CA1293090C - Polymeres olefiniques de benzocyclobutene et procede pour sa preparation - Google Patents

Polymeres olefiniques de benzocyclobutene et procede pour sa preparation

Info

Publication number: CA1293090C
Authority: CA; Canada
Prior art keywords: copolymer; benzocyclobutene; general formula; monomer; block
Prior art date: 1986-09-29
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 - Fee Related

Application number

CA000519263A

Other languages

English (en)

Inventor

Pui Kwan Wong

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

Priority date (The priority date 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 date listed.)

1986-09-29

Filing date

1986-09-29

Publication date

1991-12-10

1986-09-29 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1986-09-29 Priority to CA000519263A priority Critical patent/CA1293090C/fr

1991-12-10 Application granted granted Critical

1991-12-10 Publication of CA1293090C publication Critical patent/CA1293090C/fr

2008-12-10 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 124
UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 title claims abstract description 106
238000000034 method Methods 0.000 title claims abstract description 55
230000008569 process Effects 0.000 title claims abstract description 42
238000002360 preparation method Methods 0.000 title claims abstract description 21
229920001577 copolymer Polymers 0.000 claims abstract description 87
239000000178 monomer Substances 0.000 claims abstract description 72
229920001400 block copolymer Polymers 0.000 claims abstract description 66
238000006116 polymerization reaction Methods 0.000 claims abstract description 46
239000003054 catalyst Substances 0.000 claims abstract description 43
150000001993 dienes Chemical class 0.000 claims abstract description 29
229920005604 random copolymer Polymers 0.000 claims abstract description 16
229920001519 homopolymer Polymers 0.000 claims abstract description 14
BERZDLBNIUDUQQ-UHFFFAOYSA-N C(CC=C)C1=C2C(CC2)=CC=C1 Chemical compound C(CC=C)C1=C2C(CC2)=CC=C1 BERZDLBNIUDUQQ-UHFFFAOYSA-N 0.000 claims abstract description 11
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 76
-1 diene hydrocarbon Chemical class 0.000 claims description 54
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 36
239000003999 initiator Substances 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 32
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 30
239000007822 coupling agent Substances 0.000 claims description 19
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 18
239000005977 Ethylene Substances 0.000 claims description 17
229920000098 polyolefin Polymers 0.000 claims description 17
DTGDMPJDZKDHEP-UHFFFAOYSA-N 4-ethenylbicyclo[4.2.0]octa-1(6),2,4-triene Chemical compound C=CC1=CC=C2CCC2=C1 DTGDMPJDZKDHEP-UHFFFAOYSA-N 0.000 claims description 16
WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 16
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 16
239000012967 coordination catalyst Substances 0.000 claims description 15
239000007787 solid Substances 0.000 claims description 15
229930195733 hydrocarbon Natural products 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
238000005984 hydrogenation reaction Methods 0.000 claims description 13
239000004215 Carbon black (E152) Substances 0.000 claims description 12
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 12
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 8
230000000379 polymerizing effect Effects 0.000 claims description 8
239000004411 aluminium Substances 0.000 claims description 7
229910052782 aluminium Inorganic materials 0.000 claims description 7
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
229920000578 graft copolymer Polymers 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 4
ODYAEFDPZJFCPC-UHFFFAOYSA-N C(=C)C12C(CC1)C=CC=C2 Chemical compound C(=C)C12C(CC1)C=CC=C2 ODYAEFDPZJFCPC-UHFFFAOYSA-N 0.000 claims description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
MTTFVZPJTOQFCB-UHFFFAOYSA-N 4-prop-2-enylbicyclo[4.2.0]octa-1(6),2,4,7-tetraene Chemical compound C=CCC1=CC=C2C=CC2=C1 MTTFVZPJTOQFCB-UHFFFAOYSA-N 0.000 claims description 3
OQMLXSLKGBSTJT-UHFFFAOYSA-N C(CC=C)C12C(CC1)C=CC=C2 Chemical compound C(CC=C)C12C(CC1)C=CC=C2 OQMLXSLKGBSTJT-UHFFFAOYSA-N 0.000 claims description 3
239000005062 Polybutadiene Substances 0.000 claims description 3
XIJNNDJXMGTYGK-UHFFFAOYSA-K [Cl-].[Cl-].[Cl-].[V+5] Chemical compound [Cl-].[Cl-].[Cl-].[V+5] XIJNNDJXMGTYGK-UHFFFAOYSA-K 0.000 claims description 3
229920002857 polybutadiene Polymers 0.000 claims description 3
UVPKUTPZWFHAHY-UHFFFAOYSA-L 2-ethylhexanoate;nickel(2+) Chemical compound [Ni+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O UVPKUTPZWFHAHY-UHFFFAOYSA-L 0.000 claims description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
239000011952 anionic catalyst Substances 0.000 claims 1
239000011953 free-radical catalyst Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
238000004132 cross linking Methods 0.000 description 24
239000000047 product Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000007334 copolymerization reaction Methods 0.000 description 11
150000002978 peroxides Chemical class 0.000 description 11
229920000181 Ethylene propylene rubber Polymers 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
229920001971 elastomer Polymers 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 9
238000005859 coupling reaction Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
239000004793 Polystyrene Substances 0.000 description 8
150000001336 alkenes Chemical class 0.000 description 8
229920002223 polystyrene Polymers 0.000 description 8
239000000243 solution Substances 0.000 description 8
229920003048 styrene butadiene rubber Polymers 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
230000008878 coupling Effects 0.000 description 7
238000010168 coupling process Methods 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
239000010936 titanium Substances 0.000 description 7
229910052723 transition metal Inorganic materials 0.000 description 7
150000003624 transition metals Chemical class 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000004698 Polyethylene Substances 0.000 description 6
239000004743 Polypropylene Substances 0.000 description 6
239000002174 Styrene-butadiene Substances 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
150000002430 hydrocarbons Chemical class 0.000 description 6
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
230000009467 reduction Effects 0.000 description 6
239000005060 rubber Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
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 5
239000003795 chemical substances by application Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
239000004033 plastic Substances 0.000 description 5
229920001155 polypropylene Polymers 0.000 description 5
239000003381 stabilizer Substances 0.000 description 5
229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 5
229910052719 titanium Inorganic materials 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
229920002943 EPDM rubber Polymers 0.000 description 4
229910010061 TiC13 Inorganic materials 0.000 description 4
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 4
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000499 gel Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
150000002902 organometallic compounds Chemical class 0.000 description 4
239000012071 phase Substances 0.000 description 4
229920000573 polyethylene Polymers 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
239000011115 styrene butadiene Substances 0.000 description 4
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
229910052720 vanadium Inorganic materials 0.000 description 4
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 4
229910052726 zirconium Inorganic materials 0.000 description 4
GOVAISVZGLQKDS-UHFFFAOYSA-N 4-[[4-$l^{1}-oxidanyl-3,5-bis(2-methylpropyl)phenyl]methylidene]-2,6-bis(2-methylpropyl)cyclohexa-2,5-dien-1-one Chemical group C1=C(CC(C)C)C(=O)C(CC(C)C)=CC1=CC1=CC(CC(C)C)=C([O])C(CC(C)C)=C1 GOVAISVZGLQKDS-UHFFFAOYSA-N 0.000 description 3
241001120493 Arene Species 0.000 description 3
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 3
QPPHYRYXDBCLHR-UHFFFAOYSA-N C(=C)(C)C12C(CC1)C=CC=C2 Chemical compound C(=C)(C)C12C(CC1)C=CC=C2 QPPHYRYXDBCLHR-UHFFFAOYSA-N 0.000 description 3
NNXROJYPAFWICS-UHFFFAOYSA-N C(=C)(C)C1=C2C(CC2)=CC=C1 Chemical compound C(=C)(C)C1=C2C(CC2)=CC=C1 NNXROJYPAFWICS-UHFFFAOYSA-N 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
238000010539 anionic addition polymerization reaction Methods 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
239000011651 chromium Substances 0.000 description 3
239000002131 composite material Substances 0.000 description 3
238000000748 compression moulding Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229920005669 high impact polystyrene Polymers 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
229940095102 methyl benzoate Drugs 0.000 description 3
229910052750 molybdenum Inorganic materials 0.000 description 3
239000011733 molybdenum Substances 0.000 description 3
238000000465 moulding Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
230000000737 periodic effect Effects 0.000 description 3
238000012545 processing Methods 0.000 description 3
239000002516 radical scavenger Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
150000003440 styrenes Chemical class 0.000 description 3
229920003051 synthetic elastomer Polymers 0.000 description 3
239000005061 synthetic rubber Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RLKKZSSOQABBHI-UHFFFAOYSA-N 1-[2-[(2-methylpropan-2-yl)oxy]ethoxy]butane Chemical compound CCCCOCCOC(C)(C)C RLKKZSSOQABBHI-UHFFFAOYSA-N 0.000 description 2
QNURBHLVKKDMJX-UHFFFAOYSA-N 2-(chloromethyl)bicyclo[4.2.0]octa-1(6),2,4-triene Chemical compound ClCC1=C2C(CC2)=CC=C1 QNURBHLVKKDMJX-UHFFFAOYSA-N 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
238000010504 bond cleavage reaction Methods 0.000 description 2
150000001649 bromium compounds Chemical class 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
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
230000008859 change Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
230000002950 deficient Effects 0.000 description 2
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 2
150000004673 fluoride salts Chemical class 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
239000004797 high-impact polystyrene Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
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238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000005204 segregation Methods 0.000 description 1
238000005245 sintering Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000012721 stereospecific polymerization Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229920002725 thermoplastic elastomer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
230000007704 transition Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound 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
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
239000004636 vulcanized rubber Substances 0.000 description 1
238000004260 weight control Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000519263A 1986-09-29 1986-09-29 Polymeres olefiniques de benzocyclobutene et procede pour sa preparation Expired - Fee Related CA1293090C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000519263A CA1293090C (fr)	1986-09-29	1986-09-29	Polymeres olefiniques de benzocyclobutene et procede pour sa preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000519263A CA1293090C (fr)	1986-09-29	1986-09-29	Polymeres olefiniques de benzocyclobutene et procede pour sa preparation

Publications (1)

Publication Number	Publication Date
CA1293090C true CA1293090C (fr)	1991-12-10

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000519263A Expired - Fee Related CA1293090C (fr)	1986-09-29	1986-09-29	Polymeres olefiniques de benzocyclobutene et procede pour sa preparation

Country Status (1)

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CA (1)	CA1293090C (fr)

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WO2013041958A1 (fr) *	2011-09-23	2013-03-28	Az Electronics Materials Usa Corp.	Compositions de couche neutre pour l'auto-assemblage dirigé de copolymères séquencés et procédés s'y rapportant
US8835581B2 (en)	2012-06-08	2014-09-16	Az Electronic Materials (Luxembourg) S.A.R.L.	Neutral layer polymer composition for directed self assembly and processes thereof
US9040659B2 (en)	2012-03-09	2015-05-26	Az Electronic Materials (Luxembourg) S.A.R.L.	Methods and materials for removing metals in block copolymers
US9093263B2 (en)	2013-09-27	2015-07-28	Az Electronic Materials (Luxembourg) S.A.R.L.	Underlayer composition for promoting self assembly and method of making and using
US9181449B2 (en)	2013-12-16	2015-11-10	Az Electronic Materials (Luxembourg) S.A.R.L.	Underlayer composition for promoting self assembly and method of making and using
US10457088B2 (en)	2013-05-13	2019-10-29	Ridgefield Acquisition	Template for self assembly and method of making a self assembled pattern
US11067893B2 (en)	2016-12-21	2021-07-20	Merck Patent Gmbh	Compositions and processes for self-assembly of block copolymers
CN115141157A (zh) *	2022-06-27	2022-10-04	佳化化学科技发展（上海）有限公司	一种异氰脲酸三丙烯酸酯及其制备方法和应用
US11518730B2 (en)	2016-08-18	2022-12-06	Merck Patent Gmbh	Polymer compositions for self-assembly applications
US12559644B2 (en)	2018-12-07	2026-02-24	Merck Patent Gmbh	Rapid cross-linkable neutral underlayers for contact hole self-assembly of polystyrene-b-poly(methyl methacrylate) diblock copolymers and their formulation thereof

1986
- 1986-09-29 CA CA000519263A patent/CA1293090C/fr not_active Expired - Fee Related

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WO2013041958A1 (fr) *	2011-09-23	2013-03-28	Az Electronics Materials Usa Corp.	Compositions de couche neutre pour l'auto-assemblage dirigé de copolymères séquencés et procédés s'y rapportant
US8691925B2 (en)	2011-09-23	2014-04-08	Az Electronic Materials (Luxembourg) S.A.R.L.	Compositions of neutral layer for directed self assembly block copolymers and processes thereof
EP2949702A1 (fr) *	2011-09-23	2015-12-02	Merck Patent GmbH	Compositions de couche neutre pour copolymères à bloc d'auto-assemblage dirigé et procédés correspondants
US9040659B2 (en)	2012-03-09	2015-05-26	Az Electronic Materials (Luxembourg) S.A.R.L.	Methods and materials for removing metals in block copolymers
US8835581B2 (en)	2012-06-08	2014-09-16	Az Electronic Materials (Luxembourg) S.A.R.L.	Neutral layer polymer composition for directed self assembly and processes thereof
US10457088B2 (en)	2013-05-13	2019-10-29	Ridgefield Acquisition	Template for self assembly and method of making a self assembled pattern
US9093263B2 (en)	2013-09-27	2015-07-28	Az Electronic Materials (Luxembourg) S.A.R.L.	Underlayer composition for promoting self assembly and method of making and using
US9181449B2 (en)	2013-12-16	2015-11-10	Az Electronic Materials (Luxembourg) S.A.R.L.	Underlayer composition for promoting self assembly and method of making and using
US11518730B2 (en)	2016-08-18	2022-12-06	Merck Patent Gmbh	Polymer compositions for self-assembly applications
US11067893B2 (en)	2016-12-21	2021-07-20	Merck Patent Gmbh	Compositions and processes for self-assembly of block copolymers
US12559644B2 (en)	2018-12-07	2026-02-24	Merck Patent Gmbh	Rapid cross-linkable neutral underlayers for contact hole self-assembly of polystyrene-b-poly(methyl methacrylate) diblock copolymers and their formulation thereof
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Legal Events

Date	Code	Title	Description
2006-12-11	MKLA	Lapsed

Publication	Publication Date	Title
EP0227124B1 (fr)	1992-03-04	Polymères oléfiniques de benzocyclobutène et procédés pour leur préparation
US6699941B1 (en)	2004-03-02	Block copolymer
CN1143871C (zh)	2004-03-31	热塑性模塑材料
US4089913A (en)	1978-05-16	Process for producing transparent block copolymer resin
JP3460005B2 (ja)	2003-10-27	水添重合体
US4122134A (en)	1978-10-24	Method for producing transparent block copolymer resin
US5476904A (en)	1995-12-19	Thermoplastic elastomers having improved heat resistance comprising conjugated diene/methyl methacrylate block copolymers
US4698394A (en)	1987-10-06	Reactive styrene polymers
AU686193B2 (en)	1998-02-05	Solid elastomeric block copolymers
CA1155248A (fr)	1983-10-11	Copolymeres sequences de dienes, dont les blocs terminaux sont constitues de copolymere statistique de styrene et d'alpha-methylstyrene; ou de styrene ou d'alkylstyrene, et d'un alpha-methylstyrene
WO2001062813A1 (fr)	2001-08-30	Caoutchouc de copolymere bloc, modificateur de resine, et composition de resine
US3985826A (en)	1976-10-12	Hydrogenated block copolymers of butadiene and isoprene
CA1293090C (fr)	1991-12-10	Polymeres olefiniques de benzocyclobutene et procede pour sa preparation
US4054616A (en)	1977-10-18	Process for producing transparent block copolymer resins
US5585441A (en)	1996-12-17	Elastomer - Modified thermoplastic olefin polymer compositions
CA1049686A (fr)	1979-02-27	Resine transparente d'un copolymere sequence d'un monomere de vinyle et d'un diene conjugue
US4687815A (en)	1987-08-18	Hydrogenated block copolymers
EP0192424B1 (fr)	1992-04-29	Préparation de copolymères séquencés élastomères thermoplastiques
US6143832A (en)	2000-11-07	Aromatic vinyl-conjugated diene block copolymer and production process thereof
US3660536A (en)	1972-05-02	Process for manufacture of polymers of conjugated dienes
Gausepohl et al.	2000	Super-polystyrene: a new class of engineering plastics with versatile properties
JPH02311504A (ja)	1990-12-27	ポリマーの水素化法
US4722974A (en)	1988-02-02	Novel block copolymers containing benzocyclobutene units
NO324339B1 (no)	2007-09-24	Fremgangsmate ved fremstilling av en polymer eller kopolymer ved polymerisering i naervaer av en stabil fri radikal og initiator
JP2004250679A (ja)	2004-09-09	スチレン系樹脂組成物