NO752013L - - Google Patents
Info
- Publication number
- NO752013L NO752013L NO752013A NO752013A NO752013L NO 752013 L NO752013 L NO 752013L NO 752013 A NO752013 A NO 752013A NO 752013 A NO752013 A NO 752013A NO 752013 L NO752013 L NO 752013L
- Authority
- NO
- Norway
- Prior art keywords
- triazine
- bis
- thio
- diethylamino
- mixture
- Prior art date
Links
- -1 CH-J.-S- Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 229920001971 elastomer Polymers 0.000 description 12
- 239000005060 rubber Substances 0.000 description 11
- 238000005755 formation reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004073 vulcanization Methods 0.000 description 9
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 150000003949 imides Chemical class 0.000 description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HAZJTCQWIDBCCE-UHFFFAOYSA-N 1h-triazine-6-thione Chemical class SC1=CC=NN=N1 HAZJTCQWIDBCCE-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229960002317 succinimide Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- WZOCKHCXCJYKTM-UHFFFAOYSA-N 2-(diethylamino)-6-sulfanyl-1,3-dihydrotriazine-4-thione Chemical compound CCN(CC)N1NC(S)=CC(=S)N1 WZOCKHCXCJYKTM-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- UCIQEWMDWAEICB-UHFFFAOYSA-N 2-(dimethylamino)-6-sulfanyl-1,3-dihydrotriazine-4-thione Chemical compound CN(C)N1NC(S)=CC(=S)N1 UCIQEWMDWAEICB-UHFFFAOYSA-N 0.000 description 1
- BHXUJIDKIRLKPC-UHFFFAOYSA-N 2-[(2-amino-6-butylimino-1,3-dihydrotriazin-4-yl)sulfanyl]-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound CCCCNC1=NN(N)NC(SN2C(C3C=CCCC3C2=O)=O)=C1 BHXUJIDKIRLKPC-UHFFFAOYSA-N 0.000 description 1
- NRZLEQMIDVUYLU-UHFFFAOYSA-N 2-[[2-(butylamino)-4-(1,3-dioxoisoindol-2-yl)sulfanyl-1h-triazin-6-yl]sulfanyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1=NN(NCCCC)NC(SN2C(C3=CC=CC=C3C2=O)=O)=C1 NRZLEQMIDVUYLU-UHFFFAOYSA-N 0.000 description 1
- ZAPGNLRDUYRMIK-UHFFFAOYSA-N 2-[[2-(diethylamino)-4-[(1,3-dioxo-3a,4,5,7a-tetrahydroisoindol-2-yl)sulfanyl]-1h-triazin-6-yl]sulfanyl]-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound O=C1C2CCC=CC2C(=O)N1SC1=NN(N(CC)CC)NC(SN2C(C3C=CCCC3C2=O)=O)=C1 ZAPGNLRDUYRMIK-UHFFFAOYSA-N 0.000 description 1
- DBNFWCDWQYXWEE-UHFFFAOYSA-N 2-[[2-(ethylamino)-6-ethylimino-1,3-dihydrotriazin-4-yl]sulfanyl]isoindole-1,3-dione Chemical compound C(C)NN1NC(=CC(=N1)NCC)SN1C(C=2C(C1=O)=CC=CC2)=O DBNFWCDWQYXWEE-UHFFFAOYSA-N 0.000 description 1
- GRFUECAJOQNPJB-UHFFFAOYSA-N 2-[[4-(1,3-dioxoisoindol-2-yl)sulfanyl-2-(ethylamino)-1h-triazin-6-yl]sulfanyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1=NN(NCC)NC(SN2C(C3=CC=CC=C3C2=O)=O)=C1 GRFUECAJOQNPJB-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MGFOGKFPUWJUQW-UHFFFAOYSA-N CCNN1NC(SC(=O)CNC(N)=O)=CC(N(CC)CC)=N1 Chemical compound CCNN1NC(SC(=O)CNC(N)=O)=CC(N(CC)CC)=N1 MGFOGKFPUWJUQW-UHFFFAOYSA-N 0.000 description 1
- FEOANYJSTZQVEX-UHFFFAOYSA-N CN(N1NC(=CC(=N1)N(C)C)SN1C(C2C(C1=O)CCCC2)=O)C Chemical compound CN(N1NC(=CC(=N1)N(C)C)SN1C(C2C(C1=O)CCCC2)=O)C FEOANYJSTZQVEX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CSYMKBCLDSQTJK-UHFFFAOYSA-N Cl.CCNN1NC(SCl)=CC(N(CC)CC)=N1 Chemical compound Cl.CCNN1NC(SCl)=CC(N(CC)CC)=N1 CSYMKBCLDSQTJK-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZSBDPRIWBYHIAF-UHFFFAOYSA-N N-acetyl-acetamide Natural products CC(=O)NC(C)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 description 1
- XOTYQJSFKOTUGH-UHFFFAOYSA-N NN1NC(=CC(=N1)N(CC)CC)SN1C(C=2C(C1=O)=CC=CC=2)=O Chemical compound NN1NC(=CC(=N1)N(CC)CC)SN1C(C=2C(C1=O)=CC=CC=2)=O XOTYQJSFKOTUGH-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- WTRJIHTUHNKCNM-UHFFFAOYSA-N S-[2-(butylamino)-6-butylimino-1,3-dihydrotriazin-4-yl] 2-(ethylcarbamoylamino)ethanethioate Chemical compound CCCCNN1NC(SC(=O)CNC(=O)NCC)=CC(NCCCC)=N1 WTRJIHTUHNKCNM-UHFFFAOYSA-N 0.000 description 1
- HXDMAWRHAVMSOA-UHFFFAOYSA-N S-[4-(butylamino)-6-[2-(methylcarbamoylamino)acetyl]sulfanyl-1,3,5-triazin-2-yl] 2-(methylcarbamoylamino)ethanethioate Chemical compound C(CCC)NC1=NC(=NC(=N1)SC(=O)CNC(=O)NC)SC(=O)CNC(=O)NC HXDMAWRHAVMSOA-UHFFFAOYSA-N 0.000 description 1
- MIBFYWKKGGZZQO-UHFFFAOYSA-N S-[6-butylimino-2-(methylamino)-1,3-dihydrotriazin-4-yl] 2-(propylcarbamoylamino)ethanethioate Chemical compound CCCCNC1=NN(NC)NC(SC(=O)CNC(=O)NCCC)=C1 MIBFYWKKGGZZQO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BPQWVEOPXYLDBH-UHFFFAOYSA-N [4-chlorosulfanyl-2-(diethylamino)-1h-triazin-6-yl] thiohypochlorite Chemical compound CCN(CC)N1NC(SCl)=CC(SCl)=N1 BPQWVEOPXYLDBH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004411 aluminium Substances 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
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- ILUAAIDVFMVTAU-UHFFFAOYSA-N cyclohex-4-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC=CCC1C(O)=O ILUAAIDVFMVTAU-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 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
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920003246 polypentenamer Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- KMLFNDGVSMHRFL-UHFFFAOYSA-N s-(1,3,5-triazin-2-yl)thiohydroxylamine Chemical class NSC1=NC=NC=N1 KMLFNDGVSMHRFL-UHFFFAOYSA-N 0.000 description 1
- BCIXPHQNCHGLTD-UHFFFAOYSA-N s-[2-(butylamino)-4-[2-(methylcarbamoylamino)acetyl]sulfanyl-1h-triazin-6-yl] 2-(methylcarbamoylamino)ethanethioate Chemical compound CCCCNN1NC(SC(=O)CNC(=O)NC)=CC(SC(=O)CNC(=O)NC)=N1 BCIXPHQNCHGLTD-UHFFFAOYSA-N 0.000 description 1
- DQXRJOQRSWXASY-UHFFFAOYSA-N s-[2-(diethylamino)-4-[2-(dimethylcarbamoylamino)acetyl]sulfanyl-1h-triazin-6-yl] 2-(dimethylcarbamoylamino)ethanethioate Chemical compound CCN(CC)N1NC(SC(=O)CNC(=O)N(C)C)=CC(SC(=O)CNC(=O)N(C)C)=N1 DQXRJOQRSWXASY-UHFFFAOYSA-N 0.000 description 1
- PGWYPTUBOVAYDP-UHFFFAOYSA-N s-[4-[2-(carbamoylamino)acetyl]sulfanyl-2-(dimethylamino)-1h-triazin-6-yl] 2-(carbamoylamino)ethanethioate Chemical compound CN(C)N1NC(SC(=O)CNC(N)=O)=CC(SC(=O)CNC(N)=O)=N1 PGWYPTUBOVAYDP-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- PYHOFAHZHOBVGV-UHFFFAOYSA-N triazane Chemical compound NNN PYHOFAHZHOBVGV-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2430143A DE2430143C3 (de) | 1974-06-24 | 1974-06-24 | Triazinsulfenimide von Dicarbonsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO752013L true NO752013L (fi) | 1975-12-30 |
Family
ID=5918768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO752013A NO752013L (fi) | 1974-06-24 | 1975-06-06 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3969353A (fi) |
| JP (1) | JPS5855979B2 (fi) |
| AU (1) | AU8109975A (fi) |
| BE (1) | BE830545A (fi) |
| BR (1) | BR7503921A (fi) |
| CA (1) | CA1037040A (fi) |
| DE (1) | DE2430143C3 (fi) |
| DK (1) | DK268375A (fi) |
| ES (1) | ES438791A1 (fi) |
| FI (1) | FI751554A (fi) |
| FR (1) | FR2276304A1 (fi) |
| GB (1) | GB1508022A (fi) |
| IL (1) | IL47242A0 (fi) |
| LU (1) | LU72781A1 (fi) |
| NL (1) | NL7507523A (fi) |
| NO (1) | NO752013L (fi) |
| SE (1) | SE7507187L (fi) |
| SU (1) | SU589932A3 (fi) |
| ZA (1) | ZA752962B (fi) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4178253A (en) * | 1977-04-05 | 1979-12-11 | Ciba-Geigy Corporation | Corrosion inhibited lubricant compositions |
| DE3006803A1 (de) * | 1980-02-23 | 1981-09-03 | Bayer Ag, 5090 Leverkusen | Vulkanisationsbeschleuniger auf basis von melaminderivaten, melaminderivate enthaltende kautschukmassen sowie ein verfahren zur vulkanisation von kautschuken |
| US4339577A (en) * | 1980-05-12 | 1982-07-13 | Monsanto Company | 2-(Thioamino)-4,6-diamino-1,3,5-triazines |
| JPS58106394U (ja) * | 1982-01-14 | 1983-07-20 | 株式会社二葉製作所 | 過負荷対策装置付電動式巻上機 |
| JPS58125597A (ja) * | 1982-01-18 | 1983-07-26 | 三菱電機株式会社 | 巻上装置 |
| DE3938015A1 (de) * | 1989-11-16 | 1991-05-23 | Degussa | Herstellung von s-triazinsulfenimiden und deren verwendung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1669954A1 (de) * | 1951-01-28 | 1970-08-20 | Degussa | Verfahren zur Verbesserung der Gebrauchseigenschaften von Vulkanisaten |
-
1974
- 1974-06-24 DE DE2430143A patent/DE2430143C3/de not_active Expired
-
1975
- 1975-05-06 IL IL47242A patent/IL47242A0/xx unknown
- 1975-05-07 ZA ZA00752962A patent/ZA752962B/xx unknown
- 1975-05-13 AU AU81099/75A patent/AU8109975A/en not_active Expired
- 1975-05-14 GB GB20313/75A patent/GB1508022A/en not_active Expired
- 1975-05-28 FI FI751554A patent/FI751554A/fi not_active Application Discontinuation
- 1975-06-06 NO NO752013A patent/NO752013L/no unknown
- 1975-06-13 DK DK268375A patent/DK268375A/da unknown
- 1975-06-17 CA CA229,485A patent/CA1037040A/en not_active Expired
- 1975-06-18 FR FR7519059A patent/FR2276304A1/fr active Granted
- 1975-06-19 US US05/588,649 patent/US3969353A/en not_active Expired - Lifetime
- 1975-06-20 LU LU72781A patent/LU72781A1/xx unknown
- 1975-06-23 BE BE6045064A patent/BE830545A/xx not_active IP Right Cessation
- 1975-06-23 ES ES438791A patent/ES438791A1/es not_active Expired
- 1975-06-23 BR BR5044/75A patent/BR7503921A/pt unknown
- 1975-06-23 SE SE7507187A patent/SE7507187L/xx unknown
- 1975-06-24 SU SU752149702A patent/SU589932A3/ru active
- 1975-06-24 NL NL7507523A patent/NL7507523A/xx unknown
- 1975-06-24 JP JP50078465A patent/JPS5855979B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3969353A (en) | 1976-07-13 |
| BE830545A (fr) | 1975-12-23 |
| JPS5134179A (fi) | 1976-03-23 |
| ZA752962B (en) | 1976-04-28 |
| BR7503921A (pt) | 1976-07-06 |
| FI751554A (fi) | 1975-12-25 |
| DE2430143C3 (de) | 1981-12-03 |
| FR2276304B1 (fi) | 1977-07-22 |
| AU8109975A (en) | 1976-11-18 |
| DE2430143B2 (de) | 1980-09-04 |
| ES438791A1 (es) | 1977-03-16 |
| DE2430143A1 (de) | 1976-01-15 |
| JPS5855979B2 (ja) | 1983-12-13 |
| SE7507187L (sv) | 1975-12-29 |
| SU589932A3 (ru) | 1978-01-25 |
| NL7507523A (nl) | 1975-12-30 |
| FR2276304A1 (fr) | 1976-01-23 |
| CA1037040A (en) | 1978-08-22 |
| DK268375A (da) | 1975-12-25 |
| IL47242A0 (en) | 1975-07-28 |
| LU72781A1 (fi) | 1975-10-08 |
| GB1508022A (en) | 1978-04-19 |
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