CA1068040A - Low pressure ethylene polymer based compositions - Google Patents
Low pressure ethylene polymer based compositionsInfo
- Publication number
- CA1068040A CA1068040A CA225,326A CA225326A CA1068040A CA 1068040 A CA1068040 A CA 1068040A CA 225326 A CA225326 A CA 225326A CA 1068040 A CA1068040 A CA 1068040A
- Authority
- CA
- Canada
- Prior art keywords
- ethylene polymer
- phosphonic acid
- polymer based
- composition
- based composition
- 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
Links
- 229920000573 polyethylene Polymers 0.000 title claims abstract description 94
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 238000013329 compounding Methods 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 7
- 239000011651 chromium Substances 0.000 claims abstract description 7
- -1 phosphonic acid compound Chemical class 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 30
- 239000000155 melt Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 230000000087 stabilizing effect Effects 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 claims description 3
- CQBWEBXPMRPCSI-UHFFFAOYSA-M O[Cr](O[SiH3])(=O)=O Chemical compound O[Cr](O[SiH3])(=O)=O CQBWEBXPMRPCSI-UHFFFAOYSA-M 0.000 claims description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 3
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- XMAADNOJLNKDSN-UHFFFAOYSA-N octadecoxy(octadecyl)phosphinic acid Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(=O)CCCCCCCCCCCCCCCCCC XMAADNOJLNKDSN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- WBSRIXCTCFFHEF-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WBSRIXCTCFFHEF-UHFFFAOYSA-N 0.000 claims 2
- 239000012943 hotmelt Substances 0.000 claims 2
- NBXHXWIQWFGMQE-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methoxy-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]phosphinic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(COP(O)(=O)CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 NBXHXWIQWFGMQE-UHFFFAOYSA-N 0.000 claims 1
- HCMSQVXNPZPEDQ-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-(2-ethylhexoxy)phosphinic acid Chemical compound CCCCC(CC)COP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 HCMSQVXNPZPEDQ-UHFFFAOYSA-N 0.000 claims 1
- RCSQMROITMFDTR-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-octadecoxyphosphinic acid Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RCSQMROITMFDTR-UHFFFAOYSA-N 0.000 claims 1
- SAXJAGGHMSMAFQ-UHFFFAOYSA-N pentoxy(pentyl)phosphinic acid Chemical compound CCCCCOP(O)(=O)CCCCC SAXJAGGHMSMAFQ-UHFFFAOYSA-N 0.000 claims 1
- 150000003009 phosphonic acids Chemical class 0.000 abstract description 15
- 239000002253 acid Substances 0.000 abstract description 6
- 238000004132 cross linking Methods 0.000 abstract description 6
- 150000007513 acids Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 description 17
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 14
- 239000003381 stabilizer Substances 0.000 description 11
- 229940126062 Compound A Drugs 0.000 description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 239000002671 adjuvant Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000000071 blow moulding Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 2
- 229920013716 polyethylene resin Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RCRYERQRZNATJP-UHFFFAOYSA-N 1-(4-hydroxyphenyl)pentylphosphonic acid Chemical compound CCCCC(P(O)(O)=O)C1=CC=C(O)C=C1 RCRYERQRZNATJP-UHFFFAOYSA-N 0.000 description 1
- ASLNDVUAZOHADR-UHFFFAOYSA-N 2-butyl-3-methylphenol Chemical compound CCCCC1=C(C)C=CC=C1O ASLNDVUAZOHADR-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920005638 polyethylene monopolymer Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 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
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7405343A SE392112B (sv) | 1974-04-19 | 1974-04-19 | Lagtryckspolyetenkomposition innehallande fosfonsyraderivat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068040A true CA1068040A (en) | 1979-12-11 |
Family
ID=20320889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA225,326A Expired CA1068040A (en) | 1974-04-19 | 1975-04-18 | Low pressure ethylene polymer based compositions |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4104256A (en, 2012) |
| JP (1) | JPS5715133B2 (en, 2012) |
| AU (1) | AU475804B2 (en, 2012) |
| BE (1) | BE827942A (en, 2012) |
| CA (1) | CA1068040A (en, 2012) |
| CH (1) | CH602848A5 (en, 2012) |
| DE (1) | DE2517226A1 (en, 2012) |
| DK (1) | DK142816B (en, 2012) |
| FI (1) | FI751124A7 (en, 2012) |
| FR (1) | FR2268048B1 (en, 2012) |
| GB (1) | GB1479794A (en, 2012) |
| IT (1) | IT1035340B (en, 2012) |
| NL (1) | NL164883C (en, 2012) |
| NO (1) | NO751397L (en, 2012) |
| SE (1) | SE392112B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2735160A1 (de) * | 1977-08-04 | 1979-02-22 | Hoechst Ag | Fuellstoff enthaltende kunststoff- formmasse |
| EP0003058B1 (de) * | 1978-01-09 | 1983-02-16 | Ciba-Geigy Ag | Stabilisiertes Polypropylen |
| RU2212480C2 (ru) * | 2001-09-05 | 2003-09-20 | Барулин Николай Юрьевич | Способ создания сменяемых нетканых ворсовых покрытий декоративных изделий |
| KR100551810B1 (ko) * | 2003-06-24 | 2006-02-13 | 현대자동차주식회사 | 자동차의 테일러드 블랭크용 레이저 용접방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2952658A (en) * | 1955-12-19 | 1960-09-13 | Dow Chemical Co | Linear polyethylene stabilized with alkali phosphates |
| US3155704A (en) * | 1960-09-01 | 1964-11-03 | Ethyl Corp | O, o-dialkyl 3, 5-dialkyl 4-hydroxyphenylalkyl phosphonates and process for preparing same |
| US3281505A (en) * | 1963-09-12 | 1966-10-25 | Geigy Chem Corp | Dialkylhydroxyethanephosphonates and dialkylhydroxybenzylphosphonates |
| NL135065C (en, 2012) * | 1965-05-14 | |||
| US3493538A (en) * | 1966-11-30 | 1970-02-03 | Monsanto Co | Discoloration inhibitors for polyethylene |
-
1974
- 1974-04-19 SE SE7405343A patent/SE392112B/xx unknown
-
1975
- 1975-04-09 DK DK153275AA patent/DK142816B/da not_active IP Right Cessation
- 1975-04-11 AU AU80062/75A patent/AU475804B2/en not_active Expired
- 1975-04-15 BE BE155412A patent/BE827942A/xx unknown
- 1975-04-16 FI FI751124A patent/FI751124A7/fi not_active Application Discontinuation
- 1975-04-16 IT IT49134/75A patent/IT1035340B/it active
- 1975-04-17 FR FR7511927A patent/FR2268048B1/fr not_active Expired
- 1975-04-17 GB GB15885/75A patent/GB1479794A/en not_active Expired
- 1975-04-18 CA CA225,326A patent/CA1068040A/en not_active Expired
- 1975-04-18 NL NL7504668.A patent/NL164883C/xx not_active IP Right Cessation
- 1975-04-18 JP JP4658375A patent/JPS5715133B2/ja not_active Expired
- 1975-04-18 CH CH501375A patent/CH602848A5/xx not_active IP Right Cessation
- 1975-04-18 NO NO751397A patent/NO751397L/no unknown
- 1975-04-18 DE DE19752517226 patent/DE2517226A1/de not_active Withdrawn
- 1975-04-21 US US05/569,666 patent/US4104256A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4104256A (en) | 1978-08-01 |
| JPS50145452A (en, 2012) | 1975-11-21 |
| BE827942A (fr) | 1975-10-15 |
| NO751397L (en, 2012) | 1975-10-21 |
| DE2517226A1 (de) | 1975-10-23 |
| IT1035340B (it) | 1979-10-20 |
| FR2268048A1 (en, 2012) | 1975-11-14 |
| NL7504668A (nl) | 1975-10-21 |
| NL164883C (nl) | 1981-02-16 |
| FI751124A7 (en, 2012) | 1975-10-20 |
| DK142816C (en, 2012) | 1981-08-24 |
| SE7405343L (sv) | 1975-10-20 |
| AU475804B2 (en) | 1976-09-02 |
| GB1479794A (en) | 1977-07-13 |
| AU8006275A (en) | 1976-09-02 |
| SE392112B (sv) | 1977-03-14 |
| NL164883B (nl) | 1980-09-15 |
| DK153275A (en, 2012) | 1975-10-20 |
| FR2268048B1 (en, 2012) | 1978-02-24 |
| JPS5715133B2 (en, 2012) | 1982-03-29 |
| CH602848A5 (en, 2012) | 1978-08-15 |
| DK142816B (da) | 1981-02-02 |
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