CA1043494A - High heat stability composition of ring-opening polymerization product - Google Patents
High heat stability composition of ring-opening polymerization productInfo
- Publication number
- CA1043494A CA1043494A CA225,423A CA225423A CA1043494A CA 1043494 A CA1043494 A CA 1043494A CA 225423 A CA225423 A CA 225423A CA 1043494 A CA1043494 A CA 1043494A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- radicals
- alkyl
- rubber
- group
- 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
- 238000007151 ring opening polymerisation reaction Methods 0.000 title claims abstract description 155
- 239000000203 mixture Substances 0.000 title claims abstract description 130
- 229920001577 copolymer Polymers 0.000 claims abstract description 108
- 229920001519 homopolymer Polymers 0.000 claims abstract description 57
- 150000002989 phenols Chemical class 0.000 claims abstract description 47
- 125000004185 ester group Chemical group 0.000 claims abstract description 26
- 150000001923 cyclic compounds Chemical class 0.000 claims abstract description 19
- 125000001033 ether group Chemical group 0.000 claims abstract description 15
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 claims abstract description 14
- 125000004122 cyclic group Chemical class 0.000 claims abstract description 8
- 125000005462 imide group Chemical group 0.000 claims abstract description 4
- -1 hydrocarbon radicals Chemical group 0.000 claims description 404
- 125000004432 carbon atom Chemical group C* 0.000 claims description 333
- 239000000178 monomer Substances 0.000 claims description 107
- 150000003254 radicals Chemical class 0.000 claims description 85
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 66
- 229930195733 hydrocarbon Natural products 0.000 claims description 57
- 239000004215 Carbon black (E152) Substances 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000000463 material Substances 0.000 claims description 44
- 150000005840 aryl radicals Chemical class 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 229920001971 elastomer Polymers 0.000 claims description 38
- 239000005060 rubber Substances 0.000 claims description 37
- 150000003568 thioethers Chemical class 0.000 claims description 34
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 29
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 27
- 229940102838 methylmethacrylate Drugs 0.000 claims description 27
- 229920002554 vinyl polymer Polymers 0.000 claims description 26
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 24
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 22
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 21
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 17
- 239000012260 resinous material Substances 0.000 claims description 15
- 125000002560 nitrile group Chemical group 0.000 claims description 13
- 229920006235 chlorinated polyethylene elastomer Polymers 0.000 claims description 12
- 239000005062 Polybutadiene Substances 0.000 claims description 10
- 229920002857 polybutadiene Polymers 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 229920002681 hypalon Polymers 0.000 claims description 9
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 8
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 7
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 4
- 229940000425 combination drug Drugs 0.000 claims 6
- 150000002430 hydrocarbons Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 abstract description 31
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 156
- 239000003381 stabilizer Substances 0.000 description 133
- 239000000306 component Substances 0.000 description 92
- 238000006116 polymerization reaction Methods 0.000 description 83
- 150000002848 norbornenes Chemical class 0.000 description 82
- 229920000642 polymer Polymers 0.000 description 70
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 57
- 230000003197 catalytic effect Effects 0.000 description 57
- 239000000243 solution Substances 0.000 description 52
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 20
- 150000003949 imides Chemical class 0.000 description 19
- 229960005419 nitrogen Drugs 0.000 description 19
- 150000003462 sulfoxides Chemical class 0.000 description 19
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 19
- 229910052721 tungsten Inorganic materials 0.000 description 19
- 239000010937 tungsten Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 17
- 238000002156 mixing Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 16
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical class C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 16
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 14
- 229910052750 molybdenum Inorganic materials 0.000 description 14
- 239000011733 molybdenum Substances 0.000 description 14
- 150000001399 aluminium compounds Chemical class 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 12
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229940077746 antacid containing aluminium compound Drugs 0.000 description 12
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000002841 Lewis acid Substances 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 150000007517 lewis acids Chemical class 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 238000007142 ring opening reaction Methods 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 10
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- 229920000578 graft copolymer Polymers 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
- 150000002846 norbornadienes Chemical class 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 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 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000007720 emulsion polymerization reaction Methods 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000000087 stabilizing effect Effects 0.000 description 6
- 150000003457 sulfones Chemical class 0.000 description 6
- 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 5
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- 238000005698 Diels-Alder reaction Methods 0.000 description 5
- 239000004411 aluminium Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 4
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 4
- 238000012662 bulk polymerization Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 230000037048 polymerization activity Effects 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000010557 suspension polymerization reaction Methods 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 239000000057 synthetic resin Substances 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 3
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 3
- SDCYWERHEYVPHL-UHFFFAOYSA-N 3,9-diphenoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound O1CC2(COP(OC=3C=CC=CC=3)OC2)COP1OC1=CC=CC=C1 SDCYWERHEYVPHL-UHFFFAOYSA-N 0.000 description 3
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 229960004132 diethyl ether Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- ZTVZLYBCZNMWCF-UHFFFAOYSA-N homocystine Chemical compound [O-]C(=O)C([NH3+])CCSSCCC([NH3+])C([O-])=O ZTVZLYBCZNMWCF-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 2
- IBLDPSVRDLMMHJ-UHFFFAOYSA-H 1,1-diethoxyethane hexachlorotungsten Chemical compound C(C)OC(C)OCC.[W](Cl)(Cl)(Cl)(Cl)(Cl)Cl IBLDPSVRDLMMHJ-UHFFFAOYSA-H 0.000 description 2
- POPHMOPNVVKGRW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydronaphthalene Chemical compound C1CCC2CCCCC2=C1 POPHMOPNVVKGRW-UHFFFAOYSA-N 0.000 description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- HWPKTNAANOPIRV-UHFFFAOYSA-N 2,4,5-trihydroxy-1-phenyloctadecan-1-one Chemical compound CCCCCCCCCCCCCC(O)C(O)CC(O)C(=O)C1=CC=CC=C1 HWPKTNAANOPIRV-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MYOXWOWYELCAJM-UHFFFAOYSA-N 2,6-dioctylphenol Chemical compound CCCCCCCCC1=CC=CC(CCCCCCCC)=C1O MYOXWOWYELCAJM-UHFFFAOYSA-N 0.000 description 2
- LBOGPIWNHXHYHN-UHFFFAOYSA-N 2-(2-hydroxy-5-octylphenyl)sulfanyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(SC=2C(=CC=C(CCCCCCCC)C=2)O)=C1 LBOGPIWNHXHYHN-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 2
- CNSRYNJMLOJSLU-UHFFFAOYSA-N 3-hexyl-4-methoxyphenol Chemical compound CCCCCCC1=CC(O)=CC=C1OC CNSRYNJMLOJSLU-UHFFFAOYSA-N 0.000 description 2
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- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- KVDWNTBVZBXLFQ-UHFFFAOYSA-N tetradecyl 4-(4-oxo-4-tetradecoxybutyl)sulfanylbutanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCSCCCC(=O)OCCCCCCCCCCCCCC KVDWNTBVZBXLFQ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical group Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- GQAYTTVSMIZIMJ-UHFFFAOYSA-N trihydroxy-(10-nonylheptacosan-10-yl)-(2-phenoxyethyl)-lambda5-phosphane Chemical compound CCCCCCCCCCCCCCCCCC(CCCCCCCCC)(CCCCCCCCC)P(O)(O)(O)CCOC1=CC=CC=C1 GQAYTTVSMIZIMJ-UHFFFAOYSA-N 0.000 description 1
- SUXIKHBBPQWLHO-UHFFFAOYSA-N trihydroxy-(8-methylnonyl)-(8-methyl-1-phenylnonyl)-lambda5-phosphane Chemical compound CC(C)CCCCCCCP(O)(O)(O)C(CCCCCCC(C)C)C1=CC=CC=C1 SUXIKHBBPQWLHO-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JBXUHJUOOSISGB-UHFFFAOYSA-N tris(2,3-dimethylphenyl) phosphite Chemical compound CC1=CC=CC(OP(OC=2C(=C(C)C=CC=2)C)OC=2C(=C(C)C=CC=2)C)=C1C JBXUHJUOOSISGB-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- NURJXHUITUPBOD-UHFFFAOYSA-N tris(2-methylpropyl) phosphite Chemical compound CC(C)COP(OCC(C)C)OCC(C)C NURJXHUITUPBOD-UHFFFAOYSA-N 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-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
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical group Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49045051A JPS50138050A (enExample) | 1974-04-23 | 1974-04-23 | |
| JP7646874A JPS516251A (ja) | 1974-07-05 | 1974-07-05 | Anteiseinokairyosareta kaikanjugotaisoseibutsu |
| JP13050274A JPS5156860A (ja) | 1974-11-14 | 1974-11-14 | Anteiseinokairyosaretakaikanjugotaisoseibutsu |
| JP13115974A JPS5157756A (en) | 1974-11-15 | 1974-11-15 | Anteiseinosugureta kaikanjugotaisoseibutsu |
| JP13522874A JPS5161556A (en) | 1974-11-26 | 1974-11-26 | Anteiseino kairyosareta kaikanjugotaikongobutsu |
| JP13769274A JPS5164563A (en) | 1974-12-03 | 1974-12-03 | Anteiseino kairyosareta kaikanjugotaisoseibutsu |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043494A true CA1043494A (en) | 1978-11-28 |
Family
ID=27550172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA225,423A Expired CA1043494A (en) | 1974-04-23 | 1975-04-22 | High heat stability composition of ring-opening polymerization product |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1043494A (enExample) |
| DE (1) | DE2518055C3 (enExample) |
| FR (3) | FR2366329A1 (enExample) |
| GB (1) | GB1503703A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4324717A (en) * | 1980-06-23 | 1982-04-13 | The B. F. Goodrich Company | Norbornene polymers stabilized with hindered aromatic alcohols |
| US4849486A (en) * | 1985-07-10 | 1989-07-18 | Nippon Oil Co., Ltd. | Polyphenylene ether resin composition |
-
1975
- 1975-04-22 CA CA225,423A patent/CA1043494A/en not_active Expired
- 1975-04-22 GB GB16587/75A patent/GB1503703A/en not_active Expired
- 1975-04-23 FR FR7512675A patent/FR2366329A1/fr active Granted
- 1975-04-23 DE DE2518055A patent/DE2518055C3/de not_active Expired
- 1975-11-27 FR FR7536333A patent/FR2283175A1/fr active Granted
- 1975-11-27 FR FR7536334A patent/FR2283176A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2283175B1 (enExample) | 1982-10-08 |
| GB1503703A (en) | 1978-03-15 |
| DE2518055A1 (de) | 1975-10-30 |
| FR2283175A1 (fr) | 1976-03-26 |
| DE2518055B2 (de) | 1981-06-19 |
| FR2283176A1 (fr) | 1976-03-26 |
| FR2366329B1 (enExample) | 1983-10-07 |
| FR2366329A1 (fr) | 1978-04-28 |
| FR2283176B1 (enExample) | 1982-10-08 |
| DE2518055C3 (de) | 1982-05-27 |
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