DE1223540B - Formmassen aus Olefinpolymerisaten und einer Stabilisatormischung - Google Patents
Formmassen aus Olefinpolymerisaten und einer StabilisatormischungInfo
- Publication number
- DE1223540B DE1223540B DEF38804A DEF0038804A DE1223540B DE 1223540 B DE1223540 B DE 1223540B DE F38804 A DEF38804 A DE F38804A DE F0038804 A DEF0038804 A DE F0038804A DE 1223540 B DE1223540 B DE 1223540B
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- bis
- acid
- methane
- contain
- 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
- 239000003381 stabilizer Substances 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 title claims description 12
- 238000000465 moulding Methods 0.000 title claims description 8
- 229920000098 polyolefin Polymers 0.000 title claims description 7
- 150000002148 esters Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 24
- -1 aliphatic sulfur compound Chemical class 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000002989 phenols Chemical class 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 229920001021 polysulfide Polymers 0.000 claims description 3
- 239000005077 polysulfide Substances 0.000 claims description 3
- 150000008117 polysulfides Polymers 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 description 11
- XOUGZRFGOBEBSK-UHFFFAOYSA-N OC1=C(C=C(C=C1C)CCCCCCCC)CC1=C(C(=CC(=C1)CCCCCCCC)C)O Chemical compound OC1=C(C=C(C=C1C)CCCCCCCC)CC1=C(C(=CC(=C1)CCCCCCCC)C)O XOUGZRFGOBEBSK-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- XDILCINHTMZTGG-UHFFFAOYSA-N 3-(3-dodecoxy-3-oxopropyl)sulfanylpropanoic acid Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(O)=O XDILCINHTMZTGG-UHFFFAOYSA-N 0.000 description 7
- 239000004743 Polypropylene Substances 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- YNGUXAKJEVGKCF-UHFFFAOYSA-N 2-octadecylsulfanylacetic acid Chemical compound CCCCCCCCCCCCCCCCCCSCC(O)=O YNGUXAKJEVGKCF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000003490 Thiodipropionic acid Substances 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000019303 thiodipropionic acid Nutrition 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- HKYYJZABVBDWJU-UHFFFAOYSA-N 1-(octadecyltrisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSSCCCCCCCCCCCCCCCCCC HKYYJZABVBDWJU-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 1
- KNGHQUFQZLYRKP-UHFFFAOYSA-N 10-butoxy-10-oxodecanoic acid Chemical compound CCCCOC(=O)CCCCCCCCC(O)=O KNGHQUFQZLYRKP-UHFFFAOYSA-N 0.000 description 1
- LSEDQAPMYXQDRC-UHFFFAOYSA-N 11-dodecylsulfanylundecanoic acid Chemical compound CCCCCCCCCCCCSCCCCCCCCCCC(O)=O LSEDQAPMYXQDRC-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- FHTRYIHBMTYTQT-UHFFFAOYSA-N 2,4-dibromo-6-[(3,5-dibromo-2-hydroxyphenyl)methyl]phenol Chemical compound OC1=C(Br)C=C(Br)C=C1CC1=CC(Br)=CC(Br)=C1O FHTRYIHBMTYTQT-UHFFFAOYSA-N 0.000 description 1
- LRWFGWJHJQPCCC-UHFFFAOYSA-N 2-(carboxymethyltrisulfanyl)acetic acid Chemical compound OC(=O)CSSSCC(O)=O LRWFGWJHJQPCCC-UHFFFAOYSA-N 0.000 description 1
- CNGCNMVXDKZYNN-UHFFFAOYSA-N 2-[(2-dodecoxy-2-oxoethyl)disulfanyl]acetic acid Chemical compound CCCCCCCCCCCCOC(=O)CSSCC(=O)O CNGCNMVXDKZYNN-UHFFFAOYSA-N 0.000 description 1
- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 1
- YXNWKYMLMYBZSA-UHFFFAOYSA-N 2-dodecylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCSC(C)C(O)=O YXNWKYMLMYBZSA-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 1
- UGJYGWNQFXIHMS-UHFFFAOYSA-N 4-methoxy-2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound COC1=CC=C(O)C(C(C)(C)CC(C)(C)C)=C1 UGJYGWNQFXIHMS-UHFFFAOYSA-N 0.000 description 1
- UDHHXYYEUWKHMF-UHFFFAOYSA-N 6-butoxy-6-oxohexanoic acid Chemical compound CCCCOC(=O)CCCCC(O)=O UDHHXYYEUWKHMF-UHFFFAOYSA-N 0.000 description 1
- IHLDEDLAZNFOJB-UHFFFAOYSA-N 6-octoxy-6-oxohexanoic acid Chemical compound CCCCCCCCOC(=O)CCCCC(O)=O IHLDEDLAZNFOJB-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 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
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38804A DE1223540B (de) | 1963-01-19 | 1963-01-19 | Formmassen aus Olefinpolymerisaten und einer Stabilisatormischung |
| NL302768D NL302768A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1963-01-19 | 1963-12-30 | |
| FR960645A FR1379565A (fr) | 1963-01-19 | 1964-01-17 | Procédé de stabilisation d'homo-et copolymères d'oléfines |
| AT34464A AT248691B (de) | 1963-01-19 | 1964-01-17 | Stabilisierte Formmassen aus Olefinpolymerisaten |
| BE642713A BE642713A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1963-01-19 | 1964-01-20 | |
| GB246364A GB1043147A (en) | 1963-01-19 | 1964-01-20 | Process for stabilising homopolymers and copolymers of olefines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38804A DE1223540B (de) | 1963-01-19 | 1963-01-19 | Formmassen aus Olefinpolymerisaten und einer Stabilisatormischung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1223540B true DE1223540B (de) | 1966-08-25 |
Family
ID=7097498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF38804A Pending DE1223540B (de) | 1963-01-19 | 1963-01-19 | Formmassen aus Olefinpolymerisaten und einer Stabilisatormischung |
Country Status (5)
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1259294A (fr) * | 1959-06-10 | 1961-04-21 | Hoechst Ag | Procédé d'amélioration de polyoléfines |
| FR1277190A (fr) * | 1960-01-04 | 1961-11-24 | Eastman Kodak Co | Nouvelle composition de poly-alpha-oléfine stabilisée |
-
1963
- 1963-01-19 DE DEF38804A patent/DE1223540B/de active Pending
- 1963-12-30 NL NL302768D patent/NL302768A/xx unknown
-
1964
- 1964-01-17 AT AT34464A patent/AT248691B/de active
- 1964-01-20 BE BE642713A patent/BE642713A/xx unknown
- 1964-01-20 GB GB246364A patent/GB1043147A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1259294A (fr) * | 1959-06-10 | 1961-04-21 | Hoechst Ag | Procédé d'amélioration de polyoléfines |
| FR1277190A (fr) * | 1960-01-04 | 1961-11-24 | Eastman Kodak Co | Nouvelle composition de poly-alpha-oléfine stabilisée |
Also Published As
| Publication number | Publication date |
|---|---|
| BE642713A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-07-22 |
| NL302768A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-05-11 |
| GB1043147A (en) | 1966-09-21 |
| AT248691B (de) | 1966-08-10 |
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