MXPA99005923A - Rubber compositions containing acrylates estear metacrylate - Google Patents
Rubber compositions containing acrylates estear metacrylateInfo
- Publication number
- MXPA99005923A MXPA99005923A MXPA/A/1999/005923A MX9905923A MXPA99005923A MX PA99005923 A MXPA99005923 A MX PA99005923A MX 9905923 A MX9905923 A MX 9905923A MX PA99005923 A MXPA99005923 A MX PA99005923A
- Authority
- MX
- Mexico
- Prior art keywords
- rubber
- composition
- phr
- copolymer
- bis
- Prior art date
Links
- 229920001971 elastomer Polymers 0.000 title claims abstract description 84
- 239000005060 rubber Substances 0.000 title claims abstract description 70
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 150000001252 acrylic acid derivatives Chemical class 0.000 title 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims abstract description 19
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000806 elastomer Substances 0.000 claims abstract description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 239000011593 sulfur Substances 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 16
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 13
- -1 vinyl aromatic compound Chemical class 0.000 claims description 13
- 239000005062 Polybutadiene Substances 0.000 claims description 12
- 239000006229 carbon black Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000945 filler Substances 0.000 claims description 10
- 229920002857 polybutadiene Polymers 0.000 claims description 10
- 229920001195 polyisoprene Polymers 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 7
- 229920003052 natural elastomer Polymers 0.000 claims description 7
- 229920001194 natural rubber Polymers 0.000 claims description 7
- 244000043261 Hevea brasiliensis Species 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229920005549 butyl rubber Polymers 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 4
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-UHFFFAOYSA-N 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 229920005690 natural copolymer Polymers 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229920002943 EPDM rubber Polymers 0.000 claims 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 15
- 239000000377 silicon dioxide Substances 0.000 description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 238000004073 vulcanization Methods 0.000 description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- 150000003961 organosilicon compounds Chemical class 0.000 description 5
- 239000006057 Non-nutritive feed additive Substances 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 230000000930 thermomechanical effect Effects 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000010074 rubber mixing Methods 0.000 description 3
- 229920003051 synthetic elastomer Polymers 0.000 description 3
- 239000005061 synthetic rubber Substances 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- SUPOBRXPULIDDX-UHFFFAOYSA-N [[4-amino-6-(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound NC1=NC(NCO)=NC(NCO)=N1 SUPOBRXPULIDDX-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 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 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- ASZRKZHREYGNIX-UHFFFAOYSA-N 1-(2-dimethoxysilylbutyltrisulfanyl)butan-2-yl-dimethoxysilane Chemical compound C(C)C(CSSSCC(CC)[SiH](OC)OC)[SiH](OC)OC ASZRKZHREYGNIX-UHFFFAOYSA-N 0.000 description 1
- LYPJSBQIFJESQY-UHFFFAOYSA-N 1-(3-diethoxysilylhexyldisulfanyl)hexan-3-yl-diethoxysilane Chemical compound C(CC)C(CCSSCCC(CCC)[SiH](OCC)OCC)[SiH](OCC)OCC LYPJSBQIFJESQY-UHFFFAOYSA-N 0.000 description 1
- BULPGPDAJKQNHS-UHFFFAOYSA-N 1-(3-dimethoxysilylheptyltrisulfanyl)heptan-3-yl-dimethoxysilane Chemical compound C(CCC)C(CCSSSCCC(CCCC)[SiH](OC)OC)[SiH](OC)OC BULPGPDAJKQNHS-UHFFFAOYSA-N 0.000 description 1
- IXVLQYYLJLOXNV-UHFFFAOYSA-M 1-(dodecoxymethyl)pyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCOC[N+]1=CC=CC=C1 IXVLQYYLJLOXNV-UHFFFAOYSA-M 0.000 description 1
- VJZJVMFSALQEMK-UHFFFAOYSA-M 1-(ethoxymethyl)pyridin-1-ium;chloride Chemical compound [Cl-].CCOC[N+]1=CC=CC=C1 VJZJVMFSALQEMK-UHFFFAOYSA-M 0.000 description 1
- LLMLGZUZTFMXSA-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzenethiol Chemical compound SC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LLMLGZUZTFMXSA-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- SEHILZUPYWMWKV-UHFFFAOYSA-N 2-n,4-n,6-n-tris(2-methoxyethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCCNC1=NC(NCCOC)=NC(NCCOC)=N1 SEHILZUPYWMWKV-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- ANJNKZRLWOBAOR-UHFFFAOYSA-N C(COCCSSSCCOCCC1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(COCCSSSCCOCCC1=CC=CC=C1)C1=CC=CC=C1 ANJNKZRLWOBAOR-UHFFFAOYSA-N 0.000 description 1
- JXWBEOBROLXBGC-UHFFFAOYSA-N CO[SiH2]C(C)(C)CSSCC(C)(C)[SiH2]OC Chemical compound CO[SiH2]C(C)(C)CSSCC(C)(C)[SiH2]OC JXWBEOBROLXBGC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000252505 Characidae Species 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229920004941 NATSYN® 2200 Polymers 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
- SKFWHOBZYWUYMC-UHFFFAOYSA-N [2-[(2-diethoxysilyl-2-methoxyethyl)tetrasulfanyl]-1-methoxyethyl]-diethoxysilane Chemical compound CCO[SiH](OCC)C(OC)CSSSSCC(OC)[SiH](OCC)OCC SKFWHOBZYWUYMC-UHFFFAOYSA-N 0.000 description 1
- PWRCPTKSXMCQLS-UHFFFAOYSA-N [3-[(3,3-diphenyl-3-propan-2-yloxysilylpropyl)tetrasulfanyl]-1,1-diphenylpropyl]-propan-2-yloxysilane Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([SiH2]OC(C)C)CCSSSSCCC([SiH2]OC(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 PWRCPTKSXMCQLS-UHFFFAOYSA-N 0.000 description 1
- AIQUYWRDQFFHKH-UHFFFAOYSA-N [3-[(3-dimethoxysilyl-3-phenylpropyl)tetrasulfanyl]-1-phenylpropyl]-dimethoxysilane Chemical compound C1(=CC=CC=C1)C(CCSSSSCCC(C1=CC=CC=C1)[SiH](OC)OC)[SiH](OC)OC AIQUYWRDQFFHKH-UHFFFAOYSA-N 0.000 description 1
- UHBSMIYRAQANCI-UHFFFAOYSA-N [3-ethyl-1-[(3-ethyl-3-methoxysilylpentyl)tetrasulfanyl]pentan-3-yl]-methoxysilane Chemical compound C(C)C(CCSSSSCCC(CC)(CC)[SiH2]OC)([SiH2]OC)CC UHBSMIYRAQANCI-UHFFFAOYSA-N 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000000 cycloalkoxy 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
- GPRMZRVUGCUUCQ-UHFFFAOYSA-N cyclohexyloxy-[3-[(3-cyclohexyloxysilyl-3,3-diphenylpropyl)disulfanyl]-1,1-diphenylpropyl]silane Chemical compound C1(=CC=CC=C1)C(CCSSCCC(C1=CC=CC=C1)(C1=CC=CC=C1)[SiH2]OC1CCCCC1)([SiH2]OC1CCCCC1)C1=CC=CC=C1 GPRMZRVUGCUUCQ-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- LAQYGVFTFKGFLA-UHFFFAOYSA-N dimethoxymethyl-[5-[5-(dimethoxymethylsilyl)pentyltrisulfanyl]pentyl]silane Chemical compound COC(OC)[SiH2]CCCCCSSSCCCCC[SiH2]C(OC)OC LAQYGVFTFKGFLA-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- YGSXCBZAEOMZFW-UHFFFAOYSA-N ethoxy-[1-[(3-ethoxysilyl-3-methylheptyl)tetrasulfanyl]-3-methylheptan-3-yl]silane Chemical compound CCCCC(C)([SiH2]OCC)CCSSSSCCC(C)(CCCC)[SiH2]OCC YGSXCBZAEOMZFW-UHFFFAOYSA-N 0.000 description 1
- AWJOGEUUYZRGOU-UHFFFAOYSA-N ethylsulfanyl-[4-[(3-ethylsulfanylsilyl-3-methylbutyl)tetrasulfanyl]-2-methylbutan-2-yl]silane Chemical compound CC(CCSSSSCCC(C)(C)[SiH2]SCC)([SiH2]SCC)C AWJOGEUUYZRGOU-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940091868 melamine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N penta-1,3-diene Chemical compound CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical group [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- RHCICBOBTHGGEY-UHFFFAOYSA-N tri(propan-2-yloxy)-[12-[12-tri(propan-2-yloxy)silyldodecyldisulfanyl]dodecyl]silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCCCCCCCCCCSSCCCCCCCCCCCC[Si](OC(C)C)(OC(C)C)OC(C)C RHCICBOBTHGGEY-UHFFFAOYSA-N 0.000 description 1
- ATYIZISYPACGCO-UHFFFAOYSA-N tributoxy-[3-(3-tributoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCSSCCC[Si](OCCCC)(OCCCC)OCCCC ATYIZISYPACGCO-UHFFFAOYSA-N 0.000 description 1
- NMPPNPIZYXDMMY-UHFFFAOYSA-N tricyclohexyloxy-[3-(3-tricyclohexyloxysilylpropyltetrasulfanyl)propyl]silane Chemical compound C1CCCCC1O[Si](OC1CCCCC1)(OC1CCCCC1)CCCSSSSCCC[Si](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 NMPPNPIZYXDMMY-UHFFFAOYSA-N 0.000 description 1
- RLQRJIRGQDCNKY-UHFFFAOYSA-N tricyclopentyloxy-[3-(3-tricyclopentyloxysilylpropyltrisulfanyl)propyl]silane Chemical compound C1CCCC1O[Si](OC1CCCC1)(OC1CCCC1)CCCSSSCCC[Si](OC1CCCC1)(OC1CCCC1)OC1CCCC1 RLQRJIRGQDCNKY-UHFFFAOYSA-N 0.000 description 1
- ASAOXGWSIOQTDI-UHFFFAOYSA-N triethoxy-[2-(2-triethoxysilylethyltetrasulfanyl)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCSSSSCC[Si](OCC)(OCC)OCC ASAOXGWSIOQTDI-UHFFFAOYSA-N 0.000 description 1
- XGVRSFOOQXXSDO-UHFFFAOYSA-N trihexoxy-[3-(3-trihexoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCCCCCO[Si](OCCCCCC)(OCCCCCC)CCCSSCCC[Si](OCCCCCC)(OCCCCCC)OCCCCCC XGVRSFOOQXXSDO-UHFFFAOYSA-N 0.000 description 1
- SVNJQEIWNMNTBW-UHFFFAOYSA-N trimethoxy-[18-(18-trimethoxysilyloctadecyltetrasulfanyl)octadecyl]silane Chemical compound CO[Si](OC)(OC)CCCCCCCCCCCCCCCCCCSSSSCCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SVNJQEIWNMNTBW-UHFFFAOYSA-N 0.000 description 1
- IPBOZRUUILDBBF-UHFFFAOYSA-N trimethoxy-[2-methyl-1-[(2-methyl-1-trimethoxysilylpropyl)tetrasulfanyl]propyl]silane Chemical compound CO[Si](OC)(OC)C(C(C)C)SSSSC(C(C)C)[Si](OC)(OC)OC IPBOZRUUILDBBF-UHFFFAOYSA-N 0.000 description 1
- NQRACKNXKKOCJY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSCCC[Si](OC)(OC)OC NQRACKNXKKOCJY-UHFFFAOYSA-N 0.000 description 1
- JTTSZDBCLAKKAY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSSCCC[Si](OC)(OC)OC JTTSZDBCLAKKAY-UHFFFAOYSA-N 0.000 description 1
- KOFGNZOFJYBHIN-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltrisulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSCCC[Si](OC)(OC)OC KOFGNZOFJYBHIN-UHFFFAOYSA-N 0.000 description 1
- BPBNXPYFZUPVRY-UHFFFAOYSA-N trimethoxy-[3-(4-trimethoxysilylbut-1-en-2-yltetrasulfanyl)but-3-enyl]silane Chemical compound CO[Si](OC)(OC)CCC(=C)SSSSC(=C)CC[Si](OC)(OC)OC BPBNXPYFZUPVRY-UHFFFAOYSA-N 0.000 description 1
- WUMASLCNJBRHDA-UHFFFAOYSA-N trimethoxy-[4-(4-trimethoxysilylbutyltetrasulfanyl)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCSSSSCCCC[Si](OC)(OC)OC WUMASLCNJBRHDA-UHFFFAOYSA-N 0.000 description 1
- ORMMMPDHLQZPEB-UHFFFAOYSA-N trioctoxy-[3-(3-trioctoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCCCCCCCO[Si](OCCCCCCCC)(OCCCCCCCC)CCCSSSSCCC[Si](OCCCCCCCC)(OCCCCCCCC)OCCCCCCCC ORMMMPDHLQZPEB-UHFFFAOYSA-N 0.000 description 1
- VKJFZCCNSAEGRS-UHFFFAOYSA-N tripropoxy-[18-(18-tripropoxysilyloctadec-1-enyltetrasulfanyl)octadec-17-enyl]silane Chemical compound CCCO[Si](OCCC)(OCCC)CCCCCCCCCCCCCCCCC=CSSSSC=CCCCCCCCCCCCCCCCC[Si](OCCC)(OCCC)OCCC VKJFZCCNSAEGRS-UHFFFAOYSA-N 0.000 description 1
- HRAOIWWIABULSC-UHFFFAOYSA-N tripropoxy-[2-(2-tripropoxysilylethylpentasulfanyl)ethyl]silane Chemical compound CCCO[Si](OCCC)(OCCC)CCSSSSSCC[Si](OCCC)(OCCC)OCCC HRAOIWWIABULSC-UHFFFAOYSA-N 0.000 description 1
- IRNPVNAUHNTHDI-UHFFFAOYSA-N tris(6-methylheptoxy)-[3-[3-[tris(6-methylheptoxy)silyl]propyltetrasulfanyl]propyl]silane Chemical compound CC(C)CCCCCO[Si](OCCCCCC(C)C)(OCCCCCC(C)C)CCCSSSSCCC[Si](OCCCCCC(C)C)(OCCCCCC(C)C)OCCCCCC(C)C IRNPVNAUHNTHDI-UHFFFAOYSA-N 0.000 description 1
- CONCKWGHNZAEBO-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[3-[3-[tris[(2-methylpropan-2-yl)oxy]silyl]propyldisulfanyl]propyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)CCCSSCCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C CONCKWGHNZAEBO-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Abstract
The present invention relates to a rubber composition containing: (i) an elastomer containing olefinic unsaturation and (ii) from 0.5 to 25 phr of stearyl acrylate, stearyl methacrylate or mixtures thereof.
Description
RUBBER COMPOSITIONS CONTAINING ACRYLATE OR ESTEARYL METACRYLATE
FIELD OF THE INVENTION The present invention relates to a rubber composition containing (i) an elastomer having olefinic unsaturation and (ii) stearyl acrylate, stearyl methacrylate or mixtures thereof.
BACKGROUND OF THE INVENTION Processing aids are commonly used in natural and synthetic rubber compositions.
Such processing aids are used during mixing, allowing the incorporation of filling materials and other ingredients quickly with low energy consumption.
SUMMARY OF THE INVENTION The present invention relates to the use of stearyl acrylate, stearyl methacrylate or mixtures thereof in a rubber composition.
DETAILED DESCRIPTION OF THE INVENTION A method for processing a silica-added rubber composition is disclosed, which consists in mixing: (i) 100 parts by weight of at least one elastomer containing olefinic unsaturation selected from the group consisting of natural rubber and copolymers and homopolymers of dienes with uqados and copolymers of at least one conjugated diene and vinyl aromatic compounds; with (ii) 0.5 to 25 phr of stearyl acrylate, stearyl methacrylate or mixtures thereof. Also disclosed is a rubber composition comprising at least one elastomer containing (i) olefinic unsaturation and (ii) from 0.5 to 25 phr of stearyl acrylate, stearyl methacrylate or mixtures thereof. The present invention can be used in rubber or elastomer processes having olefinic unsaturation. The phrase "rubber or elastomer containing olefinic unsaturation" is meant to include natural rubbers and their various raw materials and recovered forms, as well as various synthetic rubbers In the description of this invention, the terms "rubber" and "elastomer" can be used interchangeably, unless otherwise indicated The terms "rubber composition", "compound rubber" and "rubber compounds" are used interchangeably to refer to rubber that has been combined or mixed with various ingredients and materials, such as The terms are well known to those skilled in the rubber or combined rubber mixing art.The representative synthetic polymers are the products of bu oropolymerization and their homologues and derivatives, for example, methylbutadiene, di-ethylbutadiene and pentadiene, as well as as polymers such as those formed of butadienes or their homologs or derivatives with other mo unsaturated nomena Among the latter are acetylenes, for example, vinyl acetylene; olefins, for example isobutylene, which are copolymerized with isoprene to form butyl rubber; vinyl compounds, for example acrylic acid, acrylonitrile (which polymerizes with butadiene to form NBR), methacrylic acid and styrene, the latter compound is polymerized with butadiene to form SBR, as well as vinyl esters and the different unsaturated aldehydes, ketones and esters, for example, acrolein, methyl isopropenii ketone and vinylethyl ether. Specific examples of synthetic rubbers include neoprene
(polychloroprene), polybutadiene (which includes cis-1,4-polybutadiene), polyisoprene (including cis-1,4-polyisoprene), butyl rubber, styrene / isoprene / butadiene rubber, copolymers of 1,3-butadiene or isoprene with monomers such as styrene, acrylonitrile and methyl methacrylate, as well as ethylene / propylene terpolymer, also known as ethylene / propylene / diene monomer (EPDM) and, in particular, ethylene / propylene / diciolopentadiene terpolymers. The preferred rubber or elastomers are polybutadiene and SBR. In one aspect, the rubber is preferably at least two diene-based rubbers, for example, a combination of two or more rubbers such as cis-1-polyisoprene rubber (natural or synthetic) is preferred., although natural is preferred), 3, 4-polyisoprene rubber, styrene / isoprene / butadiene rubber, styrene / butadiene rubbers derived from emulsion and solution polymerization, cis 1, 4-polybutadiene rubbers and butadiene copolymers / acrylonitrile prepared by emulsion polymerization. In one aspect of this invention, an (E-SBR) styrene / butadiene derivative of emulsion polymerization is likely to be used having a relatively conventional styrene content of from about 20 to about 28% bound styrene or, for some applications , an E-SBR having a styrene content bound from medium to relatively high; specifically, a bound styrene content of from about 30 up to about 45%. The relatively high styrene content of about 30 to about 45 for the E-SBR can be considered beneficial for a purpose of improving the traction, or resistance to skidding of the tread. The presence of the E-SBR itself is considered beneficial for the purpose of improving the processability of the uncured elastomer composition mixture, especially as compared to the use of an SBR (S-SBR) prepared by solution polymerization. By E-SBR prepared by emulsion polymerization, it is understood that styrene and 1,3-butadiene sseean copolymerize as an aqueous emulsion. These are well known to those who have experience in the art. The bound styrene content can vary, for example, from about 5 to about 50%. In one aspect, the E-SBR may also contain acrylonitrile to form a terpolymer rubber, such as E-SBAR, in amounts, for example, from about 2 to about 30 weight percent bound acrylonitrile in the terpolymer. Styrene / butadiene / acrylonitrile terpolymer rubbers prepared by emulsion polymerization containing from 2 to about 408 by weight of bound acrylonitrile in the terpolymer are also contemplated as diene based rubbers for use in this invention. SBR (S-SBR) prepared by solution polymerization usually has a bound styrene content in a range from about 5 to about 50, preferably from about 9 to about 36 percent. The S-SBR can be prepared conveniently, for example, by catalyzing organolithium in the presence of an organic hydrocarbon solvent. One purpose of using S-SBR is to improve rolling resistance of the rim as a result of low hysteresis when used in a tire tread composition. The 3,4-polyisoprene (3,4-PI) rubber is considered beneficial for a purpose of increasing the traction of the rim when it is used in a tire tread composition. 3,4-PI and the use thereof is described extensively in U.S. Patent No. 5,087,668, which is incorporated herein by reference. The Tg refers to the glass transition temperature which can be conveniently determined by a differential scanning calorimeter at a heating rate of 10 ° C per minute. The rubber of cis 1, -polybutadiene (BR) is considered beneficial for a purpose of improving the use of the tire treads, or deterioration of the treads. Such BR can be prepared, for example, by polymerization in organic solution of 1,3-butadiene. BR can be conveniently characterized, for example, by having at least 90% cis content Natural rubber cis 1, polyisoprene and cis 1/4-polyisoprene are well known to those skilled in the rubber art. The term 'phr', as used herein, and in accordance with conventional practice, refers to "parts by weight of a respective material per 100 parts by weight of rubber or elastomer." Stearyl acrylate, methacrylate stearyl and mixtures thereof are used in the present invention Preferably, stearyl acrylate is used The stearyl acrylate or stearyl methacrylate used in the present invention can be added to the rubber by any conventional technique, such as a mill or a Banbury The amount of stearyl acrylate or stearyl methacrylate can vary widely depending on the type of rubber and other compounds present in the rubber composition.Usually, the amount of stearyl acrylate or stearyl methacrylate is used in a range from about 0.5 to about 25 phr, with a range from 1 to about 10 phr being preferred.Stearyl acrylate or stearyl methacrylate can be r added during the non-productive stage or productive stage of mixing, but is preferably added in the non-productive stage.
For ease of handling, stearyl acrylate or stearyl methacrylate can be used per se or can be deposited in suitable carrier materials. Examples of carrier materials that can be used in the present invention include silica, carbon black, alumina, kieselguhr, silica gel and calcium silicate. In another preferred embodiment the rubber composition contains a sufficient amount of filler material to contribute to a reasonably high modulus and high tear resistance. The filler material can be added in quantities within the limits from 10 to 250 phr. Representative types of fillers include silica, carbon black and mixtures thereof. When the filler material is silica, the silica is usually present in an amount within the limits of 10 to 80 phr. Preferably, the silica is present in an amount within the limits of from 15 to 70 phr. When the filler material is carbon black, the amount of carbon black will vary from 0 to 80 phr. Preferably, the amount of carbon black varies in the range from 0 to 40 phr. It can also be appreciated that stearyl acrylate, stearyl methacrylate, or mixtures thereof, can be used in conjunction with a carbon black; specifically, pre-mixed with a carbon black prior to addition to the rubber composition, and such a carbon black can be included in the above amount of carbon black for the formulation of the rubber composition. The precipitated, particulate, commonly used silica that is used in rubber composition applications can be used as the silica of this invention. These precipitated silicas include, for example, those obtained by the acidification of a soluble silicate; for example sodium silicate. Such silicas can be characterized, for example, by having a BET surface area, measured using nitrogen gas, preferably in the range of about 40 to about 600, and more usually in a range of about 50 to about 300 square meters. per gram. The BET method of surface area measurement is described in the Journal of the American Chemical Society, volume 60, page 304 (1930). Silica can also usually be characterized as having an absorption value of dibutyl phthalate (DBP) in a range from about 100 to about 400, and more usually from about 150 to about 300. It can be expected that silica have an average final particle size, for example, in the range from 0.01 to 0.05 microns determined by the electron microscope, although the silica particles may be even smaller, or possibly larger, in size. Some commercially available silicas can be considered for use in this invention, such as, for example only herein, without limitations, silicas commercially available by PPG Industries, under the trademark Hi-Sil with designations 210, 243, etc.; the silicas available from Rhone-Poulenc, with, for example, Z1165MP and Z165GR designations and silicas available from Degussa AG with, for example, designations VN2 and VN3, etcetera. The processing of the vulcanizable rubber by sulfur can be carried out in the presence of an organosilicon compound containing sulfur. Examples of suitable sulfur-containing organosilicon compounds are of the formula:
Z-Alk-Sn-Alk-Z, 1 /
in which Z is selected from the group consisting of
wherein R os rm alkyl group of 1 to 4 carbon atoms, cyclohexyl or phenyl;
2 R is alkoxy of 1 to 8 carbon atoms, or cycloalkoxy of 5 to 8 carbon atoms; Alk is a divalent hydrocarbon of 1 to 18 carbon atoms and n is an integer of 2 to 8. Specific examples of the organosilicon compounds containing sulfur, which may be used in accordance with the present invention include:, 3'-bis (trimethoxysilylpropyl) disulfide, 3,3'-bis (triethoxysilylpropyl) tetrasulfide, 3,3'-bis (triethoxysilylpropyl) octasulfide, 3,3'-bis (trimethoxysilylpropyl) tetrasulfide, 2,2'-bis (triethoxysilylethyl) tetrasulfide, 3, 3'-bis (trimethoxysilylpropyl) trisulfide 3,3'-bis (triethoxysilylpropyl) trisulfide 3,3'-bis (tributoxysilylpropyl) disulphide 3,3'-bis (trimethoxysilylpropyl) exasulfide 3, 3 '- bis (trimethoxysilylpropyl) octasulfide 3, 3'-bis (trioctoxysilylpropyl) tetrasulfide 3, 3'-bis (trihexoxysilylpropyl) disulfide, 3,3'-bis (tri-2"-ethylhexoxysilylpropyl) trisulfide, 3,3'-bis (triisooctoxysilylpropyl) tetrasulfide, 3, 3 'bis (tri-t-butoxysilylpropyl) disulfide, 2,2'-bis (methoxydiethoxysilylethyl) tetrasulfide, 2,2'-bis (tripropoxysilylethyl) pentasulfide, 3, 3'-bis (tricyclohexoxysilylpropyl) tetrasulfide, 3, 3' bis (tricyclopentoxysilylpropyl) trisulfide, 2,2 'bis (tri-2"-methylcyclohexoxysilylethyl) tetrasulfide, bis (trimethoxysilylmethyl) tetras ulfuro, 3-methoxyethoxypropoxysilyl 3'-diethylbutoxypropyl tetrasulfide, 2,2'-bis (dimethylmethoxysilylethyl) disulfide, 2,2'-bis (dimethylsec.butoxysilylethyl) trisulfide, 3,3'-bis (methylbutylethoxysilylpropyl) tetrasulfide 3, 3 '- bis (di t-butylmethoxysilylpropyl) tetrasulfide 2,2'-bis (phenylmethylmethoxylethyl) trisulfide, 3,3'-bis (diphenylisopropoxysilylpropyl) tetrasulfide, 3, 3 * -bi s (diphenylcyclohexoxysilylpropyl) disulfide, 3,3'-bis (dimethylethylmercaptosilylpropyl) tetrasulfide, 2,2'-bis (ethyldimethoxysilylethyl) trisulfide, 2,2'-bis (ethylexypropoxysilylethyl) tetrasulfide, 3,3'-bis (diethylmethoxysilylpropyl) tetrasulfide 3, 3'-bis (ethyldi-sec.butoxysilylpropyl) disulfide, , 3'-bis (propyldiethoxysilylpropyl) disulfide, 3,3'-bis (butyldimethoxysilylpropyl) trisulphide, 3,3'-bis (phenyldimethoxysilylpropyl) tetrasulfide, 3-phenylethoxybutoxysilyl 3'-trimethoxysilylpropyl tetrasulfide, 4,4'-bis (trimethoxysilylbutyl) tetrasulfide, 6,6 '-bis (trietoxy if lilhexyl) t etrasulfide, 12,12'-bis (triisopropoxysilyldodecyl) disulfide, 18,18'-bis (trimethoxysilyloctadecyl) tetrasulfide, 18,18'-bis (tripropoxysilyloctadecenyl) tetrasulfide, 4,4'-bis (trimethoxysilyl-buten-2-yl) tetrasulfide, 4,4'-bis (trimethoxysilylcyclohexylene) ethersulfide, 5, 5'-bis (dimethoxymethylsilylpentyl) trisulfide, 3,3'-bis (trimethoxysilyl-2-methylpropyl) tetrasulfide, 3,3'-bis (dimethoxyphenylsilyl-2-) methylpropyl) disulfide.
The preferred sulfur-containing orqanosilicic compounds are the 3,3'-bis (tri ethoxy or triethoxy silylpropyl) sulfides. Most preferred compound EJ is 3,3'-bis (triethoxysilylpropyl) tetrasulfide. Therefore, for Formula I, Z preferably is R2 I - Si - R2 I R2 2 where R r. n to the r.oxi from? Up to 4 carbon atoms, two carbon atoms were particularly preferred; Alk is a divalent hydrocarbon of 2 to 4 carbon atoms, with 3 carbon atoms being particularly preferred; and n is an integer from 3 to 5, with 4 being particularly preferred.
The amount of sulfur-containing organosilicon compounds of the formula I in a rubber composition will vary depending on the level of silica used. Generally speaking, the amount of the compound of the formula II, if used, will be in the limits from 0.01 to 1.0 parts by weight per parts by weight of the silica. Preferably, the amount will be in the range from 0.05 to 0.4 parts by weight per parts by weight of the silica. Those skilled in the art will readily understand that the rubber composition can be compounded by the methods generally known in the rubber composition art, such as by mixing the various sulfur-vulcanizable constituent rubbers with various commonly used additive materials, such as , for example, sulfur donors, curing aids, as activators and retarders and process additives, such as oils, resins that include thickener or tackifying resins and plasticizers, fillers, pigments, fatty acids, zinc oxide, waxes, antioxidants and antiozonants and peptizers. As is known to those of skill in the art, depending on the intended use of the material (rubbers) vulcanized by sulfur and vulcanizable by sulfur, the aforementioned additives are selected and commonly used in conventional amounts. Typical typical amounts of black (s) of reinforcing type smoke for this invention, if used, are set forth herein. Representative examples of sulfur donors include elemental sulfur (free sulfur), amine disulfide, polymeric polysulfide, and sulfur olefin adducts. Preferably, the sulfur vulcanizing agent is elemental sulfur. The vulcanizing agent for sulfur can be used in an amount within the limits of 0.5 to 8 phr, with a limit of 1.5 to 6 phr being preferred. Common amounts of thickener resins, if used, range from 0.5 to about 10 phr, usually from 1 to 5 phr. The common amounts of processing aids range from about 1 to about 50 phr. Such processing aids may include, for example, aromatic, naphthenic and / or paraffinic processing oils. Common amounts of antioxidants range from about 1 to about 5 phr. Representative antioxidants may be, for example, diphenyl-p-phenylenediamine and others, such as those described in Vanderbilt Rubber Handbook (1978), pages 344-346. The common amounts of antiozonants comprise from about 1 to 5 phr. Common amounts of fatty acids, if used, which may include stearic acid, range from about 0.5 to about 3 phr. The common amounts of zinc oxide range from about 2 to about 5 phr. The common amounts of waxes comprise about 1 to about 5 phr. Microcrystalline waxes are often used. The common amounts of peptizers comprise about 0.1 to about 1 phr. Common peptizers can be, for example, pentachlorothiophenol and dibenzamidodiphenyl disulfide. In one aspect of the present invention, the rubber composition vulcanizable by sulfur is then cured by sulfur or vulcanized. Accelerators are used to control the time and / or temperatures required for vulcanization and to improve the vulcanization properties. In one embodiment, a simple accelerator system can be used; for example, primary accelerator. The primary accelerator (s) may be used in total amounts within the limits of from about 0.5 to about 4, preferably from about 0.8 to about 1.5 phr. In another embodiment, combinations of a primary accelerator and a secondary accelerator could be used, with a secondary accelerator being used in small quantities, such as from about 0.05 to about 3 phr, to activate and improve the properties of the vulcanizate. It could be expected that the combinations of these accelerators produce a synergistic effect on the final properties and be somewhat better than those produced by the use of any accelerator alone. In addition, delayed action accelerators can be used when they are not affected by normal processing temperatures but produce a satisfactory cure at ordinary vulcanization temperatures. It is also possible to use vulcanization retarders. Suitable types of accelerators that can be used in the present invention are amines, disulfides, guanidines, thioureas, thiazoles, thiourams, sulfenamides, dithiocarbamates and xanthates. Preferably, the primary accelerator is a sulfenamide. If a second accelerator is used, the second accelerator is preferably a guanidine, dithiocarbamate or thiouram compound. The rubber compositions of the present invention may contain methylene donors and methylene acceptors. The term "methylene donor" is understood to mean a compound capable of reacting with a methylene acceptor (such as resorcinol or its equivalent containing a hydroxyl group present) and generating the resin in-situ. Examples of methylene donors that are suitable for use in the present invention include hexamethylene tetraamine, hexaethoxyethylmelamine, hexethoxymethoxymelamine, lauryloxymethyl pyridinium chloride, ethoxymethylpyridinium chloride, trioxane hexametoxymethylmelamine, hydroxy groups from which they can be esterified or partially esterified, and formaldehyde polymers, such as paraformaldehyde. Moreover, the methylene donors may be N-substituted oxymethylmelamine of the general formula:
wherein X is an alkyl having from 1 to 8 carbon atoms, R, R, R, R and R are individually selected from the group consisting of hydrogen, an alkyl having from 1 to 8 carbon atoms and the group - CHvOX. Specific methylene donors include hexakis- (methoxymethyl) mel amine, N, N ', N "-trimet.il / N, N', N" -trimethylolmelamine, hexamethylolmelamine, N, N ', N "-dimethylolmelamine, N- methylolmelamine, N, N'-dimethylolmelamine, N, N ', N "-tris (methoxy ethyl) melamine and N, N'-N" -tributyl-N, N', N "-trimethylol-melamine. The N-methylol derivatives of melamine are prepared by known methods. The amount of methylene donors and methylene acceptors that are present and the rubber material may vary. Typically, the amount of methylene donors and methylene acceptors that are present will be in the range from about 0.1 phr to 10.0 phr. Preferably, the amount of methylene donors and methylene acceptor will be in limits from about 2.0 phr to 5.0 phr for each. The weight ratio of the methylene donor to the methylene acceptor can vary. Generally speaking, the weight ratio will vary in the range from about 1:10 to about 10: 1. Preferably, the limits of the weight ratio will be from about 1: 3 to 3: 1. The mixing of the rubber composition can be carried out by methods known to those skilled in the rubber mixing art. For example, the ingredients are usually mixed in at least two stages; specifically, at least one non-productive stage followed by a productive mixing stage. Final curatives that include sulfur vulcanizing agents are usually mixed in the final stage which is conventionally called the 'productive' mixing step in which mixing is usually done at a temperature, or ultimate temperature, less than temperature (s) of the mixture than in the preceding nonproductive mixing stage (s) Rubber and stearyl acrylate or stearyl methacrylate are mixed in one or more non-productive mixing stages. of "non-productive" and "productive" mixing stages are well known to those who have experience in the technique of rubber mixing. The rubber composition containing stearyl acrylate or stearyl methacrylate, silica rubber and organosilicon compound containing sulfur, if used, can be subjected to a thermomechanical mixing step. The thermomechanical mixing step usually comprises mechanical work in a mixer or extruder for a suitable time to produce a temperature in the rubber between 140 ° C and 190 ° C. The proper duration of the thermomechanical work varies as a function of the operating conditions and the volume and nature of the components. For example, the thermomechanical work can be from 4 to 20 minutes. The vulcanization of the rubber composition of the present invention is, in general, carried out at conventional temperatures within the limits of about 100 ° C to 200 ° C, preferably, the vulcanization is carried out at temperatures within the limits. from approximately 110 ° C to 180 ° C. Any normal vulcanization process can be used, such as heating in a press or mold, heating with superheated steam or hot air or in a salt bath. With the vulcanization of the composition vulcanized by sulfur, the rubber composition of this invention can be used for various purposes. For example, the rubber composition vulcanized with sulfur can be in the form of a rim, band or hose. In the case of a tire, it may be in different components of the tire. Such rims can be constructed, formed, molded and cured by the different methods that are known and will be readily apparent to those of skill in the art. Preferably, the rubber compositions are used in the tire treads. As can be seen, the tire can be a car tire, an airplane tire, a truck tire and the like. Preferably, the rim is a car tire. The rim may also be biased or radial, with a radial rim being preferred. The invention can be better understood by reference to the following examples, in which the parts and percentages are by weight unless otherwise indicated.
The following examples are presented in order to illustrate, but will not limit the present invention. Curing properties were determined using a Monsanto oscillating disc rheometer that was operated at a temperature of 150 ° C and at a frequency of 1 hertz. A description of oscillating disc rheometers can be found in the Vanderbilt Rubber Handbook edited by Robert O. Ohm (Norwalk, Conn., R. T. Vanderbilt Company, Inc., 1990), pages 554-557. The use of this curing measure and the registered standardized values of the curve are specified in ASTM D-2084. A common curing curve obtained in an oscillating disc revolution is shown on page 555 of the 1990 edition of the Vanderbilt Rubber Handbook. In the oscillating disc rheometer, the composite rubber samples are subjected to an oscillating cutting action of constant amplitude. The torque of the oscillating disk, imbedded in the material being tested, is measured, which is required to oscillate the rotor at the vulcanization temperature. The values obtained using this curing test are very significant since the changes in the rubber or in the compound formula are very quickly detected. It is obvious that it is usually advantageous to have a fast curing speed. The invention may be better understood by reference to the following examples, in which parts and percentages are by weight unless otherwise indicated.
Example 1 In this example, stearyl methacrylate was evaluated in a rubber compound containing carbon black. The rubber compositions containing the materials indicated in Tables 1 and 2 were prepared in a BR Banbury ™ mixer using three separate stages of addition (mixing); specifically, two non-productive mixing stages and one productive mixing stage. The first non-productive stage was mixed for 4 minutes at a rubber temperature of 160 ° C. The second non-productive stage was mixed for 4 minutes at a rubber temperature of 1 0 ° C. The mixing time for the productive stage was at a rubber temperature of 1? 0 ° C per? minutes The rubber compositions were identified herein as samples 1 and 2. Sample 1 is considered herein as a control without the use of stearyl methacrylate. In sample 2, 5 phr of stearyl methacrylate was used instead of 5 phr of processing oil. The samples were cured at about 150 ° C for approximately 36 minutes. Table 2 illustrates the behavior and physical properties of the cured samples 1 and 2. It is clearly evident from the results that the use of stearyl methacrylate in a rubber compound provides less DIN abrasion, which suggests a use of Improved tread when used on the tread of a tire.
Table 1
i cis 1, 4-po and synthetic isoprene which is commercially available from The Goodyear Tire & Rubber Company under the name Natsyn® 2200 2 N299 3 obtained from Aldri ch © Fl exon ™ 641 from Exxon 5 Mixtures of stearic acid, oleic acid and palrpitic acid. Type, 2-dlhid.ro 2, 2, 4-trimeti Iquinol ina pol imeri zade Table 2
Although certain representative embodiments and details have been shown for the purpose of illustrating the invention, it will be apparent to those skilled in the art that various changes and modifications may be made therein without departing from the spirit or scope of the invention.
Claims (10)
1. A method of processing a rubber composition characterized by mixing (i) 100 parts by weight of at least one elastomer containing olefinic unsaturation, selected from the group consisting of natural rubber, copolymers and homopolymers of conjugated dienes and copolymers of at least one conjugated diene and vinyl aromatic compound; with (ii) 0.5 to 25 phr of stearyl acrylate, stearyl methacrylate or mixtures thereof.
2. The method of claim 1, characterized in that a filler material is present from 10 to 250 phr.
3. The method of claim 2 characterized in that said filler material is carbon black.
4. The method of claim 1 is characterized in that said elastomer containing olefinic unsaturation is selected from the group consisting of natural rubber, neoprene, polyisoprene, butyl rubber, polybutadiene, styrene-butadiene copolymer, styrene / isoprene / butadiene rubber, methyl methacrylate-butadiene copolymer, isoprene-styrene copolymer, methyl methacrylate-isoprene copolymer, acrylonitrile-isoprene copolymer, acrylonitrile-butadiene copolymer, EPDM and mixtures thereof.
5. A rubber composition characterized by (i) an elastomer containing olefinic unsaturation and (ii) 0.5 to 25 phr of stearyl acrylate, stearyl methacrylate or mixtures thereof.
6. The composition of claim 5 is characterized in that a filler material of 10 to 250 phr is present. The composition of claim 6 characterized in that said filler material is carbon black. The composition of claim 5 characterized in that said elastomer containing olefinic unsaturation was selected from the group consisting of natural rubber, neoprene, polyisoprene, butyl rubber, polybutadiene, styrene-butadiene copolymer, styrene / isprene / butadiene rubber , methyl methacrylate butadiene copolymer, isoprene-styrene copolymer, methyl methacrylate-isoprene copolymer, acrylonitrile-isoprene copolymer, acrylonitrile-butadiene EPDM copolymer and mixtures thereof. 9. A rubber composition vulcanized by sulfur which is characterized by being prepared by heating the composition of claim 9 at a temperature between the limits of 100 ° C to 200 ° C in the presence of a sulfur vulcanizing agent, said composition It is in the form of a tire, band or hose. 10. A tire having a tread characterized by the composition of claim 9.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9/111445 | 1990-07-07 | ||
| US111445 | 1998-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA99005923A true MXPA99005923A (en) | 2000-04-24 |
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