WO2007042229A1 - Composition comprising sulfurized particle - Google Patents
Composition comprising sulfurized particle Download PDFInfo
- Publication number
- WO2007042229A1 WO2007042229A1 PCT/EP2006/009704 EP2006009704W WO2007042229A1 WO 2007042229 A1 WO2007042229 A1 WO 2007042229A1 EP 2006009704 W EP2006009704 W EP 2006009704W WO 2007042229 A1 WO2007042229 A1 WO 2007042229A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- sulfur
- particle
- weight
- rubber
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 99
- 239000002245 particle Substances 0.000 title claims abstract description 34
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 70
- 239000011593 sulfur Substances 0.000 claims abstract description 69
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 69
- 229920001971 elastomer Polymers 0.000 claims abstract description 49
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 23
- 238000004073 vulcanization Methods 0.000 claims abstract description 21
- 239000011159 matrix material Substances 0.000 claims abstract description 18
- 239000005077 polysulfide Substances 0.000 claims abstract description 14
- 229920001021 polysulfide Polymers 0.000 claims abstract description 14
- 150000008117 polysulfides Polymers 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000000806 elastomer Substances 0.000 claims abstract description 8
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 2
- 239000008188 pellet Substances 0.000 claims description 57
- 239000000835 fiber Substances 0.000 claims description 43
- 239000001993 wax Substances 0.000 claims description 18
- 239000004760 aramid Substances 0.000 claims description 17
- 229920003235 aromatic polyamide Polymers 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 5
- 229920003052 natural elastomer Polymers 0.000 claims description 5
- 229920001194 natural rubber Polymers 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 239000008199 coating composition Substances 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000011324 bead Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 238000004513 sizing Methods 0.000 claims description 3
- 229920003051 synthetic elastomer Polymers 0.000 claims description 3
- 239000005061 synthetic rubber Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000004200 microcrystalline wax Substances 0.000 claims description 2
- 235000019808 microcrystalline wax Nutrition 0.000 claims description 2
- 229920003366 poly(p-phenylene terephthalamide) Polymers 0.000 claims description 2
- 229910006067 SO3−M Inorganic materials 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 2
- 239000005060 rubber Substances 0.000 description 41
- 239000000126 substance Substances 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 12
- 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 11
- 235000021355 Stearic acid Nutrition 0.000 description 10
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 10
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 10
- 239000008117 stearic acid Substances 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 7
- 229920000561 Twaron Polymers 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 238000010058 rubber compounding Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 5
- 229920006231 aramid fiber Polymers 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000010059 sulfur vulcanization Methods 0.000 description 4
- PGNWIWKMXVDXHP-UHFFFAOYSA-L zinc;1,3-benzothiazole-2-thiolate Chemical compound [Zn+2].C1=CC=C2SC([S-])=NC2=C1.C1=CC=C2SC([S-])=NC2=C1 PGNWIWKMXVDXHP-UHFFFAOYSA-L 0.000 description 4
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical group CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KMYAABORDFJSLR-UHFFFAOYSA-N (carbamothioyltrisulfanyl) carbamodithioate Chemical compound NC(=S)SSSSC(N)=S KMYAABORDFJSLR-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 239000004484 Briquette Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229960004424 carbon dioxide Drugs 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000010603 pastilles Nutrition 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004636 vulcanized rubber Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- CPGFMWPQXUXQRX-UHFFFAOYSA-N 3-amino-3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC=C(F)C=C1 CPGFMWPQXUXQRX-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 1
- BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-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
- ZOXBWJMCXHTKNU-UHFFFAOYSA-N 5-methyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=C2C(=O)OC(=O)C2=C1 ZOXBWJMCXHTKNU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000276489 Merlangius merlangus Species 0.000 description 1
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004614 Process Aid Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 229920001494 Technora Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 1
- PGAXJQVAHDTGBB-UHFFFAOYSA-N dibutylcarbamothioylsulfanyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SSC(=S)N(CCCC)CCCC PGAXJQVAHDTGBB-UHFFFAOYSA-N 0.000 description 1
- RCGBHLSDSJSVGM-UHFFFAOYSA-L disodium;oxido-(6-oxidosulfonothioyloxyhexoxy)-oxo-sulfanylidene-$l^{6}-sulfane;dihydrate Chemical compound O.O.[Na+].[Na+].[O-]S(=O)(=S)OCCCCCCOS([O-])(=O)=S RCGBHLSDSJSVGM-UHFFFAOYSA-L 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NNYHMCFMPHPHOQ-UHFFFAOYSA-N mellitic anhydride Chemical compound O=C1OC(=O)C2=C1C(C(OC1=O)=O)=C1C1=C2C(=O)OC1=O NNYHMCFMPHPHOQ-UHFFFAOYSA-N 0.000 description 1
- OFHMODDLBXETIK-UHFFFAOYSA-N methyl 2,3-dichloropropanoate Chemical compound COC(=O)C(Cl)CCl OFHMODDLBXETIK-UHFFFAOYSA-N 0.000 description 1
- 239000012764 mineral filler Substances 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
- WGARMULIELDQEH-UHFFFAOYSA-N n-cyclohexyl-1,3-benzothiazole-2-sulfinamide Chemical compound N=1C2=CC=CC=C2SC=1S(=O)NC1CCCCC1 WGARMULIELDQEH-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 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
- 239000003826 tablet Substances 0.000 description 1
- 239000004950 technora Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003579 thiophosphoric acid derivatives 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
- 229960002447 thiram Drugs 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/10—Reinforcing macromolecular compounds with loose or coherent fibrous material characterised by the additives used in the polymer mixture
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B9/00—Making granules
- B29B9/12—Making granules characterised by structure or composition
- B29B9/14—Making granules characterised by structure or composition fibre-reinforced
-
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
Definitions
- the invention pertains to a composition comprising a particle and a matrix.
- the invention further relates to a vulcanization process using said compositions, to an elastomer composition obtainable by said process, and to a skim product, a tire, and a tire tread, undertread or belt comprising said elastomer composition.
- the invention pertains to a composition
- a composition comprising a particle and a matrix, the particle being at least partially coated with a composition comprising a Bunte salt, a polysulfide, and sulfur or a sulfur donor.
- a wax can be used, which wax also can act as solvent for the Bunte salt, a polysulfide and sulfur making the process simpler avoiding the use of solvent/water dispersion and drying step.
- the composition can be a particle or a pellet made thereof.
- Pellets as such are known in the art. For instance, in EP 0 889 072 the coating of aramid fiber pellets with a polymeric component, e.g. a wax, are disclosed. These pellets are however not coated with a Bunte salt. In US 6,068,922 pellets comprising aramid fibers and an extrudable polymer, e.g. polyethylene, polypropylene or polyamides are disclosed. The fibers may be coated by typical sizing agents (RF, epoxy, silicone), but a Bunte salt is not mentioned.
- RF sizing agents
- A Bunte salt
- B polysulfide
- TESPT Bis-3-triethoxysilylpropyl tetrasulfide
- Zinc mercaptobenzothiazole wherein R is independently selected from hydrogen, halogen, nitro, hydroxy, C1- C12 alkyl, C1-C12 alkoxy, and C1-C12 aralkyl.
- a particularly suitable polysulfide has the formula:
- compositions provide a solution to the above problems in the sulfur vulcanization of rubbers and provide rubber compositions that solve a longstanding problem of reducing hysteresis and heat generation.
- pellet includes terms, apart from pellet, that are synonymous or closely related such as tablet, briquette, pastilles, granule and the like. Pellets can be made from any particle, including short cut fibers, chopped fiber, staple fiber, pulp, fibrils, fibrid, beads, and powder, by mixing these particles with a matrix of a wax and/or an extrudable polymer and the required sulfur chemicals.
- Preferred particles are selected from aramid, polyester, polyamide, cellulose, glass, and carbon.
- Aramid fibers and powders have the preference, more specifically of poly(p-phenylene-terephthalamide) or co-poly- (paraphenylene/3,4'-oxydiphenylene terephthalamide). Most preferred are staple fiber, chopped fiber, and powder. Powder and beads have the additional advantage that they do not need a spinning step and can directly be obtained from the polymer. If the particle is a fiber, for many applications it is further of an additional advantage to pre-treat the fiber with a sizing.
- Pellets can be prepared in any manner known in the art. For instance, pellets can be made from any particle, by mixing these particles with a wax and/or an extrudable polymer and optionally the required sulfur chemicals. This mixture can be extruded to pellets and used as such. Furthermore, the mixture and/or the extruded mixture can be compressed in the shape of a pellet, tablet, briquette, pastille, or the like. If not yet added sulfur chemicals can be applied to the pellet. Optionally, before compression the mixture is heated to provide a better dispersion of the sulfur chemicals and the particles in the wax and/or extrudable polymer. In WO 0058064 another method is described for preparing pellets from staple fiber and an extrudable polymer matrix. According to this method pellets are made by mixing staple fiber and polymer, heating the fibers to at least the melting or softening point of the wax and/or extrudable polymer.
- pellets can be treated with sulfur chemicals and optionally a wax.
- Continuous fiber can be treated with the sulfur chemicals prior to or after cutting the fiber to chopped fiber.
- the continuous fiber can be cut to staple fiber and used for the production of sulfurized pellets. If the particles are staple fiber these can be mixed with an extrudable polymer matrix, heated to at least the melting or softening point of the extrudable polymer, cooled, shaped to a strand and cut to pellets.
- the matrix is a wax, an extrudable polymer, or a mixture thereof.
- the invention relates to a waxed sulfurized particle or pellet having enhanced rubber properties in an elastomer, wherein 10 to 90 wt.% of the composition consists of matrix, preferably wax.
- suitable waxes are microcrystalline wax of higher alkyl chains, such as C22-C38 alkyl chains, paraffin wax or alkyl long chain fatty acid waxes, such as C16-C22 alkanecarboxylic acids.
- extrudable polymers are polyethylene, polypropylene, and polyamide. The extrudable polymers may be modified or unmodified polymers and copolymers. Mixtures of an extrudable polymer and a wax are particularly useful as matrix.
- the composition further comprises a coating composition wherein the weight ratio of compounds A : B : C is 4-80 : 0.1-25 : 0.05-15.
- M is selected from Na 1 K, Li, V 2 Ca, 14 Mg, and ⁇
- R 1 is selected from C1-C12 alkylene, C1-C12 alkoxylene, and C7-C12 aralkylene.
- the most preferred Bunte salt has m is 2, m' is 0, and R 1 is C1-C12 alkylene.
- the treatment of the particle is based on the above Bunte salt and/or polysulfide compound sulfur chemicals, disodium hexamethylene-1 ,6-bis(thiosulfate) dihydrate, 2-mercaptobenzothiazyl disulfide, and preferably aliphatic fatty acid waxes, which chemicals further contain sulfur and/or a sulfur donor.
- the treatment of the particles can be carried out using a wax containing disodium hexamethylene-1 ,6-bis(thiosulfate) dihydrate, 2-mercaptobenzothiazyl disulfide, or in a mixture of sulfur-containing chemicals.
- Sulfur can additionally be used.
- 2-Mercaptobenzothiazyl disulfide (MBTS) can be replaced by other benzothiazole derivatives.
- a particularly useful sulfur chemical of the present invention is a mixture consisting of: i. a Bunte salt, NaSO 3 -S-(CH 2 ) 6 -S-SO 3 Na. 2H 2 O ii. MBTS,
- the invention relates to a rubber composition which is the vulcanization reaction product of a rubber, sulfur and optionally sulfur donor, and said compositions.
- the composition improves processing, acts as a modulus enhancer, strength improver, as well lowers hysteresis.
- a vulcanization process carried out in the presence of the compositions containing sulfur chemicals and the use of these compositions in the sulfur-vulcanization of rubbers.
- the present invention relates to a vulcanization process carried out in the presence of the sulfurized composition and the use of this composition in the sulfur-vulcanization of rubbers. Further, the invention also encompasses rubber products which comprise at least some rubber which has been vulcanized, preferably vulcanized with sulfur, in the presence of said sulfurized compositions.
- the present invention provides excellent processing behavior in addition to improved hysteresis behavior as well as improvements in several rubber properties without having a significant adverse effect on the remaining properties, when compared with similar sulfur-vulcanization systems without any sulfurized composition.
- the present invention is applicable to all natural and synthetic rubbers.
- rubbers include, but are not limited to, natural rubber, styrene- butadiene rubber, butadiene rubber, isoprene rubber, acrylonitrile-butadiene rubber, chloroprene rubber, isoprene-isobutylene rubber, brominated isoprene- isobutylene rubber, chlorinated isoprene-isobutylene rubber, ethylene- propylene-diene terpolymers, as well as combinations of two or more of these rubbers and combinations of one or more of these rubbers with other rubbers and/or thermoplastics.
- Sulfur optionally together with sulfur donors, provides the required level of sulfur during the vulcanization process.
- sulfur donors include, but are not limited to, tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetra- butylthiuram disulfide, dipentamethylene thiuram hexasulfide, dipentamethylene thiuram tetrasulfide, dithiodimorpholine, and mixtures thereof.
- Sulfur donors may be used instead or in addition to the sulfur.
- the term "sulfur” further also includes the mixture of sulfur and sulfur donor(s).
- references to the quantity of sulfur employed in the vulcanization process, when applied to sulfur donors mean a quantity of sulfur donor which is required to provide the equivalent amount of sulfur that is specified.
- the present invention relates to a sulfur-vulcanized rubber composition which comprises the vulcanization reaction product of: (a) 100 parts by weight of at least one natural or synthetic rubber; (b) 0.1 to 25 parts by weight of an amount of sulfur, or sulfur and/or a sulfur donor, to provide the equivalent of 0.1 to 25 parts by weight of sulfur; and (c) 0.1 to 20 parts by weight of a (preferably) waxed sulfurized compositions, preferably aramid pellets.
- the sulfurized fibers of the present invention are based on natural and synthetic yarns.
- yarns include, but not limited to, aramid, such as para-aramid, polyamide, polyester, cellulose, such as rayon, glass, and carbon as well as combinations of two or more of these yarns.
- the other sulfurized particles of the present invention can be made of the same compounds or combinations thereof.
- the particle is poly(para-phenylene-terephthalamide), which as fiber is commercially available under the trade name Twaron®, or co-poly-(para- phenylene/3,4'-oxydiphenylene terephthalamide, which as fiber is commercially available under the trade name Technora®.
- the amount of sulfur to be compounded with the rubber is, based on 100 parts of rubber, usually 0.1 to 25 parts by weight, and more preferably 0.2 to 8 parts by weight.
- the amount of sulfur donor to be compounded with the rubber is an amount to provide an equivalent amount of sulfur, i.e. an amount which gives the same amount of sulfur, as if sulfur itself were used.
- the amount of sulfurized composition to be compounded with the rubber is, based on 100 parts of rubber, 0.1 to 25 parts by weight, and more preferably 0.2 to 10.0 parts by weight, and most preferably 0.5 to 5 parts by weight.
- These ingredients may be employed as a pre-mix, or added simultaneously or separately, and they may be added together with other rubber compounding ingredients as well.
- a vulcanization accelerator in the rubber compound. Conventional, known vulcanization accelerators may be employed.
- the preferred vulcanization accelerators include mercaptobenzothiazole, 2,2'-mercaptobenzothiazole disulfide, sulfenamide accelerators including N-cyclohexyl-2-benzothiazole sulfenamide, N-tert-butyl-2- benzothiazole sulfenamide, N,N-dicyclohexyl-2-benzothiazole sulfenamide, and 2-(morpholinothio)benzothiazole; thiophosphoric acid derivative accelerators, thiurams, dithiocarbamates, diphenyl guanidine, diorthotolyl guanidine, dithiocarbamylsulfenamides, xanthates, triazine accelerators and mixtures thereof.
- the vulcanization accelerator When the vulcanization accelerator is employed, quantities of from 0.1 to 8 parts by weight, based on 100 parts by weight of rubber composition, are used. More preferably, the vulcanization accelerator comprises 0.3 to 4.0 parts by weight, based on 100 parts by weight of rubber. Other conventional rubber additives may also be employed in their usual amounts. For example, reinforcing agent such as carbon black, silica, clay, whiting, and other mineral fillers, as well as mixtures of fillers, may be included in the rubber composition.
- reinforcing agent such as carbon black, silica, clay, whiting, and other mineral fillers, as well as mixtures of fillers, may be included in the rubber composition.
- scorch retarders such as phthalic anhydride, pyromellitic anhydride, benzene hexacarboxylic trianhydride, 4-methylphthalic anhydride, trimellitic anhydride, 4-chlorophthalic anhydride, N-cyclohexyl-thiophthalimide, salicylic acid, benzoic acid, maleic anhydride and N-nitrosodiphenylamine may also be included in the rubber composition in conventional, known amounts.
- steel-cord adhesion promoters such as cobalt salts and dithiosulfates in conventional, known quantities.
- the process is carried out at a temperature of 110-220° C over a period of up to 24 hours. More preferably, the process is carried out at a temperature of 120-
- the vulcanization is carried out at a temperature of 120-190° C over a period of up to 8 hours and in the presence of 0.1 to 8 parts by weight, based on 100 parts by weight of rubber, of at least one vulcanization accelerator.
- the present invention also includes articles of manufacture, such as skim products, tires, tire treads, tire undertreads, or belts, which comprise sulfur- vulcanized rubber which is vulcanized in the presence of the sulfurized composition of the present invention.
- articles of manufacture such as skim products, tires, tire treads, tire undertreads, or belts, which comprise sulfur- vulcanized rubber which is vulcanized in the presence of the sulfurized composition of the present invention.
- Vulcanization ingredients were added to the compounds on a Schwabenthane.
- Cure characteristics were determined using a MonsantoTM rheometer MDR 2000E (arc 0.5°) according to ISO 6502/1999. Delta S is defined as extent of crosslinking is derived from subtraction of lowest torque (ML) from highest torque (MH).
- Sheets and test specimens were vulcanized by compression molding in a
- Abrasion was determined using a Zwick abrasion tester as volume loss per 40 m path travelled (DIN 53516). Heat build-up and compression set after dynamic loading were determined using a GoodrichTM Flexometer (load 1 MPa, stroke 0.445 cm, frequency 30 Hz, start temperature 100° C, running time 120 min or till blow out; ASTM D 623-78).
- Pellets (25 g) consisting of polyethylene matrix and Twaron® p-aramid staple fiber were added to a mixture of the required sulfur chemicals in molten stearic acid at a temperature of 60 to 80 0 C.
- the stearic acid was rubber grade BM 100 supplied by Behn Meyer.
- the sulfur chemicals and their ratios to stearic acid are specified in Tables 1 , 7, and 12.
- the mixture of pellets and sulfur chemicals containing molten stearic acid was stirred until uptake of the sulfur chemicals and molten stearic acid into the pellets had occurred.
- the stearic acid- containing pellets were transferred into a dry-ice containing polyethylene bag and kept in continuous motion while cooling down to a temperature below the stearic acid melting point. Finally, the contents of the bag were emptied on a sieve to remove remaining dry-ice and some stearic acid flakes.
- AFW which is a mixture of an anionic copolymer and a C-16 hydrocarbon supplied by Bozzetto Gmbh. Under vigorous stirring the aqueous solution was added to the toluene solution. An ultraturrax was applied to the mixture resulting in a stable dispersion. Then, 25 g of pellets consisting of polyethylene matrix and Twaron® p-aramid staple fiber were dipped in about 150 ml_ of the dispersion for five minutes at room temperature, filtered off, and dried in air for approximately 18 hours and then under vacuum for about 6 hours.
- Example 3 A premix of stearic acid, HTS, MBTS and sulfur was prepared in the weight ratio
- Twaron® p-aramid staple fibers were prepared according to Example 1 (T2 and T4) and Example 2 (T3) and are the following:
- SA is stearic acid
- S is sulfur
- PE is polyethylene
- MBTS 2-mercaptobenzo- thiazyl disulfide
- CBS N-cyclohexyl-2-benzothiazole sulfenamide
- NR is natural rubber
- BR is polybutadiene
- 6PPD is N-1 ,3-dimethylbutyl-N'- phenyl-p-phenylenediamine
- TMQ is polymerized 2,2,4-trimethyl-1 ,2- dihydoquinoline antioxidant
- CBS is N-cyclohexyl benzothiazyl sulfenamide.
- the vulcanized rubbers listed in Table 2 were tested according to ASTM/ISO norms.
- a and B are control experiments
- C-D are comparison experiments
- 1 and 2 are experiments according to the invention.
- the results are given in Tables 3-6.
- waxed sulfurized pellet (mix 2) shows similar properties as the sulfurized pellet (mix 1 ) with additional advantage in processing plus lower dosage with respect to the total fiber content.
- DPTT is dicylcopentamethylene thiuram tetrasulfide
- TESPT is bis-3-triethoxy- silylpropyl tetrasulfide
- APPS is alkyl phenol polysulfide (APPS).
- Zinc mercaptobenzothiazole (ZMBT) was evaluated in this experiment.
- the fiber pellets were all based on Twaron® p-aramid staple fiber and were prepared as in Example 1.
- the compositions of Table 12 were obtained.
- the accelerator employed was N-cyclohexyl-2-benzothiazole sulfenamide
- aramid pellets were based on Twaron® p-aramid powder, pulp or chopped fiber.
- the composition of the pellets is aramid : SA : HTS : MBTS : S
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002625637A CA2625637A1 (en) | 2005-10-10 | 2006-10-06 | Composition comprising sulfurized particle |
JP2008534907A JP2009511680A (en) | 2005-10-10 | 2006-10-06 | Composition comprising sulfurized particles |
AU2006301553A AU2006301553A1 (en) | 2005-10-10 | 2006-10-06 | Composition comprising sulfurized particle |
US11/992,937 US20090258988A1 (en) | 2005-10-10 | 2006-10-06 | Composition Comprising Sulfurized Particles |
BRPI0617218A BRPI0617218A2 (en) | 2005-10-10 | 2006-10-06 | composition, vulcanization process for producing an elastomeric composition, skim product, tire, and tire tread, tread or belt |
EP06792393A EP1940924A1 (en) | 2005-10-10 | 2006-10-06 | Composition comprising sulfurized particle |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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EP05022046 | 2005-10-10 | ||
EP05022046.6 | 2005-10-10 | ||
EP06012200.9 | 2006-06-14 | ||
EP06012200 | 2006-06-14 |
Publications (1)
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WO2007042229A1 true WO2007042229A1 (en) | 2007-04-19 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2006/009704 WO2007042229A1 (en) | 2005-10-10 | 2006-10-06 | Composition comprising sulfurized particle |
Country Status (10)
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US (1) | US20090258988A1 (en) |
EP (1) | EP1940924A1 (en) |
JP (1) | JP2009511680A (en) |
KR (1) | KR20080055896A (en) |
AU (1) | AU2006301553A1 (en) |
BR (1) | BRPI0617218A2 (en) |
CA (1) | CA2625637A1 (en) |
RU (1) | RU2008118209A (en) |
TW (1) | TW200730560A (en) |
WO (1) | WO2007042229A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008150436A (en) * | 2006-12-14 | 2008-07-03 | Toyo Tire & Rubber Co Ltd | Pneumatic tire |
US20090050250A1 (en) * | 2007-08-24 | 2009-02-26 | Tetsuya Kunisawa | Rubber composition and pneumatic tire |
EP2072283A1 (en) | 2007-12-18 | 2009-06-24 | The Goodyear Tire & Rubber Company | Tire with component containing aramid fibers |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5637950B2 (en) * | 2011-07-22 | 2014-12-10 | 四国化成工業株式会社 | Coupling agent for rubber and carbon black and tire rubber composition containing the same |
KR101383559B1 (en) * | 2011-12-23 | 2014-04-09 | 한국타이어 주식회사 | Rubber composition for tire sidewall and tire manufactured by using the same |
KR101382202B1 (en) * | 2011-12-26 | 2014-04-08 | 한국타이어 주식회사 | Rubber composition for tire belt and tire manufactured by using the same |
KR101381840B1 (en) * | 2011-12-27 | 2014-04-04 | 한국타이어 주식회사 | Rubber composition for tire tread and tire manufactured by using the same |
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US5241108A (en) * | 1989-12-12 | 1993-08-31 | Huels Aktiengesellschaft | Polysulfide derivatives |
EP0889072A1 (en) * | 1997-06-30 | 1999-01-07 | Basf Corporation | Improved process for producing customized thermoplastic resins |
EP0900820A1 (en) * | 1997-09-03 | 1999-03-10 | The Goodyear Tire & Rubber Company | A rubber compound containing a hydrated thiosulfate and a bismaleimide |
US20050032945A1 (en) * | 2003-08-08 | 2005-02-10 | Moniotte Philippe G. | Vulcanizable rubber having increased scorch time |
WO2006087161A1 (en) * | 2005-02-18 | 2006-08-24 | Teijin Twaron B.V. | Method for enhancing rubber properties by using bunte salt-treated fiber |
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US5830395A (en) * | 1997-08-12 | 1998-11-03 | E. I. Du Pont De Nemours And Company | Process for making a uniform dispersion of aramid fibers and polymer |
-
2006
- 2006-10-06 AU AU2006301553A patent/AU2006301553A1/en not_active Abandoned
- 2006-10-06 US US11/992,937 patent/US20090258988A1/en not_active Abandoned
- 2006-10-06 BR BRPI0617218A patent/BRPI0617218A2/en not_active IP Right Cessation
- 2006-10-06 EP EP06792393A patent/EP1940924A1/en not_active Withdrawn
- 2006-10-06 RU RU2008118209/04A patent/RU2008118209A/en not_active Application Discontinuation
- 2006-10-06 KR KR1020087008449A patent/KR20080055896A/en not_active Application Discontinuation
- 2006-10-06 CA CA002625637A patent/CA2625637A1/en not_active Abandoned
- 2006-10-06 JP JP2008534907A patent/JP2009511680A/en not_active Withdrawn
- 2006-10-06 WO PCT/EP2006/009704 patent/WO2007042229A1/en active Application Filing
- 2006-10-11 TW TW095137332A patent/TW200730560A/en unknown
Patent Citations (5)
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US5241108A (en) * | 1989-12-12 | 1993-08-31 | Huels Aktiengesellschaft | Polysulfide derivatives |
EP0889072A1 (en) * | 1997-06-30 | 1999-01-07 | Basf Corporation | Improved process for producing customized thermoplastic resins |
EP0900820A1 (en) * | 1997-09-03 | 1999-03-10 | The Goodyear Tire & Rubber Company | A rubber compound containing a hydrated thiosulfate and a bismaleimide |
US20050032945A1 (en) * | 2003-08-08 | 2005-02-10 | Moniotte Philippe G. | Vulcanizable rubber having increased scorch time |
WO2006087161A1 (en) * | 2005-02-18 | 2006-08-24 | Teijin Twaron B.V. | Method for enhancing rubber properties by using bunte salt-treated fiber |
Cited By (4)
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JP2008150436A (en) * | 2006-12-14 | 2008-07-03 | Toyo Tire & Rubber Co Ltd | Pneumatic tire |
US20090050250A1 (en) * | 2007-08-24 | 2009-02-26 | Tetsuya Kunisawa | Rubber composition and pneumatic tire |
US8418736B2 (en) * | 2007-08-24 | 2013-04-16 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
EP2072283A1 (en) | 2007-12-18 | 2009-06-24 | The Goodyear Tire & Rubber Company | Tire with component containing aramid fibers |
Also Published As
Publication number | Publication date |
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KR20080055896A (en) | 2008-06-19 |
AU2006301553A1 (en) | 2007-04-19 |
EP1940924A1 (en) | 2008-07-09 |
CA2625637A1 (en) | 2007-04-19 |
BRPI0617218A2 (en) | 2016-08-23 |
US20090258988A1 (en) | 2009-10-15 |
TW200730560A (en) | 2007-08-16 |
JP2009511680A (en) | 2009-03-19 |
RU2008118209A (en) | 2009-11-20 |
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