DE1116897B - Stabilized blend of polyolefins for the manufacture of molded products - Google Patents
Stabilized blend of polyolefins for the manufacture of molded productsInfo
- Publication number
- DE1116897B DE1116897B DEB56912A DEB0056912A DE1116897B DE 1116897 B DE1116897 B DE 1116897B DE B56912 A DEB56912 A DE B56912A DE B0056912 A DEB0056912 A DE B0056912A DE 1116897 B DE1116897 B DE 1116897B
- Authority
- DE
- Germany
- Prior art keywords
- polyolefins
- stabilized
- mercapto
- minutes
- manufacture
- 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.)
- Pending
Links
- 229920000098 polyolefin Polymers 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 5
- 150000005840 aryl radicals Chemical group 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 4
- 150000004866 oxadiazoles Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- -1 2-mercapto-5-aminooxyphenyl- Chemical group 0.000 description 20
- 239000004743 Polypropylene Substances 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 7
- AFTBJQDQENGCPC-UHFFFAOYSA-N 2,5-ditert-butyl-4-methylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C=C1C(C)(C)C AFTBJQDQENGCPC-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005338 heat storage Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
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)
Description
Stabilisierte Mischung aus Polyolefinen zur Herstellung von geformten Produkten Polyolefine werden bekanntlich durch Hitze, Sauerstoff oder Licht angegriffen. Zum Stabilisieren von Polyolefinen wurden schon zahlreiche Verbindungen, z.B. Phenole, Amine oder Harnstoffe, verwendet. Stabilized mixture of polyolefins for the production of molded Products Polyolefins are known to be attacked by heat, oxygen or light. Numerous compounds have already been used to stabilize polyolefins, e.g. phenols, Amines or ureas are used.
Diese bekannten Stabilisatoren weisen jedoch erhebliche Nachteile auf.However, these known stabilizers have considerable disadvantages on.
So wurden z. B. schon Zusätze von Phenyl-ß-naphthylamin, N,N'-Diphenyl-p-phenylendiamin und ähnliche Verbindungen zum Stabilisieren von Polyolefinen verwendet. Diese Verbindungen besitzen zwar eine gute Schutzwirkung gegen Licht- und Hitzeeinflüsse. So were z. B. already additions of phenyl-ß-naphthylamine, N, N'-diphenyl-p-phenylenediamine and similar compounds used to stabilize polyolefins. These connections have a good protective effect against the effects of light and heat.
Sie verfärben aber bei der Verarbeitung, z. B. beim Spritzgießen, die Materialien sehr stark, so daß sie in der Praxis zur Herstellung von hellen Gegenständen nicht zu gebrauchen sind. Weiter wurden zum Stabilisieren von Polyolefinen schon Phenole, wie z. B.But they discolor during processing, e.g. B. in injection molding, the materials very strong, so that they can be used in practice for the production of bright Objects are not usable. They were also used to stabilize polyolefins already phenols, such as B.
4-Methyl-2,5-di-tertiär- butyl -phenol, vorgeschlagen.4-methyl-2,5-di-tert-butyl-phenol, proposed.
Diese sterisch gehinderten Phenole liefern zwar farblose Produkte; ihre Wirkungsdauer ist aber oft nur kurz, so daß sie technisch noch nicht genügen.These sterically hindered phenols give colorless products; however, their duration of action is often only short, so that they are not technically sufficient.
Es wurde nun gefunden, daß Mischungen aus Polyolefinen und Oxadiazolderivaten der allgemeinen Formel in der R1 einen Arylrest, der weitere Substituenten tragen kann, und R2 Wasserstoff, einen Alkyl- oder Arylrest oder den Rest bedeutet, sehr stabil gegen den Abbau in der Hitze in Gegenwart von Sauerstoff und Licht sind.It has now been found that mixtures of polyolefins and oxadiazole derivatives of the general formula in which R1 is an aryl radical which can carry further substituents, and R2 is hydrogen, an alkyl or aryl radical or the radical means that they are very stable against degradation in the heat in the presence of oxygen and light.
Geeignete Oxadiazolderivate sind beispielsweise: 2-Mercapto-5-oxyphenyl-, 2-Mercapto-5-dioxyphenyl-, 2-Mercapto-5-trioxyphenyl-, 2-Mercapto-5-aminooxyphenyl-, 2-Mercapto-5-chloroxyphenyl-, 2-Mercapto-5- [di-tert.-butyloxyphenylj-, 2-Mercapto-5-oxynaphthyl-, 2-Mercapto-5-oxymethoxyphenyl-, 2-Mercapto-5-(3,4-methylenbisoxy)-phenyl-, 2-Mercapto-5-mercaptophenyl-1,3,4-oxadiazol, ferner 2-Methylmercapto-5-oxyphenyl-, 2 - Methylmercapto - 5 - dioxyphenyl-, 2-Methylmercapto-5-trioxyphenyl-,2-Methylmercapto-5-aminooxyphenyl-, 2-Methylmercapto-5-chloroxyphenyl-, 2-Methylmercapto-5- [di-tert. -butyloxyphenyl]- oder 2-Methylmercapto-5-oxynaphthyl- 1,3,4-oxadiazol sowie auch 2-Benzylmercapto-5-oxyphenyl-, 2-Benzylmercapto-5-dioxyphenyl-, 2-Benzylmercapto-5-trioxyphenyl-, 2-Benzylmercapto-5-aminooxyphenyl-, 2-Benzylmercapto -5 - chloroxyphenyl -, 2 - Benzylmercapto-5-[di-tert.-butyloxyphenyl]-, 2-Benzylmercapto-5-oxynaphthyl-1,3,4-oxadiazol und 2-Oxyäthyl-mercapto-5-trioxyphenyl-1,3,4-oxadiazol. Suitable oxadiazole derivatives are, for example: 2-mercapto-5-oxyphenyl-, 2-mercapto-5-dioxyphenyl-, 2-mercapto-5-trioxyphenyl-, 2-mercapto-5-aminooxyphenyl-, 2-mercapto-5-chloroxyphenyl-, 2-mercapto-5- [di-tert-butyloxyphenyl-, 2-mercapto-5-oxynaphthyl-, 2-mercapto-5-oxymethoxyphenyl-, 2-mercapto-5- (3,4-methylenebisoxy) -phenyl-, 2-mercapto-5-mercaptophenyl-1,3,4-oxadiazole, also 2-methylmercapto-5-oxyphenyl-, 2-methylmercapto-5-dioxyphenyl-, 2-methylmercapto-5-trioxyphenyl-, 2-methylmercapto-5-aminooxyphenyl-, 2-methylmercapto-5-chloroxyphenyl-, 2-methylmercapto-5- [di-tert. -butyloxyphenyl] - or 2-methylmercapto-5-oxynaphthyl- 1,3,4-oxadiazole and also 2-benzylmercapto-5-oxyphenyl-, 2-benzylmercapto-5-dioxyphenyl-, 2-benzylmercapto-5-trioxyphenyl-, 2-benzylmercapto-5-aminooxyphenyl-, 2-Benzylmercapto -5 - chloroxyphenyl -, 2 - Benzylmercapto-5- [di-tert-butyloxyphenyl] -, 2-benzylmercapto-5-oxynaphthyl-1,3,4-oxadiazole and 2-oxyethyl-mercapto-5-trioxyphenyl-1,3,4-oxadiazole.
Ferner eignen sich die entsprechenden Disulfide, die man leicht aus den entsprechenden 5-substituierten 2-Mercapto-oxadiazolen durch Oxydation darstellen kann. Solche Verbindungen sind beispielsweise: Bis-(5-oxyphenyl-1 ,3,4-oxadiazolyl-(2))-disulfld und Bis-(5-trioxyphenyl-l,3,4-oxadiazolyi- (2)) -disulfld. Polyolefine, die sich mit Hilfe dieser Oxadiazolderivate gegen den Einfluß von Licht, Wärme und Sauerstoff stabilisieren lassen, sind z. B. Hoch- und Niederdruckpolyäthylen, Polypropylen, Polyisobutylen, Mischpolymerisate aus Äthylen und Propylen oder Isobutylen sowie Mischungen dieser Polyolefine. Die Stabilisatoren werden zweckmäßigerweise in Mengen von 0,05 bis 15 Gewichtsprozent, bezogen auf die Menge an Polyolefin, verwendet. Mengen von 0,1 bis 2Gewichtsprozent sind in den meisten Fällen ausreichend. Man kann die Stabilisatoren in üblicher Weise, z. B. mit Hilfe einer Schneckenpresse oder eines Kneters oder durch Mischen der pulverförmigen Polyolefine mit einer Lösung des Stabilisators, einarbeiten. Die genannten Verbindungen können in an sich üblicher Weise mit anderen Stabilisatoren kombiniert werden, wobei sich oft sehr starke synergistische Stabilisierungseffekte ergeben. Furthermore, the corresponding disulfides, which can be easily found, are suitable represent the corresponding 5-substituted 2-mercapto-oxadiazoles by oxidation can. Such compounds are, for example: bis- (5-oxyphenyl-1, 3,4-oxadiazolyl- (2)) - disulfide and bis (5-trioxyphenyl-1,3,4-oxadiazolyi (2)) disulfide. Polyolefins that are with the help of these oxadiazole derivatives against the influence of light, heat and oxygen let stabilize, are z. B. high and low pressure polyethylene, polypropylene, Polyisobutylene, copolymers of ethylene and propylene or isobutylene as well Mixtures of these polyolefins. The stabilizers are expediently used in quantities from 0.05 to 15 percent by weight, based on the amount of polyolefin, is used. Amounts of 0.1 to 2 percent by weight are sufficient in most cases. Man can the stabilizers in the usual way, for. B. with the help of a screw press or a kneader or by mixing the powdered polyolefins with a solution of the stabilizer. The compounds mentioned can be more customary per se Can be combined with other stabilizers, often very strong synergistic Stabilization effects result.
Die in den Beispielen genannten Teile sind Gewichtsteile. The parts mentioned in the examples are parts by weight.
Beispiel 1 100 Teile Polypropylen werden in einem Mischwerk innig mit 0,1 bzw. 1 Teil 2-Mercapto-5-(3,4,5-trioxyphenyl)-1,3,4-oxadiazol vermischt und anschließend 20 Minuten auf einem Walzwerk bei einer Temperatur von 1700C gewalzt. Example 1 100 parts of polypropylene are intimately mixed in a mixer mixed with 0.1 or 1 part of 2-mercapto-5- (3,4,5-trioxyphenyl) -1,3,4-oxadiazole and then rolled for 20 minutes on a rolling mill at a temperature of 1700C.
Zum Vergleich werden ebenso 100 Teile Polypropylen mit 0,1 bzw. 1 Teil 4-Methyl-2,5-di-tertiärbutyl-phenol vermischt und ebenso wie die erfindungsgemäß stabilisierten Produkte thermisch behandelt. For comparison, 100 parts of polypropylene are also 0.1 or 1 Part of 4-methyl-2,5-di-tert-butyl-phenol mixed and just like that according to the invention thermally treated stabilized products.
Das verwendete Polypropylen hatte einen K-Wert von 138. Nach dem Verwalzen hatte eine unstabilisierte Probe einen K-Wert unterhalb 80, während die ertindungsgemäß mit 0,1 Stabilisator stabilisierte Probe den K-Wert 137 und die mit 1%Stabilisator vermischte Probe denK-Wert 138 aufwies. Ein thermischer Abbau hat hier nicht stattgefunden. Die zum Vergleich mit 0,1 bzw. 1 Teil 4-Methyl-2,5-di-tertiär-butyl-phenol stabilisierten Proben hatten K-Werte von 85 bzw. 102. The polypropylene used had a K value of 138. According to the An unstabilized sample had a K value below 80, while the According to the invention, the sample stabilized with 0.1 stabilizer has a K value of 137 and the Sample mixed with 1% stabilizer had a K value of 138. A thermal breakdown did not take place here. For comparison with 0.1 or 1 part of 4-methyl-2,5-di-tertiary-butyl-phenol stabilized samples had K values of 85 and 102, respectively.
Die Prüfung des mit 0,1 Teilen 2-Mercapto-5-trioxyphenyl-1,3,4-oxadiazol stabilisierten Polypropylens wird wie folgt vorgenommen: Das stabilisierte Produkt wird bei 170"C so lange verwalzt, bis das Polymere infolge der geringen Schmelzviskosität abtropft. Dazu werden 260 Minuten benötigt. Das mit 0,1 Teilen 4-Methyl-2,5-di-tertiärbutyl-phenol stabilisierte Polypropylen tropft aber unter den gleichen Bedingungen schon nach 45 Minuten infolge seiner geringen Schmelzviskosität ab. Testing of 0.1 part of 2-mercapto-5-trioxyphenyl-1,3,4-oxadiazole stabilized polypropylene is made as follows: The stabilized product is rolled at 170 "C until the polymer due to the low melt viscosity drips off. This takes 260 minutes. That with 0.1 part of 4-methyl-2,5-di-tert-butyl-phenol stabilized polypropylene drips under the same conditions 45 minutes due to its low melt viscosity.
Beispiel 2 100 Teile Polypropylen werden in einem Mischwerk innig mit 0,1 bzw. 1 Teil 2-Mercapto-5-oxynaphthyl-1,3,4-oxadiazol vermischt und anschließend 20 Minuten auf einem Walzwerk bei einer Temperatur von 170"C gewalzt. Example 2 100 parts of polypropylene are intimately mixed in a mixer mixed with 0.1 or 1 part of 2-mercapto-5-oxynaphthyl-1,3,4-oxadiazole and then Rolled on a rolling mill at a temperature of 170 "C for 20 minutes.
Das verwendete Polypropylen hatte einen K-Wert von 138. Nach dem Verwalzen hatte das mit 0,1 Teilen 2-Mercapto-5-oxynaphthyl- 1,3,4-oxydiazol erfindungsgemäß stabilisierte Produkt einen K-Wert von 124 und das mit 1 °/o stabilisierte Produkt den K-Wert 137. The polypropylene used had a K value of 138. According to the According to the invention, it was rolled with 0.1 part of 2-mercapto-5-oxynaphthyl-1,3,4-oxydiazole The stabilized product had a K value of 124 and the product stabilized with 1% the K-value 137.
Beispiel 3 Auf einem Mischwerk werden 100 Teile Polyäthylen und 0,1 Teil 2-Mercapto-5-(2-oxynaphthyl)-1,3,4-oxadiazol innig vermischt. Man preßt anschließend kleine Plättchen, die man einer Wärmelagerung bei 180°C unterwirft. Durch einen hochgereinigten Luftstrom werden die entstehenden Zersetzungsgase in Leitfähigkeitswasser geleitet und der entstehende pa-Abfall gemessen. Die Länge der Zeit, in der der pH-Wert von 7 auf einen bestimmten p-Wert absinkt, ist ein Maß für die Beständigkeit der Polyäthylenprobe. Example 3 100 parts of polyethylene and 0.1 Part of 2-mercapto-5- (2-oxynaphthyl) -1,3,4-oxadiazole intimately mixed. You then press small platelets that are subjected to heat storage at 180 ° C. Through a The resulting decomposition gases are converted into conductive water in a highly purified air stream and the resulting pa waste is measured. The length of time the The pH-value drops from 7 to a certain p-value, is a measure of the resistance the polyethylene sample.
Gemessen: Abbauzeit: unstabilisiert ................... 35 Minuten erfindungsgemäß stabilisiert ...... 153 Minuten Beispiel 4 100 Teile Polyäthylen und 0,1 Teile Bis-[5-(3,4,5-trioxyphenyl)-oxadiazolyl-(2)]-disulfid Measured: Degradation time: unstabilized ................... 35 minutes stabilized according to the invention ...... 153 minutes Example 4 100 parts of polyethylene and 0.1 part of bis [5th - (3,4,5-trioxyphenyl) oxadiazolyl (2)] disulfide
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB56912A DE1116897B (en) | 1960-03-03 | 1960-03-03 | Stabilized blend of polyolefins for the manufacture of molded products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB56912A DE1116897B (en) | 1960-03-03 | 1960-03-03 | Stabilized blend of polyolefins for the manufacture of molded products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1116897B true DE1116897B (en) | 1961-11-09 |
Family
ID=6971498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB56912A Pending DE1116897B (en) | 1960-03-03 | 1960-03-03 | Stabilized blend of polyolefins for the manufacture of molded products |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1116897B (en) |
-
1960
- 1960-03-03 DE DEB56912A patent/DE1116897B/en active Pending
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