CA3001197C - Rubber composition including a specific hydrocarbon resin - Google Patents
Rubber composition including a specific hydrocarbon resin Download PDFInfo
- Publication number
- CA3001197C CA3001197C CA3001197A CA3001197A CA3001197C CA 3001197 C CA3001197 C CA 3001197C CA 3001197 A CA3001197 A CA 3001197A CA 3001197 A CA3001197 A CA 3001197A CA 3001197 C CA3001197 C CA 3001197C
- Authority
- CA
- Canada
- Prior art keywords
- rubber composition
- resin
- composition according
- content
- elastomer
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 149
- 229920001971 elastomer Polymers 0.000 title claims abstract description 116
- 239000005060 rubber Substances 0.000 title claims abstract description 55
- 239000013032 Hydrocarbon resin Substances 0.000 title description 2
- 229920006270 hydrocarbon resin Polymers 0.000 title description 2
- 229920005989 resin Polymers 0.000 claims abstract description 120
- 239000011347 resin Substances 0.000 claims abstract description 120
- 239000000806 elastomer Substances 0.000 claims abstract description 61
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 47
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 47
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000012763 reinforcing filler Substances 0.000 claims abstract description 19
- 238000004132 cross linking Methods 0.000 claims abstract description 16
- 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 abstract description 14
- 238000001542 size-exclusion chromatography Methods 0.000 claims abstract description 14
- 230000009477 glass transition Effects 0.000 claims abstract description 13
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920001577 copolymer Polymers 0.000 claims description 23
- 229920003244 diene elastomer Polymers 0.000 claims description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 19
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- 239000005062 Polybutadiene Substances 0.000 claims description 14
- 229920002857 polybutadiene Polymers 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 20
- 239000000178 monomer Substances 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 13
- 150000001993 dienes Chemical class 0.000 description 12
- 239000006229 carbon black Substances 0.000 description 11
- 235000019241 carbon black Nutrition 0.000 description 11
- 238000004073 vulcanization Methods 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000945 filler Substances 0.000 description 9
- 239000005077 polysulfide Substances 0.000 description 9
- 229920001021 polysulfide Polymers 0.000 description 9
- 150000008117 polysulfides Polymers 0.000 description 9
- 239000004793 Polystyrene Substances 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 239000007822 coupling agent Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- -1 alkylalkoxysilanes Chemical class 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000002897 diene group Chemical group 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 230000003014 reinforcing effect Effects 0.000 description 4
- 238000005096 rolling process Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 150000002019 disulfides Chemical class 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 239000012766 organic filler Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical group CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical class COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 2
- LJQLQCAXBUHEAZ-UWTATZPHSA-N 3-phospho-D-glyceroyl dihydrogen phosphate Chemical compound OP(=O)(O)OC[C@@H](O)C(=O)OP(O)(O)=O LJQLQCAXBUHEAZ-UWTATZPHSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical class [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- OAOZZYBUAWEDRA-UHFFFAOYSA-N 3,4-dimethylidenehexane Chemical compound CCC(=C)C(=C)CC OAOZZYBUAWEDRA-UHFFFAOYSA-N 0.000 description 1
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 238000011993 High Performance Size Exclusion Chromatography Methods 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 230000035508 accumulation Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- VILGDADBAQFRJE-UHFFFAOYSA-N n,n-bis(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SN(SC=3SC4=CC=CC=C4N=3)C(C)(C)C)=NC2=C1 VILGDADBAQFRJE-UHFFFAOYSA-N 0.000 description 1
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 1
- CMAUJSNXENPPOF-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-cyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)SC1=NC2=CC=CC=C2S1 CMAUJSNXENPPOF-UHFFFAOYSA-N 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000006235 reinforcing carbon black Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012936 vulcanization activator Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
-
- 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
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1559874 | 2015-10-16 | ||
| FR1559874A FR3042504B1 (fr) | 2015-10-16 | 2015-10-16 | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
| PCT/EP2016/074669 WO2017064235A1 (fr) | 2015-10-16 | 2016-10-14 | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA3001197A1 CA3001197A1 (en) | 2017-04-20 |
| CA3001197C true CA3001197C (en) | 2023-10-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3001197A Active CA3001197C (en) | 2015-10-16 | 2016-10-14 | Rubber composition including a specific hydrocarbon resin |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US11365308B2 (enExample) |
| EP (1) | EP3362512B1 (enExample) |
| JP (1) | JP6976936B2 (enExample) |
| CN (1) | CN108137869A (enExample) |
| CA (1) | CA3001197C (enExample) |
| FR (1) | FR3042504B1 (enExample) |
| WO (1) | WO2017064235A1 (enExample) |
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| FR3061184A1 (fr) | 2016-12-22 | 2018-06-29 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
| FR3061185A1 (fr) | 2016-12-22 | 2018-06-29 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
| FR3065221A1 (fr) | 2017-04-14 | 2018-10-19 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
| JP2019006880A (ja) * | 2017-06-22 | 2019-01-17 | 株式会社ブリヂストン | ゴム組成物及びタイヤ |
| EP3645311B1 (fr) * | 2017-06-30 | 2024-12-25 | Compagnie Générale des Etablissements Michelin | Pneumatique d'avion |
| FR3071842A1 (fr) | 2017-10-04 | 2019-04-05 | Compagnie Generale Des Etablissements Michelin | Compositions de caoutchouc comprenant une combinaison specifique d'un agent de couplage et d'une resine hydrocarbonee |
| FR3071841A1 (fr) * | 2017-10-04 | 2019-04-05 | Compagnie Generale Des Etablissements Michelin | Compositions de caoutchouc comprenant une combinaison specifique d'un agent de couplage et d'une resine hydrocarbonee |
| WO2019115954A1 (fr) * | 2017-12-14 | 2019-06-20 | Compagnie Generale Des Etablissements Michelin | Pneumatique de véhicule de génie civil |
| JP2021523959A (ja) | 2018-05-04 | 2021-09-09 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | タイヤトレッドゴム組成物 |
| WO2019213229A1 (en) | 2018-05-04 | 2019-11-07 | Bridgestone Americas Tire Operations, Llc | Tire tread rubber composition |
| EP3788101A4 (en) | 2018-05-04 | 2022-01-12 | Bridgestone Americas Tire Operations, LLC | RUBBER COMPOSITION FOR TIRE TREAD |
| US12365202B2 (en) | 2018-05-04 | 2025-07-22 | Bridgestone Americas Tire Operations, Llc | Tire tread rubber composition |
| US12365787B2 (en) | 2019-05-29 | 2025-07-22 | Bridgestone Americas Tire Operations, Llc | Tire tread rubber composition and related methods |
| JP7445681B2 (ja) | 2019-05-29 | 2024-03-07 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | タイヤトレッドゴム組成物及び関連方法 |
| WO2020243308A1 (en) | 2019-05-29 | 2020-12-03 | Bridgestone Americas Tire Operations, Llc | Tire tread rubber composition and related methods |
| FR3099168B1 (fr) | 2019-07-26 | 2021-07-02 | Michelin & Cie | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
| WO2021021417A1 (en) * | 2019-07-26 | 2021-02-04 | Exxonmobil Chemical Patents Inc. | Hydrocarbon polymer modifiers having high aromaticity and uses thereof |
| FR3099167B1 (fr) | 2019-07-26 | 2021-07-02 | Michelin & Cie | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
| FR3099169B1 (fr) | 2019-07-26 | 2021-07-02 | Michelin & Cie | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
| FR3099166B1 (fr) | 2019-07-26 | 2022-02-11 | Michelin & Cie | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
| CN114466889B (zh) * | 2019-07-26 | 2023-12-08 | 埃克森美孚化学专利公司 | 具有低芳香性的烃聚合物改性剂及其用途 |
| JP7512610B2 (ja) * | 2020-02-25 | 2024-07-09 | 住友ゴム工業株式会社 | タイヤ用組成物及びタイヤ |
| JP7521284B2 (ja) * | 2020-07-10 | 2024-07-24 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及びタイヤ |
| FR3119168B1 (fr) | 2021-01-26 | 2023-01-13 | Michelin & Cie | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
| FR3119169B1 (fr) * | 2021-01-26 | 2022-12-30 | Michelin & Cie | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
| EP4284847A1 (en) * | 2021-01-26 | 2023-12-06 | ExxonMobil Chemical Patents Inc. | Hydrocarbon polymer modifiers having high aromaticity and low molecular weight and uses thereof |
| JPWO2024203764A1 (enExample) | 2023-03-28 | 2024-10-03 | ||
| EP4692203A1 (en) | 2023-03-28 | 2026-02-11 | ENEOS Materials Corporation | Polymer composition and rubber product |
| JPWO2024203767A1 (enExample) | 2023-03-28 | 2024-10-03 |
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| FR2673187B1 (fr) | 1991-02-25 | 1994-07-01 | Michelin & Cie | Composition de caoutchouc et enveloppes de pneumatiques a base de ladite composition. |
| FR2732351B1 (fr) | 1995-03-29 | 1998-08-21 | Michelin & Cie | Composition de caoutchouc pour enveloppe de pneumatique renfermant de la silice dopee aluminium a titre de charge renforcante |
| DE69739057D1 (de) | 1996-04-01 | 2008-12-04 | Cabot Corp | Neue elastomere verbundwerkstoffe, verfahren und vorrichtung zur herstellung derselben |
| FR2749313A1 (fr) | 1996-05-28 | 1997-12-05 | Michelin & Cie | Composition de caoutchouc dienique a base d'alumine en tant que charge renforcante et son utilisation pour la fabrication d'enveloppes de pneumatiques |
| CN100473684C (zh) | 1997-09-30 | 2009-04-01 | 卡伯特公司 | 弹性体复合共混料及其制备方法 |
| BR9912334A (pt) | 1998-07-22 | 2001-04-17 | Michelin Soc Tech | Composição de borracha utilizável para a fabricação de pneumáticos, processo para preparar uma composição de borracha, utilização de uma composição de borracha, de um sistema de aclopamento e em combinação de uma enamina e de um derivado guanìdico, pneumático, produto semi-acabado em borracha para pneumático e sistema de aclopamento (carga branca/elastÈmero diênico) para composição de borracha. |
| KR20010072049A (ko) | 1998-07-22 | 2001-07-31 | 미첼 롤리에르 | 폴리설파이드 알콕시실란, 아연 디티오포스페이트 및구아니딘 유도체를 기본으로 하는 커플링 시스템(백색충전제/디엔 엘라스토머) |
| BR0114614B1 (pt) | 2000-10-13 | 2011-06-14 | composiÇço elastomÉrica, processo para preparar uma composiÇço elastomÉrica com cinÉtica de vulcanizaÇço melhorada, utilizaÇço de uma composiÇço de borracha, pneumÁtico, e, produto semi-acabado para pneumÁtico compreendendo uma composiÇço de borracha. | |
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| FR2823215B1 (fr) | 2001-04-10 | 2005-04-08 | Michelin Soc Tech | Pneumatique et bande de roulement de pneumatique comportant a titre d'agent de couplage un tetrasulfure de bis-alkoxysilane |
| WO2003002649A1 (fr) | 2001-06-28 | 2003-01-09 | Societe De Technologie Michelin | Bande de roulement pour pneumatique renforcee d'une silice a tres basse surface specifique |
| EP1419195B1 (fr) | 2001-06-28 | 2010-04-21 | Société de Technologie Michelin | Bande de roulement pour pneumatique renforcee d'une silice a basse surface specifique |
| DE60225300T2 (de) | 2001-08-13 | 2009-02-26 | Société de Technologie Michelin | Dienkautschukzusammensetzung für reifen mit einem speziellen silikon als verstärkendem füllstoff |
| SE519792C2 (sv) | 2001-08-17 | 2003-04-08 | Volvo Lastvagnar Ab | Metod för estimering av massan hos ett fordon vilket framförs på en väg med en varierande lutning samt metod för estimering av lutningen av den väg där ett fordon framförs |
| JP4955191B2 (ja) * | 2002-08-21 | 2012-06-20 | 住友ゴム工業株式会社 | タイヤトレッド用ゴム組成物 |
| FR2880349B1 (fr) | 2004-12-31 | 2009-03-06 | Michelin Soc Tech | Nanoparticules de polyvinylaromatique fonctionnalise |
| FR2880354B1 (fr) | 2004-12-31 | 2007-03-02 | Michelin Soc Tech | Composition elastomerique renforcee d'une charge de polyvinylaromatique fonctionnalise |
| FR2886305B1 (fr) | 2005-05-26 | 2007-08-10 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un agent de couplage organosilicique et un agent de recouvrement de charge inorganique |
| FR2886304B1 (fr) | 2005-05-26 | 2007-08-10 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un systeme de couplage organosilicique |
| FR2886306B1 (fr) | 2005-05-26 | 2007-07-06 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un agent de couplage organosiloxane |
| FR2903416B1 (fr) | 2006-07-06 | 2008-09-05 | Michelin Soc Tech | Composition elastomerique renforcee d'une charge de polymere vinylique non aromatique fonctionnalise |
| FR2903411B1 (fr) | 2006-07-06 | 2012-11-02 | Soc Tech Michelin | Nanoparticules de polymere vinylique fonctionnalise |
| JP2008174696A (ja) * | 2007-01-22 | 2008-07-31 | Bridgestone Corp | タイヤ用ゴム組成物及びそれを用いた空気入りタイヤ |
| JP5629422B2 (ja) * | 2007-12-03 | 2014-11-19 | 株式会社ブリヂストン | タイヤ用ゴム組成物及びそれを用いたタイヤ |
| JP2011088998A (ja) | 2009-10-21 | 2011-05-06 | Bridgestone Corp | ゴム組成物及びタイヤ |
| FR2955587B1 (fr) * | 2010-01-28 | 2012-02-17 | Michelin Soc Tech | Composition d'elastomere pour objet pneumatique, a propriete auto-obturante |
| US8735500B2 (en) * | 2010-10-13 | 2014-05-27 | Exxonmobil Chemical Patents Inc. | Hydrocarbon polymer modifiers |
| FR2974808B1 (fr) * | 2011-05-06 | 2013-05-03 | Michelin Soc Tech | Pneumatique dont la bande de roulement comporte un sbr emulsion a haut taux de trans. |
| JP5097862B1 (ja) * | 2011-05-25 | 2012-12-12 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及び空気入りタイヤ |
| JP5559234B2 (ja) * | 2011-08-09 | 2014-07-23 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及び空気入りタイヤ |
| FR2980480B1 (fr) * | 2011-09-26 | 2013-10-11 | Michelin Soc Tech | Pneumatique a adherence amelioree sur sol mouille |
| FR2984900B1 (fr) | 2011-12-21 | 2014-02-07 | Michelin Soc Tech | Pneumatique comprenant une composition essentiellement depourvue de derive guanidique et comprenant une hydroxyalkylpiperazine |
| CN104334368B (zh) * | 2012-05-25 | 2017-11-24 | 埃克森美孚化学专利公司 | 基于二环戊二烯的树脂组合物以及由其制造的制品 |
| EP2853558B1 (de) | 2013-09-27 | 2016-11-09 | Continental Reifen Deutschland GmbH | Schwefelvernetzbare Kautschukmischung |
| FR3014443B1 (fr) | 2013-12-10 | 2016-01-15 | Michelin & Cie | Bande de roulement de pneumatique |
| FR3017871B1 (fr) * | 2014-02-21 | 2016-02-19 | Michelin & Cie | Composition de caoutchouc comprenant un systeme plastifiant a base de resine hydrocarbonee de faible temperature de transition vitreuse |
| FR3021971B1 (fr) | 2014-06-05 | 2016-06-03 | Michelin & Cie | Pneumatique a faible resistance au roulement |
| FR3021972B1 (fr) | 2014-06-05 | 2016-06-03 | Michelin & Cie | Pneumatique a faible resistance au roulement |
| FR3030545B1 (fr) | 2014-12-22 | 2018-05-25 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
-
2015
- 2015-10-16 FR FR1559874A patent/FR3042504B1/fr active Active
-
2016
- 2016-10-14 JP JP2018519412A patent/JP6976936B2/ja active Active
- 2016-10-14 WO PCT/EP2016/074669 patent/WO2017064235A1/fr not_active Ceased
- 2016-10-14 US US15/768,114 patent/US11365308B2/en active Active
- 2016-10-14 CA CA3001197A patent/CA3001197C/en active Active
- 2016-10-14 CN CN201680060165.5A patent/CN108137869A/zh active Pending
- 2016-10-14 EP EP16781786.5A patent/EP3362512B1/fr active Active
-
2022
- 2022-05-17 US US17/746,489 patent/US11802194B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US11802194B2 (en) | 2023-10-31 |
| EP3362512A1 (fr) | 2018-08-22 |
| CN108137869A (zh) | 2018-06-08 |
| FR3042504B1 (fr) | 2018-01-05 |
| CA3001197A1 (en) | 2017-04-20 |
| FR3042504A1 (fr) | 2017-04-21 |
| EP3362512B1 (fr) | 2022-01-26 |
| US11365308B2 (en) | 2022-06-21 |
| JP2018536044A (ja) | 2018-12-06 |
| WO2017064235A1 (fr) | 2017-04-20 |
| US20180340055A1 (en) | 2018-11-29 |
| US20220363875A1 (en) | 2022-11-17 |
| JP6976936B2 (ja) | 2021-12-08 |
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