DE2818982C3 - Di-(3,5-dicyclopentyl-4-hydroxybenzyl)sulfid und dessen Verwendung - Google Patents
Di-(3,5-dicyclopentyl-4-hydroxybenzyl)sulfid und dessen VerwendungInfo
- Publication number
- DE2818982C3 DE2818982C3 DE2818982A DE2818982A DE2818982C3 DE 2818982 C3 DE2818982 C3 DE 2818982C3 DE 2818982 A DE2818982 A DE 2818982A DE 2818982 A DE2818982 A DE 2818982A DE 2818982 C3 DE2818982 C3 DE 2818982C3
- Authority
- DE
- Germany
- Prior art keywords
- hydroxybenzyl
- sulfide
- compound
- dicyclopentyl
- samples
- 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
- IFIYLJGEJULLJW-UHFFFAOYSA-N 2,6-dicyclopentyl-4-[(3,5-dicyclopentyl-4-hydroxyphenyl)methylsulfanylmethyl]phenol Chemical compound C1=C(C2CCCC2)C(O)=C(C2CCCC2)C=C1CSCC(C=C(C=1O)C2CCCC2)=CC=1C1CCCC1 IFIYLJGEJULLJW-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000003963 antioxidant agent Substances 0.000 claims description 13
- 229920000098 polyolefin Polymers 0.000 claims description 11
- -1 polypropylene Polymers 0.000 claims description 8
- 239000004743 Polypropylene Substances 0.000 claims description 7
- 230000003078 antioxidant effect Effects 0.000 claims description 7
- 229920001155 polypropylene Polymers 0.000 claims description 7
- 238000012360 testing method Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 5
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QFSOOAFBCXAKJL-UHFFFAOYSA-N 2,6-dicyclohexyl-4-[(3,5-dicyclohexyl-4-hydroxyphenyl)methylsulfanylmethyl]phenol Chemical compound C1=C(C2CCCCC2)C(O)=C(C2CCCCC2)C=C1CSCC(C=C(C=1O)C2CCCCC2)=CC=1C1CCCCC1 QFSOOAFBCXAKJL-UHFFFAOYSA-N 0.000 description 2
- BMTAWHXOXODJBS-UHFFFAOYSA-N 2,6-dicyclopentylphenol Chemical compound OC1=C(C2CCCC2)C=CC=C1C1CCCC1 BMTAWHXOXODJBS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LEJGVIMZYNLICP-UHFFFAOYSA-N [hydroxy(phenyl)methyl]sulfanyl-phenylmethanol Chemical class C=1C=CC=CC=1C(O)SC(O)C1=CC=CC=C1 LEJGVIMZYNLICP-UHFFFAOYSA-N 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- LLFJRLMETQSMGO-UHFFFAOYSA-N butane 2-tert-butyl-5-methylphenol Chemical compound CCCC.CC1=CC=C(C(C)(C)C)C(O)=C1.CC1=CC=C(C(C)(C)C)C(O)=C1.CC1=CC=C(C(C)(C)C)C(O)=C1 LLFJRLMETQSMGO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- JJPZOIJCDNHCJP-UHFFFAOYSA-N dibutyl(sulfanylidene)tin Chemical class CCCC[Sn](=S)CCCC JJPZOIJCDNHCJP-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 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
- 239000000243 solution Substances 0.000 description 1
- AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical class [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio 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
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (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 |
|---|---|---|---|
| US05/792,645 US4104255A (en) | 1977-05-02 | 1977-05-02 | Thioether bis phenolic antioxidants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2818982A1 DE2818982A1 (de) | 1978-11-16 |
| DE2818982B2 DE2818982B2 (de) | 1980-01-17 |
| DE2818982C3 true DE2818982C3 (de) | 1980-09-18 |
Family
ID=25157586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2818982A Expired DE2818982C3 (de) | 1977-05-02 | 1978-04-28 | Di-(3,5-dicyclopentyl-4-hydroxybenzyl)sulfid und dessen Verwendung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4104255A (enExample) |
| JP (1) | JPS5439452A (enExample) |
| CA (1) | CA1078875A (enExample) |
| DE (1) | DE2818982C3 (enExample) |
| FR (1) | FR2389651B3 (enExample) |
| GB (1) | GB1576090A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4330462A (en) * | 1980-05-12 | 1982-05-18 | The Goodyear Tire & Rubber Company | Stabilized polyester composition |
| JPH02247902A (ja) * | 1989-03-17 | 1990-10-03 | Tokyo Electric Co Ltd | 照明器具 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3704326A (en) * | 1970-01-22 | 1972-11-28 | American Cyanamid Co | Hydrocarbon-bridged thiomethylenephenol antioxidants |
| DE2334163A1 (de) * | 1973-07-05 | 1975-01-30 | Bayer Ag | Nicht verfaerbende stabilisierungsmittel |
-
1977
- 1977-05-02 US US05/792,645 patent/US4104255A/en not_active Expired - Lifetime
-
1978
- 1978-04-27 CA CA302,115A patent/CA1078875A/en not_active Expired
- 1978-04-28 FR FR7812673A patent/FR2389651B3/fr not_active Expired
- 1978-04-28 DE DE2818982A patent/DE2818982C3/de not_active Expired
- 1978-05-02 JP JP5325078A patent/JPS5439452A/ja active Granted
- 1978-05-02 GB GB17328/78A patent/GB1576090A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2818982A1 (de) | 1978-11-16 |
| FR2389651B3 (enExample) | 1980-12-05 |
| FR2389651A1 (enExample) | 1978-12-01 |
| US4104255A (en) | 1978-08-01 |
| GB1576090A (en) | 1980-10-01 |
| JPS5439452A (en) | 1979-03-26 |
| JPS5618612B2 (enExample) | 1981-04-30 |
| CA1078875A (en) | 1980-06-03 |
| DE2818982B2 (de) | 1980-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |