CA2424912C - Composition comprenant un nitroxyde, un promoteur et eventuellement un initiateur de radicaux libres - Google Patents
Composition comprenant un nitroxyde, un promoteur et eventuellement un initiateur de radicaux libres Download PDFInfo
- Publication number
- CA2424912C CA2424912C CA002424912A CA2424912A CA2424912C CA 2424912 C CA2424912 C CA 2424912C CA 002424912 A CA002424912 A CA 002424912A CA 2424912 A CA2424912 A CA 2424912A CA 2424912 C CA2424912 C CA 2424912C
- Authority
- CA
- Canada
- Prior art keywords
- group
- composition according
- nitroxide
- radical
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 50
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 239000003999 initiator Substances 0.000 title claims description 26
- 150000003254 radicals Chemical class 0.000 title claims description 23
- 238000004132 cross linking Methods 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 71
- -1 t-butyl-peroxy Chemical group 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000002978 peroxides Chemical class 0.000 claims description 9
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 8
- 229920001169 thermoplastic Polymers 0.000 claims description 8
- 239000000806 elastomer Substances 0.000 claims description 7
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 150000001451 organic peroxides Chemical class 0.000 claims description 5
- 229920000193 polymethacrylate Polymers 0.000 claims description 5
- IHPKGUQCSIINRJ-CSKARUKUSA-N (E)-beta-ocimene Chemical compound CC(C)=CC\C=C(/C)C=C IHPKGUQCSIINRJ-CSKARUKUSA-N 0.000 claims description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 claims description 4
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims description 4
- SFXHWRCRQNGVLJ-UHFFFAOYSA-N 4-methoxy-TEMPO Chemical group COC1CC(C)(C)N([O])C(C)(C)C1 SFXHWRCRQNGVLJ-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- RPDUDBYMNGAHEM-UHFFFAOYSA-N PROXYL Chemical group CC1(C)CCC(C)(C)N1[O] RPDUDBYMNGAHEM-UHFFFAOYSA-N 0.000 claims description 4
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229920001897 terpolymer Polymers 0.000 claims description 3
- CWABICBDFJMISP-UHFFFAOYSA-N 1,3,5-tris(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC(C(C)=C)=CC(C(C)=C)=C1 CWABICBDFJMISP-UHFFFAOYSA-N 0.000 claims description 2
- UPJVEXRKOWFEIG-UHFFFAOYSA-N 1-[2-methyl-4-(3-propan-2-ylphenyl)pent-4-en-2-yl]-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(C(=C)CC(C)(C)C=2C=C(C=CC=2)C(C)C)=C1 UPJVEXRKOWFEIG-UHFFFAOYSA-N 0.000 claims description 2
- ICRPDMMPXGVIQA-UHFFFAOYSA-N 1-[2-methyl-4-(3-propan-2-ylphenyl)pent-4-en-2-yl]-4-propan-2-ylbenzene Chemical compound C1=CC(C(C)C)=CC=C1C(C)(C)CC(=C)C1=CC=CC(C(C)C)=C1 ICRPDMMPXGVIQA-UHFFFAOYSA-N 0.000 claims description 2
- PWLJXFFLHZAFNN-UHFFFAOYSA-N 1-[2-methyl-4-(4-propan-2-ylphenyl)pent-4-en-2-yl]-3-propan-2-ylbenzene Chemical compound C1=CC(C(C)C)=CC=C1C(=C)CC(C)(C)C1=CC=CC(C(C)C)=C1 PWLJXFFLHZAFNN-UHFFFAOYSA-N 0.000 claims description 2
- JHOZPXIJSJRIOJ-UHFFFAOYSA-N 1-methyl-3-[2-methyl-4-(3-methylphenyl)pent-4-en-2-yl]benzene Chemical compound CC1=CC=CC(C(=C)CC(C)(C)C=2C=C(C)C=CC=2)=C1 JHOZPXIJSJRIOJ-UHFFFAOYSA-N 0.000 claims description 2
- JAHVAVMRZBZGSU-UHFFFAOYSA-N 1-methyl-4-[2-methyl-4-(4-methylphenyl)pent-4-en-2-yl]benzene Chemical compound C1=CC(C)=CC=C1C(=C)CC(C)(C)C1=CC=C(C)C=C1 JAHVAVMRZBZGSU-UHFFFAOYSA-N 0.000 claims description 2
- JMXKDHSUNNENAQ-UHFFFAOYSA-N 1-propan-2-yl-2,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)=C)=C1C(C)=C JMXKDHSUNNENAQ-UHFFFAOYSA-N 0.000 claims description 2
- DEERRLKEFILJCL-UHFFFAOYSA-N 1-propan-2-yl-2,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)=C)C=C1C(C)=C DEERRLKEFILJCL-UHFFFAOYSA-N 0.000 claims description 2
- PELHLNBYGSCPEK-UHFFFAOYSA-N 1-propan-2-yl-3,5-bis(prop-1-en-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)=C)=CC(C(C)=C)=C1 PELHLNBYGSCPEK-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- BXAAQNFGSQKPDZ-UHFFFAOYSA-N 3-[1,2,2-tris(prop-2-enoxy)ethoxy]prop-1-ene Chemical compound C=CCOC(OCC=C)C(OCC=C)OCC=C BXAAQNFGSQKPDZ-UHFFFAOYSA-N 0.000 claims description 2
- GEPIUTWNBHBHIO-UHFFFAOYSA-N 3-carboxy-PROXYL Chemical compound CC1(C)CC(C(O)=O)C(C)(C)N1[O] GEPIUTWNBHBHIO-UHFFFAOYSA-N 0.000 claims description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- VSZHZSRGOYJISY-UHFFFAOYSA-N 4-propan-2-yl-1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)=C)C(C(C)=C)=C1 VSZHZSRGOYJISY-UHFFFAOYSA-N 0.000 claims description 2
- NNWNNQTUZYVQRK-UHFFFAOYSA-N 5-bromo-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound BrC1=NC=C2NC(C(=O)O)=CC2=C1 NNWNNQTUZYVQRK-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229920002574 CR-39 Polymers 0.000 claims description 2
- 239000004709 Chlorinated polyethylene Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229920001973 fluoroelastomer Polymers 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004700 high-density polyethylene Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920002681 hypalon Polymers 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229920001684 low density polyethylene Polymers 0.000 claims description 2
- 239000004702 low-density polyethylene Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229920002379 silicone rubber Polymers 0.000 claims description 2
- 239000004945 silicone rubber Substances 0.000 claims description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 2
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 claims description 2
- IHPKGUQCSIINRJ-UHFFFAOYSA-N β-ocimene Natural products CC(C)=CCC=C(C)C=C IHPKGUQCSIINRJ-UHFFFAOYSA-N 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 3
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- XLFOYVHYOLEKPZ-UHFFFAOYSA-N 1-[2-methyl-4-(4-propan-2-ylphenyl)pent-4-en-2-yl]-4-propan-2-ylbenzene Chemical compound C1=CC(C(C)C)=CC=C1C(=C)CC(C)(C)C1=CC=C(C(C)C)C=C1 XLFOYVHYOLEKPZ-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- GQVMHMFBVWSSPF-TUDXIOLJSA-N CC=C(C)\C=C\C=C(C)C Chemical compound CC=C(C)\C=C\C=C(C)C GQVMHMFBVWSSPF-TUDXIOLJSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical group CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
- SXPLGYBFGPYAHS-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SXPLGYBFGPYAHS-UHFFFAOYSA-N 0.000 claims 1
- BKXRKRANFLFTFU-UHFFFAOYSA-N bis(prop-2-enyl) oxalate Chemical compound C=CCOC(=O)C(=O)OCC=C BKXRKRANFLFTFU-UHFFFAOYSA-N 0.000 claims 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229920001038 ethylene copolymer Polymers 0.000 claims 1
- 239000005038 ethylene vinyl acetate Substances 0.000 claims 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- PLCFYBDYBCOLSP-UHFFFAOYSA-N tris(prop-2-enyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=CCOC(=O)CC(O)(CC(=O)OCC=C)C(=O)OCC=C PLCFYBDYBCOLSP-UHFFFAOYSA-N 0.000 claims 1
- 230000001588 bifunctional effect Effects 0.000 abstract description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 description 32
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 26
- 239000000178 monomer Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 4
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007863 gel particle Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 229940070710 valerate Drugs 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- GPQGZUDRUAEAQL-UHFFFAOYSA-N 1,2,4-tris(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C(C(C)=C)=C1 GPQGZUDRUAEAQL-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- DBMSQTNESXMLCH-UHFFFAOYSA-N 1-[1-[2-(2,5-dioxopyrrol-1-yl)propoxy]propan-2-yl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C)COCC(C)N1C(=O)C=CC1=O DBMSQTNESXMLCH-UHFFFAOYSA-N 0.000 description 1
- OEUTXEVXKFXZPB-UHFFFAOYSA-N 1-[12-(2,5-dioxopyrrol-1-yl)dodecyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCCCCCCCN1C(=O)C=CC1=O OEUTXEVXKFXZPB-UHFFFAOYSA-N 0.000 description 1
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- WHQGTBWKCDUZBX-UHFFFAOYSA-N 1-[5-(2,5-dioxopyrrol-1-yl)-2,4-dimethylphenyl]pyrrole-2,5-dione Chemical compound CC1=CC(C)=C(N2C(C=CC2=O)=O)C=C1N1C(=O)C=CC1=O WHQGTBWKCDUZBX-UHFFFAOYSA-N 0.000 description 1
- VVXPQQWFPJRVDH-UHFFFAOYSA-N 1-[5-(2,5-dioxopyrrol-1-yl)-5-methylcyclohexa-1,3-dien-1-yl]pyrrole-2,5-dione Chemical compound C=1C=CC(C)(N2C(C=CC2=O)=O)CC=1N1C(=O)C=CC1=O VVXPQQWFPJRVDH-UHFFFAOYSA-N 0.000 description 1
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- PHIGUQOUWMSXFV-UHFFFAOYSA-N 2-methyl-2-[2-(2-methylbutan-2-ylperoxy)propan-2-ylperoxy]butane Chemical compound CCC(C)(C)OOC(C)(C)OOC(C)(C)CC PHIGUQOUWMSXFV-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- CCOJJJCQUHWYAT-UHFFFAOYSA-N 4-methyl-4-(2-methylbutan-2-ylperoxy)pentan-2-ol Chemical compound CCC(C)(C)OOC(C)(C)CC(C)O CCOJJJCQUHWYAT-UHFFFAOYSA-N 0.000 description 1
- WSGDRFHJFJRSFY-UHFFFAOYSA-N 4-oxo-TEMPO Chemical compound CC1(C)CC(=O)CC(C)(C)N1[O] WSGDRFHJFJRSFY-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JNSWFNBIZLIBPH-UHFFFAOYSA-N 4-tert-butylperoxy-4-methylpentan-2-ol Chemical compound CC(O)CC(C)(C)OOC(C)(C)C JNSWFNBIZLIBPH-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
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- 125000002877 alkyl aryl group Chemical group 0.000 description 1
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- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- MKGMCCVHOVSDTI-UHFFFAOYSA-N ethyl 2-(3,6,6,9,9-pentamethyl-1,2,4,5-tetraoxonan-3-yl)acetate Chemical compound CCOC(=O)CC1(C)OOC(C)(C)CCC(C)(C)OO1 MKGMCCVHOVSDTI-UHFFFAOYSA-N 0.000 description 1
- HARQWLDROVMFJE-UHFFFAOYSA-N ethyl 3,3-bis(tert-butylperoxy)butanoate Chemical compound CCOC(=O)CC(C)(OOC(C)(C)C)OOC(C)(C)C HARQWLDROVMFJE-UHFFFAOYSA-N 0.000 description 1
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- 125000005842 heteroatom Chemical group 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 230000003746 surface roughness Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- 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
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- 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
- C08K5/01—Hydrocarbons
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/32—Compounds containing nitrogen bound to oxygen
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
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)
- Dental Preparations (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Graft Or Block Polymers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerization Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
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| FR00/12580 | 2000-10-03 | ||
| FR0012580A FR2819517B1 (fr) | 2000-10-03 | 2000-10-03 | Composition comprenant un nitroxyde, un promoteur et eventuellement un initiateur de radicaux libres |
| PCT/FR2001/003011 WO2002028946A1 (fr) | 2000-10-03 | 2001-09-28 | Composition comprenant un nitroxyde, un promoteur et eventuellement un initiateur de radicaux libres |
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| CA2424912A1 CA2424912A1 (fr) | 2002-04-11 |
| CA2424912C true CA2424912C (fr) | 2009-05-12 |
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| DE (1) | DE60105183T2 (enExample) |
| ES (1) | ES2227278T3 (enExample) |
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| PT (1) | PT1322696E (enExample) |
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| FR2814749B1 (fr) * | 2000-10-03 | 2003-06-13 | Atofina | Composition retardant le grillage |
| CA2551018A1 (en) * | 2003-12-24 | 2005-07-21 | Dow Global Technologies Inc. | Free-radical crosslinkable polymers: improved process for crosslinking and compositions |
| FR2875502B1 (fr) | 2004-09-22 | 2007-01-05 | Arkema Sa | Composition retardant le grillage |
| US7465769B2 (en) * | 2006-10-09 | 2008-12-16 | Dow Global Technologies Inc. | Nitroxide compounds for minimizing scorch in crosslinkable compositions |
| CN101652417B (zh) * | 2007-02-05 | 2013-10-30 | 陶氏环球技术有限责任公司 | 可交联聚乙烯组合物、其制备方法和由其制得的制品 |
| JP5133983B2 (ja) * | 2007-04-25 | 2013-01-30 | 日本ケミコン株式会社 | 電解コンデンサの封口体とその封口体を用いた電解コンデンサ |
| EP2014707B1 (en) * | 2007-07-12 | 2014-04-23 | Borealis Technology Oy | Modified polymer compositions, modification process and free radical generating agents for i.a. wire and cable applications |
| US9234093B2 (en) | 2008-03-31 | 2016-01-12 | Exxonmobil Chemical Patents Inc. | Thermoplastic vulcanizates |
| US8644470B2 (en) | 2008-04-15 | 2014-02-04 | Cequint, Inc. | Methods and systems for improved caller name identification on a telephone network |
| US8983540B2 (en) | 2008-09-22 | 2015-03-17 | Cequint, Inc. | Delivery of caller identification data to a mobile device using application directed short messaging service |
| US8877867B2 (en) | 2008-11-06 | 2014-11-04 | Exxonmobil Chemical Patents Inc. | Process for forming thermoplastic vulcanizates and extruded articles therefrom |
| US8620281B2 (en) | 2009-04-13 | 2013-12-31 | Cequint, Inc. | System and method for determination and display of “in-network caller” notification on a mobile device |
| US8160554B2 (en) | 2009-04-13 | 2012-04-17 | Cequint, Inc. | System and method for enhanced display of in-network caller information on a mobile device |
| US8160556B2 (en) | 2009-04-13 | 2012-04-17 | Cequint, Inc. | System and method for local handset check of the NXX local exchange to determine carrier |
| US8160555B2 (en) | 2009-04-13 | 2012-04-17 | Cequint, Inc. | System and method for determination of network and conditional execution of applications and promotions |
| CN101820001B (zh) * | 2010-04-30 | 2011-08-31 | 南京红宝丽新材料有限公司 | 太阳能电池封装胶膜 |
| JP5533208B2 (ja) * | 2010-05-06 | 2014-06-25 | 横浜ゴム株式会社 | ゴム組成物およびホース |
| TWI491675B (zh) * | 2012-04-20 | 2015-07-11 | Asahi Kasei E Materials Corp | Polyoxometallic compositions containing free crosslinking groups |
| US20150132513A1 (en) * | 2012-04-20 | 2015-05-14 | Hilti Aktiengesellschaft | Indoline-Nitroxide Radical as Stabiliser and Inhibitor for Reaction Resins, Reaction Resins Containing Same and Use Thereof |
| FR2995313B1 (fr) * | 2012-09-12 | 2015-08-21 | Arkema France | Melange primaire d'initiateur et de promoteur de reticulation |
| CN103206541B (zh) * | 2013-04-23 | 2015-07-15 | 广州机械科学研究院有限公司 | 一种夹布油封及其制备方法与应用 |
| KR20160132958A (ko) * | 2014-03-14 | 2016-11-21 | 밀리켄 앤드 캄파니 | 개질된 헤테로상 폴리올레핀 조성물 |
| JP6355375B2 (ja) * | 2014-03-18 | 2018-07-11 | 日本バルカー工業株式会社 | パーフルオロエラストマー組成物及びシール材 |
| EP2995631A1 (en) | 2014-09-12 | 2016-03-16 | Borealis AG | Process for producing graft copolymers on polyolefin backbone |
| JP6713464B2 (ja) * | 2014-12-09 | 2020-06-24 | アーケマ・インコーポレイテッド | スコーチ防止性のペルオキシドの液体状および溶融性固体状グレード |
| MX2017007414A (es) * | 2014-12-09 | 2017-09-28 | Arkema Inc | Composiciones y metodos de reticulacion de polimeros en presencia de oxigeno atmosferico. |
| CA3019189C (en) * | 2016-03-30 | 2024-01-16 | Dow Global Technologies Llc | Crosslinkable polymeric compositions with methyl-radical scavengers and articles made therefrom |
| US10508179B2 (en) | 2017-02-28 | 2019-12-17 | Exxonmobil Chemical Patents Inc. | Thermoplastic vulcanizate prepared with oil-extended, bimodal metallocene-synthesized EPDM |
| US20200109259A1 (en) | 2017-06-28 | 2020-04-09 | Nok Corporation | Rubber composition and a sealing material for fuel cell separators |
| KR102551057B1 (ko) | 2017-11-08 | 2023-07-05 | 다우 글로벌 테크놀로지스 엘엘씨 | 공기 경화성 에틸렌/알파-올레핀/디엔 혼성중합체 조성물 |
| WO2020023193A1 (en) | 2018-07-23 | 2020-01-30 | Exxonmobil Chemical Patents Inc. | Preparation of bimodal rubber, thermoplastic vulcanizates, and articles made therefrom |
| BR112022024071A2 (pt) | 2020-05-27 | 2022-12-20 | Axial Therapeutics Inc | Compostos moduladores de tlr2, composições farmacêuticas e usos dos mesmos |
| US11674024B2 (en) | 2020-05-29 | 2023-06-13 | Exxonmobil Chemical Patents Inc. | Sequential, double elastomer vulcanization system, method and composition |
| EP4176005A1 (en) | 2020-07-02 | 2023-05-10 | Celanese International Corporation | Thermoplastic vulcanizate compositions containing metallocene multimodal copolymer rubber and processes for making same |
| FR3139825A1 (fr) | 2022-09-21 | 2024-03-22 | Arkema France | Composition comprenant au moins un peroxyde de dialkyle ou de peroxycétal et au moins un peroxyde organique insaturé |
| EP4715006A3 (en) | 2024-09-19 | 2026-06-03 | Nouryon Chemicals International B.V. | Unsaturated scorch retarders |
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| DE59208668D1 (de) * | 1991-02-13 | 1997-08-14 | Ciba Geigy Ag | Stabilisierte Polymermischung |
| US6084015A (en) * | 1996-10-25 | 2000-07-04 | The Yokohama Rubber Co., Ltd. | Rubber composition |
| JPH1149865A (ja) * | 1997-07-31 | 1999-02-23 | Nof Corp | エチレン系ポリマーの架橋用組成物、架橋方法及びポリマー組成物 |
| FR2768739B1 (fr) * | 1997-09-19 | 2004-08-06 | Atochem Elf Sa | Polymere vinylaromatique choc obtenu a partir d'un caoutchouc porteur d'un groupement generateur d'un radical libre stable |
| SE9802386D0 (sv) * | 1998-07-03 | 1998-07-03 | Borealis As | Composition for elektric cables |
| FR2791060A1 (fr) * | 1999-03-18 | 2000-09-22 | Atochem Elf Sa | Procede de preparation d'un caoutchouc porteur de radical libre stable et utilisation dudit caoutchouc porteur pour la preparation d'un polymere vinylaromatique choc |
-
2000
- 2000-10-03 FR FR0012580A patent/FR2819517B1/fr not_active Expired - Fee Related
-
2001
- 2001-09-28 KR KR1020037004684A patent/KR100735589B1/ko not_active Expired - Lifetime
- 2001-09-28 CN CNB018200095A patent/CN100564430C/zh not_active Expired - Lifetime
- 2001-09-28 PT PT01974408T patent/PT1322696E/pt unknown
- 2001-09-28 WO PCT/FR2001/003011 patent/WO2002028946A1/fr not_active Ceased
- 2001-09-28 CA CA002424912A patent/CA2424912C/fr not_active Expired - Lifetime
- 2001-09-28 AT AT01974408T patent/ATE274545T1/de active
- 2001-09-28 JP JP2002532523A patent/JP4086144B2/ja not_active Expired - Lifetime
- 2001-09-28 DE DE60105183T patent/DE60105183T2/de not_active Expired - Lifetime
- 2001-09-28 EP EP01974408A patent/EP1322696B1/fr not_active Expired - Lifetime
- 2001-09-28 ES ES01974408T patent/ES2227278T3/es not_active Expired - Lifetime
- 2001-09-28 AU AU2001293932A patent/AU2001293932A1/en not_active Abandoned
-
2007
- 2007-07-02 JP JP2007174536A patent/JP2007327063A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP4086144B2 (ja) | 2008-05-14 |
| EP1322696A1 (fr) | 2003-07-02 |
| DE60105183D1 (de) | 2004-09-30 |
| AU2001293932A1 (en) | 2002-04-15 |
| KR20030060902A (ko) | 2003-07-16 |
| WO2002028946A1 (fr) | 2002-04-11 |
| ES2227278T3 (es) | 2005-04-01 |
| JP2007327063A (ja) | 2007-12-20 |
| ATE274545T1 (de) | 2004-09-15 |
| CN100564430C (zh) | 2009-12-02 |
| PT1322696E (pt) | 2004-12-31 |
| DE60105183T2 (de) | 2005-10-20 |
| KR100735589B1 (ko) | 2007-07-04 |
| EP1322696B1 (fr) | 2004-08-25 |
| JP2004510858A (ja) | 2004-04-08 |
| CA2424912A1 (fr) | 2002-04-11 |
| FR2819517A1 (fr) | 2002-07-19 |
| FR2819517B1 (fr) | 2003-03-21 |
| CN1478118A (zh) | 2004-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20210928 |