DE2261884C3 - Verwendung von Bis-Cdimethy!phenol)sulfiden zum Stabilisieren von chemisch quervernetztem Polyäthylen - Google Patents
Verwendung von Bis-Cdimethy!phenol)sulfiden zum Stabilisieren von chemisch quervernetztem PolyäthylenInfo
- Publication number
- DE2261884C3 DE2261884C3 DE2261884A DE2261884A DE2261884C3 DE 2261884 C3 DE2261884 C3 DE 2261884C3 DE 2261884 A DE2261884 A DE 2261884A DE 2261884 A DE2261884 A DE 2261884A DE 2261884 C3 DE2261884 C3 DE 2261884C3
- Authority
- DE
- Germany
- Prior art keywords
- bis
- polyethylene
- cross
- sulfides
- linked polyethylene
- 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.)
- Expired
Links
- 229920003020 cross-linked polyethylene Polymers 0.000 title claims description 25
- 239000004703 cross-linked polyethylene Substances 0.000 title claims description 24
- 150000003568 thioethers Chemical class 0.000 title description 5
- 239000003381 stabilizer Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 12
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 239000002656 Distearyl thiodipropionate Substances 0.000 claims description 3
- 235000019305 distearyl thiodipropionate Nutrition 0.000 claims description 3
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 claims description 2
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 claims 1
- -1 polyethylene Polymers 0.000 description 13
- 229940126062 Compound A Drugs 0.000 description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 7
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 230000006641 stabilisation Effects 0.000 description 5
- 238000011105 stabilization Methods 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- JPSMTGONABILTP-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)sulfanyl-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(SC=2C=C(C)C(O)=C(C)C=2)=C1 JPSMTGONABILTP-UHFFFAOYSA-N 0.000 description 4
- GULCEJMDIVLNIZ-UHFFFAOYSA-N 5,6-dimethyl-7-thiabicyclo[4.1.0]hepta-2,4-dien-1-ol Chemical class CC=1C2(C(C=CC=1)(O)S2)C GULCEJMDIVLNIZ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000010525 oxidative degradation reaction Methods 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920013716 polyethylene resin Polymers 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IPMAYNUPBOOWDK-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)disulfanyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(SSC=2C=C(C)C(O)=C(C)C=2)=C1 IPMAYNUPBOOWDK-UHFFFAOYSA-N 0.000 description 2
- WCDJAWUZIBZVED-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)trisulfanyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(SSSC=2C=C(C)C(O)=C(C)C=2)=C1 WCDJAWUZIBZVED-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229920001342 Bakelite® Polymers 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000004637 bakelite Substances 0.000 description 2
- 238000010382 chemical cross-linking Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 1
- IEQAUACQFUWVAH-UHFFFAOYSA-N 2,6-dimethyl-4-sulfanylphenol Chemical compound CC1=CC(S)=CC(C)=C1O IEQAUACQFUWVAH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WJTLVJIYLSUQHM-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)tetrasulfanyl]-2,6-dimethylphenol Chemical compound CC=1C=C(C=C(C=1O)C)SSSSC1=CC(=C(C(=C1)C)O)C WJTLVJIYLSUQHM-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 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
- 229920000877 Melamine resin Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 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
- 239000008199 coating composition Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GTIBACHAUHDNPH-JYFOCSDGSA-N n,n'-bis[(e)-benzylideneamino]oxamide Chemical compound C=1C=CC=CC=1/C=N/NC(=O)C(=O)N\N=C\C1=CC=CC=C1 GTIBACHAUHDNPH-JYFOCSDGSA-N 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 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
- C08K5/375—Thiols containing six-membered aromatic rings
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21060371A | 1971-12-21 | 1971-12-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2261884A1 DE2261884A1 (de) | 1973-06-28 |
| DE2261884B2 DE2261884B2 (de) | 1975-02-27 |
| DE2261884C3 true DE2261884C3 (de) | 1975-10-09 |
Family
ID=22783549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2261884A Expired DE2261884C3 (de) | 1971-12-21 | 1972-12-18 | Verwendung von Bis-Cdimethy!phenol)sulfiden zum Stabilisieren von chemisch quervernetztem Polyäthylen |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3763095A (OSRAM) |
| JP (1) | JPS4870756A (OSRAM) |
| AT (1) | AT316150B (OSRAM) |
| AU (1) | AU458550B2 (OSRAM) |
| BE (1) | BE793111A (OSRAM) |
| BR (1) | BR7208996D0 (OSRAM) |
| CA (1) | CA990886A (OSRAM) |
| CH (1) | CH577537A5 (OSRAM) |
| DD (1) | DD101906A5 (OSRAM) |
| DE (1) | DE2261884C3 (OSRAM) |
| FR (1) | FR2164737B1 (OSRAM) |
| GB (1) | GB1369729A (OSRAM) |
| IT (1) | IT972678B (OSRAM) |
| NL (1) | NL7217308A (OSRAM) |
| SE (1) | SE394681B (OSRAM) |
| SU (1) | SU471726A3 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028332A (en) * | 1975-10-14 | 1977-06-07 | Phillips Petroleum Company | Stabilization of cross-linked polyolefins |
| JPS6016976B2 (ja) * | 1976-06-17 | 1985-04-30 | アデカ・ア−ガス化学株式会社 | 安定化された架橋エチレン系重合体組成物 |
| EP0041617A1 (en) * | 1980-05-09 | 1981-12-16 | High Voltage Engineering Corporation | Crosslinked polyolefin compositions stabilized with thiodialkanoate polyesters |
| JPS58171421A (ja) * | 1982-04-02 | 1983-10-08 | Konishiroku Photo Ind Co Ltd | 光学用樹脂組成物及び光学用素子 |
| DE3610595A1 (de) * | 1985-12-06 | 1987-06-11 | Bayer Ag | Verstaerkte polyamide mit verbessertem fliessverhalten |
| US6191230B1 (en) * | 1999-07-22 | 2001-02-20 | Union Carbide Chemicals & Plastics Technology Corporation | Polyethylene crosslinkable composition |
| CN113993719B (zh) * | 2019-06-07 | 2024-01-02 | 住友化学株式会社 | 三硫化物化合物 |
-
0
- BE BE793111D patent/BE793111A/xx unknown
-
1971
- 1971-12-21 US US00210603A patent/US3763095A/en not_active Expired - Lifetime
-
1972
- 1972-11-20 CA CA156,932A patent/CA990886A/en not_active Expired
- 1972-12-12 SE SE7216182A patent/SE394681B/xx unknown
- 1972-12-13 AU AU50011/72A patent/AU458550B2/en not_active Expired
- 1972-12-18 DE DE2261884A patent/DE2261884C3/de not_active Expired
- 1972-12-19 GB GB5865772A patent/GB1369729A/en not_active Expired
- 1972-12-19 NL NL7217308A patent/NL7217308A/xx unknown
- 1972-12-20 SU SU1860156A patent/SU471726A3/ru active
- 1972-12-20 CH CH1852972A patent/CH577537A5/xx not_active IP Right Cessation
- 1972-12-20 DD DD167855A patent/DD101906A5/xx unknown
- 1972-12-20 FR FR7245424A patent/FR2164737B1/fr not_active Expired
- 1972-12-20 IT IT33303/72A patent/IT972678B/it active
- 1972-12-20 AT AT1086572A patent/AT316150B/de not_active IP Right Cessation
- 1972-12-20 BR BR8996/72A patent/BR7208996D0/pt unknown
- 1972-12-21 JP JP47128742A patent/JPS4870756A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SU471726A3 (ru) | 1975-05-25 |
| BR7208996D0 (pt) | 1973-09-25 |
| DE2261884B2 (de) | 1975-02-27 |
| FR2164737B1 (OSRAM) | 1976-04-23 |
| NL7217308A (OSRAM) | 1973-06-25 |
| DD101906A5 (OSRAM) | 1973-11-20 |
| AU5001172A (en) | 1974-06-13 |
| CH577537A5 (OSRAM) | 1976-07-15 |
| CA990886A (en) | 1976-06-08 |
| DE2261884A1 (de) | 1973-06-28 |
| GB1369729A (en) | 1974-10-09 |
| US3763095A (en) | 1973-10-02 |
| IT972678B (it) | 1974-05-31 |
| FR2164737A1 (OSRAM) | 1973-08-03 |
| AU458550B2 (en) | 1975-02-27 |
| JPS4870756A (OSRAM) | 1973-09-25 |
| BE793111A (fr) | 1973-06-21 |
| AT316150B (de) | 1974-06-25 |
| SE394681B (sv) | 1977-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |