JPH0315656B2 - - Google Patents
Info
- Publication number
- JPH0315656B2 JPH0315656B2 JP56146484A JP14648481A JPH0315656B2 JP H0315656 B2 JPH0315656 B2 JP H0315656B2 JP 56146484 A JP56146484 A JP 56146484A JP 14648481 A JP14648481 A JP 14648481A JP H0315656 B2 JPH0315656 B2 JP H0315656B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- norbornene
- hydrogen
- alkyl
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 21
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 19
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- -1 norbornenyl phenol Chemical compound 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 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 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000002848 norbornenes Chemical group 0.000 claims description 6
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- HANKSFAYJLDDKP-UHFFFAOYSA-N dihydrodicyclopentadiene Chemical compound C12CC=CC2C2CCC1C2 HANKSFAYJLDDKP-UHFFFAOYSA-N 0.000 claims description 4
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 claims description 4
- 239000013638 trimer Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001925 cycloalkenes Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 239000003963 antioxidant agent Substances 0.000 description 28
- 239000000178 monomer Substances 0.000 description 24
- 230000003078 antioxidant effect Effects 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- XEDOURVJTJGZAF-UHFFFAOYSA-N 2,6-ditert-butyl-4-prop-2-enylphenol Chemical compound CC(C)(C)C1=CC(CC=C)=CC(C(C)(C)C)=C1O XEDOURVJTJGZAF-UHFFFAOYSA-N 0.000 description 3
- PCBPVYHMZBWMAZ-UHFFFAOYSA-N 5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C)CC1C=C2 PCBPVYHMZBWMAZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000593 degrading effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RMDKEBZUCHXUER-UHFFFAOYSA-N 4-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(C)C2 RMDKEBZUCHXUER-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005041 Mylar™ Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- PPQUYYAZSOKTQD-UHFFFAOYSA-M diethylalumanylium;iodide Chemical compound CC[Al](I)CC PPQUYYAZSOKTQD-UHFFFAOYSA-M 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002751 molybdenum Chemical class 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002954 polymerization reaction product Substances 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003657 tungsten Chemical class 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- LGAQJENWWYGFSN-PLNGDYQASA-N (z)-4-methylpent-2-ene Chemical compound C\C=C/C(C)C LGAQJENWWYGFSN-PLNGDYQASA-N 0.000 description 1
- LAZHUUGOLCHESB-UHFFFAOYSA-N 2,3-dimethylbicyclo[2.2.1]hept-5-ene Chemical compound C1C2C(C)C(C)C1C=C2 LAZHUUGOLCHESB-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- HMCZBYVXVKBQQH-UHFFFAOYSA-N 2-[2-methyl-6-(2-methylbutan-2-yl)cyclohexyl]phenol Chemical compound CCC(C)(C)C1CCCC(C)C1C1=CC=CC=C1O HMCZBYVXVKBQQH-UHFFFAOYSA-N 0.000 description 1
- YTJBEQVMHNEDQE-UHFFFAOYSA-N 2-cyclohexyl-6-hexylphenol Chemical compound CCCCCCC1=CC=CC(C2CCCCC2)=C1O YTJBEQVMHNEDQE-UHFFFAOYSA-N 0.000 description 1
- MLAVZJVREFPERL-UHFFFAOYSA-N 2-tert-butyl-6-cyclohexylphenol Chemical compound CC(C)(C)C1=CC=CC(C2CCCCC2)=C1O MLAVZJVREFPERL-UHFFFAOYSA-N 0.000 description 1
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
- OQFRBGQKZQCIGT-UHFFFAOYSA-N 2-tert-butyl-6-octylphenol Chemical compound CCCCCCCCC1=CC=CC(C(C)(C)C)=C1O OQFRBGQKZQCIGT-UHFFFAOYSA-N 0.000 description 1
- NBLAIVADEWCFJN-UHFFFAOYSA-N 4-bromooct-1-ene Chemical compound CCCCC(Br)CC=C NBLAIVADEWCFJN-UHFFFAOYSA-N 0.000 description 1
- VEEKCIOFMIAGSF-UHFFFAOYSA-N 4-butylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCC)C2 VEEKCIOFMIAGSF-UHFFFAOYSA-N 0.000 description 1
- YHESWXAODSYVCO-UHFFFAOYSA-N 5-but-1-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=CCC)CC1C=C2 YHESWXAODSYVCO-UHFFFAOYSA-N 0.000 description 1
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 1
- QHJIJNGGGLNBNJ-UHFFFAOYSA-N 5-ethylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CC)CC1C=C2 QHJIJNGGGLNBNJ-UHFFFAOYSA-N 0.000 description 1
- TWFUDEZNRMIBSM-UHFFFAOYSA-N 5-ethyloct-3-ene Chemical compound CCCC(CC)C=CCC TWFUDEZNRMIBSM-UHFFFAOYSA-N 0.000 description 1
- RCLWVKWEZCRGGS-UHFFFAOYSA-N 5-pentadecylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCCCCCCC)CC1C=C2 RCLWVKWEZCRGGS-UHFFFAOYSA-N 0.000 description 1
- CJQNJRMLJAAXOS-UHFFFAOYSA-N 5-prop-1-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=CC)CC1C=C2 CJQNJRMLJAAXOS-UHFFFAOYSA-N 0.000 description 1
- BLMIXWDJHNJWDT-UHFFFAOYSA-N 6-chlorohex-1-ene Chemical compound ClCCCCC=C BLMIXWDJHNJWDT-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 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
- 150000001412 amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001599 direct drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003658 tungsten compounds Chemical class 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/188,397 US4355148A (en) | 1980-09-18 | 1980-09-18 | Norbornene polymers containing bound phenolic antioxidant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5783522A JPS5783522A (en) | 1982-05-25 |
| JPH0315656B2 true JPH0315656B2 (enExample) | 1991-03-01 |
Family
ID=22692970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56146484A Granted JPS5783522A (en) | 1980-09-18 | 1981-09-18 | Norbornene polymer containing bonded antioxidant |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4355148A (enExample) |
| EP (1) | EP0048439B1 (enExample) |
| JP (1) | JPS5783522A (enExample) |
| CA (1) | CA1162350A (enExample) |
| DE (1) | DE3169557D1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666974A (en) * | 1985-06-06 | 1987-05-19 | The Dow Chemical Company | Antioxidant thickening compositions |
| US4690995A (en) * | 1985-06-06 | 1987-09-01 | The Dow Chemical Company | Copolymers containing high concentrations of phenol antioxidant units |
| EP0308809A3 (en) * | 1987-07-27 | 1990-10-31 | Nippon Zeon Kabushiki Kaisha | Machinable stock and machined shaped article |
| JPH0791448B2 (ja) * | 1987-09-18 | 1995-10-04 | 日本ゼオン株式会社 | 切削加工用素材および切削成形品 |
| US4952348A (en) * | 1987-09-18 | 1990-08-28 | Nippon Zeon Co., Ltd. | Process for preparing shaped article having thick section |
| EP0313838A3 (en) * | 1987-10-01 | 1990-08-22 | The B.F. Goodrich Company | Cycloolefin polymers obtained from resinous monomers |
| US4822839A (en) * | 1987-11-25 | 1989-04-18 | Hercules Incorporated | Polyunsaturated hydrocarbon polymer-compatible antioxidant compositions |
| US4812543A (en) * | 1988-03-01 | 1989-03-14 | Hercules Incorporated | Co-polymer-bound amine antioxidants |
| DE69122323T2 (de) * | 1990-07-10 | 1997-05-07 | Dsm Nv | Polymerisierbares Antioxidans und gebundenes Antioxidans enthaltende Olefinpolymere |
| GB2309694B (en) * | 1996-02-01 | 2000-02-16 | Ciba Sc Holding Ag | Norbornene-substituted bisphenol antioxidants |
| WO1999042502A1 (en) * | 1998-02-23 | 1999-08-26 | The B.F. Goodrich Company | Polycyclic resist compositions with increased etch resistance |
| KR100739482B1 (ko) | 1998-12-09 | 2007-07-13 | 스미토모 베이클라이트 가부시키가이샤 | 제 10족 금속 착물을 사용하는 노르보르넨형 단량체의 몰드내 첨가 중합반응 |
| US6861123B2 (en) * | 2000-12-01 | 2005-03-01 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogel contact lens |
| JP2005522564A (ja) * | 2002-04-05 | 2005-07-28 | ユニバーシティ オブ マサチューセッツ ロウエル | ポリマー抗酸化剤 |
| US7595074B2 (en) * | 2002-04-05 | 2009-09-29 | University Of Massachusetts Lowell | Polymeric antioxidants |
| US7323511B2 (en) * | 2004-01-21 | 2008-01-29 | University Of Massachusetts Lowell | Post-coupling synthetic approach for polymeric antioxidants |
| WO2006014605A2 (en) * | 2004-07-23 | 2006-02-09 | Polnox Corporation | Anti-oxidant macromonomers and polymers and methods of making and using the same |
| US7902317B2 (en) | 2004-12-03 | 2011-03-08 | Polnox Corporation | Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers |
| US7678877B2 (en) * | 2004-12-03 | 2010-03-16 | Polnox Corporation | Process for the synthesis of polyalkylphenol antioxidants |
| US20060128939A1 (en) * | 2004-12-03 | 2006-06-15 | Vijayendra Kumar | One pot process for making polymeric antioxidants |
| US20060128930A1 (en) * | 2004-12-03 | 2006-06-15 | Ashish Dhawan | Synthesis of sterically hindered phenol based macromolecular antioxidants |
| WO2006091705A2 (en) | 2005-02-22 | 2006-08-31 | Polnox Corporation | Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications |
| US7705185B2 (en) | 2005-03-25 | 2010-04-27 | Polnox Corporation | Alkylated and polymeric macromolecular antioxidants and methods of making and using the same |
| WO2007050985A2 (en) | 2005-10-27 | 2007-05-03 | Polnox Corporation | Macromolecular antioxidants based on stξrically hindered phenolic phosphites |
| EP1966293A1 (en) * | 2005-10-27 | 2008-09-10 | Polnox Corporation | Stabilized polyolefin compositions |
| US20070106059A1 (en) * | 2005-10-27 | 2007-05-10 | Cholli Ashok L | Macromolecular antioxidants and polymeric macromolecular antioxidants |
| US20070161522A1 (en) | 2005-12-02 | 2007-07-12 | Cholli Ashok L | Lubricant oil compositions |
| WO2008005358A2 (en) | 2006-07-06 | 2008-01-10 | Polnox Corporation | Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same |
| US7767853B2 (en) | 2006-10-20 | 2010-08-03 | Polnox Corporation | Antioxidants and methods of making and using the same |
| US10294423B2 (en) | 2013-11-22 | 2019-05-21 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
| US20180251695A1 (en) | 2017-03-01 | 2018-09-06 | Polnox Corporation | Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017669A (en) * | 1969-06-02 | 1977-04-12 | E. I. Du Pont De Nemours And Company | Functionally substituted terpolymers and tetrapolymers of alpha-olefins and process for manufacturing functional substituted copolymers |
| US3652487A (en) * | 1970-02-05 | 1972-03-28 | Goodyear Tire & Rubber | Process for the polymerization of alicyclic monomer masterbatches |
| US3974092A (en) * | 1970-06-06 | 1976-08-10 | Chemische Werke Huls Aktiengesellschaft | Catalyst for the preparation of polyalkenamers |
| US3962187A (en) * | 1970-07-20 | 1976-06-08 | The Goodyear Tire & Rubber Company | Stabilized polymers of ditertiary alkyl-4-hydroxybenzyloxy alkyl acrylates and dienes |
| GB1489470A (en) * | 1974-07-04 | 1977-10-19 | Showa Denko Kk | Norbornene polymers |
| US4010140A (en) * | 1974-10-02 | 1977-03-01 | The Goodyear Tire & Rubber Company | Age resistant resin compositions and admixtures useful as adhesives |
| US4129557A (en) * | 1976-05-26 | 1978-12-12 | Sumitomo Chemical Company, Limited | Process for producing copolymerized resins |
| JPS54150500A (en) * | 1978-05-19 | 1979-11-26 | Showa Denko Kk | Production of ring-opening polymer with high oxidative stability |
-
1980
- 1980-09-18 US US06/188,397 patent/US4355148A/en not_active Expired - Lifetime
-
1981
- 1981-08-31 CA CA000384912A patent/CA1162350A/en not_active Expired
- 1981-09-16 EP EP81107311A patent/EP0048439B1/en not_active Expired
- 1981-09-16 DE DE8181107311T patent/DE3169557D1/de not_active Expired
- 1981-09-18 JP JP56146484A patent/JPS5783522A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5783522A (en) | 1982-05-25 |
| US4355148A (en) | 1982-10-19 |
| DE3169557D1 (en) | 1985-05-02 |
| EP0048439B1 (en) | 1985-03-27 |
| CA1162350A (en) | 1984-02-14 |
| EP0048439A1 (en) | 1982-03-31 |
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