DE1297865B - Verfahren zum Stabilisieren von Polyaethylen oder Polypropylen - Google Patents
Verfahren zum Stabilisieren von Polyaethylen oder PolypropylenInfo
- Publication number
- DE1297865B DE1297865B DEI32030A DEI0032030A DE1297865B DE 1297865 B DE1297865 B DE 1297865B DE I32030 A DEI32030 A DE I32030A DE I0032030 A DEI0032030 A DE I0032030A DE 1297865 B DE1297865 B DE 1297865B
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- polypropylene
- weight
- percent
- group
- 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
- -1 polyethylene Polymers 0.000 title claims description 19
- 239000004743 Polypropylene Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 229920001155 polypropylene Polymers 0.000 title claims description 9
- 230000000087 stabilizing effect Effects 0.000 title claims description 7
- 239000004698 Polyethylene Substances 0.000 title claims description 6
- 229920000573 polyethylene Polymers 0.000 title claims description 6
- 229920000642 polymer Polymers 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 5
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DNXFLSLDTGZEFO-UHFFFAOYSA-N 2-tert-butyl-5-methyl-4-[1,4,4-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]phenol Chemical compound C(C)(C)(C)C=1C(=CC(=C(C1)C(CCC(C1=C(C=C(C(=C1)C(C)(C)C)O)C)C1=C(C=C(C(=C1)C(C)(C)C)O)C)C1=C(C=C(C(=C1)C(C)(C)C)O)C)C)O DNXFLSLDTGZEFO-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical group CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KVJHGPAAOUGYJX-UHFFFAOYSA-N 1,1,3,3-tetraethoxypropane Chemical compound CCOC(OCC)CC(OCC)OCC KVJHGPAAOUGYJX-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
- VZJFPIXCMVSTID-UHFFFAOYSA-N 2-ethoxy-3,4-dihydro-2h-pyran Chemical compound CCOC1CCC=CO1 VZJFPIXCMVSTID-UHFFFAOYSA-N 0.000 description 1
- DPGBHRJHIOTIOI-UHFFFAOYSA-N 4-[[4-[bis(4-hydroxy-2,5-dimethylphenyl)methyl]phenyl]-(4-hydroxy-2,5-dimethylphenyl)methyl]-2,5-dimethylphenol Chemical compound C1=C(O)C(C)=CC(C(C=2C=CC(=CC=2)C(C=2C(=CC(O)=C(C)C=2)C)C=2C(=CC(O)=C(C)C=2)C)C=2C(=CC(O)=C(C)C=2)C)=C1C DPGBHRJHIOTIOI-UHFFFAOYSA-N 0.000 description 1
- JXSRRBVHLUJJFC-UHFFFAOYSA-N 7-amino-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound N1=CC(C#N)=C(N)N2N=C(SC)N=C21 JXSRRBVHLUJJFC-UHFFFAOYSA-N 0.000 description 1
- ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- PPRNRQYITYWTIS-UHFFFAOYSA-N dodecyl 4-(4-dodecoxy-4-oxobutyl)sulfanylbutanoate Chemical compound CCCCCCCCCCCCOC(=O)CCCSCCCC(=O)OCCCCCCCCCCCC PPRNRQYITYWTIS-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- JKBYAWVSVVSRIX-UHFFFAOYSA-N octadecyl 2-(1-octadecoxy-1-oxopropan-2-yl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)SC(C)C(=O)OCCCCCCCCCCCCCCCCCC JKBYAWVSVVSRIX-UHFFFAOYSA-N 0.000 description 1
- YVQOUDHDIAUWPN-UHFFFAOYSA-N octadecyl 4-(4-octadecoxy-4-oxobutyl)sulfanylbutanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCSCCCC(=O)OCCCCCCCCCCCCCCCCCC YVQOUDHDIAUWPN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/115—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using acetals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2110161A GB942594A (en) | 1961-06-12 | 1961-06-12 | Polyhydric phenols |
| GB2391461 | 1961-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1297865B true DE1297865B (de) | 1969-06-19 |
Family
ID=26255135
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI32030A Pending DE1297865B (de) | 1961-06-12 | 1962-06-08 | Verfahren zum Stabilisieren von Polyaethylen oder Polypropylen |
| DEJ21906A Pending DE1235582B (de) | 1961-06-12 | 1962-06-08 | Verfahren zum Stabilisieren von Polyaethylen oder Polypropylen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ21906A Pending DE1235582B (de) | 1961-06-12 | 1962-06-08 | Verfahren zum Stabilisieren von Polyaethylen oder Polypropylen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3309337A (en, 2012) |
| BE (1) | BE618841A (en, 2012) |
| DE (2) | DE1297865B (en, 2012) |
| NL (1) | NL279609A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3379875A (en) * | 1966-02-21 | 1968-04-23 | Gen Electric | Stabilized polyphenylene oxide composition |
| US3480581A (en) * | 1966-10-20 | 1969-11-25 | Nat Distillers Chem Corp | Enhancement of resistance of olefin polymers to heat deterioration |
| US3547875A (en) * | 1969-04-11 | 1970-12-15 | Hercules Inc | Polyolefins stabilized with tertiary amine groups-containing compounds |
| US3941850A (en) * | 1972-05-12 | 1976-03-02 | The Quaker Oats Company | α,α,α',α'-TETRAKIS(4-HYDROXY-3,5-DISUBSTITUTED PHENYL)XYLENE |
| IT1060705B (it) * | 1976-05-28 | 1982-08-20 | Montedison Spa | Composizioni polimeriche autoestinguenti |
| US4529556A (en) * | 1983-08-19 | 1985-07-16 | The Dow Chemical Company | Bis((aryl)vinyl)benzenes |
| CN104761703A (zh) * | 2008-03-12 | 2015-07-08 | 陶氏环球技术有限责任公司 | 多酚化合物和包括脂环族基团的环氧树脂及其制备方法 |
| DE102009029050A1 (de) * | 2009-08-31 | 2011-03-03 | Evonik Oxeno Gmbh | Organophosphorverbindungen basierend auf Tetraphenol(TP)-substituierten Strukturen |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3207794A (en) * | 1965-09-21 | Novel process for alkylated bisphenols | ||
| US2482748A (en) * | 1948-05-28 | 1949-09-27 | Dow Chemical Co | 4,4'-isopropylidene bis |
| US2730502A (en) * | 1951-03-31 | 1956-01-10 | Monsanto Chemicals | Antiseptic detergent composition |
| US2862787A (en) * | 1953-05-27 | 1958-12-02 | Paul F Seguin | Process and apparatus for the preparation of semi-conductors from arsenides and phosphides and detectors formed therefrom |
| US2779800A (en) * | 1954-11-30 | 1957-01-29 | Shell Dev | Process for the production of poly-(hydroxyaryl) alkane compounds and new products thereof |
| IT559929A (en, 2012) * | 1955-09-02 | |||
| DE1092026B (de) * | 1958-02-10 | 1960-11-03 | Basf Ag | Verfahren zur Herstellung von antioxydierend wirkenden, mehrkernigen, phenolische Ringe enthaltenden Kondensationsprodukten |
| BE582162A (en, 2012) * | 1958-09-18 | |||
| US3496128A (en) * | 1959-02-05 | 1970-02-17 | Avisun Corp | Stabilization of polypropylene |
| FR1247236A (fr) * | 1959-02-06 | 1960-11-25 | Eastman Kodak Co | Nouvelle composition de polyoléfine stabilisée |
| US3210428A (en) * | 1959-09-04 | 1965-10-05 | Union Carbide Corp | Polyols from 2-hydroxymethyl-1, 3-dioxolane and phenolic compounds |
| US3378518A (en) * | 1959-09-28 | 1968-04-16 | Shell Oil Co | Polypropylene stabilizer with durylene bis-phenols |
| BE597932A (en, 2012) * | 1959-12-09 | |||
| BE593476A (en, 2012) * | 1960-04-14 |
-
0
- NL NL279609D patent/NL279609A/xx unknown
- BE BE618841D patent/BE618841A/xx unknown
-
1962
- 1962-06-07 US US200677A patent/US3309337A/en not_active Expired - Lifetime
- 1962-06-08 DE DEI32030A patent/DE1297865B/de active Pending
- 1962-06-08 DE DEJ21906A patent/DE1235582B/de active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| NL279609A (en, 2012) | |
| US3309337A (en) | 1967-03-14 |
| DE1235582B (de) | 1967-03-02 |
| BE618841A (en, 2012) |
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