DK3280766T3 - Elastomere copolymerer på basis af [bis(trihydrocarbylsilyl)aminosilyl]-funktionaliseret styren og deres anvendelse til fremstilling af gummistoffer - Google Patents
Elastomere copolymerer på basis af [bis(trihydrocarbylsilyl)aminosilyl]-funktionaliseret styren og deres anvendelse til fremstilling af gummistoffer Download PDFInfo
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- DK3280766T3 DK3280766T3 DK16719032.1T DK16719032T DK3280766T3 DK 3280766 T3 DK3280766 T3 DK 3280766T3 DK 16719032 T DK16719032 T DK 16719032T DK 3280766 T3 DK3280766 T3 DK 3280766T3
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- Prior art keywords
- carbon atoms
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- copolymer
- aryl
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- 229920001971 elastomer Polymers 0.000 title claims description 70
- 239000005060 rubber Substances 0.000 title claims description 65
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- 229920001198 elastomeric copolymer Polymers 0.000 title claims description 55
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000000178 monomer Substances 0.000 claims description 103
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
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- 238000006116 polymerization reaction Methods 0.000 claims description 52
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 36
- -1 tin halide Chemical class 0.000 claims description 36
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- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000945 filler Substances 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 14
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
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- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
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- 229920002857 polybutadiene Polymers 0.000 claims description 7
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
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- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 claims description 6
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
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- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 3
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- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 claims description 3
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- HVOKBODBWQEEGI-UHFFFAOYSA-N 1-ethenyl-3,5-diethylbenzene Chemical compound CCC1=CC(CC)=CC(C=C)=C1 HVOKBODBWQEEGI-UHFFFAOYSA-N 0.000 claims description 3
- XSHXURIGVYRXAD-UHFFFAOYSA-N 1-ethenyl-3,5-diphenylbenzene Chemical compound C=1C(C=C)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XSHXURIGVYRXAD-UHFFFAOYSA-N 0.000 claims description 3
- LFZRKMOWVSTEMD-UHFFFAOYSA-N 1-ethenyl-3-ethylnaphthalene Chemical compound C1=CC=CC2=CC(CC)=CC(C=C)=C21 LFZRKMOWVSTEMD-UHFFFAOYSA-N 0.000 claims description 3
- XTUJFEHBYGQMFD-UHFFFAOYSA-N 1-ethenyl-3-hexyl-5-methylbenzene Chemical compound CCCCCCC1=CC(C)=CC(C=C)=C1 XTUJFEHBYGQMFD-UHFFFAOYSA-N 0.000 claims description 3
- VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 claims description 3
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- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 3
- ABERXULXRGIGTD-UHFFFAOYSA-N 2-dodecyl-7-ethenylnaphthalene Chemical compound C1=CC(C=C)=CC2=CC(CCCCCCCCCCCC)=CC=C21 ABERXULXRGIGTD-UHFFFAOYSA-N 0.000 claims description 3
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 claims description 3
- OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 claims description 3
- DXFURPHVJQITAC-UHFFFAOYSA-N 4-benzyl-1-ethenyl-2-ethylbenzene Chemical compound C1=C(C=C)C(CC)=CC(CC=2C=CC=CC=2)=C1 DXFURPHVJQITAC-UHFFFAOYSA-N 0.000 claims description 3
- GYLGGODPGFTNRX-UHFFFAOYSA-N 6-cyclohexyl-1-ethenylnaphthalene Chemical compound C=1C=C2C(C=C)=CC=CC2=CC=1C1CCCCC1 GYLGGODPGFTNRX-UHFFFAOYSA-N 0.000 claims description 3
- IMJGQTCMUZMLRZ-UHFFFAOYSA-N buta-1,3-dien-2-ylbenzene Chemical compound C=CC(=C)C1=CC=CC=C1 IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 claims description 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- DMBOORLKGDADEQ-UHFFFAOYSA-N dichloro-bis[[dichloro(methyl)silyl]methyl]silane Chemical compound C[Si](Cl)(Cl)C[Si](Cl)(Cl)C[Si](C)(Cl)Cl DMBOORLKGDADEQ-UHFFFAOYSA-N 0.000 claims description 2
- ZRACHDWEPBOVAJ-UHFFFAOYSA-N dichloro-methyl-[2-[2,3,4,5,6-pentakis[2-[dichloro(methyl)silyl]ethyl]phenyl]ethyl]silane Chemical compound C[Si](Cl)(Cl)CCC1=C(CC[Si](C)(Cl)Cl)C(CC[Si](C)(Cl)Cl)=C(CC[Si](C)(Cl)Cl)C(CC[Si](C)(Cl)Cl)=C1CC[Si](C)(Cl)Cl ZRACHDWEPBOVAJ-UHFFFAOYSA-N 0.000 claims description 2
- VQKBYKIKHWSKDL-UHFFFAOYSA-N difluoro-bis(trifluorosilyl)silane Chemical compound F[Si](F)(F)[Si](F)(F)[Si](F)(F)F VQKBYKIKHWSKDL-UHFFFAOYSA-N 0.000 claims description 2
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- 229920005555 halobutyl Polymers 0.000 claims description 2
- 150000002466 imines Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 claims description 2
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005068 thioepoxy group Chemical group S(O*)* 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical group Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- ASWZNPOTXAXUPB-UHFFFAOYSA-N tribromo(tribromosilyl)silane Chemical compound Br[Si](Br)(Br)[Si](Br)(Br)Br ASWZNPOTXAXUPB-UHFFFAOYSA-N 0.000 claims description 2
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 claims description 2
- QHAHOIWVGZZELU-UHFFFAOYSA-N trichloro(trichlorosilyloxy)silane Chemical compound Cl[Si](Cl)(Cl)O[Si](Cl)(Cl)Cl QHAHOIWVGZZELU-UHFFFAOYSA-N 0.000 claims description 2
- SDNBGJALFMSQER-UHFFFAOYSA-N trifluoro(trifluorosilyl)silane Chemical compound F[Si](F)(F)[Si](F)(F)F SDNBGJALFMSQER-UHFFFAOYSA-N 0.000 claims description 2
- CIEKVFFSPFYSHN-UHFFFAOYSA-N triiodo(triiodosilyl)silane Chemical compound I[Si](I)(I)[Si](I)(I)I CIEKVFFSPFYSHN-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 2
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- 230000015572 biosynthetic process Effects 0.000 description 13
- 229910052744 lithium Inorganic materials 0.000 description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 12
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 150000002642 lithium compounds Chemical class 0.000 description 5
- BVWUEIUNONATML-UHFFFAOYSA-N n-benzylethenamine Chemical compound C=CNCC1=CC=CC=C1 BVWUEIUNONATML-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229920006978 SSBR Polymers 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 238000013329 compounding Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
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- 238000010348 incorporation Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
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- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
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- XOXRRQOIDCIGAX-UHFFFAOYSA-N lithium ethyl(propyl)azanide Chemical compound [Li+].CCC[N-]CC XOXRRQOIDCIGAX-UHFFFAOYSA-N 0.000 description 1
- LHPXHKQJYVVXKC-UHFFFAOYSA-N lithium;benzyl(ethyl)azanide Chemical compound [Li+].CC[N-]CC1=CC=CC=C1 LHPXHKQJYVVXKC-UHFFFAOYSA-N 0.000 description 1
- UYCQPCJALIRKBP-UHFFFAOYSA-N lithium;butyl(ethyl)azanide Chemical compound [Li+].CCCC[N-]CC UYCQPCJALIRKBP-UHFFFAOYSA-N 0.000 description 1
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- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
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- HOLCSXZMVPOUQR-UHFFFAOYSA-N lithium;dihexylazanide Chemical compound [Li+].CCCCCC[N-]CCCCCC HOLCSXZMVPOUQR-UHFFFAOYSA-N 0.000 description 1
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- OKMANNMCASEBSW-UHFFFAOYSA-N lithium;methyl(2-phenylethyl)azanide Chemical compound [Li+].C[N-]CCC1=CC=CC=C1 OKMANNMCASEBSW-UHFFFAOYSA-N 0.000 description 1
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- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
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- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
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- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
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- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- JHGCXUUFRJCMON-UHFFFAOYSA-J silicon(4+);tetraiodide Chemical compound [Si+4].[I-].[I-].[I-].[I-] JHGCXUUFRJCMON-UHFFFAOYSA-J 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
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- PZKOFHKJGUNVTM-UHFFFAOYSA-N trichloro-[dichloro(trichlorosilyl)silyl]silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)[Si](Cl)(Cl)Cl PZKOFHKJGUNVTM-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- VOSJXMPCFODQAR-UHFFFAOYSA-N trisilylamine group Chemical class [SiH3]N([SiH3])[SiH3] VOSJXMPCFODQAR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/26—Nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/26—Nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/06—Butadiene
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/54—Silicon-containing compounds
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
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Claims (24)
1. Anvendelse af et styrenderivat med formlen (I)
(i) hvor R1 og R2 kan være ens eller forskellige og betegner et medlem udvalgt fra gruppen bestående af: a) en enkeltbinding; b) -(CH2)n-, hvor n står for et heltal fra 1 til 12; c) - (CH2CH2Y)n-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; d) -CH2-(CH2CH2Y)n-CH2-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; e) -(CH2CH2NR)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; f) -CH2-(CH2CH2NR)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; g) -(CH2SiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; h) -CH2-(CH2SiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; i) -(OSiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og j) -CH2- (OSiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; hvor R3, R4, R5 og R5 kan være ens eller forskellige og står for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og R7 og R8 kan være ens eller forskellige, og hver R7 og R8 betegner uafhængigt en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer, til fremstilling af en elastomer copolymer.
2. Anvendelse ifølge krav 1, hvor copolymeren ud over enheder afledt af
styrenderivatet med formlen (I) omfatter enheder afledt fra en eller flere dienmonomerer og eventuelt en eller flere vinylaromatiske monomerer, fortrinsvis hvor dienmonomeren er en konjugeret dienmonomer.
3. Fremgangsmåde til fremstilling af en elastomer copolymer, hvilken fremgangsmåde omfatter at underkaste en eller flere dienmonomerer, - eventuelt en eller flere vinylaromatiske monomerer og - et eller flere styrenderivater med formlen (I)
(i), hvor R1 og R2 kan være ens eller forskellige og betegner et led udvalgt fra gruppen bestående af: a) en enkeltbinding; b) - (CH2)n-, hvor n står for et heltal fra 1 til 12; c) - (CH2CH2Y)n-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; d) -CH2-(CH2CH2Y)n-CH2-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; e) - (CH2CH2NR)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; f) -CH2-(CH2CH2NR)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til cirka 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; g) -(CH2SiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til cirka 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; h) -CH2-(CH2SiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; i) -(OSiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og j) -CH2-(OSiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til cirka 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; hvor R3, R4, R5 og R5 kan være ens eller forskellige og står for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10
carbonatomer; og R7 og R8 kan være ens eller forskellige, og hver R7 og R8 betegner uafhængigt en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer, anioniske polymeriseringsbetingelser, fortrinsvis hvor polymeriseringen er portionsvis eller kontinuerlig.
4. Elastomer copolymer omfattende gentagelsesenheder, som er afledt af A) 20 % til 99,95 % efter vægt af copolymeren af en eller flere dienmonomerer; B) 0 % til 60 % efter vægt af copolymeren af en eller flere vinylaromatiske monomerer; og C) 0,05 % til 50 % efter vægt af copolymeren af et eller flere styrenderivater med formlen (I)
(I), hvor R1 og R2 kan være ens eller forskellige og betegner et medlem udvalgt fra gruppen bestående af: a) en enkeltbinding; b) -(CH2)n-, hvor n står for et heltal fra 1 til 12; c) - (CH2CH2Y)n-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; d) -CH2-(CH2CH2Y)n-CH2-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; e) -(CH2CH2NR)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; f) -CH2-(CH2CH2NR)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til cirka 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; g) -(CH2SiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til cirka 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; h) -CH2-(CH2SiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; i) -(OSiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og j) -CH2-(OSiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt betegne en alkylgruppe indeholdende fra 1 til cirka 10 carbonatomer, eller en aryl- eller aralkylgruppe
indeholdende fra 6 til 10 carbonatomer; hvor R3, R4, R5 og R5 kan være ens eller forskellige og står for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og R7 og R8 kan være ens eller forskellige, og hver R7 og R8 betegner uafhængigt en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer.
5. Elastomer copolymer ifølge krav 4, hvor dienmonomeren er en konjugeret dienmonomer, fortrinsvis hvor den konjugerede dienmonomer er udvalgt blandt 1,3-butadien, isopren, 1,3-pentadien, 2,3-dimethyl-l,3-butadien, 2-methyl-l,3-pentadien, 2,3-dimethyl-l,3-pentadien, 2-phenyl-l,3-butadien og 4,5-diethyl-l,3-oktadien, mere foretrukket hvor den konjugerede dienmonomer er udvalgt blandt 1,3-butadien og isopren, især hvor den konjugerede dienmonomer er 1,3-butadien.
6. Elastomer copolymer ifølge krav 5, hvor mængden af A) konjugerede dienmonomerer er 40 til 90 % efter vægt af copolymeren, fortrinsvis 50 til 90 % efter vægt af copolymeren, navnlig 60 til 90 % efter vægt af copolymeren .
7. Elastomer copolymer ifølge et hvilket som helst af kravene 4 til 6, hvor den vinylaromatiske monomer er udvalgt blandt styren, 1-vinylnaphthalen, 3-methylstyren, 3,5-diethylstyren, 4-propylstyren, 2,4,6-trimethylstyren, 4-dodecylstyren, 3-methyl-5-n-hexylstyren, 4-phenylstyren, 2-ethyl-4-benzyl-styren, 3,5-diphenylstyren, 2,3,4,5-tetraethylstyren, 3-ethyl-l-vinylnaphthalen, 6-isopropyl-l-vinylnaphthalen, 6-cyclohexyl-1-vinylnaphthalen, 7-dodecyl-2-vinylnaphthalen, og a-methylstyren, fortrinsvis hvor den vinylaromatiske monomer er udvalgt blandt styren, 3-methylstyren og a-methylstyren, navnlig hvor den vinylaromatiske monomer er styren.
8. Elastomer copolymer ifølge et hvilket som helst af kravene 4 til 7, hvor mængden af B) vinylaromatiske monomerer er 10 til 60 % efter vægt af copolymeren, fortrinsvis 10 til 50 % efter vægt af copolymeren, navnlig 20 til 50 % efter vægt af copolymeren.
9. Elastomer copolymer ifølge et hvilket som helst af kravene 4 til 8, hvor R2 i styrenderivatet med formlen (I) er (CEFL; fortrinsvis hvor styrenderivatet er udvalgt blandt en hvilken som helst af formlerne (1), (2), (3), (4), (5) og (6)
mere foretrukket hvor styrenderivatet med formlen (I) er udvalgt blandt en hvilken som helst af formlerne (1), (2), (4), og (5); mest foretrukket hvor styrenderivatet med formlen (I) er udvalgt blandt en hvilken som helst af formlerne (1), (4), og (5).
10. Elastomer copolymer ifølge et hvilket som helst af kravene 4 til 9, hvor mængden af C) er 0,05 til 50 % efter vægt af copolymeren, fortrinsvis 0,2 til 10 % efter vægt af copolymeren, navnlig 0,5 til 2 % efter vægt af copolymeren.
11. Elastomer copolymer ifølge et hvilket som helst af kravene 4 til 10, hvor copolymeren omfatter enheder med en stjernestruktur, som dannes ved omsætning af metalterminerede levende lineær copolymer med et eller flere bindemidler.
12. Elastomer copolymer ifølge krav 11, hvor bindemidlet er et tinhaloidbindemiddel, fortrinsvis hvor tinhaloidbindemidlet er tintetrachlorid.
13. Copolymer ifølge krav 11, hvor bindemidlet er et siliciumhaloidbindemiddel, fortrinsvis hvor siliciumhaloidbindemidlet er udvalgt blandt siliciumtetrachlorid, siliciumtetrabromid, siliciumtetrafluorid, siliciumtetraiodid, hexachlordisilan, hexabromdisilan, hexafluordisilan, hexaioddisilan, oktachlortrisilan, oktabromtrisilan, oktafluortrisilan, oktaiodtrisilan, hexachlordisiloxan, 2,2,4,4,6,6-hexachlor-2,4,6-trisilaheptan,l,2,3,4,5,6-hexakis[2-(methyldichlorsilyl)ethyl]benzen, og alkylsiliciumhaloid med den almene formel (III) R9n-Si-X4-n (III),
hvor R9 er en monovalent alifatisk carbonhydridgruppe med 1 til 20 carbonatomer eller en monovalent aromatisk carbonhydridgruppe med 6 til 18 carbonatomer; n er et heltal på 0 til 2; og X kan være et chlor-, brom-, fluor- eller iodatom.
14. Elastomer copolymer ifølge et hvilket som helst af kravene 11 til 13, hvor andelen af enheder med stjernestruktur er mellem 15 og 75 % efter vægt af copolymeren.
15. Elastomer copolymer ifølge et hvilket som helst af kravene 4 til 14, hvor et eller flere partier, der er reaktive over for siliciumoverflade, er til stede, fortrinsvis hvor partiet er afledt af enheder med den almene formel (IV) eller (V) R10n-Si- (OR11)4-n (IV),
(V), hvor R10 og R11 i den almene formel (IV) hver især uafhængigt er en monovalent alifatisk carbonhydridgruppe med 1 til 20 carbonatomer eller en monovalent aromatisk carbonhydridgruppe med 6 til 18 carbonatomer; n er et heltal på 0 til 2; når der er flere OR11, kan de flere OR11 være ens eller forskellige fra hinanden, og der er ingen aktiv proton i molekylet, og hvor A i den almene formel (V) er en monovalent gruppe med mindst en funktionel gruppe udvalgt fra gruppen bestående af epoxy, thioepoxy, isocyanat, imin, cyklisk tertiær amin, acyklisk tertiær amin, pyridin, silazan og disulfid; R14 er en enkeltbinding eller en divalent carbonhydridgruppe; R12 og R13 er hver især uafhængigt en monovalent alifatisk carbonhydridgruppe med 1 til 20 carbonatomer eller en monovalent aromatisk carbonhydridgruppe med 6 til 18 carbonatomer; b er et heltal på 0 til 2; når der er flere OR13, kan de flere OR13 være ens eller forskellige fra hinanden; og der er ingen aktiv proton i molekylet.
16. Fremgangsmåde til fremstilling af en gummi omfattende at vulkanisere den elastomere copolymer ifølge et hvilket som helst af kravene 4 til 15 i nærvær af et eller flere vulkaniseringsmidler.
17. Gummi, der kan opnås ifølge fremgangsmåden ifølge krav 16.
18. Gummisammensætning omfattende x) en gummibestanddel omfattende gummien ifølge krav 17.
19. Gummisammensætning ifølge krav 18, yderligere omfattende y) et eller flere fyldstoffer, fortrinsvis hvor fyldstoffet er udvalgt fra gruppen bestående af silicium og kønrøg, fortrinsvis hvor gummisammensætningen omfatter y) både silicium og kønrøg.
20. Gummisammensætning ifølge krav 19, hvor mængden af fyldstofbestanddelen y) er 10 til 150 dele efter masse i forhold til 100 dele efter masse af gummibestanddelen x) (phr), fortrinsvis hvor mængden af bestanddel y) er 20 til 140 phr, mere foretrukket hvor mængden af bestanddel y) er 30 til 130 phr.
21. Gummisammensætning ifølge et hvilket som helst af kravene 18 til 20, hvor
gummibestanddelen x) også omfatter en eller flere yderligere gummiagtige polymerer.
22. Gummisammensætning ifølge krav 21, hvor den yderligere gummiagtige polymer er udvalgt fra gruppen bestående af naturlig gummi, syntetisk isoprengummi, butadiengummi, styren-butadiengummi, ethylen-a-olefincopolymergummi, ethylen-a-olefin-diencopolymergummi, akrylnitril-butadiencopolymergummi, chlorprengummi og halogeneret butylgummi.
23. Dækbestanddel omfattende gummisammensætningen ifølge krav 22, fortrinsvis hvor dækbestanddelen er en slidbane.
24. Dæk omfattende dækbestanddelen ifølge krav 23.
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KR102195791B1 (ko) | 2016-10-06 | 2020-12-30 | 신도스 두리 7 스폴카 츠 오그라니크초나 오드포비드치알노스치아 스폴카 야브나 | [비스(트리하이드로카르빌실릴)아미노실릴]-관능화 스티렌 기반의 탄성 공중합체 및 고무 제조에서의 그의 용도 |
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PL2516478T3 (pl) | 2009-12-21 | 2014-11-28 | Trinseo Europe Gmbh | Modyfikowane kompozycje polimerowe |
US9120890B2 (en) | 2011-11-24 | 2015-09-01 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
JP6062662B2 (ja) * | 2012-06-01 | 2017-01-18 | 住友ゴム工業株式会社 | 共重合体、ゴム組成物及び空気入りタイヤ |
JP2014105241A (ja) * | 2012-11-26 | 2014-06-09 | Sumitomo Rubber Ind Ltd | トレッド用ゴム組成物及び空気入りタイヤ |
ES2692043T3 (es) * | 2015-04-10 | 2018-11-29 | Synthos S.A. | Estireno funcionalizado con [bis (trihidrocarbilsilil) aminosililo] y un método para su preparación |
-
2016
- 2016-04-08 RS RS20181345A patent/RS57960B1/sr unknown
- 2016-04-08 HU HUE16719032A patent/HUE039953T2/hu unknown
- 2016-04-08 SG SG11201707986VA patent/SG11201707986VA/en unknown
- 2016-04-08 ES ES16719032.1T patent/ES2692025T3/es active Active
- 2016-04-08 CN CN201680033817.6A patent/CN107849194B/zh not_active Expired - Fee Related
- 2016-04-08 BR BR112017021159A patent/BR112017021159A2/pt active Search and Examination
- 2016-04-08 TR TR2018/16162T patent/TR201816162T4/tr unknown
- 2016-04-08 EA EA201792251A patent/EA201792251A1/ru unknown
- 2016-04-08 AU AU2016246006A patent/AU2016246006A1/en not_active Abandoned
- 2016-04-08 EP EP16719032.1A patent/EP3280766B1/en active Active
- 2016-04-08 DK DK16719032.1T patent/DK3280766T3/da active
- 2016-04-08 US US15/565,346 patent/US20180072101A1/en not_active Abandoned
- 2016-04-08 MX MX2017013011A patent/MX2017013011A/es active IP Right Grant
- 2016-04-08 TN TNP/2017/000434A patent/TN2017000434A1/en unknown
- 2016-04-08 WO PCT/EP2016/057834 patent/WO2016162528A1/en active Application Filing
- 2016-04-08 KR KR1020177032698A patent/KR20180002682A/ko active IP Right Grant
- 2016-04-08 JP JP2017552924A patent/JP6725921B2/ja not_active Expired - Fee Related
- 2016-04-08 CA CA2981128A patent/CA2981128A1/en not_active Abandoned
- 2016-04-08 PL PL16719032T patent/PL3280766T3/pl unknown
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2017
- 2017-10-03 IL IL254882A patent/IL254882A0/en unknown
- 2017-11-09 ZA ZA2017/07595A patent/ZA201707595B/en unknown
Also Published As
Publication number | Publication date |
---|---|
CN107849194A (zh) | 2018-03-27 |
CA2981128A1 (en) | 2016-10-13 |
JP6725921B2 (ja) | 2020-07-22 |
EP3280766B1 (en) | 2018-08-15 |
KR20180002682A (ko) | 2018-01-08 |
TR201816162T4 (tr) | 2018-11-21 |
JP2018513897A (ja) | 2018-05-31 |
US20180072101A1 (en) | 2018-03-15 |
EP3280766A1 (en) | 2018-02-14 |
MX2017013011A (es) | 2018-04-24 |
ES2692025T3 (es) | 2018-11-29 |
CN107849194B (zh) | 2020-09-04 |
WO2016162528A1 (en) | 2016-10-13 |
AU2016246006A1 (en) | 2017-11-02 |
BR112017021159A2 (pt) | 2018-07-03 |
SG11201707986VA (en) | 2017-10-30 |
TN2017000434A1 (en) | 2019-04-12 |
IL254882A0 (en) | 2017-12-31 |
HUE039953T2 (hu) | 2019-02-28 |
ZA201707595B (en) | 2018-11-28 |
RS57960B1 (sr) | 2019-01-31 |
EA201792251A1 (ru) | 2018-02-28 |
PL3280766T3 (pl) | 2019-01-31 |
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