DE1265409B - Verfahren zum Stabilisieren von Polyolefinen - Google Patents
Verfahren zum Stabilisieren von PolyolefinenInfo
- Publication number
- DE1265409B DE1265409B DEF28654A DEF0028654A DE1265409B DE 1265409 B DE1265409 B DE 1265409B DE F28654 A DEF28654 A DE F28654A DE F0028654 A DEF0028654 A DE F0028654A DE 1265409 B DE1265409 B DE 1265409B
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- general formula
- nucleus
- naphthalene
- 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 10
- 230000000087 stabilizing effect Effects 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 claims description 11
- 150000002989 phenols Chemical class 0.000 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 150000003568 thioethers Chemical class 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002898 organic sulfur compounds Chemical class 0.000 claims description 5
- 150000001454 anthracenes Chemical class 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 150000003577 thiophenes Chemical class 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- -1 B. based on 4 Chemical class 0.000 description 25
- 239000003381 stabilizer Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000007859 condensation product Chemical class 0.000 description 12
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 12
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 11
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 230000003712 anti-aging effect Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 238000005496 tempering Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ISTBRWPQCNZBHI-UHFFFAOYSA-N 1-(4-octadecylsulfanylbutylsulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCSCCCCCCCCCCCCCCCCCC ISTBRWPQCNZBHI-UHFFFAOYSA-N 0.000 description 2
- MPKIZIGHGVKHDY-UHFFFAOYSA-N 2-tert-butyl-5-methylbenzene-1,4-diol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1O MPKIZIGHGVKHDY-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ILOBCCAMDOHZGW-UHFFFAOYSA-N 1,2-bis(chloromethyl)naphthalene Chemical compound C1=CC=CC2=C(CCl)C(CCl)=CC=C21 ILOBCCAMDOHZGW-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 1
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
- DPSSCGNZHMOEPK-UHFFFAOYSA-N 1-(2-octadecylsulfanylethylsulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCSCCCCCCCCCCCCCCCCCC DPSSCGNZHMOEPK-UHFFFAOYSA-N 0.000 description 1
- FZKQBXSRAKKKJQ-UHFFFAOYSA-N 1-(dichloromethyl)-2,3,4,5-tetramethylbenzene Chemical compound ClC(Cl)C=1C(=C(C(=C(C1)C)C)C)C FZKQBXSRAKKKJQ-UHFFFAOYSA-N 0.000 description 1
- HIFOOTCDYPUYIK-UHFFFAOYSA-N 2,3-bis(chloromethyl)thiophene Chemical compound ClCC=1C=CSC=1CCl HIFOOTCDYPUYIK-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- SAEBHJAMCVLRAK-UHFFFAOYSA-N 4,6-bis(dodecylsulfanyl)-1,3,4,6-tetramethylcyclohexene Chemical compound CC1C(CC(C(=C1)C)(SCCCCCCCCCCCC)C)(SCCCCCCCCCCCC)C SAEBHJAMCVLRAK-UHFFFAOYSA-N 0.000 description 1
- OILMLWAZYNVPMG-UHFFFAOYSA-N 4-methyl-2-nonylphenol Chemical compound CCCCCCCCCC1=CC(C)=CC=C1O OILMLWAZYNVPMG-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
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 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
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 230000003244 pro-oxidative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent 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
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 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
- 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)
- 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 |
|---|---|---|---|
| NL133211D NL133211C (enrdf_load_stackoverflow) | 1959-06-10 | ||
| NL106397D NL106397C (enrdf_load_stackoverflow) | 1959-06-10 | ||
| NL104900D NL104900C (enrdf_load_stackoverflow) | 1959-06-10 | ||
| NL252465D NL252465A (enrdf_load_stackoverflow) | 1959-06-10 | ||
| NL254604D NL254604A (enrdf_load_stackoverflow) | 1959-06-10 | ||
| NL276505D NL276505A (enrdf_load_stackoverflow) | 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 |
| FR829667A FR1259294A (fr) | 1959-06-10 | 1960-06-10 | Procédé d'amélioration de polyoléfines |
| GB20569/60A GB953447A (en) | 1959-06-10 | 1960-06-10 | Process for improving polyolefines |
| 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 (3)
| 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 |
| DEF0053846 | 1969-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1265409B true DE1265409B (de) | 1968-04-04 |
Family
ID=33101674
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28654A Pending DE1265409B (de) | 1959-06-10 | 1959-06-10 | Verfahren zum Stabilisieren von Polyolefinen |
| DE19691694210 Granted DE1694210B2 (de) | 1959-06-10 | 1969-06-10 | Stabilisierung von polyolefinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691694210 Granted DE1694210B2 (de) | 1959-06-10 | 1969-06-10 | Stabilisierung von polyolefinen |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE1265409B (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963607A (en) * | 1984-10-10 | 1990-10-16 | Pennwalt Corporation | Compositions and methods using organosulfides for stabilization of polyolefins against photodegradation |
| US5070124A (en) * | 1989-10-31 | 1991-12-03 | Atochem North America, Inc. | Sulfide antioxidants for stabilizing crosslinked polyolefins |
| US5081169A (en) * | 1989-10-31 | 1992-01-14 | Atochem North America, Inc. | Organic sulfide stabilized polymeric engineering resins |
| US5284886A (en) * | 1989-10-31 | 1994-02-08 | Elf Atochem North America, Inc. | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
| US5340862A (en) * | 1988-10-07 | 1994-08-23 | Elf Atochem North America, Inc. | Stabilizers for halogen containing polymers |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5096947A (en) * | 1989-10-31 | 1992-03-17 | Atochem North America, Inc. | Organic peroxide and organic sulfide antioxidant composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT202774B (de) * | 1956-11-29 | 1959-04-10 | Western Electric Co | Stabilisierte Mischung |
| AT203211B (de) * | 1956-11-29 | 1959-05-11 | Western Electric Co | Stabilisierte Mischung |
| AT203209B (de) * | 1956-11-29 | 1959-05-11 | Western Electric Co | Stabilisierte Mischung |
-
1959
- 1959-06-10 DE DEF28654A patent/DE1265409B/de active Pending
-
1969
- 1969-06-10 DE DE19691694210 patent/DE1694210B2/de active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT202774B (de) * | 1956-11-29 | 1959-04-10 | Western Electric Co | Stabilisierte Mischung |
| AT203211B (de) * | 1956-11-29 | 1959-05-11 | Western Electric Co | Stabilisierte Mischung |
| AT203209B (de) * | 1956-11-29 | 1959-05-11 | Western Electric Co | Stabilisierte Mischung |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963607A (en) * | 1984-10-10 | 1990-10-16 | Pennwalt Corporation | Compositions and methods using organosulfides for stabilization of polyolefins against photodegradation |
| US5340862A (en) * | 1988-10-07 | 1994-08-23 | Elf Atochem North America, Inc. | Stabilizers for halogen containing polymers |
| US5070124A (en) * | 1989-10-31 | 1991-12-03 | Atochem North America, Inc. | Sulfide antioxidants for stabilizing crosslinked polyolefins |
| US5081169A (en) * | 1989-10-31 | 1992-01-14 | Atochem North America, Inc. | Organic sulfide stabilized polymeric engineering resins |
| US5284886A (en) * | 1989-10-31 | 1994-02-08 | Elf Atochem North America, Inc. | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1694210A1 (de) | 1971-04-22 |
| DE1694210B2 (de) | 1973-04-26 |
| DE1694210C3 (enrdf_load_stackoverflow) | 1974-01-03 |
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