CA1096878A - Sulfonyl-hydrazines disubstituees en n,n' - Google Patents

Sulfonyl-hydrazines disubstituees en n,n'

Info

Publication number: CA1096878A
Authority: CA; Canada
Prior art keywords: hydrazine; carbon atoms; sulfonyl; radical; carbamyl
Prior art date: 1977-09-28
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

Application number

CA287,697A

Other languages

English (en)

Inventor

Byron A. Hunter

Franklin H. Barrows

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Uniroyal Inc

Original Assignee

Uniroyal Inc

Priority date (The priority date 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 date listed.)

1977-09-28

Filing date

1977-09-28

Publication date

1981-03-03

1977-09-28 Application filed by Uniroyal Inc filed Critical Uniroyal Inc

1977-09-28 Priority to CA287,697A priority Critical patent/CA1096878A/fr

1981-03-03 Application granted granted Critical

1981-03-03 Publication of CA1096878A publication Critical patent/CA1096878A/fr

Status Expired legal-status Critical Current

Links

ISNKSXRJJVWFIL-UHFFFAOYSA-N (sulfonylamino)amine Chemical class NN=S(=O)=O ISNKSXRJJVWFIL-UHFFFAOYSA-N 0.000 title claims description 17
-1 N,N'-disubstituted sulfonyl hydrazines Chemical class 0.000 claims abstract description 54
125000004432 carbon atom Chemical group C* 0.000 claims description 39
150000003254 radicals Chemical group 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000002877 alkyl aryl group Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
125000001118 alkylidene group Chemical group 0.000 claims description 3
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
239000004604 Blowing Agent Substances 0.000 abstract description 26
229920000642 polymer Polymers 0.000 abstract description 22
150000001875 compounds Chemical class 0.000 abstract description 16
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 102
238000000034 method Methods 0.000 description 42
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 17
239000000203 mixture Substances 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
239000007789 gas Substances 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
229920003023 plastic Polymers 0.000 description 10
239000004033 plastic Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
229920002492 poly(sulfone) Polymers 0.000 description 7
239000000243 solution Substances 0.000 description 7
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
230000005484 gravity Effects 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 4
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 4
238000004458 analytical method Methods 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
229920001971 elastomer Polymers 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000008188 pellet Substances 0.000 description 4
CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
238000007630 basic procedure Methods 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
230000001413 cellular effect Effects 0.000 description 3
229910000071 diazene Inorganic materials 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000004156 Azodicarbonamide Substances 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
VRFNYSYURHAPFL-UHFFFAOYSA-N [(4-methylphenyl)sulfonylamino]urea Chemical compound CC1=CC=C(S(=O)(=O)NNC(N)=O)C=C1 VRFNYSYURHAPFL-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000013019 agitation Methods 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 2
235000019399 azodicarbonamide Nutrition 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000013882 gravy Nutrition 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002429 hydrazines Chemical class 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
229920000515 polycarbonate Polymers 0.000 description 2
239000004417 polycarbonate Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920001225 polyester resin Polymers 0.000 description 2
239000004645 polyester resin Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000012545 processing Methods 0.000 description 2
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000007787 solid Substances 0.000 description 2
241000894007 species Species 0.000 description 2
238000012360 testing method Methods 0.000 description 2
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
XSXAKPVYYUCSMQ-UHFFFAOYSA-N (carbamoylsulfonylamino)sulfamoylformamide Chemical class NC(=O)S(=O)(=O)NNS(=O)(=O)C(N)=O XSXAKPVYYUCSMQ-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FZYWMWPSJFFJDZ-UHFFFAOYSA-N 1-(n-methylsulfonylanilino)-1-phenylurea Chemical compound C=1C=CC=CC=1N(S(=O)(=O)C)N(C(N)=O)C1=CC=CC=C1 FZYWMWPSJFFJDZ-UHFFFAOYSA-N 0.000 description 1
LHYKTQVFLKHQSR-UHFFFAOYSA-N 1-amino-3-methylurea Chemical compound CNC(=O)NN LHYKTQVFLKHQSR-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
RHAXKFFKGZJUOE-UHFFFAOYSA-N 7-acetyl-6-ethyl-3,5,8-trihydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid Chemical compound O=C1C2=CC(O)=C(C(O)=O)C(C(O)=O)=C2C(=O)C2=C1C(O)=C(CC)C(C(C)=O)=C2O RHAXKFFKGZJUOE-UHFFFAOYSA-N 0.000 description 1
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CLSRAWKQRZESHO-UHFFFAOYSA-N CC(C)OC(=O)NN(C(=O)OC(C)C)S(=O)(=O)C1CCCCC1 Chemical compound CC(C)OC(=O)NN(C(=O)OC(C)C)S(=O)(=O)C1CCCCC1 CLSRAWKQRZESHO-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
241000243251 Hydra Species 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000007664 blowing Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920005549 butyl rubber Polymers 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000002666 chemical blowing agent Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000005038 ethylene vinyl acetate Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229920002313 fluoropolymer Polymers 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229920000578 graft copolymer Polymers 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
229920001903 high density polyethylene Polymers 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
BPJLPBVJCYVEAC-UHFFFAOYSA-N methyl n-(methoxycarbonylamino)carbamate Chemical compound COC(=O)NNC(=O)OC BPJLPBVJCYVEAC-UHFFFAOYSA-N 0.000 description 1
SYWIXHZXHQDFOO-UHFFFAOYSA-N methyl n-phenyliminocarbamate Chemical compound COC(=O)N=NC1=CC=CC=C1 SYWIXHZXHQDFOO-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000000465 moulding Methods 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000002667 nucleating agent Substances 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000090 poly(aryl ether) Polymers 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920000069 polyphenylene sulfide Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NSRWUXNOJJCMSB-UHFFFAOYSA-N propan-2-yl n-methylsulfonyl-n-(propan-2-yloxycarbonylamino)carbamate Chemical compound CC(C)OC(=O)NN(S(C)(=O)=O)C(=O)OC(C)C NSRWUXNOJJCMSB-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 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
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
229920000638 styrene acrylonitrile Polymers 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
239000004753 textile Substances 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
238000012546 transfer Methods 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
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 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA287,697A 1977-09-28 1977-09-28 Sulfonyl-hydrazines disubstituees en n,n' Expired CA1096878A (fr)

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Application Number	Priority Date	Filing Date	Title
CA287,697A CA1096878A (fr)	1977-09-28	1977-09-28	Sulfonyl-hydrazines disubstituees en n,n'

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Application Number	Priority Date	Filing Date	Title
CA287,697A CA1096878A (fr)	1977-09-28	1977-09-28	Sulfonyl-hydrazines disubstituees en n,n'

Publications (1)

Publication Number	Publication Date
CA1096878A true CA1096878A (fr)	1981-03-03

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ID=4109650

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Application Number	Title	Priority Date	Filing Date
CA287,697A Expired CA1096878A (fr)	1977-09-28	1977-09-28	Sulfonyl-hydrazines disubstituees en n,n'

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CA (1)	CA1096878A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US12183479B2 (en)	2018-06-15	2024-12-31	Dow Global Technologies Llc	Chemical foaming agents containing tosyl groups

1977
- 1977-09-28 CA CA287,697A patent/CA1096878A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US12183479B2 (en)	2018-06-15	2024-12-31	Dow Global Technologies Llc	Chemical foaming agents containing tosyl groups

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Date	Code	Title	Description
1998-03-03	MKEX	Expiry

Publication	Publication Date	Title
US3544597A (en)	1970-12-01	Process for manufacturing sulfonated amides
CA1039900A (fr)	1978-10-03	Carbazates de sulfonyle comme agents de soufflage
US3235519A (en)	1966-02-15	Sulfonyl semicarbazides as blowing agents for polymeric materials
CA1096878A (fr)	1981-03-03	Sulfonyl-hydrazines disubstituees en n,n'
US3894974A (en)	1975-07-15	Hydrazoidicarboxylates used as blowing agents to form gas expandable polymeric materials
US4175200A (en)	1979-11-20	N,N-Disubstituted sulfonyl hydrazines
CA1043354A (fr)	1978-11-28	Semicarbazides sulfonyles
US4158724A (en)	1979-06-19	Tris-tetrazoles as chemical blowing agents
US4127718A (en)	1978-11-28	Tris-tetrazoles as chemical blowing agents
CA1089875A (fr)	1980-11-18	Bis (hydrocarbylsulfonyl) carbohydrazines comme agents de gonflement
US4126590A (en)	1978-11-21	Sulphonyltetrazoles as chemical blowing agents
WO1990010030A1 (fr)	1990-09-07	5-amidotetrazoles a substitution
US3152176A (en)	1964-10-06	Sulfonyl semicarbazides
KR20170049245A (ko)	2017-05-10	가열분해 화합물 및 이를 이용한 가스 발생 방법
US3332936A (en)	1967-07-25	Bis(phenylsulfonyl)diazomethanes and their preparation
US3946064A (en)	1976-03-23	Hydrazodicarboxylates and use thereof as blowing agents
US4209632A (en)	1980-06-24	Sulfonyl carbazates
CA1100529A (fr)	1981-05-05	Agents de soufflage - bis(hydrocarbylsulfonyl) carbohydrazides
CA1100700A (fr)	1981-05-05	Bis (hydrocarbylsulfonyl) carbohydrazides comme agents soufflants.
US3629227A (en)	1971-12-21	Azoacyl compounds containing a group
US4135049A (en)	1979-01-16	Sulfonyl carbazates as blowing agents
DE2602808C2 (de)	1986-12-04	N,N'-disubstituierte Sulfonylhydrazine, Verfahren zu ihrer Herstellung und ihre Verwendung
US4012432A (en)	1977-03-15	Sulfonyl carbazates as blowing agents
CA1132295A (fr)	1982-09-21	Reticulation croisee de polymeres avec des azo-esters
US4921965A (en)	1990-05-01	Method of producing alkyl substituted 5-amidotetrazoles

CA1096878A - Sulfonyl-hydrazines disubstituees en n,n' - Google Patents

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Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4109650

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

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