 * are added.
Unter Polyaromaten werden höhermolekulare Produkte verstanden, die nicht linear aufgebaut und - entsprechend den in para-Stellung verknüpften Polyphenylenes, sondern sog. polycyclische aromatische Kohlenwasserstoffe sind undPolyaromatics are understood to mean higher molecular weight products that are not built up linearly and - corresponding to the Polyphenylenes linked in the para position, but so-called. are polycyclic aromatic hydrocarbons and
^5 anellierte Benzolkerne enthalten - entsprechend den Angaben E. Clar "Aromatische Kohlenwasserstoffe" II. Auflage 1952, Springer Verlag, Heidelberg S. VI-II - und mehr als zwei Benzolkerne in polycyclischen System enthalten und Molgewichte zwischen 300 und 3000, vorzugsweise zwischen^ 5 fused benzene nuclei contain - according to the information E. Clar "Aromatic Hydrocarbons" II Edition 1952, Springer Verlag, Heidelberg S. VI-II - and contain more than two benzene nuclei in the polycyclic system and Molecular weights between 300 and 3000, preferably between
20 400 und 1500 enthalten.20 400 and 1500 included.
Bevorzugte polycyclische Kohlenwasserstoffe sind: Tetraphenylen, 1,2,7,8-Dibenzperylen, Bianthen, 3,4,8,9-Dibenzpyren, Terylen, Peropyren, Anthanthren, Zethren, Fluoranthen, 11,12-peri Naphthylenfluoranthen, Dekacyclen, Naphtho[2',7',l,8]-anthren, Dihydro-triangulen.Preferred polycyclic hydrocarbons are: tetraphenylene, 1,2,7,8-dibenzperylene, bianthen, 3,4,8,9-dibenzpyrene, Terylene, peropyrene, anthanthrene, zethrene, fluoranthene, 11,12-peri naphthylene fluoranthene, decacycles, Naphtho [2 ', 7', l, 8] -anthrene, dihydro-triangulene.
Die Synthese des oben aufgeführten polycyclischen Kohlenwasserstoffs ist in dem cit. Buch von E. Clar angegeben.The synthesis of the polycyclic hydrocarbon listed above is in the cit. Book given by E. Clar.
Die elektrischen Leitfähigkeitswerte werden in S/cm bei 300C gemessen, die Messung selbst erfolgt nach der Methode von P. Beck, Berichte Bunsengesellschaft, Physikalische Chemie" 68_ (1964) Seiten 558 bis 567. Die elektrischen Leitfähigkeitswerte der erfindungsgemäßen leitfähigenThe electrical conductivity values are measured in S / cm at 30 ° C., the measurement itself takes place according to the method of P. Beck, Reports Bunsengesellschaft, Physikalische Chemie "68_ (1964) pages 558 to 567. The electrical conductivity values of the conductive according to the invention
^Polyaromaten ist größer als 10~^S/cm. j^ Polyaromatic is greater than 10 ~ ^ S / cm. j
130034/0296130034/0296
BASF Aktiengesellschaft - y>- O.Z. 0050/034292BASF Aktiengesellschaft - y> - OZ 0050/034292
rNach dem erfindungsgemäßen Verfahren wird den Polyaromaten unter Ausschluß von Wasserfeuchtigkeit und von Sauerstoff 0,5 bis 5 Gew.%, bezogen auf das eingesetzte PoIyphenylen, an Natrium, Kalium, Rubidium, Cäsium oder deren Amine zugesetzt. r According to the method according to the invention is the polyaromatics under the absence of moisture and of oxygen, 0.5 to 5 wt.%, based on the charged PoIyphenylen, sodium, potassium, rubidium, cesium or the amines added.
Das Einarbeiten der Zusätze erfolgt unter Ausschluß von Feuchtigkeit (Wasser) sowie Sauerstoff (Luft), es wird daher vorzugsweise unter Argonatmosphäre gearbeitet.The additives are incorporated with the exclusion of moisture (water) and oxygen (air) therefore preferably worked under an argon atmosphere.
Vorzugsweise werden Hilfsflüssigkeiten wie Tetrahydrofuran, Dimethoxyglykol, Anthrazen, Naphthalin oder<i -Methylstyrol, jeweils Im Molverhältnis 1:1 bis 1:50 eingesetzt, die nach dem Einarbeiten bei Temperaturen unter 300C im Vakuum abgezogenAuxiliary liquids such as tetrahydrofuran, dimethoxyglycol, anthracene, naphthalene or <i -methylstyrene, in each case in a molar ratio of 1: 1 to 1:50, are preferably used, which are removed after incorporation at temperatures below 30 ° C. in vacuo
15 ist bevorzugt 1:2 bis 1:315 is preferably 1: 2 to 1: 3
300C im Vakuum abgezogen werden. Das obige Molverhältnis30 0 C are drawn off in a vacuum. The above molar ratio
Durch die genannten Zusätze können elektrische Leitfähigkeitsanstiege von einigen Größenordnungen erreicht werden. Die Ausgangsleitfähigkeiten der Polyaromaten betrugen ca. 10 S/cm, liefern aber nach der Zugabe der erfindungsgemäßen Zusätze Leitfähigkeiten größer als 10~2 S/cm.With the additives mentioned, increases in electrical conductivity of several orders of magnitude can be achieved. The output conductances of the polyaromatics were approximately 10 S / cm, but the addition of the additives provide to the invention conductivities greater than 10 -2 S / cm.
Die erfindungsgemäß hergestellten elektrisch leitfähigen Polyaromaten mit elektrischen Leitfähigkeiten größer als 10 S/cm sind zur antistatischen Ausrüstung von Kunststoffen, zur Herstellung von Sonnenzellen, zur Umwandlung und Fixierung von Strahlung sowie zur Herstellung elektrischer und magnetischer Schalter geeignet. Durch die Zusätze der starken Lewis-Säure zum Polyaromaten ent-The electrically conductive polyaromatics produced according to the invention with electrical conductivities greater than 10 S / cm are for the antistatic treatment of plastics, for the production of solar cells, for conversion and fixation of radiation as well as for the production of electrical and magnetic switches. Through the Additions of the strong Lewis acid to the polyaromatic
30 stehen sog. n-Leiter.30 are so-called n-conductors.
Die in den folgenden Beispielen genannten Teile sind Gewichtsteile, bzw. bei den Zusatzstoffen Molprozent.The parts mentioned in the following examples are parts by weight or, in the case of additives, mol percent.
13003A/029613003A / 0296
30Q530030Q5300
BASF Aktiengesellschaft _ Jr _ O. Z. 0050/0^4292BASF Aktiengesellschaft _ Jr _ O. Z. 0050/0 ^ 4292
-S--S-
'"Beispiele 1 bis 7 '" Examples 1 to 7
10 Teile eines Polyaromaten werden unter Argonatmosphäre und Ausschluß von Feuchtigkeit mit dem jeweiligen Zusatzmittel versetzt, die Messung der elektr. Leitfähigkeit erfolgt nach F. Beck, "Ber. Bunsengesellschaft, Phys. Chem." 68, 558 bis 567 (1964).10 parts of a polyaromatic are in an argon atmosphere and exclusion of moisture with the respective additive added, the measurement of the electr. conductivity takes place according to F. Beck, "Ber. Bunsengesellschaft, Phys. Chem. "68: 558-567 (1964).
L·L
13003A/029613003A / 0296
ο? βο? β
•"Nr. Polyphenylen Dopingmittel Leitfähigkeit S/cm 300C 1 >• "No. Polyphenylene doping agent conductivity S / cm 30 0 C 1 >
Typ und Menge Art und Menge vor d.Dopen, nach d.Dopen 5Type and amount Type and amount before dope, after dope 5
Mol. Si 3"Mol. Si 3 "
~1 1 Teil Tetraphenylen Nao]i.10"14 4,9 . 10"2 . « ~ 1 1 part tetraphenylene Na o] i. 10 " 14 4.9. 10" 2 . «
1 Teil " .Na 0,5 " 3,1 . 10"2 j=1 part ".Na 0.5" 3.1. 10 " 2 j =
1 Teil 1,2,4,8-Dibenzperylen Na 1,0 " 0,4 . ΙΟ"2 g"1 part 1,2,4,8-dibenzperylene Na 1.0 "0.4. ΙΟ" 2 g "
1 Teil Bianthen Na 0,2 10"l3 3,6 . 10"1 ~1 part Bianthene Na 0.2 10 "l 3 3.6. 10" 1 ~
1 Teil 3,4,8,9-Dibenzpyren Na 0,2 10"11 2,8 . 1O+2 1 part 3,4,8,9-dibenzpyrene Na 0.2 10 " 11 2.8. 1O +2
1 Teil Zethren Na 0,2 10"l2 1,5 . io+2
*£ 7 1 Teil Dikacyclen K 0,2 10""1^ 7,8 . 10""1 1 part Zethren Na 0.2 10 "l 2 1.5. Io +2
* £ 7 1 part dicacycles K 0.2 10 "" 1 ^ 7.8. 10 "" 1
O O
O O Ul OO O Ul O
Claims (4)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803005300 DE3005300A1 (en) | 1980-02-13 | 1980-02-13 | METHOD FOR THE PRODUCTION OF ELECTRICALLY CONDUCTIVE POLYAROMATS AND THEIR USE IN ELECTROTECHNICS AND FOR THE ANTISTATIC EQUIPMENT OF PLASTICS |
| EP81100583A EP0034273A3 (en) | 1980-02-13 | 1981-01-28 | Process for preparing electrically conductive polyaromatic substances and their use in electrotechnics and in the antistatic equipment of synthetics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803005300 DE3005300A1 (en) | 1980-02-13 | 1980-02-13 | METHOD FOR THE PRODUCTION OF ELECTRICALLY CONDUCTIVE POLYAROMATS AND THEIR USE IN ELECTROTECHNICS AND FOR THE ANTISTATIC EQUIPMENT OF PLASTICS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3005300A1 true DE3005300A1 (en) | 1981-08-20 |
Family
ID=6094468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803005300 Withdrawn DE3005300A1 (en) | 1980-02-13 | 1980-02-13 | METHOD FOR THE PRODUCTION OF ELECTRICALLY CONDUCTIVE POLYAROMATS AND THEIR USE IN ELECTROTECHNICS AND FOR THE ANTISTATIC EQUIPMENT OF PLASTICS |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0034273A3 (en) |
| DE (1) | DE3005300A1 (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1178529B (en) * | 1963-04-11 | 1964-09-24 | Basf Ag | Use of organic polycondensation products as electrical, especially light-electrical, semiconductor bodies |
| EP0016305B1 (en) * | 1979-03-20 | 1984-09-12 | Allied Corporation | Electrically conducting compositions derived from poly(phenylene), and shaped article comprising such a composition |
| DE2929367A1 (en) * | 1979-07-20 | 1981-02-12 | Basf Ag | METHOD FOR THE PRODUCTION OF ELECTRICALLY CONDUCTIVE POLYPHENYLENES AND THEIR USE IN ELECTROTECHNICS AND FOR THE ANTISTATIC EQUIPMENT OF PLASTICS |
-
1980
- 1980-02-13 DE DE19803005300 patent/DE3005300A1/en not_active Withdrawn
-
1981
- 1981-01-28 EP EP81100583A patent/EP0034273A3/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0034273A2 (en) | 1981-08-26 |
| EP0034273A3 (en) | 1981-11-18 |
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