DE1234387B - Verfahren zum Stabilisieren von Polyolefinen - Google Patents
Verfahren zum Stabilisieren von PolyolefinenInfo
- Publication number
- DE1234387B DE1234387B DE1963G0037526 DEG0037526A DE1234387B DE 1234387 B DE1234387 B DE 1234387B DE 1963G0037526 DE1963G0037526 DE 1963G0037526 DE G0037526 A DEG0037526 A DE G0037526A DE 1234387 B DE1234387 B DE 1234387B
- Authority
- DE
- Germany
- Prior art keywords
- tert
- group
- hydroxy
- alkyl
- butyl
- 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 11
- 230000000087 stabilizing effect Effects 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- -1 succinic acid diester Chemical class 0.000 claims description 57
- 239000003381 stabilizer Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 150000005690 diesters Chemical class 0.000 claims description 5
- 238000002474 experimental method Methods 0.000 claims description 4
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000003508 Dilauryl thiodipropionate Substances 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 description 20
- 239000004743 Polypropylene Substances 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 4
- QRLSTWVLSWCGBT-UHFFFAOYSA-N 4-((4,6-bis(octylthio)-1,3,5-triazin-2-yl)amino)-2,6-di-tert-butylphenol Chemical compound CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 QRLSTWVLSWCGBT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ZHBRSHSRMYZHLS-UHFFFAOYSA-N (4-hydroxyphenyl)methylphosphonic acid Chemical compound OC1=CC=C(CP(O)(O)=O)C=C1 ZHBRSHSRMYZHLS-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- TUYBEVLJKZQJPO-UHFFFAOYSA-N 19-(3,5-ditert-butyl-4-hydroxyphenyl)heptatriacontan-19-ylphosphonic acid Chemical compound CCCCCCCCCCCCCCCCCCC(CCCCCCCCCCCCCCCCCC)(P(O)(O)=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 TUYBEVLJKZQJPO-UHFFFAOYSA-N 0.000 description 2
- XJQMSHDKNMKUKH-UHFFFAOYSA-N 2,4-bis(octylsulfanyl)-1,3,5-triazine Chemical compound CCCCCCCCSC1=NC=NC(SCCCCCCCC)=N1 XJQMSHDKNMKUKH-UHFFFAOYSA-N 0.000 description 2
- UXWOYLIQDTXRCQ-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)sulfanyl-1,3,5-triazine Chemical compound CC1=C(C=CC=C1C)SC1=NC=NC=N1 UXWOYLIQDTXRCQ-UHFFFAOYSA-N 0.000 description 2
- LOKLQECQYONTKU-UHFFFAOYSA-N 2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]-1,3,5-triazine Chemical compound C(C)(C)(CC(C)(C)C)C1=CC=C(OC2=NC=NC=N2)C=C1 LOKLQECQYONTKU-UHFFFAOYSA-N 0.000 description 2
- CSROXWZGOYTBLX-UHFFFAOYSA-N 2-cyclohexylsulfanyl-1,3,5-triazine Chemical compound C1CCC(CC1)SC1=NC=NC=N1 CSROXWZGOYTBLX-UHFFFAOYSA-N 0.000 description 2
- QPJBIIGPGACOAD-UHFFFAOYSA-N 2-octadecylsulfanyl-1,3,5-triazine Chemical compound CCCCCCCCCCCCCCCCCCSC1=NC=NC=N1 QPJBIIGPGACOAD-UHFFFAOYSA-N 0.000 description 2
- WUMHXYIAFLKPFU-UHFFFAOYSA-N P(O)(O)=O.CC Chemical compound P(O)(O)=O.CC WUMHXYIAFLKPFU-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003900 succinic acid esters Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- STWTVTCBSVFAMN-UHFFFAOYSA-N 2-octylsulfanyl-1,3,5-triazine Chemical compound CCCCCCCCSC1=NC=NC=N1 STWTVTCBSVFAMN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- WOVNSXDQELBQCI-UHFFFAOYSA-N O[PH2]=O.c1ccccc1 Chemical compound O[PH2]=O.c1ccccc1 WOVNSXDQELBQCI-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-L benzyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-L 0.000 description 1
- HHPZCHTVGBYBEC-UHFFFAOYSA-N benzyl-hydroxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(=S)CC1=CC=CC=C1 HHPZCHTVGBYBEC-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920002397 thermoplastic olefin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting 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'
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 |
|---|---|---|---|
| US18827562A | 1962-04-17 | 1962-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1234387B true DE1234387B (de) | 1967-02-16 |
Family
ID=22692483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1963G0037526 Pending DE1234387B (de) | 1962-04-17 | 1963-04-16 | Verfahren zum Stabilisieren von Polyolefinen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE631163A (enrdf_load_stackoverflow) |
| CH (1) | CH433724A (enrdf_load_stackoverflow) |
| DE (1) | DE1234387B (enrdf_load_stackoverflow) |
| GB (1) | GB964647A (enrdf_load_stackoverflow) |
| NL (2) | NL291568A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449446A (en) * | 1968-07-08 | 1969-06-10 | Continental Oil Co | Purification of alcohols |
| US4446264A (en) * | 1982-04-15 | 1984-05-01 | The Goodyear Tire & Rubber Company | Synergistic antioxidant mixtures |
-
0
- NL NL125563D patent/NL125563C/xx active
- BE BE631163D patent/BE631163A/xx unknown
- NL NL291568D patent/NL291568A/xx unknown
-
1963
- 1963-04-06 CH CH436463A patent/CH433724A/de unknown
- 1963-04-16 DE DE1963G0037526 patent/DE1234387B/de active Pending
- 1963-04-16 GB GB1489463A patent/GB964647A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE631163A (enrdf_load_stackoverflow) | |
| CH433724A (de) | 1967-04-15 |
| NL291568A (enrdf_load_stackoverflow) | |
| NL125563C (enrdf_load_stackoverflow) | |
| GB964647A (en) | 1964-07-22 |
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