JPH0520419B2 - - Google Patents
Info
- Publication number
- JPH0520419B2 JPH0520419B2 JP4269483A JP4269483A JPH0520419B2 JP H0520419 B2 JPH0520419 B2 JP H0520419B2 JP 4269483 A JP4269483 A JP 4269483A JP 4269483 A JP4269483 A JP 4269483A JP H0520419 B2 JPH0520419 B2 JP H0520419B2
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- butyl
- tert
- hydroxy
- methylphenyl
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 30
- -1 1,3 , 5-benzenetriyl Chemical group 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 12
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 description 11
- 230000003078 antioxidant effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- CKFORTVTZVJLKQ-UHFFFAOYSA-N 2-tert-butyl-6-(3-hydroxypropyl)-4-methylphenol Chemical compound CC1=CC(CCCO)=C(O)C(C(C)(C)C)=C1 CKFORTVTZVJLKQ-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 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 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 229920001059 synthetic polymer Polymers 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- WDHFZDCLBDGCGJ-UHFFFAOYSA-N tris[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propyl] benzene-1,3,5-tricarboxylate Chemical compound CC(C)(C)C1=CC(C)=CC(CCCOC(=O)C=2C=C(C=C(C=2)C(=O)OCCCC=2C(=C(C=C(C)C=2)C(C)(C)C)O)C(=O)OCCCC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O WDHFZDCLBDGCGJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-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
- YZBHSZNVZPHSFN-UHFFFAOYSA-N 3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCC1=CC(C)=CC(C(C)(C)C)=C1O YZBHSZNVZPHSFN-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 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 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- WLJVNTCWHIRURA-UHFFFAOYSA-M pimelate(1-) Chemical compound OC(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-M 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical group [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical class O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 1
- RGCHNYAILFZUPL-UHFFFAOYSA-N trimethyl benzene-1,3,5-tricarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(C(=O)OC)=C1 RGCHNYAILFZUPL-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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BACKGROUND OF THE INVENTION The present invention relates to novel phenol derivatives.
The compounds of the present invention are effective in preventing the oxidation of various organic substances. Since organic substances such as natural polymers, synthetic polymers, oils and fats, lubricating oils, and hydraulic oils are subject to oxidation and their usefulness is reduced, various antioxidants have been devised and added to these organic substances. For example, hindered phenols, organic sulfur compounds, organic phosphorous compounds,
It is known that aromatic amines and the like are effective when used alone or in combination. Specific examples of derivatives having a hindered phenol skeleton include Japanese Patent Publications Nos. 33-2488, 38-17164, and 42
-9651 The compounds described in each publication are known and are currently in practical use. Japanese Patent Publication No. 57-59835
No. 57-128656 and No. 57-128679 also propose hindered phenol derivatives as deterioration inhibitors for organic substances. however,
These conventional antioxidant compounds are not always fully effective under very harsh conditions. SUMMARY OF THE INVENTION The present invention aims to provide a solution to the above points and attempts to achieve this objective by means of specific phenol derivatives. The phenol derivative according to the invention is therefore a compound of formula [ ]. However, R 1 is a secondary or tertiary chain or cyclic hydrocarbon residue having 3 to 8 carbon atoms, R 2 is an alkyl group having 1 to 12 carbon atoms, and R 3 is an alkylene group having 1 to 4 carbon atoms. group, an organic group selected from the group of compounds consisting of the following (a) to (f), and n is an integer of 1 to 8, respectively. (a) C 1 to 17 alkyl, (b) C 1 to 10 alkylene, (c) C 3 to 10 trivalent to octavalent aliphatic hydrocarbon residue, (d) phenyl, (e) 1,3 , 5-benzenetriyl, (f) 1,2,4,5-benzenetetryl, (g) -R a -S-R b - where R a and R b are each C 1 to 10 alkylene (H) R c (-S-R d )- p where R c is a divalent or trivalent cyclic saturated hydrocarbon residue, p is 2 or 3, and R d is C 1 to Ten
(Li) indicates the alkylene of
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âïŒïŒãããã³[Formula] Here, R s represents C 1-10 alkylene. The compound of formula [] is effective in preventing the oxidation of various organic substances, but it cannot be exposed to severe oxidizing conditions during molding and product use. Synthetic polymeric materials that are often exposed, such as polyolefins such as polyethylene, polypropylene, ethylene-propylene copolymer, polystyrene, polyvinyl chloride, ABS
Effective in preventing oxidation of resins, etc. Detailed Description of the Invention Compound Definition The phenol derivative according to the present invention is represented by the above formula []. The groups R 1 to R 3 are not only limited individually, but also limited in the bonding position to the phenol core. The group R 1 is a secondary or tertiary hydrocarbon residue having 3 to 8 carbon atoms. Specifically, for example, isopropyl, 1-methylpropyl, tert-butyl,
and linear structures such as pentyl, hexyl, heptyl and octyl of secondary to tertiary structure, 1-methylcyclohexyl, 1-
There are those with a cyclic structure such as phenylethyl and norbornyl. Most preferred among these are tert-butyl and 1-methylcyclohexyl. The group R 2 is an alkyl group having 1 to 12 carbon atoms.
Specific examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl. R 2 is preferably methyl because it has a large antioxidant effect during molding. The group R3 is alkylene having 1 to 4 carbon atoms.
Specifically, for example, there are methylene, ethylene, trimethylene, propylene, tetramethylene, and ethylethylene (these examples also apply to other alkylenes described later). Most preferred among these is ethylene. Z is an n-valent organic group. One group of Z is hydrocarbon residues. Specifically, for example, alkyl of about C1 to C17 , alkylene of about C1 to C10 , C3 to about
C 10 or so trivalent to octavalent aliphatic hydrocarbon residues (e.g. 1,2,3-propanetriyl), phenyl,
1,3,5-benzenetriyl and 1,2,
There is 4,5-benzenetetryl. Another group of Z includes sulfur atoms. Specifically, for example, -R a -S-R b - (R a and R b are each C1 to C10 alkylene. Preferably R a = R b = -CH 2 CH 2 -), R c (âSâR d )â p
(R c is a divalent or trivalent cyclic saturated hydrocarbon residue (e.g., 2 (or 3), 5 (or 6)-bicyclo[2,2,1]heptanediyl, 3 (or 4 or 5), 8 (or 9)-tricyclo[5,
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ã«ãMSã¹ãã¯ãã«ãããã®æ§é ã確èªããã[Formula] (R w is C 1 to C 10 alkylene). Another group of Z includes nitrogen atoms.
Specifically, for example, N(-R e ) -3 (three R e are
Each is a C1 to C10 alkylene (preferably both -CH2- ). Another group of Z includes oxygen atoms.
Specifically, for example, âR f âOâR g â(R f and
R g is a C 1 to C 10 alkylene (preferably both -CH 2 -)), C (-R h -O-R i ) - 4 (each of four
R h and R i are each C 1 to C 10 alkylene (preferably both R h is -CH 2 - and R i is both -
CH 2 CH 2 â)), and another group of Z have at least two of a sulfur atom, a nitrogen atom, and an oxygen atom. Specifically, for example, (R m to R p are C 1 to C 10 alkylene), and ( Rs is C1 - C10 alkylene). The most preferred of these are It is. Some specific examples of these compounds are:
It is as follows. The numbers assigned to these compounds will be used to designate these compounds in the Examples below. Bis[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propyl]=3,3'-thiodipropionate Bis[3-(3-tert-butyl-5-ethyl-2
-hydroxyphenyl)propyl] = 3,3'-thiodipropionate Bis[3-(3-tert-butyl-2-hydroxy-5-isopropylphenyl)propyl] = 3,
3â²-thiodipropionate Bis[3-(3,5-di-tert-butyl-2-hydroxyphenyl)propyl]=3,3'-thiodipropionate Bis[3-(3-tert-butyl-2-hydroxy-5-nonylphenyl)propyl]=3,3'-thiodipropionate Bis[3-(3-tert-butyl-2-hydroxy-5-dodecylphenyl)propyl] = 3,3'-
Thiodipropionate Bis[3-(2-hydroxy-3-isopropyl-5-methylphenyl)propyl] = 3,3'-
Thiodipropionate Bis[3-[2-hydroxy-3-(1-methylcyclohexyl)-5-methylphenyl)]propyl] = 3,3'-thiodipropionate Bis[2-(3-tert-butyl-2-hydroxy-5-methylphenyl)ethyl]=3,3'-thiodipropionate Bis[4-(3-tert-butyl-2-hydroxy-5-methylphenyl)butyl]=3,3'-thiodipropionate Bis[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propyl]=heptanedioate Bis[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propoxycarbonylmethyl]ether 3-(3-tert-butyl-2-hydroxy-5-
methylphenyl)propyl octadecanoate 3-(3-tert-butyl-2-hydroxy-5-
methylphenyl)propyl]=3-[3-[2-
(3,5-di-tert-butyl-4-hydroxyphenyl)ethylcarbonyloxy]propylthio]
Propionate Tris[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propoxycarbonylmethyl]amine Tris[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propyl] = 1,2,
3-propanetricarboxylate Tris[3-(3,5-di-tert-butyl-2-
Hydroxyphenyl)propyl]=1,2,3-
Propanetricarboxylate Tetrakis[2-[3-(3-tert-butyl-2-
hydroxy-5-methylphenyl)propoxycarbonyl]ethyloxymethyl]methane Tetrakis[2-[3-(3,5-di-tert-butyl-2-hydroxyphenyl)propoxycarbonyl]ethyloxymethyl]methane 1,3,5-Tris[3-(3-tert-butyl-
2-Hydroxy-5-methylphenyl)propoxycarbonyl]benzene 1,2,4,5-tetrakis[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)
propoxycarbonyl]benzene 1,3,5-Tris[3-[2-[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propoxycarbonyl]ethylthio]propyl]-1,3,5-triazine-2,4 ,6(1H,
3H, 5H) â trion 1,3,5-Tris[3-[2-[3-[2-hydroxy-3-(1-methylcyclohexyl)-5]
-methylphenyl]propyloxycarbonyl]
Ethylthio]propyl]-1,3-5-triazine-2,4,6(1H,3H,5H)-trione 1,3,5-tris [3-[2-[3-[3,5
-di-tert-butyl-2-hydroxyphenyl)propoxycarbonyl]ethylthio]propyl]-
1,3,5-triazine-2,4,6 (1H,3H,
5H) â Trion 2 (or 3), 5 (or 6)-bis[2-[3
-(3-tert-butyl-2-hydroxy-5-methylphenyl)propoxycarbonyl]ethylthio]bicyclo[2,2,1]heptane 3 (or 4 or 5), 8 (or 9)-bis[2-[3-(3-tert-butyl-2-hydroxy-
5-methylphenyl)propoxycarbonyl]ethylthio]tricyclo[5,2,1,0 2,6 ]decane Tris[2-[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propoxycarbonyl]ethylthio]cyclododecane Tris[2-[3-(3,5-di-tert-butyl-
2-Hydroxyphenyl)propoxycarbonyl]ethylthio]cyclododecane Tetrakis[3-[4-[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propoxycarbonyl]butylthio]propionyloxymethyl]methane Tetrakis[3-[4-[3-(3,5-di-tert-butyl-2-hydroxy-5-methylphenyl)propoxycarbonyl]butylthio]propionyloxymethyl]methane Bis[2-[2,4-bis[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propoxycarbonyl]butylthio]ethyl]ether Bis[2,4-bis[3-(3-tert-butyl-
2-Hydroxy-5-methylphenyl)propoxycarbonyl]butyl]sulfide Dipentaerythritol and 3-[4-[3-(3,
5-di-tert-butyl-2-hydroxyphenyl)
Hexakis ester with propoxycarbonyl]butylthio]propionic acid Satsucrose and 3-[4-[3-(3,5-di-
Synthesis of octakis ester compound with tert-butyl-2-hydroxyphenyl)propoxycarbonyl]butylthio]propionic acid The compound of the present invention can be prepared by any method suitable for forming or introducing a specific group or bond. can be synthesized. One specific example of such a method consists of reacting an alcohol compound of formula [] with a carboxylic acid compound of formula [] under ester-forming conditions. (R 1 , R 2 , R 3 , Z and n are as defined for the compound of formula []) Here, "to react under ester-forming conditions" means that both compounds are preferably reacted under the esterification catalyst. Either the carboxylic acid compounds are reacted directly in the form of their active derivatives such as acid halides, acid anhydrides or acid lower alkyl esters, or the alcohol compounds are reacted in the form of their active derivatives such as lower carboxylic esters. Do you want me to do it?
means. Specifically, for example, when a carboxylic acid is used, the esterification reaction is carried out in an inert solvent in the presence of an acid catalyst. As the acid catalyst, sulfuric acid, paratoluenesulfonic acid, strongly acidic ion exchange resin, etc. are used. As the reaction solvent, aliphatic hydrocarbons such as n-pentane, n-hexane, and n-heptane, alicyclic hydrocarbons such as cyclohexane, and aromatic hydrocarbons such as benzene, toluene, and xylene are used. To increase the rate of ester production,
A method is adopted in which water produced by the reaction is removed from the reaction system by azeotropy with an inert solvent. When using an acid lower alkyl ester, the transesterification reaction is suitably carried out by heating in an inert organic solvent in the presence of a strong base while removing the lower alcohol produced outside the reaction system. As the reaction solvent, amides such as dimethylformamide, dimethylacetamide, and hexamethylphosphonamide, and organic solvents such as toluene and dimethyl sulfoxide can be used. Examples of strong bases include:
sodium methylate, sodium ethylate,
Strongly basic alkali metal compounds such as potassium hydroxide, sodium amide, or titanic acid compounds such as tetraisopropyl or tetrabutyl titanate are preferably used. The reaction is usually 30 to
It proceeds preferably by heating to 180°C. When using an acid halide, the reaction is carried out in an inert solvent in the presence of a dehydrohalogenating agent at 0 to 130°C.
Preferably, the reaction is carried out at 20 to 70°C. As the dehydrohalogenation agent, pyridine, triethylamine, dimethylaniline, tetramethylurea, etc. are used. Examples of inert solvents include aliphatic hydrocarbons such as n-hexane and n-heptane, alicyclic hydrocarbons such as cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene, and ether compounds such as diethyl ether and tetrahydrofuran. is used. If an acid anhydride is used, the reaction is carried out in an inert solvent or in the absence of an inert solvent using an excess of the acid anhydride. As an inert solvent,
Aromatic hydrocarbons such as benzene, toluene, and xylene, and ether compounds such as diethyl ether and tetrahydrofuran are used. Use of the compound The compound [] according to the present invention is, as described above,
Useful as an antioxidant against organic substances. Although the compound of the present invention [ ] as an antioxidant is effective against various organic substances, it is particularly suitable for use by adding it to a synthetic polymer material as described above. The amount of the compound [ ] used as an antioxidant varies depending on the organic substance to be stabilized, and is determined depending on the type, property, purpose of use, etc. Generally used in amounts ranging from about 0.001 to about 10% by weight, based on the weight of the organic material, but in most applications from about 0.01 to about 5%. For example, typically 0.01-2.0% by weight for polyolefins, 0.01-1.0% by weight for polyvinyl chloride and polyvinylidene chloride, 0.1-2.0% by weight for polyethers, and 0.3% by weight for polyurethanes. ~3% by weight, for polyesters and polyamides about 0.01-1.0% by weight is sufficient. Although the compound [ ] according to the present invention is sufficiently effective as an antioxidant even when used alone, other antioxidants, such as sulfur-based antioxidants, phosphorus-based antioxidants or phenolic antioxidants, or benzophenone type UV absorbers or benztriazole type UV absorbers, or hindered amine type light stabilizers or organic nickel type light stabilizers,
Alternatively, the antioxidant effect of the compound of the present invention can be emphasized by using it in combination with a metal damage inhibitor, a filler deactivator, a metal soap, or the like. Also,
Auxiliary materials such as antistatic agents, flame retardants, anti-drop agents, voltage stabilizers, crosslinking agents, slip agents, colorants, etc. can be used in conjunction with conventional methods for using such antioxidants. Experimental Examples Example 1 Bis[3-(3-tert-butyl-2-hydroxy-5-methylphenyl)propyl]=3,3'-
Thiodipropionate (Exemplary Compound No. 1) 1.28 g of 3,3'-thiodipropionic acid in a 30 ml four-necked flask equipped with a Dean Stark trap.
(7.20 mmol), 4.00 g (17.99 mmol) of 3-(3-tert-butyl-2-hydroxy-5-methylphenyl)-1-propanol, 10 ml of toluene and 0.27 g (1.4 mmol) of para-toluenesulfonic acid hydrate.
mol) and heated under reflux for 2 hours in a nitrogen stream. After the reaction was completed, diethyl ether was added and the mixture was washed with water. Furthermore, after washing with saturated brine, dehydration was performed with anhydrous sodium sulfate, and the organic solvent was removed under reduced pressure. Isolation was carried out by silica gel column chromatography (solvent: chloroform), and 2.67 g (4.55 mmol) of the target product was obtained. Yield is 63
It was %. The physical properties of the product are as follows. (1) 1 H-NMR CDCl 3 ÎŽ [ppm] 1.40 (18H, s), 2.25 (6H, s), 1.50-3.20
(16H, m), 4.10 (4H, t), 5.05 (2H, s),
6.72 (2H, d), 6.88 (2H, d) (2) IR NaCl wavelength [cm -1 ] 3500, 2950, 1720, 1595, 1440, 1170, 860 (3) MS m/e (relative intensity) 586 ( 10, M + ), 204 (100), 189 (70), 161 (20) Examples 2 to 9 Compounds shown in Table 1 were synthesized according to the method of Example 1, and the NMR spectra, Its structure was confirmed from IR and MS spectra.
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(1) 1HâNMR CDCl3ÎŽãppmã
1.40ïŒ27HãïœïŒã1.80ã3.10ïŒ12HãïœïŒã2.23
ïŒ9HãïœïŒã4.40ïŒ6HãïœïŒã5.05ïŒ3HãïœïŒã
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ã«ãMSã¹ãã¯ãã«ãããã®æ§é ã確èªããã[Table] a) The definitions of Z, n, R 1 , R 2 and R 3 are the same as described above.
b) Para-toluenesulfonic acid monohydrate was added at 2.46 g instead of the catalytic amount so that it was not all scavenged with nitrilotriacetic acid.
(12.95mmol) used.
Example 10 1,3,5-tris[3-(3-tert-butyl-
2-Hydroxy-5-methylphenyl)propoxycarbonyl]benzene (Example Compound No.
20) In a 100 ml reactor equipped with a distillation condenser, a thermometer and a nitrogen inlet capillary, 1.54 g (6.00 mmol) of trimethyl 1,3,5-benzenetricarboxylate, 3-(3
-tert-butyl-2-hydroxy-5-methylphenyl)-1-propanol 4.00g (18.00mmol)
and 20 ml of N,N-dimethylformamide. The system is evacuated to 20 mm Hg and 75% by volume (15 ml) of the previously charged N,N-dimethylformamide is removed by distillation in order to dry the reagents, solvents and equipment. Cool to room temperature, break the vacuum by introducing dry nitrogen, and remove the sodium amide.
0.07 g (1.8 mmol) was quickly added to start the transesterification reaction. Initially 50-60â/20mm
Heat with Hg for 2 to 3 hours, then 60 to 80â/20
Heating was performed for 2 to 3 hours while distilling N,N-dimethylformamide at mmHg. After this, the reaction mixture was heated at 100-120°C/5 mmHg for an additional 2-3 hours. After the reaction was completed, the mixture was neutralized with diluted hydrochloric acid and chloroform was added. After separation, the mixture was dehydrated with anhydrous sodium sulfate, and the organic solvent was removed under reduced pressure. Silica gel column chromatography (solvent: chloroform)
2.60g of the target compound was isolated by
(3.16 mmol) was obtained. The yield was 53%.
The physical properties of the product are as follows. (1) 1 H-NMR CDCl 3 ÎŽ [ppm] 1.40 (27H, s), 1.80-3.10 (12H, m), 2.23
(9H, s), 4.40 (6H, t), 5.05 (3H, s),
6.78 (3H, d), 6.87 (3H, d) 8.76 (3H, s) (2) IR NaCl wave number [cm -1 ] 3490, 2940, 1725, 1600, 1240, 850, 735 Examples 11 to 16 Examples Compounds shown in Table 2 were synthesized according to method 10, and their structures were confirmed from NMR spectra, IR spectra, and MS spectra.
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ïŒ3HãïœïŒã2.30ã3.00ïŒ12HãïœïŒã4.06ïŒ4Hã
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ãããšã§ããã[Table] a) The definitions of Z, n, R 1 , R 2 and R 3 are the same as described above.
Example 17 3-(3-tert-butyl-2-hydroxy-5-
methylphenyl)propyl=3-[3-[2-
(3,5-di-tert-butyl-4-hydroxyphenyl)ethylcarbonyloxy]propylthio]propionate (Exemplary Compound No. 14) In a 50 ml reactor, add 3-(3-tert-butyl-2-hydroxy-5 -methylphenyl)-1-propanol 3.40g (15.29mmol), diethyl ether 20
ml, N,N-dimethylaniline 1.94g (16.00m
mol), and the inside of the reactor was purged with dry nitrogen. This mixture contains 3-[3-[3-(3,5-
7.09 g (16.00 mmol) of di-tert-butyl-4-hydroxyphenyl)propionyloxy]propylthio]propionyl chloride was added dropwise, and the mixture was heated under reflux for 6 hours in a nitrogen stream. After the reaction was completed, diethyl ether was added and the mixture was neutralized with 10% sulfuric acid. After separation, the mixture was washed with saturated brine, dehydrated with anhydrous sodium sulfate, and the organic solvent was removed under reduced pressure. Isolation was performed by silica gel column chromatography (solvent chloroform), and 6.42 g (10.20 g) of the target compound was isolated.
mmol) was obtained. The yield was 67%. The physical properties of the product are as follows. (1) 1 H-NMR CDCl 3 ÎŽ [ppm] 1.30 (27H, s), 1.50-2.30 (4H, s), 2.13
(3H, s), 2.30~3.00 (12H, m), 4.06 (4H,
t), 4.95 (1H, s), 5.03 (1H, s), 9.67 (1H,
d), 9.87 (1H, d), 9.88 (2H, s) (2) IR NaCl wavenumber [cm -1 ] 3630, 3500, 2940, 1730, 1590, 1230, 1160,
870 (3) MS m/e (relative intensity) 628 (5, M + ), 424 (10), 204 (100), 189 (40),
161(10), 147(15), 57(30) Next, the antioxidant effects of the compounds of the present invention will be illustrated by examples. Application Example 1 0.10% by weight of an antioxidant was added to polypropylene powder with an intrinsic viscosity of 1.9 as measured in tetralin at 135°C and an isotactic content of 98%, and the mixture was thoroughly mixed with a mixer. Then, the mixture was melt-kneaded and granulated using an extruder with L/D=20 and a diameter of 20 mm at a cylinder temperature of 260°C. The MFR (JISK6758) of the pellets thus obtained at 230°C was measured.
MFR was set to 1 . Furthermore, the extruder was repeatedly passed through the extruder under the same kneading and granulation conditions as above, and the pellets obtained were
The MFR at °C was defined as MFR 4 . MFR is one indicator of molecular weight, and a large MFR corresponds to a small molecular weight. In other words, the fact that MFR 1 and MFR 4 are small and the difference between MFR 1 and MFR 4 is small means that the decrease in molecular weight due to oxidative deterioration in the extruder is small. This means that it has a large antioxidant effect.
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ããŸã§ã®æèŠæéã枬å®ããã[Table] Application example 2 Add 0.10% by weight of an antioxidant to a propylene-ethylene block copolymer powder with an intrinsic viscosity of 2.3 measured in tetralin at 135°C and an ethylene content of 13% by weight, and mix thoroughly with a mixer. did. And cylinder temperature 260â, L/
D=20, the mixture was melt-kneaded and granulated using an extruder with a diameter of 20 mm. The pellets thus obtained were compression molded at 230°C into a sheet with a thickness of 0.5 mm to obtain test pieces.
Heat aging resistance was determined by heating a test piece in a circulating air oven at 150°C and measuring the time required for the test piece to brown and become brittle due to oxidative deterioration.
ãè¡šããtableã
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Claims (1)
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ã«ãã¬ã³ã瀺ãã (ã«) ãåŒã ããã§ãRsã¯C1ã10ã®ã¢ã«ãã¬ã³ã瀺ãã[Claims] 1. Compound of formula [] However, R 1 is a secondary or tertiary chain or cyclic hydrocarbon residue having 3 to 8 carbon atoms, R 2 is an alkyl group having 1 to 12 carbon atoms, and R 3 is an alkylene group having 1 to 4 carbon atoms. group, Z is an n-valent organic group, and the following (a)
A compound selected from the group of compounds consisting of ~(F), where n is 1
-8 integers, respectively. (a) C 1 to 17 alkyl, (b) C 1 to 10 alkylene, (c) C 3 to 10 trivalent to octavalent aliphatic hydrocarbon residue, (d) phenyl, (e) 1,3 , 5-benzenetriyl, (f) 1,2,4,5-benzenetetryl, (g) -R a -S-R b - where R a and R b are each C 1 to 10 alkylene (H) R c (-S-R d )- p where R c is a divalent or trivalent cyclic saturated hydrocarbon residue, p is 2 or 3, and R d is C 1 to Ten
(Li) [Formula] Here, R w represents C 1 to 10 alkylene. (NU) N(âR e ) â 3 Here, R e represents C 1 to 10 alkylene. (ru) âR f âOâR g â Here, R f and R g each represent C 1 to 10 alkylene, (wo) C(âR h âOâR i ) â 4 here , R h and R i each represent C 1-10 alkylene, (W) Here, R m , R o and R p each represent a C 1-10 alkylene, (f) [Formula] Here, R s represents a C 1-10 alkylene.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4269483A JPS59167537A (en) | 1983-03-15 | 1983-03-15 | Phenolic derivative |
| US06/584,636 US4633008A (en) | 1983-03-15 | 1984-02-29 | Anti-oxidant phenol derivatives |
| US06/866,280 US4694102A (en) | 1983-03-15 | 1986-05-23 | Calcium carboxylate phenol derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4269483A JPS59167537A (en) | 1983-03-15 | 1983-03-15 | Phenolic derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59167537A JPS59167537A (en) | 1984-09-21 |
| JPH0520419B2 true JPH0520419B2 (en) | 1993-03-19 |
Family
ID=12643150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4269483A Granted JPS59167537A (en) | 1983-03-15 | 1983-03-15 | Phenolic derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59167537A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2060685A1 (en) * | 1991-03-04 | 1992-09-05 | Mahmood Sabahi | Ether-ester lubricant |
| DE102017220555A1 (en) * | 2017-11-17 | 2019-05-23 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Stabilizing compounds, process for their preparation, compositions containing these stabilizing compounds, methods for stabilizing an organic component and use of stabilizing compounds |
-
1983
- 1983-03-15 JP JP4269483A patent/JPS59167537A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59167537A (en) | 1984-09-21 |
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