DD293477A7 - Method for stabilizing olefin polymers - Google Patents
Method for stabilizing olefin polymers Download PDFInfo
- Publication number
- DD293477A7 DD293477A7 DD22726181A DD22726181A DD293477A7 DD 293477 A7 DD293477 A7 DD 293477A7 DD 22726181 A DD22726181 A DD 22726181A DD 22726181 A DD22726181 A DD 22726181A DD 293477 A7 DD293477 A7 DD 293477A7
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- olefin polymers
- photooxidative degradation
- stabilizer
- against photooxidative
- mixtures
- Prior art date
Links
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 9
- 230000000087 stabilizing effect Effects 0.000 title abstract description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003381 stabilizer Substances 0.000 claims abstract description 13
- 230000015556 catabolic process Effects 0.000 claims abstract description 11
- 238000006731 degradation reaction Methods 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000011787 zinc oxide Substances 0.000 claims abstract description 8
- 230000006641 stabilisation Effects 0.000 claims abstract description 6
- 238000011105 stabilization Methods 0.000 claims abstract description 6
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 3
- 239000005022 packaging material Substances 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 description 3
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- -1 2,4-di-tert-butylphenyl Chemical group 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Stabilsierung von Olefinpolymerisaten oder deren Mischungen gegen photooxidativen Abbau unter Verwendung bekannter organischer Stabilisatorsysteme gegen photooxidativen Abbau und Zinkoxid, gegebenenfalls in Anwesenheit phosphororganischer Antioxidantien, im Verhaeltnis 1:3 bis 2:1 bei einer Gesamtkonzentration von 0,1 bis 0,8 * vorzugsweise 0,25 bis 0,5 * Durch dieses Verfahren wird die Konzentration an photooxidativ wirksamen Substanzen bei gleichzeitiger Verbesserung der stabilisierenden Wirkung herabgesetzt. Dadurch sind die erfindungsgemaesz ausgeruesteten Olefinpolymerisate gut als Verpackungsmaterialien fuer Lebensmittel geeignet.The invention relates to a process for the stabilization of olefin polymers or their mixtures against photooxidative degradation using known organic stabilizer systems against photooxidative degradation and zinc oxide, optionally in the presence of organophosphorus antioxidants, in the ratio 1: 3 to 2: 1 at a total concentration of 0.1 to 0 , 8 * preferably 0.25 to 0.5 * By this method, the concentration of photooxidatively active substances is reduced while improving the stabilizing effect. As a result, the olefin polymers of the invention are well suited as packaging materials for food.
Description
Anwendungsgebiet der ErfindungField of application of the invention
Die Erfindung betrifft ein Verfahren zur Stabilisierung von Olefinpolymerisaten oder deren Mischungen gegen photooxidativen Abbau.The invention relates to a process for the stabilization of olefin polymers or their mixtures against photooxidative degradation.
Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions
Es ist bekannt, zur Stabilisierung von Olefinpolymerisaten gegen photooxidativen Abbau Photostabilisatoren und deren Gemische, wieIt is known for the stabilization of olefin polymers against photooxidative degradation photostabilizers and mixtures thereof, such as
2-(2'-Hydroxy-3'-tertiär^butyl-5'-methylphenyl)-5-chlorbenztriazol (UV 1)2- (2'-hydroxy-3'-tertiarybutyl-5'-methylphenyl) -5-chlorobenzotriazole (UV 1)
2-(2'-Hydroxy-3'-5'-ditertiärbutylphenyl)-5-chlorbenztriazol (UV2)2- (2'-hydroxy-3'-5'-ditertiarybutylphenyl) -5-chlorobenzotriazole (UV2)
2-Hydroxy-4-methoxybenzophenon(UV3)2-hydroxy-4-methoxybenzophenone (UV 3)
2-Hydroxy-4-octoxy-benzophenon(UV4)2-hydroxy-4-octoxy-benzophenone (UV4)
Bis^^.e.G-tetramethyM-piperidinylsebacat (UV5) und 3,5-ditertiärbutyl(-4-hydroxylbenzoesäure) 2',4'-ditertiärbutylphenylester (UV6) gegebenenfalls in Kombination mit phenolischen und phosphorhaltigen Stabilisatoren, wie Distearylpentaerythritoldiphosphit (APD.Trisnonylphenylphosphit (AP3) sowieTetrakis (2,4-ditertiärbutylphenyl)-4,4'-diphenylendiphosphor.it (AP4) zu verwenden (US-PS 3935164, DE-OS 2409350,2606538).Bis (e) -betetramethyl-piperidinyl sebacate (UV5) and 3,5-di-tert-butyl (4-hydroxylbenzoic acid) 2 ', 4'-di-tert-butylphenyl ester (UV6) optionally in combination with phenolic and phosphorus-containing stabilizers, such as distearyl pentaerythritol diphosphite (APD.Trisnonylphenyl phosphite ( AP3) as well as tetrakis (2,4-di-tert-butylphenyl) -4,4'-diphenylendiphosphoronit (AP4) (US Pat. No. 3,935,164, DE-OS 2409350,2606538).
Es ist auch bekannt, zur Stabilisierung gegen photooxidativen Abbau von Olefinpolymerisaten Zinkoxid in Verbindung mit zinkorganischen Verbindungen einzusetzen.It is also known to use zinc oxide in combination with organozinc compounds for stabilization against photooxidative degradation of olefin polymers.
(Plastverarbeiter [Speyer] 28,1977,8,419-420) Außerdem ist bekannt, Zinkoxid in Kombination mit Kresolen als Stabilisator gegen photooxidativen Abbau von Olefinpolymerisaten einzumischen (GB-PS 1134017).(Plastverarbeiter [Speyer] 28,1977,8,419-420) In addition, it is known to mix zinc oxide in combination with cresols as a stabilizer against photooxidative degradation of olefin polymers (GB-PS 1134017).
Die bereits genannten Verbindungen können auch in Anwesenheit von anorganischen Füllstoffen, wie Oxiden, Hydroxiden, Carbonaten, Sulfiten und Silicaten des Mangans, Eisens, Zinks und Siliciums bei einer Konzentration von 30-400 Teilen, bei 100 Teilen des Olefinpolymerisats, verwendet werden (Jap. PS 1016013).The aforementioned compounds can also be used in the presence of inorganic fillers such as oxides, hydroxides, carbonates, sulfites and silicates of manganese, iron, zinc and silicon at a concentration of 30-400 parts, for 100 parts of the olefin polymer (Jap. PS 1016013).
Der Nachteil der genannten organischen Stabilisatoren bzw. Stabilisatorsysteme gegen photooxidativen Abbau besteht darin, daß sie in einer Konzentration wirksam sind, bei der höhere Migrationswerte auftreten. Weiterhin ist von Nachteil, daß in Anwesenheit von n'ihr als 1 % Zinkoxid die so behandelten Materialien auf dem Lebensmittelsektor, z. B. als Verpackungsmaterial, nicht zugelassen sind.The disadvantage of said organic stabilizers or systems against photooxidative degradation is that they are effective at a concentration at which higher migration levels occur. Furthermore, it is disadvantageous that in the presence of n'ihr than 1% zinc oxide, the materials thus treated in the food sector, for. B. as packaging material, are not allowed.
Ziel der ErfindungObject of the invention
Die Erfindung hat das Ziel, Olefinpolyinerisate gegen photooxidativen Abbau zu stabilisieren.The invention aims to stabilize olefin polyamines against photooxidative degradation.
Darlegung des Wesens der ErfindungExplanation of the essence of the invention
- Die technische Aufgabe, die durch die Erfindung gelöst werden soll- The technical problem to be solved by the invention
Der Erfindung liegt die Aufgabe zugrunde, ein Verfahren zur Stabilisierung von Olefinpolymerisaten zu entwickeln, das es gestattet, unter Verwendung bekannter Stabilisatoren, die Einsatzmenge an Stabilisator zu vermindern und dabei gleichzeitig den Stabilisierungseffekt zu erhöhen.The invention has for its object to develop a process for the stabilization of olefin polymers, which allows, using known stabilizers, to reduce the amount of stabilizer used and at the same time to increase the stabilizing effect.
- Merkmale der ErfindungFeatures of the invention
Die Aufgabe wird erfindungsgemäß gelöst, indem eine Kombination aus einem bekannten Stabilisator bzw. Stabilisatorgemisch gegen photooxidativen Abbau und Zinkoxid im Verhältnis 1:3 bis 2:1 bei einer Gesamtkonzentration von 0,1 bisO,8Ma.-%, vorzugsweise 0,25 bis 0,5 Ma.-%, verwendet wird.The object is achieved by a combination of a known stabilizer or stabilizer mixture against photooxidative degradation and zinc oxide in the ratio 1: 3 to 2: 1 at a total concentration of 0.1 to O, 8Ma .-%, preferably 0.25 to 0 , 5% by mass.
Gegebenenfalls kann die vorgenannte Kombination gemeinsam mit phosphorhaltigen organischen Stabilisatoren eingesetzt werden.Optionally, the aforementioned combination can be used together with phosphorus-containing organic stabilizers.
Erfindungsgemäß werden mit a-Olefinen Copolymerisate bzw. Homopolymerisate des Ethylens und Propens sowie deren Gemische mit obigen Verfahren ausgerüstet.According to the invention, copolymers or homopolymers of ethylene and propene and mixtures thereof are provided with α-olefins by the above processes.
Den Olefinpolymerisaten können Zusätze, wie Antioxydantien, z. B. phenolischer Art, Gleitmittel, Pigmente, Antistatika und Flammschutzmittel zugesetzt sein. Die Inkorporation der Zusätze kann in irgendeiner der üblichen Weisen erfolgen, z. B. vor der Konfektionierung bzw. Verarbeitung des Olefinpolymeren.The olefin polymers may contain additives such as antioxidants, e.g. As phenolic type, lubricants, pigments, antistatic agents and flame retardants may be added. The incorporation of the additives may be in any of the usual ways, e.g. B. prior to packaging or processing of the olefin polymer.
Ausführungsbeispieleembodiments
In die Olefinpolymerisate werden die entsprechenden Zusätze eingemischt und über einen handelsüblichen Extruder in der Schmelze homogenisiert. Die photooxidative Wirksamkeit der Verfahrensvariante wird an den aus einer Preßplatte hergestellten Probekörpern durch Zunahme der Karbonylbande mittels Infrarotspektroskopie nach Lagerung in einer Xenonstrahlung bestimmt und expositionszeitabhängig dargestellt.The corresponding additives are mixed into the olefin polymers and homogenized in the melt via a commercially available extruder. The photooxidative activity of the process variant is determined on the test specimens prepared from a press plate by increasing the carbonyl band by means of infrared spectroscopy after storage in a xenon radiation and exposure time-dependent.
In der Tabelle sind die erhaltenen Ergebnisse angeführt, wobei die Anführun^sbeispiele an folgenden Olefinpolymerisaten erläutert werden sollen:The table gives the results obtained, the examples of which are to be explained on the following olefin polymers:
Polyethylen hoher DichteHigh density polyethylene
Dichtedensity
butyl-p-kresolbutyl-p-cresol
Polyethylen hoher DichteHigh density polyethylene
Dichtedensity
Gehalt an Tetrakis-Content of tetrakis
lmethylen-3-(3',5'-ditertiär-lmethylen-3- (3 ', 5'-ditertiär-
butyl-4'-hydroxyphenyl)-butyl-4'-hydroxyphenyl) -
propionatjmethanpropionatjmethan
Polyethylen niederer DichteLow density polyethylene
N, 1901C)N, 190 1 C)
Dichtedensity
(3-methyl-6-tertiärbutyl-(3-methyl-6-tertiary butyl
phenol)phenol)
Polypropylenpolypropylene
Dichtedensity
(4'-hydroxy-3',5'-ditertiär-(4'-hydroxy-3 ', 5'-ditertiär-
butylphenyD-propionatbutylphenyD propionate
Mischung ausMix off
I und III im Verhältnis 8:2I and III in the ratio 8: 2
= 22g/10min= 22g / 10min
= 0,959 g/cm3 = 0.959 g / cm 3
= 0,04%= 0.04%
= 0,5g/10min= 0.5g / 10min
= 0,952 g/cm3 = 0.952 g / cm 3
0,05%0.05%
1,2g/10min 0,919 g/cm3 1.2 g / 10 min 0.919 g / cm 3
= 0,04%= 0.04%
= 2,3g/10min = 0,909 g/cm3 = 2.3g / 10min = 0.909 g / cm 3
= 0,07%= 0.07%
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD22726181A DD293477A7 (en) | 1981-01-28 | 1981-01-28 | Method for stabilizing olefin polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD22726181A DD293477A7 (en) | 1981-01-28 | 1981-01-28 | Method for stabilizing olefin polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD293477A7 true DD293477A7 (en) | 1991-09-05 |
Family
ID=5528835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD22726181A DD293477A7 (en) | 1981-01-28 | 1981-01-28 | Method for stabilizing olefin polymers |
Country Status (1)
| Country | Link |
|---|---|
| DD (1) | DD293477A7 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0676405A3 (en) * | 1994-04-05 | 1996-05-22 | Ciba Geigy Ag | Increase of the storage stability of organic phosphites and phosphonites. |
| EP0676187A3 (en) * | 1994-03-11 | 1997-12-29 | L'oreal | Composition containing a non photocatalytic metal oxide and tocopherol, its cosmetic and/or dermatologic use and methods for its preparation |
| US5856550A (en) * | 1994-04-05 | 1999-01-05 | Ciba Specialty Chemicals Corporation | Enhancement of the storage stability of organic phosphites and phosphonites |
-
1981
- 1981-01-28 DD DD22726181A patent/DD293477A7/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0676187A3 (en) * | 1994-03-11 | 1997-12-29 | L'oreal | Composition containing a non photocatalytic metal oxide and tocopherol, its cosmetic and/or dermatologic use and methods for its preparation |
| EP0676405A3 (en) * | 1994-04-05 | 1996-05-22 | Ciba Geigy Ag | Increase of the storage stability of organic phosphites and phosphonites. |
| US5856550A (en) * | 1994-04-05 | 1999-01-05 | Ciba Specialty Chemicals Corporation | Enhancement of the storage stability of organic phosphites and phosphonites |
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|---|---|---|---|
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