DE1302630B - Verfahren zum Vulkanisieren von Kautschuk - Google Patents
Verfahren zum Vulkanisieren von KautschukInfo
- Publication number
- DE1302630B DE1302630B DE19631302630D DE1302630DA DE1302630B DE 1302630 B DE1302630 B DE 1302630B DE 19631302630 D DE19631302630 D DE 19631302630D DE 1302630D A DE1302630D A DE 1302630DA DE 1302630 B DE1302630 B DE 1302630B
- Authority
- DE
- Germany
- Prior art keywords
- benzyl
- rubber
- sulfur
- chloride
- groups
- 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.)
- Pending
Links
- 229920001971 elastomer Polymers 0.000 title claims description 22
- 239000005060 rubber Substances 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- -1 Ethyliden- Chemical class 0.000 description 20
- 238000004073 vulcanization Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 241001441571 Hiodontidae Species 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 230000000996 additive effect Effects 0.000 description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical class ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- IOXAUPNPMJKSKQ-UHFFFAOYSA-N 1-benzyl-2,3-dimethylbenzene Chemical group CC1=CC=CC(CC=2C=CC=CC=2)=C1C IOXAUPNPMJKSKQ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000006232 furnace black Substances 0.000 description 3
- 239000004071 soot Substances 0.000 description 3
- 239000000126 substance Substances 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
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- XPKPOJYKFNMGBD-UHFFFAOYSA-N n-(2-phenylethyl)aniline;hydrochloride Chemical compound Cl.C=1C=CC=CC=1NCCC1=CC=CC=C1 XPKPOJYKFNMGBD-UHFFFAOYSA-N 0.000 description 2
- ZCXOSDRICFIHTA-UHFFFAOYSA-N n-methylaniline;hydrochloride Chemical compound [Cl-].C[NH2+]C1=CC=CC=C1 ZCXOSDRICFIHTA-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 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 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RSJNPFGDFDWDSC-UHFFFAOYSA-N 4-(2,3-dimethylphenyl)-N,N-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=CC(C)=C1C RSJNPFGDFDWDSC-UHFFFAOYSA-N 0.000 description 1
- UPMCDOMOBNMTPH-UHFFFAOYSA-N 6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC=CN2CC1C1=CC=CC=C1 UPMCDOMOBNMTPH-UHFFFAOYSA-N 0.000 description 1
- 102220586009 ATP-dependent Clp protease proteolytic subunit, mitochondrial_I20S_mutation Human genes 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YPTXWBBFTDKRCP-UHFFFAOYSA-N [Br-].C(C1=CC=CC=C1)C(CC1=CC=CC=C1)[NH2+]C1=CC=CC=C1 Chemical compound [Br-].C(C1=CC=CC=C1)C(CC1=CC=CC=C1)[NH2+]C1=CC=CC=C1 YPTXWBBFTDKRCP-UHFFFAOYSA-N 0.000 description 1
- FOSVLAVKDGSBEW-UHFFFAOYSA-N [Br-].C(C1=CC=CC=C1)C[NH2+]C1=CC=CC=C1 Chemical compound [Br-].C(C1=CC=CC=C1)C[NH2+]C1=CC=CC=C1 FOSVLAVKDGSBEW-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- VBSOBZRCUHBIDS-UHFFFAOYSA-N benzyl-(4-methoxyphenyl)-dimethylazanium Chemical compound C1=CC(OC)=CC=C1[N+](C)(C)CC1=CC=CC=C1 VBSOBZRCUHBIDS-UHFFFAOYSA-N 0.000 description 1
- YJLNDZRHVHIGDS-UHFFFAOYSA-N benzyl-diethyl-phenylazanium Chemical compound C=1C=CC=CC=1[N+](CC)(CC)CC1=CC=CC=C1 YJLNDZRHVHIGDS-UHFFFAOYSA-N 0.000 description 1
- VTIKXEBHFNJBPG-UHFFFAOYSA-M benzyl-dimethyl-(3-nitrophenyl)azanium bromide Chemical compound [Br-].C(C1=CC=CC=C1)[N+](C1=CC(=CC=C1)[N+](=O)[O-])(C)C VTIKXEBHFNJBPG-UHFFFAOYSA-M 0.000 description 1
- RRJCDSAHBGMAHC-UHFFFAOYSA-N benzyl-dimethyl-(4-nitrophenyl)azanium Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)[N+](C)(C)CC1=CC=CC=C1 RRJCDSAHBGMAHC-UHFFFAOYSA-N 0.000 description 1
- FFZVILRAPIUNAA-UHFFFAOYSA-N benzyl-dimethyl-phenylazanium Chemical compound C=1C=CC=CC=1[N+](C)(C)CC1=CC=CC=C1 FFZVILRAPIUNAA-UHFFFAOYSA-N 0.000 description 1
- VLIPDCBRZIXWMH-UHFFFAOYSA-M benzyl-dimethyl-phenylazanium benzoate Chemical compound C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)[N+](C1=CC=CC=C1)(C)C VLIPDCBRZIXWMH-UHFFFAOYSA-M 0.000 description 1
- CLCOXQROCAMRQO-UHFFFAOYSA-M benzyl-dimethyl-phenylazanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[N+](C)(C)CC1=CC=CC=C1 CLCOXQROCAMRQO-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000019788 craving Nutrition 0.000 description 1
- QFSPGQSXKARDIH-UHFFFAOYSA-N cyclohexane;dihydrochloride Chemical compound Cl.Cl.C1CCCCC1 QFSPGQSXKARDIH-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- DIYXQUIQAXGWIX-UHFFFAOYSA-M dimethyl(diphenyl)azanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[N+](C)(C)C1=CC=CC=C1 DIYXQUIQAXGWIX-UHFFFAOYSA-M 0.000 description 1
- ITQRVMZJBMZUBB-UHFFFAOYSA-M dimethyl(diphenyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[N+](C)(C)C1=CC=CC=C1 ITQRVMZJBMZUBB-UHFFFAOYSA-M 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NJZMYBSNJMHYQB-UHFFFAOYSA-N n-benzyl-n-methylaniline;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N(C)CC1=CC=CC=C1 NJZMYBSNJMHYQB-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- KGMXPXPXPAAUMD-UHFFFAOYSA-N propane;dihydrochloride Chemical compound Cl.Cl.CCC KGMXPXPXPAAUMD-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- 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
- C08K5/42—Sulfonic acids; Derivatives thereof
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)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21193/62A GB982236A (en) | 1962-06-01 | 1962-06-01 | Improved vulcanisation process for rubber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1302630B true DE1302630B (de) | 1972-03-23 |
Family
ID=10158756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631302630D Pending DE1302630B (de) | 1962-06-01 | 1963-05-29 | Verfahren zum Vulkanisieren von Kautschuk |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3357957A (en, 2012) |
| AT (1) | AT249995B (en, 2012) |
| BE (1) | BE633133A (en, 2012) |
| DE (1) | DE1302630B (en, 2012) |
| ES (1) | ES288447A1 (en, 2012) |
| GB (1) | GB982236A (en, 2012) |
| NL (1) | NL293500A (en, 2012) |
| SE (1) | SE305073B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL135331C (en, 2012) * | 1965-07-09 | |||
| DE3049196A1 (de) * | 1980-12-24 | 1982-07-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von granulaten aus organischen in form einer schmelze vorliegenden stoffen |
| US5187239A (en) * | 1988-12-28 | 1993-02-16 | The Goodyear Tire & Rubber Company | Sulfur vulcanizable rubber compositions containing a methyl trialkyl ammonium salt |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1871037A (en) * | 1930-09-11 | 1932-08-09 | Naugatuck Chem Co | Treatment of rubber |
| US1950067A (en) * | 1931-04-17 | 1934-03-06 | Rubber Service Lab Co | Salts of diphenylguanidine and process of making same |
| US1912448A (en) * | 1931-06-19 | 1933-06-06 | Naugatuck Chem Co | Vulcanization of rubber |
| US2100085A (en) * | 1932-01-05 | 1937-11-23 | Us Rubber Co | Production of vulcanized rubber |
| US2535857A (en) * | 1949-09-13 | 1950-12-26 | Goodrich Co B F | 2-mercapto-3,6-dihydropyrimidine-3-monocarboxylic acids and esters of these acids |
| US2666783A (en) * | 1950-03-13 | 1954-01-19 | Chemstrand Corp | Quaternary benzylchloride salts of 3-hydroxy 4-disubstituted aminobutene-1 |
| US2623902A (en) * | 1950-03-15 | 1952-12-30 | Sharp & Dohme Inc | Bis-quaternary ammonium salts |
| NL108645C (en, 2012) * | 1958-05-29 |
-
0
- BE BE633133D patent/BE633133A/xx unknown
- NL NL293500D patent/NL293500A/xx unknown
-
1962
- 1962-06-01 GB GB21193/62A patent/GB982236A/en not_active Expired
-
1963
- 1963-05-27 US US283527A patent/US3357957A/en not_active Expired - Lifetime
- 1963-05-28 ES ES288447A patent/ES288447A1/es not_active Expired
- 1963-05-29 DE DE19631302630D patent/DE1302630B/de active Pending
- 1963-05-31 SE SE6091/63A patent/SE305073B/xx unknown
- 1963-06-04 AT AT449363A patent/AT249995B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| GB982236A (en) | 1965-02-03 |
| AT249995B (de) | 1966-10-25 |
| BE633133A (en, 2012) | |
| NL293500A (en, 2012) | |
| ES288447A1 (es) | 1963-12-16 |
| US3357957A (en) | 1967-12-12 |
| SE305073B (en, 2012) | 1968-10-14 |
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