DE2518055C3

DE2518055C3 - Hochwärmestabile Masse aus Ringöffnungs-Polymerisationsprodukten und deren Verwendung zur Herstellung von Formgegenständen

Hochwärmestabile Masse aus Ringöffnungs-Polymerisationsprodukten und deren Verwendung zur Herstellung von Formgegenständen

Info

Publication number: DE2518055C3
Authority: DE; Germany
Prior art keywords: carbon atoms; radicals; ring; bicyclo; tert
Prior art date: 1974-04-23
Legal status : Expired

Application number

DE2518055A

Other languages

German (de)

English (en)

Other versions

DE2518055A1 (de

DE2518055B2 (de

Inventor

Hiroyasu Kawahara

Takashi Yokohama Ueshima

Current Assignee

Resonac Holdings Corp

Original Assignee

Showa Denko KK

Priority date

1974-04-23

Filing date

1975-04-23

Publication date

1982-05-27

1974-04-23 Priority claimed from JP49045051A external-priority patent/JPS50138050A/ja

1974-07-05 Priority claimed from JP7646874A external-priority patent/JPS516251A/ja

1974-11-14 Priority claimed from JP13050274A external-priority patent/JPS5156860A/ja

1974-11-15 Priority claimed from JP13115974A external-priority patent/JPS5157756A/ja

1974-11-26 Priority claimed from JP13522874A external-priority patent/JPS5161556A/ja

1974-12-03 Priority claimed from JP13769274A external-priority patent/JPS5164563A/ja

1975-04-23 Application filed by Showa Denko KK filed Critical Showa Denko KK

1975-10-30 Publication of DE2518055A1 publication Critical patent/DE2518055A1/de

1981-06-19 Publication of DE2518055B2 publication Critical patent/DE2518055B2/de

1982-05-27 Application granted granted Critical

1982-05-27 Publication of DE2518055C3 publication Critical patent/DE2518055C3/de

Status Expired legal-status Critical Current

Links

238000007151 ring opening polymerisation reaction Methods 0.000 title claims description 151
238000004519 manufacturing process Methods 0.000 title description 19
-1 alkyl radicals Chemical group 0.000 claims description 262
125000004432 carbon atom Chemical group C* 0.000 claims description 182
125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 claims description 85
229920001577 copolymer Polymers 0.000 claims description 82
150000002989 phenols Chemical class 0.000 claims description 31
229920001519 homopolymer Polymers 0.000 claims description 29
229930195733 hydrocarbon Natural products 0.000 claims description 28
239000004215 Carbon black (E152) Substances 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
150000005840 aryl radicals Chemical class 0.000 claims description 18
150000001923 cyclic compounds Chemical class 0.000 claims description 18
125000004185 ester group Chemical group 0.000 claims description 17
125000002560 nitrile group Chemical group 0.000 claims description 13
125000001033 ether group Chemical group 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 9
125000004122 cyclic group Chemical class 0.000 claims description 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
125000005462 imide group Chemical group 0.000 claims description 3
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
239000003381 stabilizer Substances 0.000 description 157
239000000047 product Substances 0.000 description 137
238000002845 discoloration Methods 0.000 description 90
239000000203 mixture Substances 0.000 description 90
239000000178 monomer Substances 0.000 description 84
229920000642 polymer Polymers 0.000 description 76
239000000243 solution Substances 0.000 description 60
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 58
150000001875 compounds Chemical class 0.000 description 48
KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 45
238000006116 polymerization reaction Methods 0.000 description 44
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
239000000463 material Substances 0.000 description 37
150000003254 radicals Chemical class 0.000 description 37
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 36
239000003054 catalyst Substances 0.000 description 31
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 29
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
229910052757 nitrogen Inorganic materials 0.000 description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
150000003568 thioethers Chemical class 0.000 description 24
239000002685 polymerization catalyst Substances 0.000 description 23
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 20
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
229920001971 elastomer Polymers 0.000 description 18
150000002148 esters Chemical class 0.000 description 18
125000001424 substituent group Chemical group 0.000 description 18
239000003795 chemical substances by application Substances 0.000 description 17
239000005060 rubber Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
150000003462 sulfoxides Chemical class 0.000 description 17
238000000034 method Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
229910052721 tungsten Inorganic materials 0.000 description 15
239000010937 tungsten Substances 0.000 description 15
150000001733 carboxylic acid esters Chemical class 0.000 description 14
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 14
125000003118 aryl group Chemical group 0.000 description 13
238000003756 stirring Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
229920000578 graft copolymer Polymers 0.000 description 12
150000003949 imides Chemical class 0.000 description 12
229910052760 oxygen Inorganic materials 0.000 description 12
239000001301 oxygen Substances 0.000 description 12
229920005989 resin Polymers 0.000 description 12
239000011347 resin Substances 0.000 description 12
DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical compound CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 description 11
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 11
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 11
238000002156 mixing Methods 0.000 description 11
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000523 sample Substances 0.000 description 10
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 9
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 9
238000000921 elemental analysis Methods 0.000 description 9
125000005843 halogen group Chemical group 0.000 description 9
JAGYXYUAYDLKNO-UHFFFAOYSA-N hepta-2,5-diene Chemical compound CC=CCC=CC JAGYXYUAYDLKNO-UHFFFAOYSA-N 0.000 description 9
238000000465 moulding Methods 0.000 description 9
125000002872 norbornadienyl group Chemical class C12=C(C=C(CC1)C2)* 0.000 description 9
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 8
150000008065 acid anhydrides Chemical class 0.000 description 8
238000000746 purification Methods 0.000 description 8
239000012260 resinous material Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
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 7
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
230000000052 comparative effect Effects 0.000 description 7
238000007334 copolymerization reaction Methods 0.000 description 7
238000004821 distillation Methods 0.000 description 7
238000001035 drying Methods 0.000 description 7
238000007720 emulsion polymerization reaction Methods 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
150000003457 sulfones Chemical class 0.000 description 7
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 description 6
229910052750 molybdenum Inorganic materials 0.000 description 6
239000011733 molybdenum Substances 0.000 description 6
230000008569 process Effects 0.000 description 6
238000010926 purge Methods 0.000 description 6
229920002554 vinyl polymer Polymers 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
238000012662 bulk polymerization Methods 0.000 description 5
229920006235 chlorinated polyethylene elastomer Polymers 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical class C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
239000004033 plastic Substances 0.000 description 5
125000003367 polycyclic group Chemical group 0.000 description 5
239000004800 polyvinyl chloride Substances 0.000 description 5
229920000915 polyvinyl chloride Polymers 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
229920001897 terpolymer Polymers 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
POPHMOPNVVKGRW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydronaphthalene Chemical compound C1CCC2CCCCC2=C1 POPHMOPNVVKGRW-UHFFFAOYSA-N 0.000 description 4
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
WAOPGHCXGUXHKF-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-1,1-diphenylpropane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C1(=CC=CC=C1)C(O)(C(CO)(CO)CO)C1=CC=CC=C1 WAOPGHCXGUXHKF-UHFFFAOYSA-N 0.000 description 4
ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical class CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-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
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
239000004743 Polypropylene Substances 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 compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
235000019304 dilauryl thiodipropionate Nutrition 0.000 description 4
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 4
238000004898 kneading Methods 0.000 description 4
239000005078 molybdenum compound Substances 0.000 description 4
150000002752 molybdenum compounds Chemical class 0.000 description 4
125000002950 monocyclic group Chemical group 0.000 description 4
150000002894 organic compounds Chemical class 0.000 description 4
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
230000037048 polymerization activity Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
229920003048 styrene butadiene rubber Polymers 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
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 3
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
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 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 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
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 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
UGCYOSYZUQPBBA-UHFFFAOYSA-N 4-methoxy-2-[(1-methylcyclohexa-2,4-dien-1-yl)methyl]phenol Chemical compound COC1=CC=C(O)C(CC2(C)C=CC=CC2)=C1 UGCYOSYZUQPBBA-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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
239000005062 Polybutadiene Substances 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
150000008064 anhydrides Chemical group 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000006866 deterioration Effects 0.000 description 3
150000001993 dienes Chemical class 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000005516 engineering process Methods 0.000 description 3
239000000835 fiber Substances 0.000 description 3
238000010528 free radical solution polymerization reaction Methods 0.000 description 3
238000001879 gelation Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
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 3
239000008240 homogeneous mixture Substances 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
229920002681 hypalon Polymers 0.000 description 3
IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
FICIMVBBIKUYAY-UHFFFAOYSA-N n-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enamide Chemical compound CC(C)(C)C1=CC(CNC(=O)C=C)=CC(C(C)(C)C)=C1O FICIMVBBIKUYAY-UHFFFAOYSA-N 0.000 description 3
LHQVKIYLZGWHES-UHFFFAOYSA-N n-[[4-hydroxy-3,5-di(propan-2-yl)phenyl]methyl]-2-methylprop-2-enamide Chemical compound CC(C)C1=CC(CNC(=O)C(C)=C)=CC(C(C)C)=C1O LHQVKIYLZGWHES-UHFFFAOYSA-N 0.000 description 3
BRNPAEUKZMBRLQ-UHFFFAOYSA-N octadecyl 3,4,5-trihydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 BRNPAEUKZMBRLQ-UHFFFAOYSA-N 0.000 description 3
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
230000000379 polymerizing effect Effects 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 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
SJXINMCGKMERBY-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a,9,9a-dodecahydroanthracene Chemical class C1=C2CCCCC2CC2C1CCCC2 SJXINMCGKMERBY-UHFFFAOYSA-N 0.000 description 2
IEGYXSAHRKJELM-UHFFFAOYSA-N 1,4-dihydro-1,4-methanonaphthalene Chemical compound C12=CC=CC=C2C2CC1C=C2 IEGYXSAHRKJELM-UHFFFAOYSA-N 0.000 description 2
150000003923 2,5-pyrrolediones Chemical class 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
GSOYMOAPJZYXTB-UHFFFAOYSA-N 2,6-ditert-butyl-4-(3,5-ditert-butyl-4-hydroxyphenyl)phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GSOYMOAPJZYXTB-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
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-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
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