AU2004234058A1 - Method for obtaining an elastomer graft with functional groups along the chain and rubber compositions - Google Patents
Method for obtaining an elastomer graft with functional groups along the chain and rubber compositions Download PDFInfo
- Publication number
- AU2004234058A1 AU2004234058A1 AU2004234058A AU2004234058A AU2004234058A1 AU 2004234058 A1 AU2004234058 A1 AU 2004234058A1 AU 2004234058 A AU2004234058 A AU 2004234058A AU 2004234058 A AU2004234058 A AU 2004234058A AU 2004234058 A1 AU2004234058 A1 AU 2004234058A1
- Authority
- AU
- Australia
- Prior art keywords
- elastomer
- grafted
- sbr
- antioxidant
- cross
- 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.)
- Abandoned
Links
- 229920001971 elastomer Polymers 0.000 title claims description 153
- 239000000203 mixture Substances 0.000 title claims description 146
- 239000000806 elastomer Substances 0.000 title claims description 103
- 239000005060 rubber Substances 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 41
- 125000000524 functional group Chemical group 0.000 title claims description 20
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 58
- 239000003963 antioxidant agent Substances 0.000 claims description 45
- 230000003078 antioxidant effect Effects 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 229920001577 copolymer Polymers 0.000 claims description 30
- 229920003244 diene elastomer Polymers 0.000 claims description 29
- 239000011256 inorganic filler Substances 0.000 claims description 28
- 150000001993 dienes Chemical class 0.000 claims description 27
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 27
- -1 vinyl aromatic compounds Chemical class 0.000 claims description 26
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 24
- 230000003014 reinforcing effect Effects 0.000 claims description 23
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 22
- 239000012763 reinforcing filler Substances 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 20
- 229920002554 vinyl polymer Polymers 0.000 claims description 20
- 150000002978 peroxides Chemical group 0.000 claims description 18
- 230000000930 thermomechanical effect Effects 0.000 claims description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000005062 Polybutadiene Substances 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 12
- 150000004982 aromatic amines Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 11
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 10
- 238000004132 cross linking Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 229920002857 polybutadiene Polymers 0.000 claims description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000000468 ketone group Chemical group 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 238000005096 rolling process Methods 0.000 claims description 6
- DYAOREPNYXXCOA-UHFFFAOYSA-N 2-sulfanylundecanoic acid Chemical compound CCCCCCCCCC(S)C(O)=O DYAOREPNYXXCOA-UHFFFAOYSA-N 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 4
- 235000013824 polyphenols Nutrition 0.000 claims description 4
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 2
- 150000005002 naphthylamines Chemical class 0.000 claims description 2
- 150000004989 p-phenylenediamines Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 95
- 229920000642 polymer Polymers 0.000 description 49
- 239000000377 silicon dioxide Substances 0.000 description 42
- 230000006870 function Effects 0.000 description 33
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 15
- 239000006229 carbon black Substances 0.000 description 15
- 235000019241 carbon black Nutrition 0.000 description 15
- 239000007822 coupling agent Substances 0.000 description 13
- 238000001542 size-exclusion chromatography Methods 0.000 description 13
- 241001441571 Hiodontidae Species 0.000 description 12
- 239000007767 bonding agent Substances 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000945 filler Substances 0.000 description 9
- 239000001993 wax Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 235000021355 Stearic acid Nutrition 0.000 description 8
- 239000005864 Sulphur Substances 0.000 description 8
- 239000010692 aromatic oil Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 8
- 239000008117 stearic acid Substances 0.000 description 8
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 7
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000005345 coagulation Methods 0.000 description 6
- 230000015271 coagulation Effects 0.000 description 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 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 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920001021 polysulfide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000002787 reinforcement Effects 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002897 diene group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000011017 operating method Methods 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011265 semifinished product Substances 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000013519 translation Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 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
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- HMWCQCYUKQZPRA-UHFFFAOYSA-N 2,4-dimethyl-3-methylidenepent-1-ene Chemical compound CC(C)C(=C)C(C)=C HMWCQCYUKQZPRA-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical class COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- PJXJBPMWCKMWLS-UHFFFAOYSA-N 2-methyl-3-methylidenepent-1-ene Chemical compound CCC(=C)C(C)=C PJXJBPMWCKMWLS-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
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- ZZJBMXLRRXWIDA-UHFFFAOYSA-N 3-sulfanylundecanoic acid Chemical compound CCCCCCCCC(S)CC(O)=O ZZJBMXLRRXWIDA-UHFFFAOYSA-N 0.000 description 1
- OXJLRZSYVVQPQJ-UHFFFAOYSA-N 4-(nitrosomethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(CN=O)C=C1 OXJLRZSYVVQPQJ-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001608711 Melo Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- SCPNGMKCUAZZOO-UHFFFAOYSA-N [3-[(3-dimethylsilyl-3-ethoxypropyl)tetrasulfanyl]-1-ethoxypropyl]-dimethylsilane Chemical compound CCOC([SiH](C)C)CCSSSSCCC([SiH](C)C)OCC SCPNGMKCUAZZOO-UHFFFAOYSA-N 0.000 description 1
- BZEZSORUWZUMNU-UHFFFAOYSA-N [Li]CCCC[Li] Chemical compound [Li]CCCC[Li] BZEZSORUWZUMNU-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical class [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000011805 ball Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000011208 chromatographic data Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000011325 microbead Substances 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003192 poly(bis maleimide) 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring 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
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 239000008096 xylene Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- 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
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/20—Incorporating sulfur atoms into the molecule
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR03/05305 | 2003-04-29 | ||
| FR0305305A FR2854404B1 (fr) | 2003-04-29 | 2003-04-29 | Procede d'obtention d'un elastomere greffe a groupes fonctionnels le long de la chaine et compositions de caoutchouc |
| PCT/EP2004/004510 WO2004096865A2 (fr) | 2003-04-29 | 2004-04-29 | Procede d’obtention d’un elastomere greffe a groupes fonctionnels le long de la chaîne et composition de caoutchouc |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004234058A1 true AU2004234058A1 (en) | 2004-11-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004234058A Abandoned AU2004234058A1 (en) | 2003-04-29 | 2004-04-29 | Method for obtaining an elastomer graft with functional groups along the chain and rubber compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7312264B2 (enExample) |
| EP (1) | EP1620471A2 (enExample) |
| JP (1) | JP4874791B2 (enExample) |
| KR (1) | KR101186129B1 (enExample) |
| CN (1) | CN1780859B (enExample) |
| AU (1) | AU2004234058A1 (enExample) |
| BR (1) | BRPI0409806A (enExample) |
| FR (1) | FR2854404B1 (enExample) |
| RU (1) | RU2337923C2 (enExample) |
| WO (1) | WO2004096865A2 (enExample) |
Families Citing this family (268)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7767755B2 (en) * | 2006-04-13 | 2010-08-03 | Bridgestone Corporation | Composition including multiple functionalized polymers |
| US20080103261A1 (en) * | 2006-10-25 | 2008-05-01 | Bridgestone Corporation | Process for producing modified conjugated diene based polymer, modified conjugated diene based polymer produced by the process, rubber composition, and tire |
| FR2910905B1 (fr) * | 2006-12-27 | 2010-08-20 | Michelin Soc Tech | Systeme plastifiant et composition de caoutchouc pour pneumatique incorporant ledit systeme |
| FR2916202B1 (fr) | 2007-05-15 | 2009-07-17 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un plastifiant diester |
| DE102007044175A1 (de) * | 2007-09-15 | 2009-03-19 | Lanxess Deutschland Gmbh | Funktionalisierte Hochvinyl-Dienkautschuke |
| FR2933417B1 (fr) | 2008-07-04 | 2011-12-30 | Michelin Soc Tech | Bande de roulement de pneumatique |
| DE102008052057A1 (de) * | 2008-10-16 | 2010-04-22 | Lanxess Deutschland Gmbh | Funktionalisierte Dienkautschuke |
| FR2940302B1 (fr) | 2008-12-22 | 2012-07-27 | Michelin Soc Tech | Composition de caoutchouc comportant un agent de couplage mercaptosilane bloque |
| FR2940301B1 (fr) | 2008-12-22 | 2012-07-27 | Michelin Soc Tech | Composition de caoutchouc comportant un agent de couplage mercaptosilane bloque |
| FR2940300B1 (fr) | 2008-12-22 | 2010-12-31 | Michelin Soc Tech | Composition de caoutchouc depourvue ou quasiment depourvue de zinc |
| FR2943065B1 (fr) | 2009-03-16 | 2011-04-22 | Michelin Soc Tech | Composition de caoutchouc |
| FR2943680B1 (fr) | 2009-03-31 | 2012-12-28 | Michelin Soc Tech | Composition de caoutchoux et pneumatique utilisant cette composition. |
| FR2945815B1 (fr) | 2009-05-20 | 2011-07-01 | Michelin Soc Tech | Composition de caoutchouc comportant un agent de couplage organosilane |
| DE102009023915A1 (de) * | 2009-05-27 | 2010-12-02 | Rhein-Chemie Rheinau Gmbh | Mischungen aus funktionalisierten Dienkautschuken mit Trimethylolpropan und Fettsäure, ein Verfahren zu deren Herstellung und deren Verwendung |
| FR2947274B1 (fr) | 2009-06-24 | 2013-02-08 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un compose acetylacetonate |
| FR2947275B1 (fr) | 2009-06-29 | 2011-08-26 | Michelin Soc Tech | Pneumatique dont la bande de roulement comprend un elastomere thermoplastique. |
| SG179033A1 (en) * | 2009-09-09 | 2012-04-27 | Bridgestone Corp | Modifying agent, method for producing modified conjugated diene polymer using modifying agent, and modified conjugated diene polymer |
| JP5597959B2 (ja) * | 2009-09-11 | 2014-10-01 | 横浜ゴム株式会社 | タイヤ用ゴム組成物 |
| FR2950064B1 (fr) | 2009-09-14 | 2011-10-14 | Michelin Soc Tech | Composition de caoutchouc comprenant une resine phenolique |
| BR112012006087A8 (pt) | 2009-09-17 | 2018-01-02 | Michelin & Cie | Pneumático e banda de rodagem de pneumático |
| IN2012DN02288A (enExample) | 2009-09-17 | 2015-08-14 | Michelin & Cie | |
| FR2951183B1 (fr) | 2009-10-08 | 2012-04-27 | Michelin Soc Tech | Composition de caoutchouc comprenant une 1,2,4-triazine |
| FR2951180B1 (fr) | 2009-10-08 | 2011-10-28 | Michelin Soc Tech | Composition de caoutchouc comprenant un thiazole |
| FR2951184B1 (fr) | 2009-10-08 | 2011-10-28 | Michelin Soc Tech | Composition de caoutchouc comprenant une thiazoline |
| FR2951181B1 (fr) | 2009-10-08 | 2011-10-28 | Michelin Soc Tech | Composition de caoutchouc comprenant un thiadiazole |
| FR2951182B1 (fr) | 2009-10-14 | 2012-09-21 | Michelin Soc Tech | Composition de caoutchouc comprenant une resine epoxyde |
| HUE035042T2 (en) * | 2009-10-21 | 2018-05-02 | Jsr Corp | Process for the production of modified conjugated diene gum, modified conjugated diene rubber and rubber composition |
| FR2952645B1 (fr) | 2009-10-27 | 2011-12-16 | Michelin Soc Tech | Bandage pneumatique dont la paroi interne est pourvue d'une couche de caoutchouc thermo-expansible |
| FR2952064B1 (fr) | 2009-10-30 | 2012-08-31 | Michelin Soc Tech | Methode de preparation d'un melange maitre d'elastomere dienique et de silice |
| FR2954775B1 (fr) | 2009-10-30 | 2012-03-30 | Michelin Soc Tech | Methode de preparation d'un melange maitre d'elastomere dienique synthetique et de silice |
| FR2952644B1 (fr) | 2009-11-17 | 2011-12-30 | Michelin Soc Tech | Pneumatique dont la bande de roulement comporte un elastomere thermoplastique |
| FR2956118B1 (fr) | 2009-12-18 | 2013-03-08 | Michelin Soc Tech | Composition de caoutchouc pour bande de roulement de pneumatique hiver. |
| FR2955584B1 (fr) | 2009-12-18 | 2014-08-22 | Michelin Soc Tech | Composition de caoutchouc pour bande de roulement de pneumatique hiver. |
| FR2954332B1 (fr) | 2009-12-22 | 2012-01-13 | Michelin Soc Tech | Article notamment pneumatique avec melange de caoutchouc externe comportant un sel de lanthanide |
| FR2954333B1 (fr) | 2009-12-23 | 2012-03-02 | Michelin Soc Tech | Pneumatique dont la zone sommet est pourvue d'une sous-couche comportant un elastomere thermoplastique |
| FR2956119B1 (fr) | 2009-12-23 | 2012-12-28 | Michelin Soc Tech | Pneumatique dont la zone sommet est pourvue d'une sous-couche comportant un elastomere thermoplastique |
| FR2955328B1 (fr) | 2010-01-18 | 2013-03-08 | Michelin Soc Tech | Composition de caoutchouc pour bande de roulement de pneumatique hiver |
| FR2955587B1 (fr) | 2010-01-28 | 2012-02-17 | Michelin Soc Tech | Composition d'elastomere pour objet pneumatique, a propriete auto-obturante |
| FR2955588B1 (fr) | 2010-01-28 | 2012-03-09 | Michelin Soc Tech | Composition d'elastomere pour objet pneumatique, a propriete auto-obturante |
| FR2955581B1 (fr) | 2010-01-28 | 2012-02-17 | Michelin Soc Tech | Procede de fabrication d'une composition d'elastomere a propriete auto-obturante |
| FR2955582B1 (fr) | 2010-01-28 | 2012-03-09 | Michelin Soc Tech | Procede de fabrication d'une composition d'elastomere a propriete auto-obturante |
| FR2957082B1 (fr) | 2010-03-05 | 2012-03-02 | Michelin Soc Tech | Pneumatique dont la bande de roulement comporte un elastomere thermoplastique. |
| FR2957600B1 (fr) | 2010-03-18 | 2012-04-20 | Soc Tech Michelin | Flanc pour pneumatique |
| FR2957601B1 (fr) * | 2010-03-18 | 2012-03-16 | Michelin Soc Tech | Pneumatique et composition de caoutchouc contenant un polymere greffe |
| FR2957602B1 (fr) | 2010-03-19 | 2012-04-13 | Michelin Soc Tech | Composition de caoutchouc pour bande de roulement de pneumatique hiver |
| FR2958295B1 (fr) | 2010-03-31 | 2012-05-04 | Michelin Soc Tech | Pneumatique dont la bande de roulement comporte une composition de caoutchouc comprenant une resine poly(vinylester). |
| FR2959744B1 (fr) | 2010-05-04 | 2012-08-03 | Michelin Soc Tech | Composition de caoutchouc, utilisable pour la fabrication d'un pneumatique dont la composition comporte un amidon et un plastifiant aqueux ou hydrosoluble |
| FR2959745B1 (fr) | 2010-05-10 | 2012-06-01 | Michelin Soc Tech | Pneumatique dont la bande de roulement comporte un elastomere thermoplastique vulcanisat (tpv). |
| FR2960567B1 (fr) | 2010-05-27 | 2012-06-22 | Michelin Soc Tech | Renfort filaire composite pour pneumatique, enrobe d'un caoutchouc a propriete de barriere a l'eau amelioree |
| FR2960879B1 (fr) | 2010-06-02 | 2012-07-13 | Michelin Soc Tech | Procede d'obtention d'une composition de caoutchouc comprenant une charge thermoplastique |
| FR2961516B1 (fr) | 2010-06-17 | 2015-06-26 | Michelin Soc Tech | Bandage pneumatique dont la ceinture est pourvue d'une gomme d'enrobage reduisant les bruits de roulage |
| FR2961818B1 (fr) | 2010-06-23 | 2012-07-20 | Michelin Soc Tech | Composition de caoutchouc comprenant une charge thermoplastique et un agent compatibilisant |
| FR2962368B1 (fr) | 2010-07-09 | 2012-08-31 | Michelin Soc Tech | Objet pneumatique pourvu d'une couche etanche aux gaz a base d'un melange d'un caoutchouc butyl et d'un elastomere thermoplastique |
| FR2962440B1 (fr) | 2010-07-12 | 2012-08-03 | Total Raffinage Marketing | Procede de preparation de polymeres greffes sans amorceur et sans solvant et compositions bitume/polymere comprenant lesdits polymeres greffes |
| FR2963014B1 (fr) | 2010-07-21 | 2012-08-31 | Michelin Soc Tech | Composition de caoutchouc comprenant des ecailles de verre notamment pour la fabrication de pneumatiques |
| FR2963579B1 (fr) | 2010-08-05 | 2013-04-26 | Michelin Soc Tech | Renfort composite |
| FR2965208B1 (fr) | 2010-09-23 | 2012-10-12 | Michelin Soc Tech | Renfort composite |
| RU2577263C2 (ru) * | 2010-10-01 | 2016-03-10 | Бриджстоун Корпорейшн | Способ получения резиновой смеси |
| CN103189439B (zh) * | 2010-10-01 | 2015-06-24 | 株式会社普利司通 | 橡胶组合物的制造方法 |
| FR2967414B1 (fr) * | 2010-11-12 | 2014-01-24 | Total Raffinage Marketing | Polymeres greffes reticules de maniere thermoreversible |
| FR2968307B1 (fr) | 2010-11-26 | 2018-04-06 | Societe De Technologie Michelin | Bande de roulement de pneumatique |
| KR101802169B1 (ko) * | 2010-11-26 | 2017-11-28 | 덴카 주식회사 | 유황변성 클로로프렌 고무, 그 성형체 및 그 제조방법 |
| FR2968006B1 (fr) | 2010-11-26 | 2012-12-21 | Michelin Soc Tech | Bande de roulement de pneumatique |
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| FR3099164B1 (fr) | 2019-07-26 | 2021-06-25 | Michelin & Cie | Composition de caoutchouc. |
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| EP4032915B1 (en) * | 2019-09-20 | 2025-11-05 | Kuraray Co., Ltd. | Conjugated diene graft polymer and method for producing the same |
| FR3105248B1 (fr) | 2019-12-18 | 2021-12-03 | Michelin & Cie | Composition de caoutchouc comprenant une resine de polyphenylene ether |
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| FR3127223B1 (fr) | 2021-09-20 | 2023-08-18 | Michelin & Cie | Procédé d’obtention par extrusion d’une composition élastomérique renforcée. |
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| US3976628A (en) | 1968-12-18 | 1976-08-24 | The Firestone Tire & Rubber Company | Process for polylithiating unsaturated polymers |
| SU550409A1 (ru) * | 1973-06-25 | 1977-03-15 | Предприятие П/Я А-7345 | Способ стабилизации бутадиенстирольных каучуков |
| US3978161A (en) | 1973-10-01 | 1976-08-31 | The General Tire & Rubber Company | Metalation of polymers |
| US4082817A (en) | 1974-03-02 | 1978-04-04 | Japan Synthetic Rubber Co., Ltd. | Process for producing maleic anhydride adduct of high molecular weight 1,2-polybutadiene |
| US4080493A (en) | 1975-10-22 | 1978-03-21 | Sumitomo Chemical Company, Limited | Process for production of the maleic anhydride adduct of a liquid polymer |
| ZA774041B (en) * | 1976-08-09 | 1978-05-30 | Goodyear Tire & Rubber | Age-resisting polymers and their preparation by reactions involving use of certain aminomercaptans |
| DE2653144C2 (de) * | 1976-11-23 | 1984-12-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von modifiziertem Polybutadien |
| US4912145A (en) | 1988-04-01 | 1990-03-27 | The Goodyear Tire & Rubber Company | Method for preparing carboxylated syndiotactic 1,2-polybutadiene |
| DE4038589A1 (de) * | 1990-12-04 | 1992-06-11 | Bayer Ag | Kautschukvulkanisate mit guten mechanischen eigenschaften und verbessertem hystereseverhalten |
| FR2740138B1 (fr) * | 1995-10-19 | 1997-11-21 | Elf Aquitaine | Elastomere fonctionnalise par des groupements carboxyliques ou esters greffes et son application a la production de compositions bitume/elastomere fonctionnalise utilisables pour la realisation de revetements |
| DE59907363D1 (de) * | 1998-11-16 | 2003-11-20 | Bayer Ag | Carboxylgruppen-haltige Lösungskautschuke enthaltende Kautschukmischungen |
| JP2000313767A (ja) | 1999-04-30 | 2000-11-14 | Yokohama Rubber Co Ltd:The | タイヤ用トレッドゴム組成物 |
| DE19920788A1 (de) * | 1999-05-06 | 2000-11-09 | Bayer Ag | Carboxylgruppen-haltige Dienkautschuke |
| RU2177961C2 (ru) * | 2000-02-01 | 2002-01-10 | Открытое акционерное общество "Нижнекамскнефтехим" | Способ стабилизации полиизопренового каучука |
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| AU2002356721A1 (en) * | 2001-11-26 | 2003-06-10 | Societe De Technologie Michelin | Rubber composition for running tread and method for obtaining same |
| US6765065B2 (en) * | 2002-01-09 | 2004-07-20 | Sumitomo Chemical Company, Limited | Process for producing modified polymer rubber |
-
2003
- 2003-04-29 FR FR0305305A patent/FR2854404B1/fr not_active Expired - Fee Related
-
2004
- 2004-04-29 KR KR1020057020539A patent/KR101186129B1/ko not_active Expired - Fee Related
- 2004-04-29 AU AU2004234058A patent/AU2004234058A1/en not_active Abandoned
- 2004-04-29 JP JP2006505312A patent/JP4874791B2/ja not_active Expired - Fee Related
- 2004-04-29 EP EP04730253A patent/EP1620471A2/fr not_active Withdrawn
- 2004-04-29 BR BRPI0409806-4A patent/BRPI0409806A/pt not_active Application Discontinuation
- 2004-04-29 RU RU2005136980/04A patent/RU2337923C2/ru not_active IP Right Cessation
- 2004-04-29 CN CN200480011490XA patent/CN1780859B/zh not_active Expired - Fee Related
- 2004-04-29 WO PCT/EP2004/004510 patent/WO2004096865A2/fr not_active Ceased
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2005
- 2005-10-25 US US11/256,986 patent/US7312264B2/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| KR101186129B1 (ko) | 2012-09-27 |
| KR20060008938A (ko) | 2006-01-27 |
| JP2006524725A (ja) | 2006-11-02 |
| FR2854404A1 (fr) | 2004-11-05 |
| RU2005136980A (ru) | 2006-03-20 |
| US20060089445A1 (en) | 2006-04-27 |
| CN1780859B (zh) | 2010-11-03 |
| FR2854404B1 (fr) | 2005-07-01 |
| WO2004096865A3 (fr) | 2005-02-10 |
| EP1620471A2 (fr) | 2006-02-01 |
| WO2004096865A2 (fr) | 2004-11-11 |
| US7312264B2 (en) | 2007-12-25 |
| RU2337923C2 (ru) | 2008-11-10 |
| BRPI0409806A (pt) | 2006-05-09 |
| JP4874791B2 (ja) | 2012-02-15 |
| CN1780859A (zh) | 2006-05-31 |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |