DE2328527A1 - Nicht-ausbluehende beschleuniger - Google Patents
Nicht-ausbluehende beschleunigerInfo
- Publication number
- DE2328527A1 DE2328527A1 DE19732328527 DE2328527A DE2328527A1 DE 2328527 A1 DE2328527 A1 DE 2328527A1 DE 19732328527 DE19732328527 DE 19732328527 DE 2328527 A DE2328527 A DE 2328527A DE 2328527 A1 DE2328527 A1 DE 2328527A1
- Authority
- DE
- Germany
- Prior art keywords
- represent
- hydrogen atom
- atom
- zinc
- mol
- 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.)
- Ceased
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 91
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 29
- 229920001971 elastomer Polymers 0.000 claims description 21
- 239000000806 elastomer Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 8
- 238000004073 vulcanization Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 3
- 229920003244 diene elastomer Polymers 0.000 claims description 2
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 229940070891 pyridium Drugs 0.000 claims 1
- 238000010058 rubber compounding Methods 0.000 claims 1
- 239000011701 zinc Substances 0.000 description 79
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 66
- 239000000047 product Substances 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000000354 decomposition reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 17
- 229910052725 zinc Inorganic materials 0.000 description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 14
- 229940057499 anhydrous zinc acetate Drugs 0.000 description 13
- 238000006253 efflorescence Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 206010037844 rash Diseases 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 229920002943 EPDM rubber Polymers 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 8
- -1 ethylene, propylene Chemical group 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 150000003751 zinc Chemical class 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229960000314 zinc acetate Drugs 0.000 description 4
- 239000004246 zinc acetate Substances 0.000 description 4
- QXTFBRRNRHKAKA-UHFFFAOYSA-L zinc;1,3-oxazolidine-3-carbodithioate Chemical compound [Zn+2].[S-]C(=S)N1CCOC1.[S-]C(=S)N1CCOC1 QXTFBRRNRHKAKA-UHFFFAOYSA-L 0.000 description 4
- DRGAZIDRYFYHIJ-UHFFFAOYSA-N 2,2':6',2''-terpyridine Chemical compound N1=CC=CC=C1C1=CC=CC(C=2N=CC=CC=2)=N1 DRGAZIDRYFYHIJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229960002447 thiram Drugs 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- MGHFHIHGKJBQAI-UHFFFAOYSA-N 1,3-oxazolidine-3-carbodithioic acid Chemical compound SC(=S)N1CCOC1 MGHFHIHGKJBQAI-UHFFFAOYSA-N 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- ALUFITGOFDIAAA-UHFFFAOYSA-N 2-(benzylideneamino)ethanol Chemical compound OCCN=CC1=CC=CC=C1 ALUFITGOFDIAAA-UHFFFAOYSA-N 0.000 description 2
- YFZMDNJBQWEQRG-UHFFFAOYSA-N 2-(trichloromethyl)-1,3-oxazolidine Chemical compound ClC(Cl)(Cl)C1NCCO1 YFZMDNJBQWEQRG-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- YNIFAXORHVZTGQ-UHFFFAOYSA-N 5-methyl-2-(trichloromethyl)-1,3-oxazolidine Chemical compound CC1CNC(C(Cl)(Cl)Cl)O1 YNIFAXORHVZTGQ-UHFFFAOYSA-N 0.000 description 2
- BGEUGIMDXKKTII-UHFFFAOYSA-N 5-phenyl-2-(trichloromethyl)-1,3-oxazolidine Chemical compound O1C(C(Cl)(Cl)Cl)NCC1C1=CC=CC=C1 BGEUGIMDXKKTII-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 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
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 2
- DVXPGTNOHDTLRU-UHFFFAOYSA-L zinc;1,3-oxazolidine-2-carbodithioate Chemical class [Zn+2].[S-]C(=S)C1NCCO1.[S-]C(=S)C1NCCO1 DVXPGTNOHDTLRU-UHFFFAOYSA-L 0.000 description 2
- JUICNTVXOLWNLB-UHFFFAOYSA-L zinc;1,3-thiazolidine-2-carbodithioate Chemical class [Zn+2].[S-]C(=S)C1NCCS1.[S-]C(=S)C1NCCS1 JUICNTVXOLWNLB-UHFFFAOYSA-L 0.000 description 2
- VRKGGEXDJHOYGC-UHFFFAOYSA-L zinc;morpholine-4-carbodithioate Chemical compound [Zn+2].[S-]C(=S)N1CCOCC1.[S-]C(=S)N1CCOCC1 VRKGGEXDJHOYGC-UHFFFAOYSA-L 0.000 description 2
- 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 description 1
- HTEZWIXNKLULNA-UHFFFAOYSA-N 1,3-oxazolidine-2-carbodithioic acid Chemical compound SC(=S)C1NCCO1 HTEZWIXNKLULNA-UHFFFAOYSA-N 0.000 description 1
- MPGQQQKGAXDBDN-UHFFFAOYSA-N 1,3-thiazolidin-3-ium;chloride Chemical compound Cl.C1CSCN1 MPGQQQKGAXDBDN-UHFFFAOYSA-N 0.000 description 1
- LPJNWRLYZZXWSS-UHFFFAOYSA-N 1,3-thiazolidine-3-carbodithioic acid Chemical compound SC(=S)N1CCSC1 LPJNWRLYZZXWSS-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- NCYYKVXOKJPSRU-UHFFFAOYSA-N 1-oxa-4-azaspiro[4.5]decane Chemical compound N1CCOC11CCCCC1 NCYYKVXOKJPSRU-UHFFFAOYSA-N 0.000 description 1
- VSHIRTNKIXRXMI-UHFFFAOYSA-N 2,2-dimethyl-1,3-oxazolidine Chemical compound CC1(C)NCCO1 VSHIRTNKIXRXMI-UHFFFAOYSA-N 0.000 description 1
- NKPNSVCEUIECCA-UHFFFAOYSA-N 2,2-dimethyl-1,3-thiazolidine;hydron;chloride Chemical compound Cl.CC1(C)NCCS1 NKPNSVCEUIECCA-UHFFFAOYSA-N 0.000 description 1
- IRAGEBXSFXWYNX-UHFFFAOYSA-N 2-(1,3,5-triazinan-1-yl)ethanol Chemical compound OCCN1CNCNC1 IRAGEBXSFXWYNX-UHFFFAOYSA-N 0.000 description 1
- CCIILNOBNOHYOX-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3-oxazolidine Chemical compound C1=CC(Cl)=CC=C1C1OCCN1 CCIILNOBNOHYOX-UHFFFAOYSA-N 0.000 description 1
- VQCSISBLWARLJL-UHFFFAOYSA-N 2-(trichloromethyl)-1,3-thiazolidine Chemical compound ClC(Cl)(Cl)C1NCCS1 VQCSISBLWARLJL-UHFFFAOYSA-N 0.000 description 1
- HUHGPYXAVBJSJV-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyethyl)-1,3,5-triazinan-1-yl]ethanol Chemical compound OCCN1CN(CCO)CN(CCO)C1 HUHGPYXAVBJSJV-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- VLMFACFSZYOTTM-UHFFFAOYSA-N 2-ethoxy-4-(1,3-oxazolidin-2-yl)phenol Chemical compound C1=C(O)C(OCC)=CC(C2OCCN2)=C1 VLMFACFSZYOTTM-UHFFFAOYSA-N 0.000 description 1
- SZFHAHACWVROGM-UHFFFAOYSA-N 2-phenyl-1,3-oxazolidine Chemical compound N1CCOC1C1=CC=CC=C1 SZFHAHACWVROGM-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- BURFZVNTXUTLLV-UHFFFAOYSA-N 5-phenyl-1,3-oxazolidine-3-carbodithioic acid Chemical compound C1N(C(=S)S)COC1C1=CC=CC=C1 BURFZVNTXUTLLV-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 101710178035 Chorismate synthase 2 Proteins 0.000 description 1
- 101710152694 Cysteine synthase 2 Proteins 0.000 description 1
- 101100272588 Escherichia coli (strain K12) bisC gene Proteins 0.000 description 1
- 101100099970 Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) torZ gene Proteins 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 101710198277 RNA polymerase sigma factor sigA Proteins 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910007541 Zn O Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 229940116901 diethyldithiocarbamate Drugs 0.000 description 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 229920013728 elastomeric terpolymer Polymers 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- IJDIONYCFIJYLK-UHFFFAOYSA-N n,n-diethylethanamine;propan-2-ol Chemical compound CC(C)O.CCN(CC)CC IJDIONYCFIJYLK-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
- RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 description 1
- AUKMRKCYADSGSB-UHFFFAOYSA-L zinc;2,2-dimethyl-1,3-oxazolidine-3-carbodithioate Chemical compound [Zn+2].CC1(C)OCCN1C([S-])=S.CC1(C)OCCN1C([S-])=S AUKMRKCYADSGSB-UHFFFAOYSA-L 0.000 description 1
- FNHDKOPJVSWNBR-UHFFFAOYSA-L zinc;2-methyl-2-phenyl-1,3-oxazolidine-3-carbodithioate Chemical compound [Zn+2].C=1C=CC=CC=1C1(C)OCCN1C([S-])=S.C=1C=CC=CC=1C1(C)OCCN1C([S-])=S FNHDKOPJVSWNBR-UHFFFAOYSA-L 0.000 description 1
- WFMLHCYWDVVTEN-UHFFFAOYSA-L zinc;2-phenyl-1,3-oxazolidine-3-carbodithioate Chemical compound [Zn+2].[S-]C(=S)N1CCOC1C1=CC=CC=C1.[S-]C(=S)N1CCOC1C1=CC=CC=C1 WFMLHCYWDVVTEN-UHFFFAOYSA-L 0.000 description 1
- PAPWWZJTTSXSNJ-UHFFFAOYSA-L zinc;5-methyl-2-(trichloromethyl)-1,3-oxazolidine-3-carbodithioate Chemical compound [Zn+2].CC1CN(C([S-])=S)C(C(Cl)(Cl)Cl)O1.CC1CN(C([S-])=S)C(C(Cl)(Cl)Cl)O1 PAPWWZJTTSXSNJ-UHFFFAOYSA-L 0.000 description 1
- PSJAFRPOMXQPCC-UHFFFAOYSA-L zinc;5-phenyl-2-(trichloromethyl)-1,3-oxazolidine-3-carbodithioate Chemical compound [Zn+2].O1C(C(Cl)(Cl)Cl)N(C(=S)[S-])CC1C1=CC=CC=C1.O1C(C(Cl)(Cl)Cl)N(C(=S)[S-])CC1C1=CC=CC=C1 PSJAFRPOMXQPCC-UHFFFAOYSA-L 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical class [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/21—Radicals derived from sulfur analogues of carbonic acid
-
- 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
- C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25990072A | 1972-06-05 | 1972-06-05 | |
| US35603473A | 1973-04-30 | 1973-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2328527A1 true DE2328527A1 (de) | 1974-01-03 |
Family
ID=26947610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732328527 Ceased DE2328527A1 (de) | 1972-06-05 | 1973-06-05 | Nicht-ausbluehende beschleuniger |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5634034B2 (enrdf_load_stackoverflow) |
| CA (1) | CA981259A (enrdf_load_stackoverflow) |
| DE (1) | DE2328527A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2187792B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1418833A (enrdf_load_stackoverflow) |
| IT (1) | IT989650B (enrdf_load_stackoverflow) |
| NL (1) | NL7307735A (enrdf_load_stackoverflow) |
| SE (2) | SE387943B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987017A (en) * | 1974-02-01 | 1976-10-19 | Pennwalt Corporation | Process for the vulcanization of epdm elastomers |
| DE2725931A1 (de) * | 1976-06-11 | 1977-12-22 | Pennwalt Corp | Epdm-elastomer-vulkanisationsbeschleuniger |
| US4314080A (en) | 1980-11-10 | 1982-02-02 | International Minerals & Chemical Corp. | N-Formylation of 2-amino-2-methyl-1-propanol with chloral hydrate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE625409A (enrdf_load_stackoverflow) * | 1961-11-30 | |||
| FR1453490A (fr) * | 1965-08-12 | 1966-06-03 | Kuhlmann Ets | Procédé de vulcanisation du caoutchouc butyle |
| US3674701A (en) * | 1971-02-17 | 1972-07-04 | Pennwalt Corp | Accelerator composition |
-
1973
- 1973-05-23 CA CA172,013A patent/CA981259A/en not_active Expired
- 1973-05-31 GB GB2603973A patent/GB1418833A/en not_active Expired
- 1973-06-04 NL NL7307735A patent/NL7307735A/xx not_active Application Discontinuation
- 1973-06-04 IT IT5043073A patent/IT989650B/it active
- 1973-06-04 FR FR7320193A patent/FR2187792B1/fr not_active Expired
- 1973-06-05 JP JP6264773A patent/JPS5634034B2/ja not_active Expired
- 1973-06-05 SE SE7307931A patent/SE387943B/xx unknown
- 1973-06-05 DE DE19732328527 patent/DE2328527A1/de not_active Ceased
-
1976
- 1976-04-09 SE SE7604221A patent/SE410972B/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987017A (en) * | 1974-02-01 | 1976-10-19 | Pennwalt Corporation | Process for the vulcanization of epdm elastomers |
| DE2725931A1 (de) * | 1976-06-11 | 1977-12-22 | Pennwalt Corp | Epdm-elastomer-vulkanisationsbeschleuniger |
| US4314080A (en) | 1980-11-10 | 1982-02-02 | International Minerals & Chemical Corp. | N-Formylation of 2-amino-2-methyl-1-propanol with chloral hydrate |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2187792B1 (enrdf_load_stackoverflow) | 1977-02-11 |
| NL7307735A (enrdf_load_stackoverflow) | 1973-12-07 |
| GB1418833A (en) | 1975-12-24 |
| SE387943B (sv) | 1976-09-20 |
| JPS5634034B2 (enrdf_load_stackoverflow) | 1981-08-07 |
| IT989650B (it) | 1975-06-10 |
| SE7604221L (sv) | 1976-04-09 |
| FR2187792A1 (enrdf_load_stackoverflow) | 1974-01-18 |
| JPS4961240A (enrdf_load_stackoverflow) | 1974-06-13 |
| CA981259A (en) | 1976-01-06 |
| SE410972B (sv) | 1979-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |