DE1265986B - Verfahren zum Stabilisieren von Polymerisaten von Olefinen - Google Patents
Verfahren zum Stabilisieren von Polymerisaten von OlefinenInfo
- Publication number
- DE1265986B DE1265986B DEF47977A DEF0047977A DE1265986B DE 1265986 B DE1265986 B DE 1265986B DE F47977 A DEF47977 A DE F47977A DE F0047977 A DEF0047977 A DE F0047977A DE 1265986 B DE1265986 B DE 1265986B
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- benzo
- carbon atoms
- ester
- octadecyl
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 230000000087 stabilizing effect Effects 0.000 title claims description 8
- 229920000642 polymer Polymers 0.000 title claims description 7
- 150000001336 alkenes Chemical class 0.000 title claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 230000015556 catabolic process Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 description 21
- -1 polypropylene Polymers 0.000 description 14
- VZWGRQBCURJOMT-UHFFFAOYSA-N Dodecyl acetate Chemical compound CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 description 10
- 150000001463 antimony compounds Chemical class 0.000 description 8
- FVGJPCFYGPKBKJ-UHFFFAOYSA-N Dodecyl propionate Chemical compound CCCCCCCCCCCCOC(=O)CC FVGJPCFYGPKBKJ-UHFFFAOYSA-N 0.000 description 7
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 7
- 239000004743 Polypropylene Substances 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PBCMRNUMIAQRBZ-UHFFFAOYSA-N 1-(octadecyltetrasulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSSSCCCCCCCCCCCCCCCCCC PBCMRNUMIAQRBZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- LZOLAOIYCPZECA-UHFFFAOYSA-N butyl undecanoate Chemical compound CCCCCCCCCCC(=O)OCCCC LZOLAOIYCPZECA-UHFFFAOYSA-N 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- PWLNAUNEAKQYLH-UHFFFAOYSA-N Octyl butanoate Chemical compound CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical group [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 2
- GAYUSSOCODCSNF-UHFFFAOYSA-N 1-(dodecyldisulfanyl)dodecane Chemical compound CCCCCCCCCCCCSSCCCCCCCCCCCC GAYUSSOCODCSNF-UHFFFAOYSA-N 0.000 description 1
- DWXUFQGAQNIMSO-UHFFFAOYSA-N 1-(dodecyltetrasulfanyl)dodecane Chemical compound CCCCCCCCCCCCSSSSCCCCCCCCCCCC DWXUFQGAQNIMSO-UHFFFAOYSA-N 0.000 description 1
- HKYYJZABVBDWJU-UHFFFAOYSA-N 1-(octadecyltrisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSSCCCCCCCCCCCCCCCCCC HKYYJZABVBDWJU-UHFFFAOYSA-N 0.000 description 1
- IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 1
- GQKDZDYQXPOXEM-UHFFFAOYSA-N 3-chlorocatechol Chemical compound OC1=CC=CC(Cl)=C1O GQKDZDYQXPOXEM-UHFFFAOYSA-N 0.000 description 1
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- JEPXJYKYHMEESP-UHFFFAOYSA-N Dodecyl butyrate Chemical compound CCCCCCCCCCCCOC(=O)CCC JEPXJYKYHMEESP-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical class C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- OIZXRZCQJDXPFO-UHFFFAOYSA-N Octadecyl acetate Chemical compound CCCCCCCCCCCCCCCCCCOC(C)=O OIZXRZCQJDXPFO-UHFFFAOYSA-N 0.000 description 1
- CEQGYPPMTKWBIU-UHFFFAOYSA-N Octyl propanoate Chemical compound CCCCCCCCOC(=O)CC CEQGYPPMTKWBIU-UHFFFAOYSA-N 0.000 description 1
- 239000003490 Thiodipropionic acid Substances 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- WBTCZEPSIIFINA-MSFWTACDSA-J dipotassium;antimony(3+);(2r,3r)-2,3-dioxidobutanedioate;trihydrate Chemical compound O.O.O.[K+].[K+].[Sb+3].[Sb+3].[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O.[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O WBTCZEPSIIFINA-MSFWTACDSA-J 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YTXCAJNHPVBVDJ-UHFFFAOYSA-N octadecyl propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CC YTXCAJNHPVBVDJ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 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
- C08K5/372—Sulfides, e.g. R-(S)x-R'
-
- 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
- C08K5/59—Arsenic- or antimony-containing compounds
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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF47977A DE1265986B (de) | 1965-12-21 | 1965-12-21 | Verfahren zum Stabilisieren von Polymerisaten von Olefinen |
| NL6616510A NL6616510A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-21 | 1966-11-23 | |
| DK637566AA DK114795B (da) | 1965-12-21 | 1966-12-08 | Fremgangsmåde til stabilisering af aliphatiske poly-α-olefiner indeholdende tertiære carbonatomer i molekylkæden mod nedbrydning som følge af påvirkninger af lys og varme. |
| GB55829/66A GB1162259A (en) | 1965-12-21 | 1966-12-13 | Stabilized Mixture of Polyolefines and process for preparing it |
| NO165995A NO121470B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-21 | 1966-12-14 | |
| AT1151466A AT266438B (de) | 1965-12-21 | 1966-12-14 | Verfahren zum Stabilisieren von Polyolefinen |
| CH1800466A CH479643A (de) | 1965-12-21 | 1966-12-16 | Gegen Abbau durch Licht und Wärme stabilisierte Polyolefinmischung und Verfahren zu ihrer Herstellung |
| US602169A US3459705A (en) | 1965-12-21 | 1966-12-16 | Stabilized polyolefins with (1) a thiobis compound and (2) an organic antimonyl compound |
| SE17451/66A SE309674B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-21 | 1966-12-20 | |
| ES334706A ES334706A1 (es) | 1965-12-21 | 1966-12-20 | Procedimiento para la estabilizacion de polimeros de olefi-nas. |
| BE691547D BE691547A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-21 | 1966-12-21 | |
| FR88367A FR1505926A (fr) | 1965-12-21 | 1966-12-21 | Stabilisants pour polyoléfines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF47977A DE1265986B (de) | 1965-12-21 | 1965-12-21 | Verfahren zum Stabilisieren von Polymerisaten von Olefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1265986B true DE1265986B (de) | 1968-04-11 |
Family
ID=7101952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF47977A Pending DE1265986B (de) | 1965-12-21 | 1965-12-21 | Verfahren zum Stabilisieren von Polymerisaten von Olefinen |
Country Status (12)
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2488975A (en) * | 1947-01-16 | 1949-11-22 | Us Rubber Co | Antimonyl derivatives of polyhydric phenols as antioxidants |
| US2581909A (en) * | 1949-03-30 | 1952-01-08 | Firestone Tire & Rubber Co | Stabilization of acrylonitrile-butadiene-1, 3 copolymers |
| US2581911A (en) * | 1949-03-30 | 1952-01-08 | Firestone Tire & Rubber Co | Acrylonitrile-butadiene-1, 3 copolymers stabilized by antimonyl pyrogallolate |
| US2581910A (en) * | 1949-03-30 | 1952-01-08 | Firestone Tire & Rubber Co | Acrylonitrile-butadiene-1, 3 copolymers stabilized by antimonyl p-phenyl catecholate |
| US2686167A (en) * | 1952-09-10 | 1954-08-10 | Firestone Tire & Rubber Co | Stabilization of synthetic rubbers with a sulfite and an antimonyl compound |
| US3255136A (en) * | 1960-05-27 | 1966-06-07 | Argus Chem | Stabilization of polypropylene with mixtures comprising organic-phosphite phenol transesterification products and esters of thiodipropionic acid |
-
1965
- 1965-12-21 DE DEF47977A patent/DE1265986B/de active Pending
-
1966
- 1966-11-23 NL NL6616510A patent/NL6616510A/xx unknown
- 1966-12-08 DK DK637566AA patent/DK114795B/da unknown
- 1966-12-13 GB GB55829/66A patent/GB1162259A/en not_active Expired
- 1966-12-14 NO NO165995A patent/NO121470B/no unknown
- 1966-12-14 AT AT1151466A patent/AT266438B/de active
- 1966-12-16 CH CH1800466A patent/CH479643A/de not_active IP Right Cessation
- 1966-12-16 US US602169A patent/US3459705A/en not_active Expired - Lifetime
- 1966-12-20 ES ES334706A patent/ES334706A1/es not_active Expired
- 1966-12-20 SE SE17451/66A patent/SE309674B/xx unknown
- 1966-12-21 BE BE691547D patent/BE691547A/xx unknown
- 1966-12-21 FR FR88367A patent/FR1505926A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE309674B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-03-31 |
| DK114795B (da) | 1969-08-04 |
| CH479643A (de) | 1969-10-15 |
| NL6616510A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-22 |
| GB1162259A (en) | 1969-08-20 |
| AT266438B (de) | 1968-11-11 |
| FR1505926A (fr) | 1967-12-15 |
| NO121470B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-01 |
| ES334706A1 (es) | 1968-06-01 |
| US3459705A (en) | 1969-08-05 |
| BE691547A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-21 |
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