DE1153894B - Stabilisierung von Polyolefinen - Google Patents
Stabilisierung von PolyolefinenInfo
- Publication number
- DE1153894B DE1153894B DEF31989A DEF0031989A DE1153894B DE 1153894 B DE1153894 B DE 1153894B DE F31989 A DEF31989 A DE F31989A DE F0031989 A DEF0031989 A DE F0031989A DE 1153894 B DE1153894 B DE 1153894B
- Authority
- DE
- Germany
- Prior art keywords
- polyolefins
- thio
- acetone
- embrittlement
- cresol
- 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 description 12
- 230000006641 stabilisation Effects 0.000 title description 2
- 238000011105 stabilization Methods 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000007859 condensation product Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 5
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 claims description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000005673 monoalkenes Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 claims 1
- 238000004513 sizing Methods 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- -1 polypropylene Polymers 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 238000005452 bending Methods 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- 125000001400 nonyl 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])[H] 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 239000012774 insulation material Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-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
- XDILCINHTMZTGG-UHFFFAOYSA-N 3-(3-dodecoxy-3-oxopropyl)sulfanylpropanoic acid Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(O)=O XDILCINHTMZTGG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 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
- 239000004698 Polyethylene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-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
- 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
- 239000011253 protective coating Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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'
-
- 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
-
- 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
- C08K5/52—Phosphorus bound to oxygen only
-
- 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
-
- 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
- C08K5/5398—Phosphorus bound to sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Insulating Materials (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE607608D BE607608A (US08080257-20111220-C00005.png) | 1960-08-27 | ||
| NL132954D NL132954C (US08080257-20111220-C00005.png) | 1960-08-27 | ||
| NL132955D NL132955C (US08080257-20111220-C00005.png) | 1960-08-27 | ||
| NL128918D NL128918C (US08080257-20111220-C00005.png) | 1960-08-27 | ||
| NL268592D NL268592A (US08080257-20111220-C00005.png) | 1960-08-27 | ||
| DEF31989A DE1153894B (de) | 1960-08-27 | 1960-08-27 | Stabilisierung von Polyolefinen |
| DEF32040A DE1130162B (de) | 1960-08-27 | 1960-09-03 | Verfahren zum Stabilisieren von Polyolefinen |
| FI1515/61A FI42631B (US08080257-20111220-C00005.png) | 1960-08-27 | 1961-08-25 | |
| CH994161A CH423232A (de) | 1960-08-27 | 1961-08-25 | Verfahren zur Wärmestabilisierung von Polyolefinen |
| FR871773A FR1299862A (fr) | 1960-08-27 | 1961-08-28 | Procédé de stabilisation de polyoléfines |
| GB30999/61A GB994344A (en) | 1960-08-27 | 1961-08-28 | Stabilized polyolefines |
| US62671467 US3354117A (en) | 1960-08-27 | 1967-03-29 | Stabilized polyolefins |
| NL6910399A NL6910399A (US08080257-20111220-C00005.png) | 1960-08-27 | 1969-07-07 | |
| NL6910400A NL6910400A (US08080257-20111220-C00005.png) | 1960-08-27 | 1969-07-07 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31989A DE1153894B (de) | 1960-08-27 | 1960-08-27 | Stabilisierung von Polyolefinen |
| DEF32040A DE1130162B (de) | 1960-08-27 | 1960-09-03 | Verfahren zum Stabilisieren von Polyolefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1153894B true DE1153894B (de) | 1963-09-05 |
Family
ID=25974760
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31989A Pending DE1153894B (de) | 1960-08-27 | 1960-08-27 | Stabilisierung von Polyolefinen |
| DEF32040A Pending DE1130162B (de) | 1960-08-27 | 1960-09-03 | Verfahren zum Stabilisieren von Polyolefinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF32040A Pending DE1130162B (de) | 1960-08-27 | 1960-09-03 | Verfahren zum Stabilisieren von Polyolefinen |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0943654A1 (de) * | 1998-03-20 | 1999-09-22 | Clariant GmbH | Oligomeres Stabilisatorgemisch |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3435097A (en) * | 1965-03-26 | 1969-03-25 | Nat Poly Chem Inc | Phenolic-sulfide-phosphite compounds |
| US3755610A (en) * | 1971-09-15 | 1973-08-28 | Hercules Inc | Electrically conductive cable |
| DE2448415A1 (de) * | 1973-10-11 | 1975-04-24 | Raychem Corp | Antioxydantien und polymermassen, die diese antioxydantien enthalten |
| US3897388A (en) * | 1973-10-11 | 1975-07-29 | Raychem Corp | Antioxidant comprising a hydroxy aromatic compound containing sulfur and organic phosphite |
| JPH02251582A (ja) * | 1989-03-24 | 1990-10-09 | Dainippon Ink & Chem Inc | 耐候性の改善された一時保護塗料用組成物 |
| US6180706B1 (en) * | 1998-06-16 | 2001-01-30 | Union Carbide Chemicals & Plastics Technology Corporation | Crosslinkable high pressure low density polyethylene composition |
| US6103374A (en) * | 1998-06-16 | 2000-08-15 | Union Carbide Chemicals & Plastics Technology Corporation | Crosslinkable polyolefin composition |
| US7270775B2 (en) * | 2002-01-22 | 2007-09-18 | Northern Technologies International Corp. | Corrosion inhibiting composition and article containing it |
| TWI425041B (zh) * | 2006-07-25 | 2014-02-01 | Clariant Finance Bvi Ltd | 在以熔融加工製備聚乙烯物件過程中該物件之改良處理條件 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE562417A (US08080257-20111220-C00005.png) * | 1955-06-06 | 1958-05-16 | ||
| GB838042A (en) * | 1958-07-01 | 1960-06-22 | Petrochemicals Ltd | Improvements in or relating to polymeric material comprising low pressure ziegler polyolefines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124551A (en) * | 1964-03-10 | Xpxox | ||
| US2839563A (en) * | 1955-12-28 | 1958-06-17 | Shea Chemical Corp | Phosphites |
-
0
- NL NL128918D patent/NL128918C/xx active
- NL NL268592D patent/NL268592A/xx unknown
- NL NL132954D patent/NL132954C/xx active
- BE BE607608D patent/BE607608A/xx unknown
- NL NL132955D patent/NL132955C/xx active
-
1960
- 1960-08-27 DE DEF31989A patent/DE1153894B/de active Pending
- 1960-09-03 DE DEF32040A patent/DE1130162B/de active Pending
-
1961
- 1961-08-25 CH CH994161A patent/CH423232A/de unknown
- 1961-08-25 FI FI1515/61A patent/FI42631B/fi active
- 1961-08-28 GB GB30999/61A patent/GB994344A/en not_active Expired
-
1967
- 1967-03-29 US US62671467 patent/US3354117A/en not_active Expired - Lifetime
-
1969
- 1969-07-07 NL NL6910400A patent/NL6910400A/xx unknown
- 1969-07-07 NL NL6910399A patent/NL6910399A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE562417A (US08080257-20111220-C00005.png) * | 1955-06-06 | 1958-05-16 | ||
| GB838042A (en) * | 1958-07-01 | 1960-06-22 | Petrochemicals Ltd | Improvements in or relating to polymeric material comprising low pressure ziegler polyolefines |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0943654A1 (de) * | 1998-03-20 | 1999-09-22 | Clariant GmbH | Oligomeres Stabilisatorgemisch |
| US6225385B1 (en) | 1998-03-20 | 2001-05-01 | Clariant Gmbh | Oligomeric stabilizer mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| GB994344A (en) | 1965-06-02 |
| FI42631B (US08080257-20111220-C00005.png) | 1970-06-01 |
| DE1130162B (de) | 1962-05-24 |
| NL132955C (US08080257-20111220-C00005.png) | |
| CH423232A (de) | 1966-10-31 |
| NL268592A (US08080257-20111220-C00005.png) | |
| US3354117A (en) | 1967-11-21 |
| NL6910400A (US08080257-20111220-C00005.png) | 1969-10-27 |
| NL6910399A (US08080257-20111220-C00005.png) | 1969-10-27 |
| BE607608A (US08080257-20111220-C00005.png) | |
| NL132954C (US08080257-20111220-C00005.png) | |
| NL128918C (US08080257-20111220-C00005.png) |
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