CA1045748A - Chlorothio-sulfonamide-modified rubbery terpolymers and their blends - Google Patents
Chlorothio-sulfonamide-modified rubbery terpolymers and their blendsInfo
- Publication number
- CA1045748A CA1045748A CA239,787A CA239787A CA1045748A CA 1045748 A CA1045748 A CA 1045748A CA 239787 A CA239787 A CA 239787A CA 1045748 A CA1045748 A CA 1045748A
- Authority
- CA
- Canada
- Prior art keywords
- chlorothio
- terpolymer
- methyl
- radicals
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920001897 terpolymer Polymers 0.000 title claims abstract description 75
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 229920001971 elastomer Polymers 0.000 claims abstract description 44
- 229920000642 polymer Polymers 0.000 claims description 59
- -1 alkyl radicals Chemical class 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- 239000005060 rubber Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- UNOPJOFCFSFPCK-UHFFFAOYSA-N ClNS(=O)=S Chemical compound ClNS(=O)=S UNOPJOFCFSFPCK-UHFFFAOYSA-N 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 150000001993 dienes Chemical class 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- NAWQKWLDGDPPJR-UHFFFAOYSA-N [methyl-(4-methylphenyl)sulfonylamino] thiohypochlorite Chemical compound ClSN(C)S(=O)(=O)C1=CC=C(C)C=C1 NAWQKWLDGDPPJR-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical group C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011324 bead Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000012188 paraffin wax Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- WHPASJHILRGNCY-UHFFFAOYSA-N (n-(4-methylphenyl)sulfonylanilino) thiohypochlorite Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(SCl)C1=CC=CC=C1 WHPASJHILRGNCY-UHFFFAOYSA-N 0.000 claims description 3
- YJXZTMTVFOKMJT-UHFFFAOYSA-N (n-methylsulfonylanilino) thiohypochlorite Chemical compound CS(=O)(=O)N(SCl)C1=CC=CC=C1 YJXZTMTVFOKMJT-UHFFFAOYSA-N 0.000 claims description 3
- 244000043261 Hevea brasiliensis Species 0.000 claims description 3
- RKURYNQAEZHSEQ-UHFFFAOYSA-N [benzenesulfonyl(methyl)amino] thiohypochlorite Chemical compound ClSN(C)S(=O)(=O)C1=CC=CC=C1 RKURYNQAEZHSEQ-UHFFFAOYSA-N 0.000 claims description 3
- LARWKEHJBYUNQQ-UHFFFAOYSA-N [dimethylsulfamoyl(methyl)amino] thiohypochlorite Chemical compound CN(C)S(=O)(=O)N(C)SCl LARWKEHJBYUNQQ-UHFFFAOYSA-N 0.000 claims description 3
- AJNATCSYYVYJAI-UHFFFAOYSA-N [methylsulfonyl(propan-2-yl)amino] thiohypochlorite Chemical compound CC(C)N(SCl)S(C)(=O)=O AJNATCSYYVYJAI-UHFFFAOYSA-N 0.000 claims description 3
- RGTLKAINSBXJHM-UHFFFAOYSA-N [n-(benzenesulfonyl)anilino] thiohypochlorite Chemical compound C=1C=CC=CC=1S(=O)(=O)N(SCl)C1=CC=CC=C1 RGTLKAINSBXJHM-UHFFFAOYSA-N 0.000 claims description 3
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 3
- 235000010446 mineral oil Nutrition 0.000 claims description 3
- 229920003052 natural elastomer Polymers 0.000 claims description 3
- 229920001194 natural rubber Polymers 0.000 claims description 3
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 3
- 229920003246 polypentenamer Polymers 0.000 claims description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 3
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 claims description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- WTQBISBWKRKLIJ-UHFFFAOYSA-N 5-methylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C)CC1C=C2 WTQBISBWKRKLIJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000459 Nitrile rubber Polymers 0.000 claims description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- ZSXOAFADVREZAE-UHFFFAOYSA-N [ethyl-(4-methylphenyl)sulfonylamino] thiohypochlorite Chemical compound CCN(SCl)S(=O)(=O)C1=CC=C(C)C=C1 ZSXOAFADVREZAE-UHFFFAOYSA-N 0.000 claims description 2
- KEXXTLGOPKSSHB-UHFFFAOYSA-N [ethylsulfonyl(methyl)amino] thiohypochlorite Chemical compound CCS(=O)(=O)N(C)SCl KEXXTLGOPKSSHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229920005557 bromobutyl Polymers 0.000 claims description 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 description 2
- 229920005556 chlorobutyl Polymers 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 238000003801 milling Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- SQHFOJGTLRUIJQ-UHFFFAOYSA-N [(4-chlorophenyl)sulfonyl-propylamino] thiohypochlorite Chemical compound CCCN(SCl)S(=O)(=O)C1=CC=C(Cl)C=C1 SQHFOJGTLRUIJQ-UHFFFAOYSA-N 0.000 claims 2
- GOBQYTBDGJPQQI-UHFFFAOYSA-N [diethylsulfamoyl(methyl)amino] thiohypochlorite Chemical compound CCN(CC)S(=O)(=O)N(C)SCl GOBQYTBDGJPQQI-UHFFFAOYSA-N 0.000 claims 2
- UQLZIIAOPHDAJV-UHFFFAOYSA-N [methyl(methylsulfonyl)amino] thiohypochlorite Chemical group ClSN(C)S(C)(=O)=O UQLZIIAOPHDAJV-UHFFFAOYSA-N 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- UFERIGCCDYCZLN-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-1h-indene Chemical compound C1C=CCC2CC=CC21 UFERIGCCDYCZLN-UHFFFAOYSA-N 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000012360 testing method Methods 0.000 description 24
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 13
- 239000004594 Masterbatch (MB) Substances 0.000 description 12
- SPOAUAVQDRRDDK-UHFFFAOYSA-N ClS(=S)(=O)N Chemical class ClS(=S)(=O)N SPOAUAVQDRRDDK-UHFFFAOYSA-N 0.000 description 11
- 238000002835 absorbance Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000011787 zinc oxide Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 235000021355 Stearic acid Nutrition 0.000 description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 8
- 239000008117 stearic acid Substances 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 7
- 235000019241 carbon black Nutrition 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 229940124530 sulfonamide Drugs 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- 229920002943 EPDM rubber Polymers 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 4
- 229960002447 thiram Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- QRYFCNPYGUORTK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yldisulfanyl)morpholine Chemical compound C1COCCN1SSC1=NC2=CC=CC=C2S1 QRYFCNPYGUORTK-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000010057 rubber processing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- RYPKRALMXUUNKS-HWKANZROSA-N 2E-hexene Chemical compound CCC\C=C\C RYPKRALMXUUNKS-HWKANZROSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical class SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 1
- GVLBNAYYKLMCSH-UHFFFAOYSA-N 4-chloro-2-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC=C1S(N)(=O)=O GVLBNAYYKLMCSH-UHFFFAOYSA-N 0.000 description 1
- USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VKJACDHLIVOBTL-UHFFFAOYSA-N [cyclohexyl(methylsulfonyl)amino] thiohypochlorite Chemical compound CS(=O)(=O)N(SCl)C1CCCCC1 VKJACDHLIVOBTL-UHFFFAOYSA-N 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- WSCFFDRRHVCCFB-UHFFFAOYSA-N chlorosulfanylsulfonyl thiohypochlorite Chemical compound ClSS(=O)(=O)SCl WSCFFDRRHVCCFB-UHFFFAOYSA-N 0.000 description 1
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 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 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 239000000178 monomer 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 230000003068 static effect Effects 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
- 150000004763 sulfides Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- 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
- B60C1/0025—Compositions of the sidewalls
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- 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
- C08K5/43—Compounds containing sulfur bound to nitrogen
-
- 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
- C08K5/43—Compounds containing sulfur bound to nitrogen
- C08K5/44—Sulfenamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T152/00—Resilient tires and wheels
- Y10T152/10—Tires, resilient
- Y10T152/10495—Pneumatic tire or inner tube
- Y10T152/10819—Characterized by the structure of the bead portion of the tire
- Y10T152/10846—Bead characterized by the chemical composition and or physical properties of elastomers or the like
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US532979A US3915907A (en) | 1974-12-16 | 1974-12-16 | Chlorothio-sulfonamide-modified rubbery terpolymers and their blends |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1045748A true CA1045748A (en) | 1979-01-02 |
Family
ID=24123967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,787A Expired CA1045748A (en) | 1974-12-16 | 1975-11-17 | Chlorothio-sulfonamide-modified rubbery terpolymers and their blends |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3915907A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5626259B2 (cg-RX-API-DMAC10.html) |
| BE (1) | BE836646A (cg-RX-API-DMAC10.html) |
| BR (1) | BR7508158A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1045748A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2552617C2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2295047A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1490387A (cg-RX-API-DMAC10.html) |
| IT (1) | IT1052839B (cg-RX-API-DMAC10.html) |
| SE (1) | SE425088B (cg-RX-API-DMAC10.html) |
| TR (1) | TR18995A (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA757245B (cg-RX-API-DMAC10.html) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051083A (en) * | 1974-02-21 | 1977-09-27 | Exxon Research & Engineering Co. | Elastomer blends for tire components |
| CA1042330A (en) * | 1976-01-13 | 1978-11-14 | Yung-Kang Wei | Radial ply pneumatic tires and process for their manufacture |
| US4085093A (en) * | 1976-07-23 | 1978-04-18 | The Goodyear Tire & Rubber Company | Sulfilimines as premature vulcanization inhibitors |
| JPS5979747A (ja) * | 1982-10-29 | 1984-05-09 | Bridgestone Corp | 加硫ゴムの表面改質剤組成物および加硫ゴムの表面改質方法 |
| US5086123A (en) * | 1984-02-27 | 1992-02-04 | Minnesota Mining And Manufacturing Company | Fluoroelastomer compositions containing fluoroaliphatic sulfonamides as curing agents |
| US5216085A (en) * | 1984-02-27 | 1993-06-01 | Minnesota Mining And Manufacturing Company | Method for curing fluoroelastomer compositions containing fluoroaliphatic sulfonamides as curing agents |
| US4617347A (en) * | 1985-09-09 | 1986-10-14 | The Goodyear Tire & Rubber Company | Sulfur curable silicone rubber |
| ZA869680B (en) * | 1985-12-30 | 1987-09-30 | Monsanto Co | Rubber blends |
| US4804028A (en) * | 1986-03-05 | 1989-02-14 | The Goodyear Tire & Rubber Company | Non-staining vulcanized elastomeric composition and tires having sidewalls comprising said composition |
| US4814384A (en) * | 1986-05-14 | 1989-03-21 | Uniroyal Chemical Company, Inc. | Tire having tread composition comprised of EPDM/unsaturated rubber blend |
| US5047530A (en) * | 1987-08-28 | 1991-09-10 | Uniroyal Chemical Company, Inc. | Arylenediamine substituted triazines |
| US4794134A (en) * | 1987-08-28 | 1988-12-27 | Uniroyal Chemical Company, Inc. | Ozone resistant elastomeric articles |
| US4946881A (en) * | 1987-08-28 | 1990-08-07 | Uniroyal Chemical Company, Inc. | Tire sidewall |
| US5120779A (en) * | 1987-08-28 | 1992-06-09 | Uniroyal Chemical Company, Inc. | Tire sidewall |
| US4820780A (en) * | 1987-10-15 | 1989-04-11 | The Goodyear Tire & Rubber Company | Modification of rubber with N-chlorothio-sulfonamide |
| US4910266A (en) * | 1987-10-15 | 1990-03-20 | The Goodyear Tire & Rubber Company | Modification process using N-chloro-thiosulfonamide and rubber |
| US4855362A (en) * | 1987-12-28 | 1989-08-08 | The Goodyear Tire & Rubber Company | Polymer alloy |
| US5187240A (en) * | 1988-09-15 | 1993-02-16 | Exxon Chemical Patents Inc. | Process for preparing N-halothiosulfonamide-modified non-rubbery thermoplastic olefins |
| US5034468A (en) * | 1988-09-15 | 1991-07-23 | Exxon Chemical Patents Inc. | N-halothiosulfonamide modified rubber products |
| US5037896A (en) * | 1988-09-15 | 1991-08-06 | Exxon Chemical Patents Inc. | Selective catalytic process for preparing N-halothiosulfonamide modified polyolefins |
| US5017662A (en) * | 1988-09-15 | 1991-05-21 | Exxon Chemical Patents, Inc. | Selective catalytic process for preparing N-halothiosulfonamide modified EPDM terpolymers |
| US4956420A (en) * | 1988-09-15 | 1990-09-11 | Exxon Chemical Patents Inc. | Selective catalytic process for controlled modification of ethylene-(alpha-olefin)-diene monomer terpolymer with halothisulfonamide |
| US5034467A (en) * | 1988-09-15 | 1991-07-23 | Exxon Chemical Patents, Inc. | N-halothiosulfonamide-modified non-rubbery thermoplastic polyolefins |
| US5151467A (en) * | 1988-09-15 | 1992-09-29 | Exxon Chemical Patents Inc. | N-halothiosulfonamide modified rubber products and process for preparing the same |
| US4972010A (en) * | 1988-09-21 | 1990-11-20 | Uniroyal Chemical Company, Inc. | Substituted triazines |
| US5120844A (en) * | 1988-09-21 | 1992-06-09 | Uniroyal Chemical Company, Inc. | Substituted triazines |
| US4877901A (en) * | 1988-10-28 | 1989-10-31 | The Goodyear Tire & Rubber Company | Process for synthesizing N,N'-dithiobis(sulfonamides) |
| US4992583A (en) * | 1989-01-06 | 1991-02-12 | The Goodyear Tire & Rubber Company | Process for synthesizing N-chlorothio-sulfonamides |
| US4973627A (en) * | 1989-10-13 | 1990-11-27 | Uniroyal Chemical Company, Inc. | Tire sidewall composition |
| US5191022A (en) * | 1990-03-09 | 1993-03-02 | Exxon Chemical Patents Inc. | Covulcanizable polymer blends and process for producing the same |
| CA2054119A1 (en) * | 1991-03-28 | 1992-09-29 | Paul Harry Sandstrom | Tread compounds containing modified epdm which exhibit good abrasion resistance and improved hysteresis properties |
| US5216066A (en) * | 1991-03-28 | 1993-06-01 | The Goodyear Tire & Rubber Company | Tread compounds containing modified EPDM which exhibit good abrasion resistance and improved hysteresis properties |
| CA2154862A1 (en) * | 1995-03-20 | 1996-09-21 | Roger John Hopper | Process for preparation of n-halothiosulfonamide modified terpolymers |
| CA2281138A1 (en) * | 1998-09-22 | 2000-03-22 | Richard Michael D'sidocky | N-halothio-amide-modified elastomers and their application as adhesives for precured elastomeric substrates |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2852497A (en) * | 1956-07-24 | 1958-09-16 | Du Pont | Unsaturated sulfonamides of chlorosulfonated olefin polymers |
| US3406142A (en) * | 1965-06-01 | 1968-10-15 | Exxon Research Engineering Co | Acyclic dienophile cure of low unsaturated polymers |
| US3687893A (en) * | 1965-06-29 | 1972-08-29 | Columbian Carbon | Rubber compounding |
| US3524826A (en) * | 1965-12-17 | 1970-08-18 | Exxon Research Engineering Co | Covulcanizable brominated terpolymers |
| US3492370A (en) * | 1966-05-09 | 1970-01-27 | Copolymer Rubber & Chem Corp | Sulfur vulcanizable blends comprising diolefin rubber and e.p.d.m. terpolymers |
| US3649573A (en) * | 1968-02-20 | 1972-03-14 | Sumitomo Chemical Co | Sulfur-curable compositions comprising amorphous olefin copolymers and diene rubbers |
| NL6818781A (cg-RX-API-DMAC10.html) * | 1968-12-28 | 1970-06-30 | ||
| BE758927A (fr) * | 1969-11-15 | 1971-05-13 | Bayer Ag | Nouveaux retardateurs de vulcanisation a base de sulfonamides substitues |
| US3791913A (en) * | 1971-05-17 | 1974-02-12 | Exxon Research Engineering Co | Free flowing elastomer pellets and process for their preparation |
| US3870768A (en) * | 1971-09-15 | 1975-03-11 | Stepan Chemical Co | Unsaturated amides of oxybis(benzenesulfonic acid) and their use as cross-linking agents |
| US3856762A (en) * | 1972-06-26 | 1974-12-24 | Goodyear Tire & Rubber | Sulfonamide additives for sulfur vulcanizable polymers |
-
1974
- 1974-12-16 US US532979A patent/US3915907A/en not_active Expired - Lifetime
-
1975
- 1975-11-17 CA CA239,787A patent/CA1045748A/en not_active Expired
- 1975-11-18 ZA ZA00757245A patent/ZA757245B/xx unknown
- 1975-11-20 GB GB47789/75A patent/GB1490387A/en not_active Expired
- 1975-11-24 DE DE2552617A patent/DE2552617C2/de not_active Expired
- 1975-12-03 FR FR7536962A patent/FR2295047A1/fr active Granted
- 1975-12-10 BR BR7508158*A patent/BR7508158A/pt unknown
- 1975-12-10 SE SE7513952A patent/SE425088B/xx not_active IP Right Cessation
- 1975-12-12 TR TR18995A patent/TR18995A/xx unknown
- 1975-12-15 IT IT52698/75A patent/IT1052839B/it active
- 1975-12-15 JP JP14942675A patent/JPS5626259B2/ja not_active Expired
- 1975-12-15 BE BE162750A patent/BE836646A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1052839B (it) | 1981-07-20 |
| DE2552617C2 (de) | 1984-08-16 |
| TR18995A (tr) | 1978-02-10 |
| GB1490387A (en) | 1977-11-02 |
| DE2552617A1 (de) | 1976-07-01 |
| AU8680275A (en) | 1977-05-26 |
| JPS5186548A (cg-RX-API-DMAC10.html) | 1976-07-29 |
| ZA757245B (en) | 1976-10-27 |
| FR2295047A1 (fr) | 1976-07-16 |
| US3915907A (en) | 1975-10-28 |
| SE7513952L (sv) | 1976-06-17 |
| SE425088B (sv) | 1982-08-30 |
| BE836646A (fr) | 1976-04-01 |
| JPS5626259B2 (cg-RX-API-DMAC10.html) | 1981-06-17 |
| BR7508158A (pt) | 1976-08-24 |
| FR2295047B1 (cg-RX-API-DMAC10.html) | 1979-01-19 |
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