DE1161688B - Gegen Alterung stabilisierte Formmassen aus Polyolefinen - Google Patents
Gegen Alterung stabilisierte Formmassen aus PolyolefinenInfo
- Publication number
- DE1161688B DE1161688B DEF29113A DEF0029113A DE1161688B DE 1161688 B DE1161688 B DE 1161688B DE F29113 A DEF29113 A DE F29113A DE F0029113 A DEF0029113 A DE F0029113A DE 1161688 B DE1161688 B DE 1161688B
- Authority
- DE
- Germany
- Prior art keywords
- stabilizer
- bis
- polyolefins
- stabilized against
- against aging
- 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 18
- 238000000465 moulding Methods 0.000 title claims description 7
- 230000032683 aging Effects 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title description 2
- 239000003381 stabilizer Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 12
- -1 Alkyl radical Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 150000002898 organic sulfur compounds Chemical class 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 229920001021 polysulfide Polymers 0.000 description 16
- 239000005077 polysulfide Substances 0.000 description 9
- 150000008117 polysulfides Polymers 0.000 description 9
- 230000000087 stabilizing effect Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000005496 tempering Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 3
- HKYYJZABVBDWJU-UHFFFAOYSA-N 1-(octadecyltrisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSSCCCCCCCCCCCCCCCCCC HKYYJZABVBDWJU-UHFFFAOYSA-N 0.000 description 3
- IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- PBCMRNUMIAQRBZ-UHFFFAOYSA-N 1-(octadecyltetrasulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSSSCCCCCCCCCCCCCCCCCC PBCMRNUMIAQRBZ-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 2
- 229930006739 camphene Natural products 0.000 description 2
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical compound [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000004071 soot Substances 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
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000010626 work up procedure 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- 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'
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 (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL252465D NL252465A (US20020128544A1-20020912-P00008.png) | 1959-06-10 | ||
| NL276505D NL276505A (US20020128544A1-20020912-P00008.png) | 1959-06-10 | ||
| NL133211D NL133211C (US20020128544A1-20020912-P00008.png) | 1959-06-10 | ||
| NL104900D NL104900C (US20020128544A1-20020912-P00008.png) | 1959-06-10 | ||
| NL254604D NL254604A (US20020128544A1-20020912-P00008.png) | 1959-06-10 | ||
| NL106397D NL106397C (US20020128544A1-20020912-P00008.png) | 1959-06-10 | ||
| DEF28654A DE1265409B (de) | 1959-06-10 | 1959-06-10 | Verfahren zum Stabilisieren von Polyolefinen |
| DEF29113A DE1161688B (de) | 1959-06-10 | 1959-08-06 | Gegen Alterung stabilisierte Formmassen aus Polyolefinen |
| US33393A US3258449A (en) | 1959-06-10 | 1960-06-02 | Polyolefins stabilized with 2, 6-ditertiary butyl-p-cresol and organic sulfides |
| GB20569/60A GB953447A (en) | 1959-06-10 | 1960-06-10 | Process for improving polyolefines |
| FR829667A FR1259294A (fr) | 1959-06-10 | 1960-06-10 | Procédé d'amélioration de polyoléfines |
| US46895A US3269980A (en) | 1959-06-10 | 1960-08-02 | Stabilization of polyolefins with sulfides and terpene reaction products of terpenes and phenols |
| FR835196A FR78236E (fr) | 1959-06-10 | 1960-08-06 | Procédé d'amélioration de polyoléfines |
| GB27479/60A GB953448A (en) | 1959-06-10 | 1960-08-08 | Improved polyolefine compositions |
| US259438A US3238179A (en) | 1959-06-10 | 1963-02-18 | Process for improving polyolefins by incorporation of condensation products of isovinyl phenol and acetone and organic poly sulfides |
| DE19691694210 DE1694210B2 (de) | 1959-06-10 | 1969-06-10 | Stabilisierung von polyolefinen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28654A DE1265409B (de) | 1959-06-10 | 1959-06-10 | Verfahren zum Stabilisieren von Polyolefinen |
| DEF29113A DE1161688B (de) | 1959-06-10 | 1959-08-06 | Gegen Alterung stabilisierte Formmassen aus Polyolefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1161688B true DE1161688B (de) | 1964-01-23 |
Family
ID=25974338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF29113A Pending DE1161688B (de) | 1959-06-10 | 1959-08-06 | Gegen Alterung stabilisierte Formmassen aus Polyolefinen |
Country Status (4)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351678A (en) * | 1964-08-12 | 1967-11-07 | Hercules Inc | Polyolefins stabilized with a combination of phenols and episulfide polymers |
| US3399251A (en) * | 1966-02-01 | 1968-08-27 | Uniroyal Inc | Alkylbenzyl adducts of polyethyleneimine blended with crystalline polyolefins |
| US3480581A (en) * | 1966-10-20 | 1969-11-25 | Nat Distillers Chem Corp | Enhancement of resistance of olefin polymers to heat deterioration |
| US3379678A (en) * | 1966-11-25 | 1968-04-23 | Stauffer Chemical Co | Olefin polymer compositions containing thiazoline polysulfide stabilizing materials |
| BE754216A (fr) * | 1969-08-08 | 1971-02-01 | Pennwalt Corp | Sulfures cycloaliphatiques pour la stabilisation de polyolefines |
| US4163006A (en) * | 1977-05-09 | 1979-07-31 | Ciba-Geigy Corporation | Compositions stabilized with polyalkylthiobenzenes |
| US4218332A (en) * | 1977-09-16 | 1980-08-19 | The United States Of America As Represented By The Secretary Of Agriculture | Tetrasulfide extreme pressure lubricant additives |
| US4229598A (en) * | 1978-12-14 | 1980-10-21 | Conoco, Inc. | Chemicals for treatment of PVC |
| US4309293A (en) * | 1979-12-10 | 1982-01-05 | Mobil Oil Corporation | Process for reducing the corrosivity of phenol sulfides |
| US4735980A (en) * | 1987-03-09 | 1988-04-05 | The Goodyear Tire & Rubber Company | Methylene bis(alkylsulfides) as antioxidant synergists in rubber |
| US5238980A (en) * | 1992-10-13 | 1993-08-24 | Phillips Petroleum Company | Corrosion inhibition of stereoregular, branched-mono-1-olefin polymers |
| ATE353352T1 (de) * | 2001-05-02 | 2007-02-15 | Borealis Tech Oy | Verwendung von polysulphiden zur stabilisierung von vernetzen silangruppen enthaltenden polymeren |
| EP3645511B1 (en) * | 2017-06-29 | 2023-08-16 | Arkema, Inc. | Polymer compositions stabilized with organopolysulfides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE562623A (US20020128544A1-20020912-P00008.png) * | 1956-11-29 | |||
| BE561944A (US20020128544A1-20020912-P00008.png) * | 1956-11-29 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA572920A (en) * | 1959-03-24 | Farbwerke Hoechst Aktiengesellschaft Vormals Meister Lucius And Bruning | Stabilized polyethylene containing a terpene phenol | |
| US2300069A (en) * | 1939-06-17 | 1942-10-27 | Jasco Inc | Process for the polymerization of olefins to high molecular weight substances |
| US2415833A (en) * | 1942-01-01 | 1947-02-18 | Standard Oil Dev Co | Lubricant |
| US2727879A (en) * | 1951-12-11 | 1955-12-20 | Du Pont | Stabilized ethylene polymer compositions |
| IT559929A (US20020128544A1-20020912-P00008.png) * | 1955-09-02 | |||
| US2843577A (en) * | 1955-10-17 | 1958-07-15 | Standard Oil Co | Process and catalyst for polymerization using polyvalent metal salts and a reducing agent plus a sulfur compound |
| US2995539A (en) * | 1956-03-01 | 1961-08-08 | Du Pont | Ethylene polymer composition containing alkanol sulfide polymer |
| BE570217A (US20020128544A1-20020912-P00008.png) * | 1957-08-08 | |||
| BE571035A (US20020128544A1-20020912-P00008.png) * | 1957-09-07 | |||
| US3056759A (en) * | 1958-08-21 | 1962-10-02 | Exxon Research Engineering Co | Polypropylene stabilized with di-tert.-octyl tri- and tetrasulfides |
| US3010937A (en) * | 1958-12-19 | 1961-11-28 | Bayer Ag | Process for stabilizing polymers of monoolefins |
-
0
- NL NL106397D patent/NL106397C/xx active
- NL NL133211D patent/NL133211C/xx active
- NL NL254604D patent/NL254604A/xx unknown
- NL NL276505D patent/NL276505A/xx unknown
- NL NL104900D patent/NL104900C/xx active
- NL NL252465D patent/NL252465A/xx unknown
-
1959
- 1959-08-06 DE DEF29113A patent/DE1161688B/de active Pending
-
1960
- 1960-06-02 US US33393A patent/US3258449A/en not_active Expired - Lifetime
- 1960-06-10 GB GB20569/60A patent/GB953447A/en not_active Expired
- 1960-08-02 US US46895A patent/US3269980A/en not_active Expired - Lifetime
- 1960-08-08 GB GB27479/60A patent/GB953448A/en not_active Expired
-
1963
- 1963-02-18 US US259438A patent/US3238179A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE562623A (US20020128544A1-20020912-P00008.png) * | 1956-11-29 | |||
| BE561944A (US20020128544A1-20020912-P00008.png) * | 1956-11-29 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL276505A (US20020128544A1-20020912-P00008.png) | |
| GB953448A (en) | 1964-03-25 |
| NL106397C (US20020128544A1-20020912-P00008.png) | |
| NL133211C (US20020128544A1-20020912-P00008.png) | |
| US3269980A (en) | 1966-08-30 |
| NL104900C (US20020128544A1-20020912-P00008.png) | |
| US3238179A (en) | 1966-03-01 |
| US3258449A (en) | 1966-06-28 |
| NL254604A (US20020128544A1-20020912-P00008.png) | |
| NL252465A (US20020128544A1-20020912-P00008.png) | |
| GB953447A (en) | 1964-03-25 |
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