CA1100700A - Bis (hydrocarbylsulfonyl) carbohydrazides comme agents soufflants. - Google Patents

Bis (hydrocarbylsulfonyl) carbohydrazides comme agents soufflants.

Info

Publication number: CA1100700A
Authority: CA; Canada
Prior art keywords: bis; carbohydrazide; carbon atoms; mole; product
Prior art date: 1976-05-24
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

CA350,318A

Other languages

English (en)

Inventor

Irwin A. Prager

Byron A. Hunter

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.)

1976-05-24

Filing date

1980-04-22

Publication date

1981-05-05

1976-05-24 Priority claimed from US05/689,448 external-priority patent/US4096100A/en

1980-04-22 Application filed by Uniroyal Inc filed Critical Uniroyal Inc

1980-04-22 Priority to CA350,318A priority Critical patent/CA1100700A/fr

1981-05-05 Application granted granted Critical

1981-05-05 Publication of CA1100700A publication Critical patent/CA1100700A/fr

Status Expired legal-status Critical Current

Links

239000004604 Blowing Agent Substances 0.000 title abstract description 21
239000000203 mixture Substances 0.000 claims abstract description 46
XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims abstract description 34
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
239000000463 material Substances 0.000 claims abstract description 16
238000000034 method Methods 0.000 claims abstract description 16
238000000354 decomposition reaction Methods 0.000 claims abstract description 14
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 6
238000010438 heat treatment Methods 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
150000005840 aryl radicals Chemical group 0.000 claims description 3
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 2
150000001875 compounds Chemical class 0.000 abstract description 15
125000000217 alkyl group Chemical group 0.000 abstract description 2
239000000047 product Substances 0.000 description 34
-1 hydrocarbyl sulfonyl carbohydrazide compounds Chemical class 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
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
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 11
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 11
229910052799 carbon Inorganic materials 0.000 description 10
239000007789 gas Substances 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
239000000908 ammonium hydroxide Substances 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
229910002092 carbon dioxide Inorganic materials 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
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
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
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
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 3
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 3
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 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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
239000001569 carbon dioxide Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000875 corresponding effect 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
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
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
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
238000007664 blowing Methods 0.000 description 2
230000005484 gravity Effects 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
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
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000002897 organic nitrogen compounds Chemical class 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
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 1
YUYNDDBGVITGMG-UHFFFAOYSA-N 1,3-bis(tert-butylsulfonylamino)urea 1,3-bis(propan-2-ylsulfonylamino)urea Chemical compound C(C)(C)(C)S(=O)(=O)NNC(=O)NNS(=O)(=O)C(C)(C)C.C(C)(C)S(=O)(=O)NNC(=O)NNS(=O)(=O)C(C)C YUYNDDBGVITGMG-UHFFFAOYSA-N 0.000 description 1
UFKYOHBGPOVGCS-UHFFFAOYSA-N 1,3-bis[(2-tert-butylphenyl)sulfonylamino]urea Chemical compound CC(C)(C)C1=CC=CC=C1S(=O)(=O)NNC(=O)NNS(=O)(=O)C1=CC=CC=C1C(C)(C)C UFKYOHBGPOVGCS-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
NBOCQTNZUPTTEI-UHFFFAOYSA-N 4-[4-(hydrazinesulfonyl)phenoxy]benzenesulfonohydrazide Chemical compound C1=CC(S(=O)(=O)NN)=CC=C1OC1=CC=C(S(=O)(=O)NN)C=C1 NBOCQTNZUPTTEI-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
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229910020364 ClSO2 Inorganic materials 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
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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
229920006397 acrylic thermoplastic 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
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
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
239000001273 butane Substances 0.000 description 1
229920005549 butyl rubber Polymers 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
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 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
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
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

Landscapes

Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Compositions Of Macromolecular Compounds (AREA)
Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

CA350,318A 1976-05-24 1980-04-22 Bis (hydrocarbylsulfonyl) carbohydrazides comme agents soufflants. Expired CA1100700A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA350,318A CA1100700A (fr)	1976-05-24	1980-04-22	Bis (hydrocarbylsulfonyl) carbohydrazides comme agents soufflants.

Applications Claiming Priority (4)

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
CA258,997A CA1089875A (fr)	1976-05-24	1976-08-13	Bis (hydrocarbylsulfonyl) carbohydrazines comme agents de gonflement
CA350,318A CA1100700A (fr)	1976-05-24	1980-04-22	Bis (hydrocarbylsulfonyl) carbohydrazides comme agents soufflants.

Publications (1)

Publication Number	Publication Date
CA1100700A true CA1100700A (fr)	1981-05-05

Family

ID=27164597

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA350,318A Expired CA1100700A (fr)	1976-05-24	1980-04-22	Bis (hydrocarbylsulfonyl) carbohydrazides comme agents soufflants.

Country Status (1)

Country	Link
CA (1)	CA1100700A (fr)

1980
- 1980-04-22 CA CA350,318A patent/CA1100700A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-05-05	MKEX	Expiry

Publication	Publication Date	Title
US4163037A (en)	1979-07-31	Method for making thermoplastic foams
JPS6134457B2 (fr)	1986-08-07
CA1089875A (fr)	1980-11-18	Bis (hydrocarbylsulfonyl) carbohydrazines comme agents de gonflement
US3925270A (en)	1975-12-09	Polymeric composition comprising sulfonyl carbazates as blowing agents
US4334030A (en)	1982-06-08	Thermoplastic foamable blends
US2830029A (en)	1958-04-08	Preparation of cellular products containing organic sulfonyl azides and composition thereof
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