CA1089875A - Blowing agents - bis(hydrocarbylsulfonyl) carbohydrazides - Google Patents
Blowing agents - bis(hydrocarbylsulfonyl) carbohydrazidesInfo
- Publication number
- CA1089875A CA1089875A CA258,997A CA258997A CA1089875A CA 1089875 A CA1089875 A CA 1089875A CA 258997 A CA258997 A CA 258997A CA 1089875 A CA1089875 A CA 1089875A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- carbohydrazide
- mole
- hydrocarbylsulfonyl
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000004604 Blowing Agent Substances 0.000 title abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 13
- 238000000354 decomposition reaction Methods 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- -1 hydrocarbyl sulfonyl carbohydrazide compounds Chemical class 0.000 description 34
- 239000000047 product Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 13
- 235000017557 sodium bicarbonate Nutrition 0.000 description 13
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VHDQWGMVEFANPD-UHFFFAOYSA-N 1,3-bis[(4-methylphenyl)sulfonylamino]urea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NNC(=O)NNS(=O)(=O)C1=CC=C(C)C=C1 VHDQWGMVEFANPD-UHFFFAOYSA-N 0.000 description 4
- HJKXLQIPODSWMB-UHFFFAOYSA-N 4-(4-chlorosulfonylphenoxy)benzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1OC1=CC=C(S(Cl)(=O)=O)C=C1 HJKXLQIPODSWMB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229920002492 poly(sulfone) Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- GLEXRKRJMYWGES-UHFFFAOYSA-N 1,3-bis(benzenesulfonamido)urea Chemical compound C=1C=CC=CC=1S(=O)(=O)NNC(=O)NNS(=O)(=O)C1=CC=CC=C1 GLEXRKRJMYWGES-UHFFFAOYSA-N 0.000 description 2
- HQJPTWMZLIPSJT-UHFFFAOYSA-N 1,3-bis(butylsulfonylamino)urea Chemical compound CCCCS(=O)(=O)NNC(=O)NNS(=O)(=O)CCCC HQJPTWMZLIPSJT-UHFFFAOYSA-N 0.000 description 2
- NTYDVOFEKOIDKZ-UHFFFAOYSA-N 1,3-bis(ethylsulfonylamino)urea Chemical compound CCS(=O)(=O)NNC(=O)NNS(=O)(=O)CC NTYDVOFEKOIDKZ-UHFFFAOYSA-N 0.000 description 2
- CYFWTGPTSMJNFX-UHFFFAOYSA-N 1,3-bis(methanesulfonamido)urea Chemical compound CS(=O)(=O)NNC(=O)NNS(C)(=O)=O CYFWTGPTSMJNFX-UHFFFAOYSA-N 0.000 description 2
- AGFKDLVKMBDGGS-UHFFFAOYSA-N 1,3-bis[(4-chlorophenyl)sulfonylamino]urea Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NNC(=O)NNS(=O)(=O)C1=CC=C(Cl)C=C1 AGFKDLVKMBDGGS-UHFFFAOYSA-N 0.000 description 2
- RRCFMPZTPWMGJB-UHFFFAOYSA-N 4,6-dimethylbenzene-1,3-disulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O RRCFMPZTPWMGJB-UHFFFAOYSA-N 0.000 description 2
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 239000004156 Azodicarbonamide Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 230000002411 adverse Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 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
- 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 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- SYJPAKDNFZLSMV-HYXAFXHYSA-N (Z)-2-methylpropanal oxime Chemical compound CC(C)\C=N/O SYJPAKDNFZLSMV-HYXAFXHYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GBZJAFUHKVFIDL-UHFFFAOYSA-N 1,3-bis(tert-butylsulfonylamino)urea Chemical compound CC(C)(C)S(=O)(=O)NNC(=O)NNS(=O)(=O)C(C)(C)C GBZJAFUHKVFIDL-UHFFFAOYSA-N 0.000 description 1
- MHJYFBKMSRVRHC-UHFFFAOYSA-N 1,3-bis[(3,4-dichlorophenyl)sulfonylamino]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NNC(=O)NNS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 MHJYFBKMSRVRHC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- CQSQUYVFNGIECQ-UHFFFAOYSA-N 1-n,4-n-dimethyl-1-n,4-n-dinitrosobenzene-1,4-dicarboxamide Chemical compound O=NN(C)C(=O)C1=CC=C(C(=O)N(C)N=O)C=C1 CQSQUYVFNGIECQ-UHFFFAOYSA-N 0.000 description 1
- KKUVWMQVIVBNEW-UHFFFAOYSA-N 2,5,5-trichloro-oxacycloundecane Chemical compound ClC1CCC(Cl)(Cl)CCCCCCO1 KKUVWMQVIVBNEW-UHFFFAOYSA-N 0.000 description 1
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-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
- YQJXYNCJTLFOFT-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(N(N)S(=O)(=O)C1=CC=C(C=C1)C)=O)N)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(N(N)S(=O)(=O)C1=CC=C(C=C1)C)=O)N)C YQJXYNCJTLFOFT-UHFFFAOYSA-N 0.000 description 1
- MWRWFPQBGSZWNV-UHFFFAOYSA-N Dinitrosopentamethylenetetramine Chemical compound C1N2CN(N=O)CN1CN(N=O)C2 MWRWFPQBGSZWNV-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 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
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229920000459 Nitrile rubber Polymers 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
- 229910005948 SO2Cl Inorganic materials 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 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
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 101150115304 cls-2 gene Proteins 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000001739 density measurement Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000006260 foam Substances 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
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229940068921 polyethylenes Drugs 0.000 description 1
- 229920001721 polyimide 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
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
- C08J9/10—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond
- C08J9/104—Hydrazines; Hydrazides; Semicarbazides; Semicarbazones; Hydrazones; Derivatives thereof
- C08J9/105—Hydrazines; Hydrazides; Semicarbazides; Semicarbazones; Hydrazones; Derivatives thereof containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/30—Polysulfonamides; Polysulfonimides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA350,318A CA1100700A (en) | 1976-05-24 | 1980-04-22 | Blowing agents - bis(hydrocarbylsulfonyl) carbohydrazides |
| CA350,317A CA1100529A (en) | 1976-05-24 | 1980-04-22 | Blowing agents - bis(hydrocarbylsulfonyl) carbohydrazides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/689,448 US4096100A (en) | 1976-05-24 | 1976-05-24 | Blowing agents-bis(hydrocarbylsulfonyl) carbohydrazides |
| US689,448 | 1976-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1089875A true CA1089875A (en) | 1980-11-18 |
Family
ID=24768516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA258,997A Expired CA1089875A (en) | 1976-05-24 | 1976-08-13 | Blowing agents - bis(hydrocarbylsulfonyl) carbohydrazides |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4096100A (en, 2012) |
| JP (1) | JPS52142765A (en, 2012) |
| BE (1) | BE854900A (en, 2012) |
| CA (1) | CA1089875A (en, 2012) |
| DE (1) | DE2723187C2 (en, 2012) |
| FR (1) | FR2352796A1 (en, 2012) |
| GB (1) | GB1561278A (en, 2012) |
| IT (1) | IT1083002B (en, 2012) |
| NL (1) | NL7705725A (en, 2012) |
| ZA (1) | ZA772658B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2912290A1 (de) * | 1979-03-28 | 1980-10-09 | Bayer Ag | Mischungen aus azodicarbonamid und alpha -amidosulfonen, deren herstellung und verwendung als treibmittel |
| JPS58150217U (ja) * | 1982-04-01 | 1983-10-08 | 株式会社東海理化電機製作所 | マグネツトスイツチのキヤツプ装置 |
| DE3322320A1 (de) * | 1983-06-21 | 1985-01-03 | Bayer Ag, 5090 Leverkusen | Arylsulfonylhydrazone als treibmittel |
| US4892887A (en) * | 1984-12-20 | 1990-01-09 | Yale University | N,N'-bis(sulfonyl)hydrazines having antineoplastic activity |
| US4684747A (en) * | 1984-12-20 | 1987-08-04 | Yale University | N,N'-bis(sulfonyl)hydrazines having antineoplastic activity |
| JP4887070B2 (ja) * | 2006-03-27 | 2012-02-29 | 永和化成工業株式会社 | Ｐ，ｐ’−オキシビス（ベンゼンスルホニルヒドラジド）の製造方法 |
| KR102540597B1 (ko) * | 2020-11-03 | 2023-06-12 | 주식회사 금양 | 발포제의 친환경적 제조방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3235519A (en) * | 1959-12-31 | 1966-02-15 | Us Rubber Co | Sulfonyl semicarbazides as blowing agents for polymeric materials |
| NL257913A (en, 2012) * | 1959-12-31 | |||
| NL129227C (en, 2012) * | 1964-12-07 | |||
| US3903151A (en) * | 1971-07-14 | 1975-09-02 | Chevron Res | Reaction products of alkali metal meborate and hydrocarbon substituted succinimide |
| US3888802A (en) * | 1973-04-26 | 1975-06-10 | Uniroyal Inc | Oxalylbis(sulfonyl hydrazides), used as blowing agents for gas-expandable polymeric material |
| US3903157A (en) * | 1974-02-06 | 1975-09-02 | Uniroyal Inc | Sulfonyl semicarbazides |
| NL184476C (nl) * | 1974-06-05 | Uniroyal Inc | Werkwijze ter bereiding van een door verhitting expandeerbaar mengsel, alsmede werkwijze ter bereiding van sulfonylcarbazaten. | |
| US3933909A (en) * | 1974-07-19 | 1976-01-20 | Armstrong Cork Company | Method for producing sulfonyl semicarbazides |
| GB1486686A (en) * | 1975-07-08 | 1977-09-21 | Quimco Gmbh | Process for the preparation of semicarbazides and carbazides |
| DE2746965A1 (de) * | 1977-10-19 | 1979-04-26 | Agfa Gevaert Ag | Verfahren zur herstellung direkt- positiver fotografischer bilder |
-
1976
- 1976-05-24 US US05/689,448 patent/US4096100A/en not_active Expired - Lifetime
- 1976-08-13 CA CA258,997A patent/CA1089875A/en not_active Expired
-
1977
- 1977-05-03 ZA ZA00772658A patent/ZA772658B/xx unknown
- 1977-05-18 FR FR7715311A patent/FR2352796A1/fr active Granted
- 1977-05-23 BE BE177792A patent/BE854900A/xx not_active IP Right Cessation
- 1977-05-23 GB GB21580/77A patent/GB1561278A/en not_active Expired
- 1977-05-23 JP JP5971777A patent/JPS52142765A/ja active Granted
- 1977-05-23 DE DE2723187A patent/DE2723187C2/de not_active Expired
- 1977-05-23 IT IT7768177A patent/IT1083002B/it active
- 1977-05-24 NL NL7705725A patent/NL7705725A/xx not_active Application Discontinuation
-
1978
- 1978-05-04 US US05/902,627 patent/US4133832A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52142765A (en) | 1977-11-28 |
| JPS561342B2 (en, 2012) | 1981-01-13 |
| ZA772658B (en) | 1978-04-26 |
| DE2723187A1 (de) | 1977-12-08 |
| BE854900A (fr) | 1977-11-23 |
| US4133832A (en) | 1979-01-09 |
| FR2352796B1 (en, 2012) | 1983-08-19 |
| DE2723187C2 (de) | 1987-02-26 |
| GB1561278A (en) | 1980-02-20 |
| US4096100A (en) | 1978-06-20 |
| FR2352796A1 (fr) | 1977-12-23 |
| NL7705725A (nl) | 1977-11-28 |
| IT1083002B (it) | 1985-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |