DE1770905C3 - Vulkanisierbare Masse und ihre Verwendung für vulkanisierte Formkörper - Google Patents
Vulkanisierbare Masse und ihre Verwendung für vulkanisierte FormkörperInfo
- Publication number
- DE1770905C3 DE1770905C3 DE1770905A DE1770905A DE1770905C3 DE 1770905 C3 DE1770905 C3 DE 1770905C3 DE 1770905 A DE1770905 A DE 1770905A DE 1770905 A DE1770905 A DE 1770905A DE 1770905 C3 DE1770905 C3 DE 1770905C3
- Authority
- DE
- Germany
- Prior art keywords
- toluenesulfinate
- zinc
- vulcanization
- acid
- benzenesulfinate
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 238000000465 moulding Methods 0.000 title 1
- 238000004073 vulcanization Methods 0.000 claims description 37
- 229920001971 elastomer Polymers 0.000 claims description 12
- 239000005060 rubber Substances 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000003111 delayed effect Effects 0.000 claims description 9
- -1 trichlorophenyl Chemical group 0.000 description 29
- 150000003455 sulfinic acids Chemical class 0.000 description 17
- DILXLMRYFWFBGR-UHFFFAOYSA-N 2-formylbenzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C(C=O)=C1 DILXLMRYFWFBGR-UHFFFAOYSA-N 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- JEHKKBHWRAXMCH-UHFFFAOYSA-M benzenesulfinate Chemical compound [O-]S(=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-M 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000011133 lead Substances 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 5
- FXJVNINSOKCNJP-UHFFFAOYSA-M 4-methylbenzenesulfinate Chemical compound CC1=CC=C(S([O-])=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-M 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- XUPCLXDANQVGBJ-UHFFFAOYSA-N butan-1-amine 4-methylbenzenesulfinic acid Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C(CCC)[NH3+] XUPCLXDANQVGBJ-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 4
- 150000003751 zinc Chemical class 0.000 description 4
- KHYUFILZGMOXBR-UHFFFAOYSA-L zinc;4-methylbenzenesulfinate Chemical compound [Zn+2].CC1=CC=C(S([O-])=O)C=C1.CC1=CC=C(S([O-])=O)C=C1 KHYUFILZGMOXBR-UHFFFAOYSA-L 0.000 description 4
- BXEXEGLXXGXRHP-UHFFFAOYSA-N (4-methylphenyl)sulfonylmethanol Chemical compound CC1=CC=C(S(=O)(=O)CO)C=C1 BXEXEGLXXGXRHP-UHFFFAOYSA-N 0.000 description 3
- JGWCPAOFUKLPIA-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)[O-])C.C(CCC)[NH2+]CCCC Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C(CCC)[NH2+]CCCC JGWCPAOFUKLPIA-UHFFFAOYSA-N 0.000 description 3
- LRDDKOUKGQWJMD-UHFFFAOYSA-L C1=C(C=CC2=CC=CC=C12)S(=O)[O-].[Zn+2].C1=C(C=CC2=CC=CC=C12)S(=O)[O-] Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)[O-].[Zn+2].C1=C(C=CC2=CC=CC=C12)S(=O)[O-] LRDDKOUKGQWJMD-UHFFFAOYSA-L 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- GYUMTAPSXISUIS-UHFFFAOYSA-L barium(2+);4-methylbenzenesulfinate Chemical compound [Ba+2].CC1=CC=C(S([O-])=O)C=C1.CC1=CC=C(S([O-])=O)C=C1 GYUMTAPSXISUIS-UHFFFAOYSA-L 0.000 description 3
- GKGINNLGHSJHDV-UHFFFAOYSA-L barium(2+);benzenesulfinate Chemical compound [Ba+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 GKGINNLGHSJHDV-UHFFFAOYSA-L 0.000 description 3
- JPLNMWITWCOINR-UHFFFAOYSA-L calcium;4-methylbenzenesulfinate Chemical compound [Ca+2].CC1=CC=C(S([O-])=O)C=C1.CC1=CC=C(S([O-])=O)C=C1 JPLNMWITWCOINR-UHFFFAOYSA-L 0.000 description 3
- CQTBCRGSMDMCKL-UHFFFAOYSA-L calcium;benzenesulfinate Chemical compound [Ca+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 CQTBCRGSMDMCKL-UHFFFAOYSA-L 0.000 description 3
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- ATDODYSAVLEMDU-UHFFFAOYSA-L magnesium;4-methylbenzenesulfinate Chemical compound [Mg+2].CC1=CC=C(S([O-])=O)C=C1.CC1=CC=C(S([O-])=O)C=C1 ATDODYSAVLEMDU-UHFFFAOYSA-L 0.000 description 3
- MUZDAAUUCSJIRK-UHFFFAOYSA-L magnesium;benzenesulfinate Chemical compound [Mg+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 MUZDAAUUCSJIRK-UHFFFAOYSA-L 0.000 description 3
- PLCIVAKCWDUURK-UHFFFAOYSA-N n,n-diethylethanamine;4-methylbenzenesulfinic acid Chemical compound CC[NH+](CC)CC.CC1=CC=C(S([O-])=O)C=C1 PLCIVAKCWDUURK-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 3
- UWFXZVCJIZYGSN-UHFFFAOYSA-N tert-butylazanium 4-methylbenzenesulfinate Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C(C)(C)(C)[NH3+] UWFXZVCJIZYGSN-UHFFFAOYSA-N 0.000 description 3
- VRQDTYPKHFIVGS-UHFFFAOYSA-L zinc butane-1,4-disulfinate Chemical compound C(CCCS(=O)[O-])S(=O)[O-].[Zn+2] VRQDTYPKHFIVGS-UHFFFAOYSA-L 0.000 description 3
- QAMKAVKKOHHAFL-UHFFFAOYSA-L zinc;4-chlorobenzenesulfinate Chemical compound [Zn+2].[O-]S(=O)C1=CC=C(Cl)C=C1.[O-]S(=O)C1=CC=C(Cl)C=C1 QAMKAVKKOHHAFL-UHFFFAOYSA-L 0.000 description 3
- UMGLWJIVIBWZCW-UHFFFAOYSA-L zinc;benzenesulfinate Chemical compound [Zn+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 UMGLWJIVIBWZCW-UHFFFAOYSA-L 0.000 description 3
- RABJFDQBMCXIBW-UHFFFAOYSA-N 2,4,5-trichlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC(Cl)=C(Cl)C=C1Cl RABJFDQBMCXIBW-UHFFFAOYSA-N 0.000 description 2
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 2
- BCBLCYBWIZBEMS-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)[O-])C.C(C)(C)(CC(C)(C)C)[NH3+] Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C(C)(C)(CC(C)(C)C)[NH3+] BCBLCYBWIZBEMS-UHFFFAOYSA-N 0.000 description 2
- RHRHDCARUUHYAF-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)[O-])C.C[NH3+] Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C[NH3+] RHRHDCARUUHYAF-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241001441571 Hiodontidae Species 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LCVMXFMNTVQRLS-UHFFFAOYSA-N N-cyclohexylcyclohexanamine 4-methylbenzenesulfinic acid Chemical compound C1(=CC=C(C=C1)S(=O)O)C.C1(CCCCC1)NC1CCCCC1 LCVMXFMNTVQRLS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DAOYJPOIOIBRSB-UHFFFAOYSA-L [Ni+2].C1(=CC=CC=C1)S(=O)[O-].C1(=CC=CC=C1)S(=O)[O-] Chemical compound [Ni+2].C1(=CC=CC=C1)S(=O)[O-].C1(=CC=CC=C1)S(=O)[O-] DAOYJPOIOIBRSB-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 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 description 2
- VKSGXPNWMDWJJR-UHFFFAOYSA-N cyclohexylazanium naphthalene-2-sulfinate Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)[O-].C1(CCCCC1)[NH3+] VKSGXPNWMDWJJR-UHFFFAOYSA-N 0.000 description 2
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003452 sulfinic acid derivatives Chemical class 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- VLUWLNIMIAFOSY-UHFFFAOYSA-N 2-methylbenzenesulfinic acid Chemical compound CC1=CC=CC=C1S(O)=O VLUWLNIMIAFOSY-UHFFFAOYSA-N 0.000 description 1
- KLEUYJCQHIYGMQ-UHFFFAOYSA-N 3-cyclohexyl-2h-1,3-benzothiazole Chemical compound C1SC2=CC=CC=C2N1C1CCCCC1 KLEUYJCQHIYGMQ-UHFFFAOYSA-N 0.000 description 1
- YDQNDKBOOVXRTL-UHFFFAOYSA-N 4-acetamidobenzenesulfinic acid Chemical compound CC(=O)NC1=CC=C(S(O)=O)C=C1 YDQNDKBOOVXRTL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- QNQCYEHITFRZLQ-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)[O-])C.C(C)[NH2+]CC Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C(C)[NH2+]CC QNQCYEHITFRZLQ-UHFFFAOYSA-N 0.000 description 1
- JCAXGQNIQVMRER-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)[O-])C.C(CCCCCCCCCCC)[NH3+] Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C(CCCCCCCCCCC)[NH3+] JCAXGQNIQVMRER-UHFFFAOYSA-N 0.000 description 1
- JCFSNRCATBJDTA-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)[O-])C.C1(CCCCC1)[NH3+] Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C1(CCCCC1)[NH3+] JCFSNRCATBJDTA-UHFFFAOYSA-N 0.000 description 1
- KMYFWBHDWBWGHG-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)[O-])C.C[NH2+]C Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C[NH2+]C KMYFWBHDWBWGHG-UHFFFAOYSA-N 0.000 description 1
- NOOBLUPTAXXDFB-UHFFFAOYSA-L C1(=CC=CC=C1)S(=O)[O-].C1(=CC=CC=C1)S(=O)[O-].[Cd+2] Chemical compound C1(=CC=CC=C1)S(=O)[O-].C1(=CC=CC=C1)S(=O)[O-].[Cd+2] NOOBLUPTAXXDFB-UHFFFAOYSA-L 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BZBYOSGPLFTLAP-UHFFFAOYSA-L ClC1=C(C=C(C(=C1)Cl)Cl)S(=O)[O-].[Zn+2].ClC1=C(C=C(C(=C1)Cl)Cl)S(=O)[O-] Chemical compound ClC1=C(C=C(C(=C1)Cl)Cl)S(=O)[O-].[Zn+2].ClC1=C(C=C(C(=C1)Cl)Cl)S(=O)[O-] BZBYOSGPLFTLAP-UHFFFAOYSA-L 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- OLOCHARBKDWIBK-UHFFFAOYSA-N benzene-1,3-disulfinic acid Chemical compound OS(=O)C1=CC=CC(S(O)=O)=C1 OLOCHARBKDWIBK-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective 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
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000012936 vulcanization activator Substances 0.000 description 1
- JUYBSQOSZYYVOG-UHFFFAOYSA-L zinc 2,5-dimethylbenzenesulfinate Chemical compound CC1=C(C=C(C=C1)C)S(=O)[O-].CC1=C(C=C(C=C1)C)S(=O)[O-].[Zn+2] JUYBSQOSZYYVOG-UHFFFAOYSA-L 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- ALVZMMLOLCSQPS-UHFFFAOYSA-L zinc;4-nitrobenzenesulfinate Chemical compound [Zn+2].[O-][N+](=O)C1=CC=C(S([O-])=O)C=C1.[O-][N+](=O)C1=CC=C(S([O-])=O)C=C1 ALVZMMLOLCSQPS-UHFFFAOYSA-L 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
- C08K5/41—Compounds containing sulfur bound to oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65470567A | 1967-07-20 | 1967-07-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1770905A1 DE1770905A1 (de) | 1972-03-02 |
| DE1770905B2 DE1770905B2 (de) | 1977-09-22 |
| DE1770905C3 true DE1770905C3 (de) | 1978-05-24 |
Family
ID=24625931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1770905A Expired DE1770905C3 (de) | 1967-07-20 | 1968-07-18 | Vulkanisierbare Masse und ihre Verwendung für vulkanisierte Formkörper |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3518236A (online.php) |
| BE (1) | BE718102A (online.php) |
| DE (1) | DE1770905C3 (online.php) |
| FR (1) | FR1581710A (online.php) |
| GB (1) | GB1205709A (online.php) |
| LU (1) | LU56467A1 (online.php) |
| NL (1) | NL152284B (online.php) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2148597A1 (de) * | 1971-09-29 | 1973-04-05 | Bayer Ag | Perfluoralkylsulfinsaeuren und verfahren zu ihrer herstellung |
| US4710323A (en) * | 1984-02-29 | 1987-12-01 | Richter Gedeon Vegyeszeti Gyar Rt | Nitrodiaryl sulfoxide derivatives, process for their preparation and pharmaceutical and pesticidal compositions containing them as active ingredient |
| US7030169B2 (en) | 2003-09-26 | 2006-04-18 | 3M Innovative Properties Company | Arylsulfinate salts in initiator systems for polymeric reactions |
| US7250452B2 (en) | 2003-09-26 | 2007-07-31 | 3M Innovative Properties Company | Dental compositions and methods with arylsulfinate salts |
| US11407721B2 (en) | 2013-02-19 | 2022-08-09 | Amgen Inc. | CIS-morpholinone and other compounds as MDM2 inhibitors for the treatment of cancer |
| WO2014151863A1 (en) | 2013-03-14 | 2014-09-25 | Amgen Inc. | Heteroaryl acid morpholinone compounds as mdm2 inhibitors for the treatment of cancer |
| MA53572A1 (fr) * | 2013-06-10 | 2021-10-29 | Amgen Inc | Procédés de production et formes cristallines d'un inhibiteur mdm2 |
| CN115925589A (zh) * | 2022-12-26 | 2023-04-07 | 诚达药业股份有限公司 | 一种脂肪族亚磺酸钙盐及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH311220A (de) * | 1950-07-17 | 1955-11-30 | Gmbh W C Heraeus | Verfahren zur Herstellung von Kunststoffen aus polymerisierbaren organischen Verbindungen mit einer doppelt gebundenen endständigen Methylengruppe. |
| GB900172A (en) * | 1958-07-21 | 1962-07-04 | American Cyanamid Co | New bis-sulphinic acid compounds |
-
1967
- 1967-07-20 US US654705A patent/US3518236A/en not_active Expired - Lifetime
-
1968
- 1968-06-27 GB GB30636/68A patent/GB1205709A/en not_active Expired
- 1968-07-11 LU LU56467D patent/LU56467A1/xx unknown
- 1968-07-11 NL NL686809803A patent/NL152284B/xx not_active IP Right Cessation
- 1968-07-15 BE BE718102D patent/BE718102A/xx unknown
- 1968-07-18 DE DE1770905A patent/DE1770905C3/de not_active Expired
- 1968-07-19 FR FR1581710D patent/FR1581710A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3518236A (en) | 1970-06-30 |
| FR1581710A (online.php) | 1969-09-19 |
| BE718102A (online.php) | 1969-01-15 |
| DE1770905A1 (de) | 1972-03-02 |
| DE1770905B2 (de) | 1977-09-22 |
| LU56467A1 (online.php) | 1970-01-15 |
| NL6809803A (online.php) | 1969-01-22 |
| NL152284B (nl) | 1977-02-15 |
| GB1205709A (en) | 1970-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |