DE2459433A1 - Antioxydationsmittel - Google Patents
AntioxydationsmittelInfo
- Publication number
- DE2459433A1 DE2459433A1 DE19742459433 DE2459433A DE2459433A1 DE 2459433 A1 DE2459433 A1 DE 2459433A1 DE 19742459433 DE19742459433 DE 19742459433 DE 2459433 A DE2459433 A DE 2459433A DE 2459433 A1 DE2459433 A1 DE 2459433A1
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- tert
- radicals
- group
- butyl
- 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.)
- Withdrawn
Links
- 239000003963 antioxidant agent Substances 0.000 title claims description 26
- 230000003078 antioxidant effect Effects 0.000 title claims description 15
- -1 alkenyl radicals Chemical class 0.000 claims description 81
- 229920000642 polymer Polymers 0.000 claims description 38
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 34
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 claims description 23
- 150000001336 alkenes Chemical class 0.000 claims description 20
- 150000004820 halides Chemical class 0.000 claims description 18
- 239000002168 alkylating agent Substances 0.000 claims description 17
- 229940100198 alkylating agent Drugs 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- BWICWBUSAUOHAM-UHFFFAOYSA-N 4-tert-butylsulfanylphenol Chemical compound CC(C)(C)SC1=CC=C(O)C=C1 BWICWBUSAUOHAM-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001400 nonyl 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])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000010525 oxidative degradation reaction Methods 0.000 claims description 2
- 125000000913 palmityl 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])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 235000006708 antioxidants Nutrition 0.000 description 23
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000376 reactant Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical class OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000005804 alkylation reaction Methods 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000002530 phenolic antioxidant Substances 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- 230000029936 alkylation Effects 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 235000019445 benzyl alcohol Nutrition 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- CZGAOHSMVSIJJZ-UHFFFAOYSA-N 2,4-dimethyl-1-heptene Chemical compound CCCC(C)CC(C)=C CZGAOHSMVSIJJZ-UHFFFAOYSA-N 0.000 description 2
- QZQLEVJVXYLVPQ-UHFFFAOYSA-N 2,6-ditert-butyl-4-tert-butylsulfanylphenol Chemical compound CC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 QZQLEVJVXYLVPQ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 2
- KJHZKRXYOKZWOA-UHFFFAOYSA-N 4-butan-2-ylsulfanylphenol Chemical compound CCC(C)SC1=CC=C(O)C=C1 KJHZKRXYOKZWOA-UHFFFAOYSA-N 0.000 description 2
- FMIHFTDZEIOVQX-UHFFFAOYSA-N 4-ethylsulfanylphenol Chemical compound CCSC1=CC=C(O)C=C1 FMIHFTDZEIOVQX-UHFFFAOYSA-N 0.000 description 2
- KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 description 2
- ULDJYJVEDGWULA-UHFFFAOYSA-N 4-nonylsulfanylphenol Chemical compound CCCCCCCCCSC1=CC=C(O)C=C1 ULDJYJVEDGWULA-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000003938 benzyl alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000004149 thio group Chemical group *S* 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- CIUVMHOEIOLVBU-UHFFFAOYSA-N 1-(bromomethyl)-2,4-diethylbenzene Chemical compound CCC1=CC=C(CBr)C(CC)=C1 CIUVMHOEIOLVBU-UHFFFAOYSA-N 0.000 description 1
- GWESGLGUMMNXDU-UHFFFAOYSA-N 1-bromononadecane Chemical compound CCCCCCCCCCCCCCCCCCCBr GWESGLGUMMNXDU-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- CNCGVWVSYGCFMD-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylsulfanylphenol Chemical compound CSC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 CNCGVWVSYGCFMD-UHFFFAOYSA-N 0.000 description 1
- SOOARYARZPXNAL-UHFFFAOYSA-N 2-(Methylthio)phenol Chemical compound CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 description 1
- OWZPCVGKLYOVLV-UHFFFAOYSA-N 2-benzylsulfanylphenol Chemical compound OC1=CC=CC=C1SCC1=CC=CC=C1 OWZPCVGKLYOVLV-UHFFFAOYSA-N 0.000 description 1
- NEBYCXAKZCQWAW-UHFFFAOYSA-N 2-bromohexane Chemical compound CCCCC(C)Br NEBYCXAKZCQWAW-UHFFFAOYSA-N 0.000 description 1
- RZJRZIHTKWZCQI-UHFFFAOYSA-N 2-butan-2-ylsulfanylphenol Chemical compound CCC(C)SC1=CC=CC=C1O RZJRZIHTKWZCQI-UHFFFAOYSA-N 0.000 description 1
- IUBAHWJEUCYURE-UHFFFAOYSA-N 2-butylsulfanylphenol Chemical compound CCCCSC1=CC=CC=C1O IUBAHWJEUCYURE-UHFFFAOYSA-N 0.000 description 1
- BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 1
- CILPECKAVHJPBO-UHFFFAOYSA-N 2-dodecylsulfanylphenol Chemical compound CCCCCCCCCCCCSC1=CC=CC=C1O CILPECKAVHJPBO-UHFFFAOYSA-N 0.000 description 1
- ASTUDXATKSODHV-UHFFFAOYSA-N 2-heptylsulfanylphenol Chemical compound CCCCCCCSC1=CC=CC=C1O ASTUDXATKSODHV-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- UCVORQZRHHHDPS-UHFFFAOYSA-N 2-tert-butyl-4-methyl-6-sulfanylphenol Chemical compound CC1=CC(S)=C(O)C(C(C)(C)C)=C1 UCVORQZRHHHDPS-UHFFFAOYSA-N 0.000 description 1
- UXMOBLWTCSCLLR-UHFFFAOYSA-N 4-benzylsulfanylphenol Chemical compound C1=CC(O)=CC=C1SCC1=CC=CC=C1 UXMOBLWTCSCLLR-UHFFFAOYSA-N 0.000 description 1
- PKUQXIYIBNRPTF-UHFFFAOYSA-N 4-butylsulfanylphenol Chemical compound CCCCSC1=CC=C(O)C=C1 PKUQXIYIBNRPTF-UHFFFAOYSA-N 0.000 description 1
- WDNUSOXJBMYPND-UHFFFAOYSA-N 4-cyclohexylsulfanyl-3-methylphenol Chemical compound CC1=CC(O)=CC=C1SC1CCCCC1 WDNUSOXJBMYPND-UHFFFAOYSA-N 0.000 description 1
- YPOAYIJFILMVRB-UHFFFAOYSA-N 4-cyclohexylsulfanylphenol Chemical compound C1=CC(O)=CC=C1SC1CCCCC1 YPOAYIJFILMVRB-UHFFFAOYSA-N 0.000 description 1
- PIFZQGAOQDAACC-UHFFFAOYSA-N 4-hexylsulfanylphenol Chemical compound CCCCCCSC1=CC=C(O)C=C1 PIFZQGAOQDAACC-UHFFFAOYSA-N 0.000 description 1
- LBKISISWVPNGGC-UHFFFAOYSA-N 4-prop-2-enylsulfanylphenol Chemical compound OC1=CC=C(SCC=C)C=C1 LBKISISWVPNGGC-UHFFFAOYSA-N 0.000 description 1
- OZTBMXXFEGZXHX-UHFFFAOYSA-N 4-tetradecylsulfanylphenol Chemical compound CCCCCCCCCCCCCCSC1=CC=C(O)C=C1 OZTBMXXFEGZXHX-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 241001481828 Glyptocephalus cynoglossus Species 0.000 description 1
- 239000000899 Gutta-Percha Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 240000000342 Palaquium gutta Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical class Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 244000001591 balata Species 0.000 description 1
- 235000016302 balata Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229920000588 gutta-percha Polymers 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
- C08K5/375—Thiols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
- C09K15/14—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen containing a phenol or quinone moiety
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/925—Natural rubber compositions having nonreactive materials, i.e. NRM, other than: carbon, silicon dioxide, glass titanium dioxide, water, hydrocarbon or halohydrocarbon
- Y10S524/929—Natural rubber broadly disclosed, nonclaimed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/436,751 US4128530A (en) | 1974-01-25 | 1974-01-25 | Mercapto phenolic and alkylthio phenolic antioxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2459433A1 true DE2459433A1 (de) | 1975-07-31 |
Family
ID=23733682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742459433 Withdrawn DE2459433A1 (de) | 1974-01-25 | 1974-12-16 | Antioxydationsmittel |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4128530A (en, 2012) |
| JP (1) | JPS5756950B2 (en, 2012) |
| BE (1) | BE824376A (en, 2012) |
| BR (1) | BR7500195A (en, 2012) |
| CA (1) | CA1067646A (en, 2012) |
| DE (1) | DE2459433A1 (en, 2012) |
| FR (1) | FR2259131B1 (en, 2012) |
| GB (2) | GB1494350A (en, 2012) |
| IT (1) | IT1026354B (en, 2012) |
| LU (1) | LU71665A1 (en, 2012) |
| ZA (1) | ZA747905B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0293895A1 (en) * | 1987-06-05 | 1988-12-07 | G.D. Searle & Co. | Phenolic thioethers as inhibitors of 5-lipoxygenase |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308199A (en) * | 1980-01-17 | 1981-12-29 | The Goodyear Tire & Rubber Company | Mercaptophenol derivatives as age resisters for polymers |
| USRE32618E (en) * | 1980-01-17 | 1988-03-01 | The Goodyear Tire & Rubber Company | Mercaptophenol derivatives as age resisters for polymers |
| US4330462A (en) * | 1980-05-12 | 1982-05-18 | The Goodyear Tire & Rubber Company | Stabilized polyester composition |
| USRE31771E (en) * | 1980-07-28 | 1984-12-18 | Ethyl Corporation | Process for the preparation of ortho-(hydrocarbylthio)-phenols |
| US4558083A (en) * | 1981-02-26 | 1985-12-10 | Morton Thiokol, Inc. | Stabilizer compositions and polymers containing same |
| US4701486A (en) * | 1981-02-26 | 1987-10-20 | Morton Thiokol, Inc. | Stabilizer compositions for PVC resins |
| US4576984A (en) * | 1982-02-04 | 1986-03-18 | Morton Thiokol, Inc. | Stabilizer compositions for PVC resins |
| US4533753A (en) * | 1982-09-30 | 1985-08-06 | Ethyl Corporation | (Hydrocarbylthio)phenols and their preparation |
| US4602113A (en) * | 1983-04-12 | 1986-07-22 | Ethyl Corporation | (Hydrocarbylthio) phenols and their preparation |
| US4508865A (en) * | 1983-07-29 | 1985-04-02 | Ciba-Geigy Corporation | S-(4-Hydroxyphenyl)thiocarboxylic ester antioxidants |
| US4552926A (en) * | 1983-09-26 | 1985-11-12 | Ciba-Geigy Corporation | Substituted 4-hydroxyphenylthio benzoate stabilizers |
| US4611023A (en) * | 1984-02-03 | 1986-09-09 | Ciba-Geigy Corporation | Di-(substituted hydroxyphenylthio) alkane and cycloalkane stabilizers and stabilized compositions |
| US4835190A (en) * | 1987-06-05 | 1989-05-30 | G. D. Searle & Co. | Phenolic thioethers as inhbitors of 5-lipoxygenase |
| GB8905747D0 (en) * | 1989-03-13 | 1989-04-26 | Secr Defence | Pyrotechnic material |
| JP5017093B2 (ja) * | 2005-03-02 | 2012-09-05 | シーシーアイ株式会社 | 燃料電池用冷却液組成物 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU283565A1 (ru) * | ПАТЕЯТКО- ,р.!1ли1Ей[ЩЧЕС1{АЯ ^^ БИБЛИОТЕКА | |||
| NL6715879A (en, 2012) * | 1966-11-30 | 1968-05-31 | ||
| GB1136639A (en) * | 1966-12-29 | 1968-12-11 | Novo Gama Sa | Dolls |
| US3468961A (en) * | 1967-09-11 | 1969-09-23 | Hooker Chemical Corp | Process for the preparation of orthomercaptophenols |
| US3553163A (en) * | 1967-08-31 | 1971-01-05 | Goodyear Tire & Rubber | Stabilizers for polymers |
| US3683054A (en) * | 1968-11-29 | 1972-08-08 | Ethyl Corp | S{8 -3,5(or 6)-dihydrocarbyl-4-hydroxy-phenyl{9 {11 phosphates or phosphites |
| JPH04214532A (ja) * | 1990-12-12 | 1992-08-05 | Matsushita Electric Ind Co Ltd | 液晶表示装置 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3103500A (en) * | 1963-09-10 | Polyolefins heat stabilized with z-alkyl- | ||
| US2549118A (en) * | 1949-10-05 | 1951-04-17 | Us Rubber Co | Vulcanized rubber and method of preserving same |
| DE842429C (de) | 1950-09-08 | 1952-06-26 | Junghans Geb Ag | Elastische Wellenlagerung fuer feinmechanische Getriebe |
| US2810765A (en) * | 1956-04-12 | 1957-10-22 | Consolidation Coal Co | 4-thiol-6-t-butyl-ortho-cresol and method of preparation |
| US3565857A (en) * | 1967-08-31 | 1971-02-23 | Goodyear Tire & Rubber | Age resisters for polymers |
| US3657370A (en) * | 1970-01-02 | 1972-04-18 | Monsanto Co | Process for the preparation of ditertiary-aromatic hydrocarbons |
| US3714264A (en) * | 1970-08-17 | 1973-01-30 | Goodyear Tire & Rubber | Alylation product of 4(methylthio) phenol |
| AT312075B (de) * | 1971-08-16 | 1973-12-10 | Karl Neumayer Erzeugung | Verfahren und Vorrichtung zur Herstellung einer Litze aus Metalldrähten, wobei die Drähte mit einer galvanisch aufgebrachten Oberflächenbeschichtung eines anderen Metalles versehen sind |
| US3751483A (en) * | 1971-10-13 | 1973-08-07 | Crown Zellerbach Corp | Phenolic thioethers and process for preparing same |
| JPS496245A (en, 2012) * | 1972-05-10 | 1974-01-19 | ||
| JPS49124038A (en, 2012) * | 1973-03-14 | 1974-11-27 |
-
1974
- 1974-01-25 US US05/436,751 patent/US4128530A/en not_active Expired - Lifetime
- 1974-12-06 CA CA215,407A patent/CA1067646A/en not_active Expired
- 1974-12-11 ZA ZA00747905A patent/ZA747905B/xx unknown
- 1974-12-16 GB GB30243/77A patent/GB1494350A/en not_active Expired
- 1974-12-16 DE DE19742459433 patent/DE2459433A1/de not_active Withdrawn
- 1974-12-16 GB GB54167/74A patent/GB1494349A/en not_active Expired
-
1975
- 1975-01-13 BR BR195/75A patent/BR7500195A/pt unknown
- 1975-01-13 FR FR7500828A patent/FR2259131B1/fr not_active Expired
- 1975-01-14 BE BE152372A patent/BE824376A/xx not_active IP Right Cessation
- 1975-01-15 IT IT47694/75A patent/IT1026354B/it active
- 1975-01-17 LU LU71665A patent/LU71665A1/xx unknown
- 1975-01-24 JP JP50010375A patent/JPS5756950B2/ja not_active Expired
-
1978
- 1978-02-22 US US05/879,842 patent/US4143076A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU283565A1 (ru) * | ПАТЕЯТКО- ,р.!1ли1Ей[ЩЧЕС1{АЯ ^^ БИБЛИОТЕКА | |||
| NL6715879A (en, 2012) * | 1966-11-30 | 1968-05-31 | ||
| GB1136639A (en) * | 1966-12-29 | 1968-12-11 | Novo Gama Sa | Dolls |
| US3553163A (en) * | 1967-08-31 | 1971-01-05 | Goodyear Tire & Rubber | Stabilizers for polymers |
| US3468961A (en) * | 1967-09-11 | 1969-09-23 | Hooker Chemical Corp | Process for the preparation of orthomercaptophenols |
| US3683054A (en) * | 1968-11-29 | 1972-08-08 | Ethyl Corp | S{8 -3,5(or 6)-dihydrocarbyl-4-hydroxy-phenyl{9 {11 phosphates or phosphites |
| JPH04214532A (ja) * | 1990-12-12 | 1992-08-05 | Matsushita Electric Ind Co Ltd | 液晶表示装置 |
Non-Patent Citations (8)
| Title |
|---|
| Ann. 645, 1961, 79 f * |
| Ann. 677, 1964, 59-64 * |
| J. Am. Chem. Soc. 46, 1924, 2334 * |
| J. med. Chem. 13, 1970, 722-725 * |
| J. med. Chem. 15, 1972, 795-802 * |
| J. Org. Chem. 24, 1959, 1598-1600 * |
| J. pr. 41, 1890, 195 * |
| Rec. Trav. 31, 1912, 30 f * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0293895A1 (en) * | 1987-06-05 | 1988-12-07 | G.D. Searle & Co. | Phenolic thioethers as inhibitors of 5-lipoxygenase |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1067646A (en) | 1979-12-04 |
| JPS50108185A (en, 2012) | 1975-08-26 |
| ZA747905B (en) | 1976-01-28 |
| GB1494349A (en) | 1977-12-07 |
| BE824376A (fr) | 1975-05-02 |
| GB1494350A (en) | 1977-12-07 |
| AU7626974A (en) | 1976-06-17 |
| FR2259131B1 (en, 2012) | 1978-03-17 |
| US4128530A (en) | 1978-12-05 |
| US4143076A (en) | 1979-03-06 |
| LU71665A1 (en, 2012) | 1975-06-24 |
| FR2259131A1 (en, 2012) | 1975-08-22 |
| IT1026354B (it) | 1978-09-20 |
| JPS5756950B2 (en, 2012) | 1982-12-02 |
| BR7500195A (pt) | 1975-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2459433A1 (de) | Antioxydationsmittel | |
| DE1495985B1 (de) | Verfahren zur herstellung von polyaddukten | |
| DE2617180A1 (de) | Substituierte sulfonamidderivate von gehinderten phenolen und damit stabilisierte mischungen | |
| DE3512057A1 (de) | Verfahren zur isomerisierung von olefinen | |
| DE1915684A1 (de) | Polymerisate von Cyclopenten | |
| DE1694359B2 (de) | Mischung auf der Basis von Kautschuk und einem klebrigmachenden Harz | |
| DE3883029T2 (de) | Autosynergistisches phenolisches antioxydierendes Reaktionsprodukt. | |
| DE69122323T2 (de) | Polymerisierbares Antioxidans und gebundenes Antioxidans enthaltende Olefinpolymere | |
| DE68920604T2 (de) | Organothioäthylalkohole als Synergisten für Antidegradantien. | |
| DE2039356C2 (de) | Verfahren zur Stabilisierung von Polyolefinen und hierzu verwendbare cycloaliphatische Sulfide | |
| DE2600204C2 (de) | Alkyliertes aralkyliertes Phenol und dessen Verwendung | |
| DE2447971A1 (de) | Antioxidationsmittel | |
| DE3887546T2 (de) | Methylen-bis(alkylsulfide) als synergistische Antioxydationsmittel in Kautschuk. | |
| DE3707434A1 (de) | Polyisoprene mit einem hohen anteil von 1,2- und 3,4-struktureinheiten, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2201538A1 (de) | Verfahren zur Verbesserung der Farbe von phenolischen Antioxidationsmitteln | |
| EP0432406B1 (de) | Polysulfidderivate, Verfahren zu ihrer Herstellung und Verwendung zur Vernetzung von Natur- und Synthesekautschuken | |
| DE2363647A1 (de) | Verfahren zur herstellung organischer sulfidverbindungen | |
| DE69206369T2 (de) | Flüssige Peroxidzusammensetzungen. | |
| CH640493A5 (de) | Verfahren zur herstellung von dicyclopentylen (2,2'-bis(4-alkyl-6-t-butylphenolen)). | |
| DE1493787A1 (de) | Verfahren zum Herstellen eines Alterungsstabilisators fuer oxidierbare organische Produkte und insbesondere Kautschuk | |
| DE69307591T2 (de) | Verfahren zur Herstellung von vernetzten Olefinpolymeren | |
| EP0222288A2 (de) | Elastomere Masse aus Polychloropren-Sol und Polychloropren-Gel und ihre Herstellung | |
| DE2150095A1 (de) | Phenolverbindungen | |
| DE1643559B1 (de) | Substituierte 2-Hydroxybenzyl-4-hydroxyphenyl-sulfide und ihre Verwendung | |
| US4308199A (en) | Mercaptophenol derivatives as age resisters for polymers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification | ||
| 8126 | Change of the secondary classification | ||
| 8130 | Withdrawal |