CA1100699A - Bis-tetrazoles as chemical blowing agents - Google Patents
Bis-tetrazoles as chemical blowing agentsInfo
- Publication number
- CA1100699A CA1100699A CA282,761A CA282761A CA1100699A CA 1100699 A CA1100699 A CA 1100699A CA 282761 A CA282761 A CA 282761A CA 1100699 A CA1100699 A CA 1100699A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- alkyl
- formula
- bis
- 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
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 title abstract description 29
- 239000002666 chemical blowing agent Substances 0.000 title abstract description 4
- -1 polypropylene Polymers 0.000 claims abstract description 38
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 10
- 239000004417 polycarbonate Substances 0.000 claims abstract description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 8
- 239000004743 Polypropylene Substances 0.000 claims abstract description 6
- 239000004952 Polyamide Substances 0.000 claims abstract description 5
- 229920002647 polyamide Polymers 0.000 claims abstract description 5
- 229920001155 polypropylene Polymers 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 229910052736 halogen Chemical group 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000005187 foaming Methods 0.000 claims description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 125000004957 naphthylene group Chemical group 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 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 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 4
- 229920002492 poly(sulfone) Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 3
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims 1
- 239000004604 Blowing Agent Substances 0.000 abstract description 27
- 238000001746 injection moulding Methods 0.000 abstract description 5
- 229920006380 polyphenylene oxide Polymers 0.000 abstract description 4
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical group C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005992 thermoplastic resin Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 47
- 235000013350 formula milk Nutrition 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 150000003536 tetrazoles Chemical group 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- 239000004033 plastic Substances 0.000 description 10
- 229920003023 plastic Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002845 discoloration Methods 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- GJNTWVASQGUIOY-UHFFFAOYSA-N 5-[2-[2-(2h-tetrazol-5-yl)ethoxy]ethyl]-2h-tetrazole Chemical compound N1=NNN=C1CCOCCC=1N=NNN=1 GJNTWVASQGUIOY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- MARUHZGHZWCEQU-UHFFFAOYSA-N 5-phenyl-2h-tetrazole Chemical compound C1=CC=CC=C1C1=NNN=N1 MARUHZGHZWCEQU-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 3
- KSCMYJXTGSEZEI-UHFFFAOYSA-N 5-[2-(2h-tetrazol-5-yl)ethyl]-2h-tetrazole Chemical compound N1=NNN=C1CCC=1N=NNN=1 KSCMYJXTGSEZEI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000012815 thermoplastic material Substances 0.000 description 3
- PVXCQHHWNDJIJP-UHFFFAOYSA-N 2,3-diphenylbutanedioic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C(C(O)=O)C1=CC=CC=C1 PVXCQHHWNDJIJP-UHFFFAOYSA-N 0.000 description 2
- BCGCCTGNWPKXJL-UHFFFAOYSA-N 3-(2-cyanoethoxy)propanenitrile Chemical compound N#CCCOCCC#N BCGCCTGNWPKXJL-UHFFFAOYSA-N 0.000 description 2
- NDVLTZFQVDXFAN-UHFFFAOYSA-N 3-(2-cyanoethylsulfanyl)propanenitrile Chemical compound N#CCCSCCC#N NDVLTZFQVDXFAN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000006004 Quartz sand Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical group NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- SDLHRUDTCAGBLQ-UHFFFAOYSA-N n-(3-benzamidophenyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1 SDLHRUDTCAGBLQ-UHFFFAOYSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
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- 125000005023 xylyl group Chemical group 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- ZYACJWRVLBPZNG-UHFFFAOYSA-N 1-n,2-n-diphenylbenzene-1,2-dicarboxamide Chemical compound C=1C=CC=C(C(=O)NC=2C=CC=CC=2)C=1C(=O)NC1=CC=CC=C1 ZYACJWRVLBPZNG-UHFFFAOYSA-N 0.000 description 1
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- YFZSRODSCHJZQY-UHFFFAOYSA-N 1-phenyl-5-[3-(1-phenyltetrazol-5-yl)phenyl]tetrazole Chemical compound C1=CC=CC=C1N1C(C=2C=C(C=CC=2)C=2N(N=NN=2)C=2C=CC=CC=2)=NN=N1 YFZSRODSCHJZQY-UHFFFAOYSA-N 0.000 description 1
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- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- QPAHNTZTUMLHOZ-UHFFFAOYSA-N 2h-pyrazine-1,2-dicarbonitrile Chemical compound N#CC1C=NC=CN1C#N QPAHNTZTUMLHOZ-UHFFFAOYSA-N 0.000 description 1
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- YNRGDPQTVDWXPB-UHFFFAOYSA-N 3-(1,2,4-triazol-3-ylidene)-1,2,4-triazole Chemical class N1=NC=NC1=C1N=NC=N1 YNRGDPQTVDWXPB-UHFFFAOYSA-N 0.000 description 1
- NPMCIHCQSNHBDX-UHFFFAOYSA-N 3-[2-cyanoethyl(methyl)amino]propanenitrile Chemical compound N#CCCN(C)CCC#N NPMCIHCQSNHBDX-UHFFFAOYSA-N 0.000 description 1
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- RCRNVWKZQROUJM-UHFFFAOYSA-N 3-[4-(2-cyanoethoxy)butoxy]propanenitrile Chemical compound N#CCCOCCCCOCCC#N RCRNVWKZQROUJM-UHFFFAOYSA-N 0.000 description 1
- PJOTXMHESXUPBD-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-4-methylanilino]propanenitrile Chemical compound CC1=CC=C(N(CCC#N)CCC#N)C=C1 PJOTXMHESXUPBD-UHFFFAOYSA-N 0.000 description 1
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- POYGMEPUQZJSCS-UHFFFAOYSA-N 4-benzoyl-4-phenylheptanedioic acid Chemical compound C=1C=CC=CC=1C(CCC(O)=O)(CCC(=O)O)C(=O)C1=CC=CC=C1 POYGMEPUQZJSCS-UHFFFAOYSA-N 0.000 description 1
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- STXRBRKZIAPBBP-UHFFFAOYSA-N 4-nitroheptanedioic acid Chemical compound OC(=O)CCC([N+]([O-])=O)CCC(O)=O STXRBRKZIAPBBP-UHFFFAOYSA-N 0.000 description 1
- NKEFYKHTHQSJOL-UHFFFAOYSA-N 5-[1,2-diphenyl-2-(2h-tetrazol-5-yl)ethyl]-2h-tetrazole Chemical compound C1=CC=CC=C1C(C1=NNN=N1)C(C=1C=CC=CC=1)C1=NNN=N1 NKEFYKHTHQSJOL-UHFFFAOYSA-N 0.000 description 1
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- RCXNKGHLBFYKHO-UHFFFAOYSA-N 5-[2-[2-(2h-tetrazol-5-yl)ethylsulfanyl]ethyl]-2h-tetrazole Chemical compound N1=NNN=C1CCSCCC=1N=NNN=1 RCXNKGHLBFYKHO-UHFFFAOYSA-N 0.000 description 1
- CXQSAFJKCHJMQV-UHFFFAOYSA-N 5-[4-(2h-tetrazol-5-yl)butyl]-2h-tetrazole Chemical compound N1=NNN=C1CCCCC=1N=NNN=1 CXQSAFJKCHJMQV-UHFFFAOYSA-N 0.000 description 1
- RJINRNDWOXJPOK-UHFFFAOYSA-N 5-[5-(2h-tetrazol-5-yl)pentyl]-2h-tetrazole Chemical compound N1=NNN=C1CCCCCC=1N=NNN=1 RJINRNDWOXJPOK-UHFFFAOYSA-N 0.000 description 1
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- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 235000019399 azodicarbonamide Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FFYAVOJIYAAUNX-UHFFFAOYSA-N n,n'-diethyloxamide Chemical compound CCNC(=O)C(=O)NCC FFYAVOJIYAAUNX-UHFFFAOYSA-N 0.000 description 1
- RAQQCMGBZRSPAR-UHFFFAOYSA-N n,n'-dimethyldecanediamide Chemical compound CNC(=O)CCCCCCCCC(=O)NC RAQQCMGBZRSPAR-UHFFFAOYSA-N 0.000 description 1
- XBXOTDRZQLRKDY-UHFFFAOYSA-N n,n'-dimethylhexanediamide Chemical compound CNC(=O)CCCCC(=O)NC XBXOTDRZQLRKDY-UHFFFAOYSA-N 0.000 description 1
- ZWXJWAPTSTYSAH-UHFFFAOYSA-N n,n'-dimethylpropanediamide Chemical compound CNC(=O)CC(=O)NC ZWXJWAPTSTYSAH-UHFFFAOYSA-N 0.000 description 1
- NOEOAZMRAXYIEK-UHFFFAOYSA-N n,n'-diphenylbutanediamide Chemical compound C=1C=CC=CC=1NC(=O)CCC(=O)NC1=CC=CC=C1 NOEOAZMRAXYIEK-UHFFFAOYSA-N 0.000 description 1
- LNCBPXWNUQBKKX-UHFFFAOYSA-N n,n-bis(2-cyanoethyl)benzamide Chemical compound N#CCCN(CCC#N)C(=O)C1=CC=CC=C1 LNCBPXWNUQBKKX-UHFFFAOYSA-N 0.000 description 1
- TWWXYDFCSCFLHT-UHFFFAOYSA-N n,n-bis(2-cyanoethyl)benzenesulfonamide Chemical compound N#CCCN(CCC#N)S(=O)(=O)C1=CC=CC=C1 TWWXYDFCSCFLHT-UHFFFAOYSA-N 0.000 description 1
- WNYIBZHOMJZDKN-UHFFFAOYSA-N n-(2-acetamidoethyl)acetamide Chemical compound CC(=O)NCCNC(C)=O WNYIBZHOMJZDKN-UHFFFAOYSA-N 0.000 description 1
- KVEDKKLZCJBVNP-UHFFFAOYSA-N n-(4-acetamidophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(NC(C)=O)C=C1 KVEDKKLZCJBVNP-UHFFFAOYSA-N 0.000 description 1
- ABRHLWPJYNIPHN-UHFFFAOYSA-N n-(4-benzamidophenyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 ABRHLWPJYNIPHN-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- MYINLNBRJVGINA-UHFFFAOYSA-N thiophene-2,5-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)S1 MYINLNBRJVGINA-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
- C08J9/108—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 in a heterocyclic ring containing at least one carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH9138/76 | 1976-07-16 | ||
| CH913876A CH623600A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-07-16 | 1976-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100699A true CA1100699A (en) | 1981-05-05 |
Family
ID=4348733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA282,761A Expired CA1100699A (en) | 1976-07-16 | 1977-07-14 | Bis-tetrazoles as chemical blowing agents |
Country Status (9)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2438064A1 (fr) * | 1978-10-05 | 1980-04-30 | Rhone Poulenc Ind | Melanges-maitres pour moulage de polyamide allege |
| US4392968A (en) * | 1980-08-13 | 1983-07-12 | Nippon Oil Company, Limited | Metal deactivator and composition containing same |
| US4308352A (en) * | 1981-04-24 | 1981-12-29 | Packaging Industries Group, Inc. | Process of extruding polysulfone foam |
| JPS62252436A (ja) * | 1986-04-24 | 1987-11-04 | Asahi Chem Ind Co Ltd | 発泡成形用ポリアミド樹脂成形材料 |
| US4871861A (en) * | 1987-07-06 | 1989-10-03 | Olin Corporation | Substituted 5-amidotetrazoles |
| US4774266A (en) * | 1987-11-27 | 1988-09-27 | Olin Corporation | N-substituted 5-phenyltetrazoles as high temperature blowing agents |
| DE4138182A1 (de) * | 1990-11-26 | 1992-05-27 | Toyo Kasei Kogyo Co Ltd | Treibmittel aus tetrazolen und ihren derivaten |
| US5359011A (en) * | 1992-10-14 | 1994-10-25 | The B.F. Goodrich Company | Process for the complete neutralization of chlorinated polyvinyl chloride and product resulting therefrom |
| US5472647A (en) * | 1993-08-02 | 1995-12-05 | Thiokol Corporation | Method for preparing anhydrous tetrazole gas generant compositions |
| US5682014A (en) * | 1993-08-02 | 1997-10-28 | Thiokol Corporation | Bitetrazoleamine gas generant compositions |
| US5468866A (en) * | 1994-01-04 | 1995-11-21 | Thiokol Corporation | Methods for synthesizing and processing bis-(1(2)H-tetrazol-5-yl)-amine |
| US5472534A (en) * | 1994-01-06 | 1995-12-05 | Thiokol Corporation | Gas generant composition containing non-metallic salts of 5-nitrobarbituric acid |
| AU1556995A (en) * | 1994-01-06 | 1995-08-01 | Thiokol Corporation | Process for making 5-nitrobarbituric acid and salts thereof |
| US5516377A (en) * | 1994-01-10 | 1996-05-14 | Thiokol Corporation | Gas generating compositions based on salts of 5-nitraminotetrazole |
| US5451682A (en) * | 1994-01-10 | 1995-09-19 | Thiokol Corporation | Method for synthesizing 5-aminotetrazole |
| JPH08337770A (ja) * | 1995-06-09 | 1996-12-24 | Toyo Kasei Kogyo Co Ltd | テトラゾ−ル系ガス発生剤 |
| US6458227B1 (en) * | 2000-04-28 | 2002-10-01 | The Regents Of The University Of California | Propellant containing 3;6-BIS(1H-1,2,3,4-Tetrazol-5-ylamino)-1,2,4,5-tetrazine or salts thereof |
| JP4721904B2 (ja) | 2004-02-05 | 2011-07-13 | Ｊｘ日鉱日石金属株式会社 | 金属の表面処理剤 |
| JP2009536207A (ja) * | 2006-05-05 | 2009-10-08 | ティー ケー ホールディングス インク | ガス生成組成物 |
| US7692024B2 (en) * | 2006-05-05 | 2010-04-06 | Tk Holdings, Inc. | Gas generant compositions |
| JP2010515664A (ja) * | 2006-09-30 | 2010-05-13 | ティー ケー ホールディングス インク | ガス生成組成物 |
| FR2926545B1 (fr) * | 2008-01-21 | 2010-09-17 | Snpe Materiaux Energetiques | Composition generatrice de gaz azote, comprenant de l'azodicarbonamide et procede de generation de gaz azote par decomposition de ladite composition |
| JP5941544B2 (ja) * | 2013-04-23 | 2016-06-29 | 積水化学工業株式会社 | テトラゾール化合物又はその塩、接着剤組成物及び接着テープ |
| US9771336B2 (en) | 2013-12-02 | 2017-09-26 | Ecolab Usa Inc. | Tetrazole based corrosion inhibitors |
| CA2934429A1 (en) * | 2013-12-23 | 2015-07-02 | Solvay Specialty Polymers Usa, Llc | New foam materials from aromatic poly(aryl ether sulfone) foamable compositions |
| WO2016191680A1 (en) | 2015-05-28 | 2016-12-01 | Ecolab Usa Inc. | Purine-based corrosion inhibitors |
| CN107667094B (zh) | 2015-05-28 | 2022-06-14 | 艺康美国股份有限公司 | 作为腐蚀抑制剂的水溶性吡唑衍生物 |
| EP3303654B1 (en) | 2015-05-28 | 2023-06-07 | Ecolab Usa Inc. | 2-substituted benzimidazole corrosion inhibitors |
| CA2987248C (en) | 2015-05-28 | 2023-09-26 | Ecolab Usa Inc. | Novel corrosion inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275608A (en) * | 1962-08-06 | 1966-09-27 | Du Pont | Polymers consisting of 1, 3, 4-oxadiazole rings linked by perfluoroalkylene and optionally, arylene radicals |
| DE1258734B (de) * | 1964-08-22 | 1968-01-11 | Kalle Ag | Lichtempfindliche Schicht |
| US3442829A (en) * | 1966-11-10 | 1969-05-06 | Borg Warner | Method of foaming thermoplastic polymeric materials using hydrocarbyltetrazoles as the foaming agent |
| GB1207855A (en) * | 1967-10-09 | 1970-10-07 | Agfa Gevaert Nv | Photographic antifoggants |
| US3873477A (en) * | 1973-12-17 | 1975-03-25 | Stepan Chemical Co | Metallic salts of tetrazoles used as blowing and intumescent agents for thermoplastic polymers |
-
1976
- 1976-07-16 CH CH913876A patent/CH623600A5/de not_active IP Right Cessation
-
1977
- 1977-07-12 US US05/814,827 patent/US4142029A/en not_active Expired - Lifetime
- 1977-07-12 DE DE19772731323 patent/DE2731323A1/de not_active Withdrawn
- 1977-07-14 NL NL7707870A patent/NL7707870A/xx not_active Application Discontinuation
- 1977-07-14 GB GB29599/77A patent/GB1568323A/en not_active Expired
- 1977-07-14 CA CA282,761A patent/CA1100699A/en not_active Expired
- 1977-07-15 BE BE179363A patent/BE856839A/xx not_active IP Right Cessation
- 1977-07-16 JP JP8555677A patent/JPS5312864A/ja active Granted
- 1977-07-18 FR FR7721935A patent/FR2358433A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE856839A (fr) | 1978-01-16 |
| NL7707870A (nl) | 1978-01-18 |
| FR2358433A1 (fr) | 1978-02-10 |
| DE2731323A1 (de) | 1978-01-26 |
| US4142029A (en) | 1979-02-27 |
| FR2358433B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-03-09 |
| GB1568323A (en) | 1980-05-29 |
| CH623600A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-06-15 |
| JPS6134457B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-08-07 |
| JPS5312864A (en) | 1978-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |