DE2504046A1 - N-cyanosulfonamidharze und zwischenprodukte fuer diese und produkte daraus - Google Patents
N-cyanosulfonamidharze und zwischenprodukte fuer diese und produkte darausInfo
- Publication number
- DE2504046A1 DE2504046A1 DE19752504046 DE2504046A DE2504046A1 DE 2504046 A1 DE2504046 A1 DE 2504046A1 DE 19752504046 DE19752504046 DE 19752504046 DE 2504046 A DE2504046 A DE 2504046A DE 2504046 A1 DE2504046 A1 DE 2504046A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- formula
- group
- groups
- cycloaliphatic
- 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.)
- Ceased
Links
- 229920005989 resin Polymers 0.000 title description 53
- 239000011347 resin Substances 0.000 title description 53
- LDABEQINUALFMV-UHFFFAOYSA-N O=S(=O)NC#N Chemical compound O=S(=O)NC#N LDABEQINUALFMV-UHFFFAOYSA-N 0.000 title description 12
- 239000000047 product Substances 0.000 title description 11
- 239000013067 intermediate product Substances 0.000 title 1
- -1 phenylene, bisphenylene Chemical group 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
- 239000011521 glass Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- 238000012644 addition polymerization Methods 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 241000534944 Thia Species 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004957 naphthylene group Chemical group 0.000 claims 4
- 239000000758 substrate Substances 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000001118 alkylidene group Chemical group 0.000 claims 3
- 125000003368 amide group Chemical group 0.000 claims 3
- 125000004467 aryl imino group Chemical group 0.000 claims 3
- 239000004760 aramid Substances 0.000 claims 2
- 229920003235 aromatic polyamide Polymers 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 48
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000155 melt Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- VBOBDSYQEZUOGV-UHFFFAOYSA-N n-cyano-n-phenylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(C#N)C1=CC=CC=C1 VBOBDSYQEZUOGV-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 230000009477 glass transition Effects 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000009835 boiling Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 239000002966 varnish Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 5
- 238000010030 laminating Methods 0.000 description 5
- 238000003475 lamination Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 238000004455 differential thermal analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DZNRWJXFRVXJBG-UHFFFAOYSA-N [3-(cyanoamino)phenyl]cyanamide Chemical compound N#CNC1=CC=CC(NC#N)=C1 DZNRWJXFRVXJBG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000004634 thermosetting polymer Substances 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- OAGUJEBHYMVZRA-UHFFFAOYSA-N 2,4,5,6-tetrachlorobenzene-1,3-disulfonyl chloride Chemical compound ClC1=C(Cl)C(S(Cl)(=O)=O)=C(Cl)C(S(Cl)(=O)=O)=C1Cl OAGUJEBHYMVZRA-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- KSXTYOOWLFRZSP-UHFFFAOYSA-N 2,5-dimethylbenzene-1,3-disulfonyl chloride Chemical compound CC1=CC(S(Cl)(=O)=O)=C(C)C(S(Cl)(=O)=O)=C1 KSXTYOOWLFRZSP-UHFFFAOYSA-N 0.000 description 1
- CAOXTJCSAJIUGW-UHFFFAOYSA-N 3-methylbutane-1-sulfonyl chloride Chemical compound CC(C)CCS(Cl)(=O)=O CAOXTJCSAJIUGW-UHFFFAOYSA-N 0.000 description 1
- BYMHXNOLUHTIDK-UHFFFAOYSA-N 4,5-dimethylbenzene-1,3-disulfonyl chloride Chemical compound CC1=CC(S(Cl)(=O)=O)=CC(S(Cl)(=O)=O)=C1C BYMHXNOLUHTIDK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IIEPAQNLXCHENX-UHFFFAOYSA-N 4-(cyanoamino)butylcyanamide Chemical compound N#CNCCCCNC#N IIEPAQNLXCHENX-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-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
- IFCUMEVTYOQGOA-UHFFFAOYSA-N 5-(cyanoamino)pentylcyanamide Chemical compound N#CNCCCCCNC#N IFCUMEVTYOQGOA-UHFFFAOYSA-N 0.000 description 1
- PLHYQJABEPDNHQ-UHFFFAOYSA-N 6-(cyanoamino)hexylcyanamide Chemical compound N#CNCCCCCCNC#N PLHYQJABEPDNHQ-UHFFFAOYSA-N 0.000 description 1
- QBBYWGSMDRMCGB-UHFFFAOYSA-N 8-(cyanoamino)octylcyanamide Chemical compound N#CNCCCCCCCCNC#N QBBYWGSMDRMCGB-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- MVDLYCMTGZZSJE-UHFFFAOYSA-N C1=CC=CC2=CC(NC#N)=CC(NC#N)=C21 Chemical compound C1=CC=CC2=CC(NC#N)=CC(NC#N)=C21 MVDLYCMTGZZSJE-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 241001077660 Molo Species 0.000 description 1
- PVGDIWOPRJBVFE-UHFFFAOYSA-N N#CNC1=CC=CC(C2N=CN(O2)C=2C=C(NC#N)C=CC=2)=C1 Chemical compound N#CNC1=CC=CC(C2N=CN(O2)C=2C=C(NC#N)C=CC=2)=C1 PVGDIWOPRJBVFE-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- HFDDMEQYUSCTJR-UHFFFAOYSA-N NC#N.NC#N.O=S(=O)NC#N Chemical compound NC#N.NC#N.O=S(=O)NC#N HFDDMEQYUSCTJR-UHFFFAOYSA-N 0.000 description 1
- UHRQYOQWVRQRFP-UHFFFAOYSA-N NC1=CC=C(C=C1)N(C#N)S(=O)(=O)C1=CC=CC=C1 Chemical compound NC1=CC=C(C=C1)N(C#N)S(=O)(=O)C1=CC=CC=C1 UHRQYOQWVRQRFP-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- IBXMOMOXCGRRCN-UHFFFAOYSA-N [2,3,5,6-tetrachloro-4-(cyanoamino)phenyl]cyanamide Chemical compound ClC1=C(Cl)C(NC#N)=C(Cl)C(Cl)=C1NC#N IBXMOMOXCGRRCN-UHFFFAOYSA-N 0.000 description 1
- HTOLFRCANOURFU-UHFFFAOYSA-N [2,5-dichloro-4-(cyanoamino)phenyl]cyanamide Chemical compound ClC1=CC(NC#N)=C(Cl)C=C1NC#N HTOLFRCANOURFU-UHFFFAOYSA-N 0.000 description 1
- NZFTUZMJJYOVNO-UHFFFAOYSA-N [3-[2-[4-[3-(cyanoamino)phenyl]-1,3-thiazol-2-yl]-1,3-thiazol-4-yl]phenyl]cyanamide Chemical compound N#CNC1=CC=CC(C=2N=C(SC=2)C=2SC=C(N=2)C=2C=C(NC#N)C=CC=2)=C1 NZFTUZMJJYOVNO-UHFFFAOYSA-N 0.000 description 1
- ZSFYOSKHMYVISE-UHFFFAOYSA-N [3-[4-[3-(cyanoamino)benzoyl]benzoyl]phenyl]cyanamide Chemical compound C=1C=CC(NC#N)=CC=1C(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC(NC#N)=C1 ZSFYOSKHMYVISE-UHFFFAOYSA-N 0.000 description 1
- NCTUSJJBCXNKRH-UHFFFAOYSA-N [4-(cyanoamino)phenyl]cyanamide Chemical compound N#CNC1=CC=C(NC#N)C=C1 NCTUSJJBCXNKRH-UHFFFAOYSA-N 0.000 description 1
- GLWYSUIDERVEKD-UHFFFAOYSA-N [4-[bis[4-(cyanoamino)phenyl]methyl]phenyl]cyanamide Chemical compound C1=CC(NC#N)=CC=C1C(C=1C=CC(NC#N)=CC=1)C1=CC=C(NC#N)C=C1 GLWYSUIDERVEKD-UHFFFAOYSA-N 0.000 description 1
- QUSGJXIGAHUQFY-UHFFFAOYSA-N [5-(cyanoamino)-2,4-dimethylphenyl]cyanamide Chemical compound CC1=CC(C)=C(NC#N)C=C1NC#N QUSGJXIGAHUQFY-UHFFFAOYSA-N 0.000 description 1
- FVYIPPJHUPSTRP-UHFFFAOYSA-N [5-(cyanoamino)naphthalen-1-yl]cyanamide Chemical compound C1=CC=C2C(NC#N)=CC=CC2=C1NC#N FVYIPPJHUPSTRP-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002390 adhesive tape Substances 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
- 150000001408 amides Chemical group 0.000 description 1
- FZAQROFXYZPAKI-UHFFFAOYSA-N anthracene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC3=CC(S(=O)(=O)Cl)=CC=C3C=C21 FZAQROFXYZPAKI-UHFFFAOYSA-N 0.000 description 1
- YEXFZSQAFQDJNW-UHFFFAOYSA-N benzene-1,3-disulfonyl bromide Chemical compound BrS(=O)(=O)C1=CC=CC(S(Br)(=O)=O)=C1 YEXFZSQAFQDJNW-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000004414 compression moulding compound Substances 0.000 description 1
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- MLDIQLUICYAELK-UHFFFAOYSA-N cyclohexane-1,1-disulfonyl chloride Chemical compound ClS(=O)(=O)C1(S(Cl)(=O)=O)CCCCC1 MLDIQLUICYAELK-UHFFFAOYSA-N 0.000 description 1
- MJWVCJUSRGLHFO-UHFFFAOYSA-N cyclohexanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CCCCC1 MJWVCJUSRGLHFO-UHFFFAOYSA-N 0.000 description 1
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- 238000000354 decomposition reaction Methods 0.000 description 1
- UHIUDPGIHAIJSV-UHFFFAOYSA-N dibenzothiophene-3,6-disulfonyl chloride Chemical compound C1=CC=C2C3=CC=C(S(=O)(=O)Cl)C=C3SC2=C1S(Cl)(=O)=O UHIUDPGIHAIJSV-UHFFFAOYSA-N 0.000 description 1
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- DKZQZHQHDMVGHE-UHFFFAOYSA-N methanedisulfonyl chloride Chemical compound ClS(=O)(=O)CS(Cl)(=O)=O DKZQZHQHDMVGHE-UHFFFAOYSA-N 0.000 description 1
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- RMLAGGOREOLNCP-UHFFFAOYSA-N n-[4-[[4-[benzenesulfonyl(cyano)amino]phenyl]methyl]phenyl]-n-cyanobenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(C#N)C(C=C1)=CC=C1CC(C=C1)=CC=C1N(C#N)S(=O)(=O)C1=CC=CC=C1 RMLAGGOREOLNCP-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BCXWMIMRDMIJGL-UHFFFAOYSA-N naphthalene-1,5-disulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1S(Cl)(=O)=O BCXWMIMRDMIJGL-UHFFFAOYSA-N 0.000 description 1
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- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- WIVNTNLDTMNDNO-UHFFFAOYSA-N octane-1-sulfonyl chloride Chemical compound CCCCCCCCS(Cl)(=O)=O WIVNTNLDTMNDNO-UHFFFAOYSA-N 0.000 description 1
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- 238000002103 osmometry Methods 0.000 description 1
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 229960000368 sulisobenzone Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
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- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
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- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
- B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
- B32B5/26—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it also being fibrous or filamentary
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
- B32B5/024—Woven fabric
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
- C08G73/0655—Preparatory processes from polycyanurates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B38/00—Ancillary operations in connection with laminating processes
- B32B2038/0052—Other operations not otherwise provided for
- B32B2038/0076—Curing, vulcanising, cross-linking
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/02—Synthetic macromolecular fibres
- B32B2262/0261—Polyamide fibres
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2305/00—Condition, form or state of the layers or laminate
- B32B2305/07—Parts immersed or impregnated in a matrix
- B32B2305/076—Prepregs
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2305/00—Condition, form or state of the layers or laminate
- B32B2305/72—Cured, e.g. vulcanised, cross-linked
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/901—Printed circuit
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2861—Coated or impregnated synthetic organic fiber fabric
- Y10T442/2893—Coated or impregnated polyamide fiber fabric
- Y10T442/2902—Aromatic polyamide fiber fabric
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2926—Coated or impregnated inorganic fiber fabric
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2926—Coated or impregnated inorganic fiber fabric
- Y10T442/2984—Coated or impregnated carbon or carbonaceous fiber fabric
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2926—Coated or impregnated inorganic fiber fabric
- Y10T442/2992—Coated or impregnated glass fiber fabric
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/439,487 US3944526A (en) | 1974-02-04 | 1974-02-04 | N-cyanosulfonamide resins and intermediates therefor and products thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2504046A1 true DE2504046A1 (de) | 1975-08-07 |
Family
ID=23744898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752504046 Ceased DE2504046A1 (de) | 1974-02-04 | 1975-01-31 | N-cyanosulfonamidharze und zwischenprodukte fuer diese und produkte daraus |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3944526A (en, 2012) |
| JP (6) | JPS5848571B2 (en, 2012) |
| BE (1) | BE825103A (en, 2012) |
| CA (1) | CA1066719A (en, 2012) |
| DD (2) | DD122816A5 (en, 2012) |
| DE (1) | DE2504046A1 (en, 2012) |
| ES (1) | ES434403A1 (en, 2012) |
| FR (2) | FR2272988B1 (en, 2012) |
| GB (2) | GB1493481A (en, 2012) |
| IT (1) | IT1031425B (en, 2012) |
| NL (1) | NL7501317A (en, 2012) |
| SU (1) | SU627751A3 (en, 2012) |
| ZA (1) | ZA75680B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2745521A1 (de) * | 1976-10-12 | 1978-04-13 | Ciba-Geigy Ag, Basel | N-cyansulfonamidharze und zwischenprodukte fuer diese und produkte daraus |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075185A (en) * | 1976-02-26 | 1978-02-21 | Ciba-Geigy Corporation | N-cyanosulfonamide resins and intermediates therefor and products thereof |
| US4383107A (en) * | 1980-08-28 | 1983-05-10 | Ciba-Geigy Corporation | Mixture containing N-cyanolactam for the preparation of nitrogen-containing polyadducts |
| JPS5879017A (ja) * | 1981-11-04 | 1983-05-12 | Hitachi Ltd | イソメラミン環を有するポリマ |
| JPH07120858B2 (ja) * | 1990-03-30 | 1995-12-20 | 株式会社日立製作所 | 多層プリント回路板およびその製造方法 |
| US5705689A (en) * | 1995-06-19 | 1998-01-06 | Associated Universities, Inc. | Aza compounds as anion receptors |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2531468A (en) * | 1949-04-14 | 1950-11-28 | Eastman Kodak Co | Polyvinyl sulfonates and process for their preparation |
| US2853475A (en) * | 1954-04-30 | 1958-09-23 | Du Pont | Nu-chlorinated polysulfonamides |
| USRE24691E (en) * | 1955-02-21 | 1959-08-25 | Process for forming films and filaments | |
| US3308101A (en) * | 1963-09-24 | 1967-03-07 | Du Pont | Novel polymeric materials |
| DE1595698C3 (de) * | 1966-12-05 | 1974-08-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Sulfonsäureamidgruppen enthaltenden Acrylnitril mischpolymeren |
| US3654192A (en) * | 1968-08-19 | 1972-04-04 | Minnesota Mining & Mfg | Poly(arylene s-triazines) |
| GB1320683A (en) * | 1969-09-29 | 1973-06-20 | Ici Ltd | Organic cyanamides |
| US3729453A (en) * | 1970-10-30 | 1973-04-24 | Celanese Corp | Process for the preparation of polyamidoximes and polybenzimidazole (pbi)type polymers derived therefrom |
-
1974
- 1974-02-04 US US05/439,487 patent/US3944526A/en not_active Expired - Lifetime
-
1975
- 1975-01-28 CA CA218,803A patent/CA1066719A/en not_active Expired
- 1975-01-31 DE DE19752504046 patent/DE2504046A1/de not_active Ceased
- 1975-02-03 ZA ZA00750680A patent/ZA75680B/xx unknown
- 1975-02-03 DD DD18396575A patent/DD122816A5/xx unknown
- 1975-02-03 FR FR7503226A patent/FR2272988B1/fr not_active Expired
- 1975-02-03 BE BE152986A patent/BE825103A/xx unknown
- 1975-02-03 DD DD18970375A patent/DD125641A5/xx unknown
- 1975-02-03 IT IT1990975A patent/IT1031425B/it active
- 1975-02-03 ES ES434403A patent/ES434403A1/es not_active Expired
- 1975-02-04 JP JP50014784A patent/JPS5848571B2/ja not_active Expired
- 1975-02-04 NL NL7501317A patent/NL7501317A/xx not_active Application Discontinuation
- 1975-02-04 SU SU752104243A patent/SU627751A3/ru active
- 1975-02-04 GB GB475275A patent/GB1493481A/en not_active Expired
- 1975-02-04 GB GB451077A patent/GB1493799A/en not_active Expired
- 1975-06-26 FR FR7520033A patent/FR2279792A1/fr active Granted
-
1982
- 1982-09-29 JP JP57170779A patent/JPS5946978B2/ja not_active Expired
- 1982-09-29 JP JP57170780A patent/JPS5946979B2/ja not_active Expired
- 1982-09-29 JP JP57170777A patent/JPS60342B2/ja not_active Expired
- 1982-09-29 JP JP57170778A patent/JPS60343B2/ja not_active Expired
-
1983
- 1983-03-07 JP JP58037228A patent/JPS5946980B2/ja not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| J. Polymer Sci., T. A-1, Bd. 4, 1966, S.1689-1702 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2745521A1 (de) * | 1976-10-12 | 1978-04-13 | Ciba-Geigy Ag, Basel | N-cyansulfonamidharze und zwischenprodukte fuer diese und produkte daraus |
| US4150051A (en) * | 1976-10-12 | 1979-04-17 | Ciba-Geigy Corporation | N-Cyanosulfonamide compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DD122816A5 (en, 2012) | 1976-11-05 |
| US3944526A (en) | 1976-03-16 |
| JPS5946978B2 (ja) | 1984-11-16 |
| JPS5946980B2 (ja) | 1984-11-16 |
| FR2279792A1 (fr) | 1976-02-20 |
| JPS58154552A (ja) | 1983-09-14 |
| GB1493481A (en) | 1977-11-30 |
| DD125641A5 (en, 2012) | 1977-05-04 |
| NL7501317A (nl) | 1975-08-06 |
| ES434403A1 (es) | 1976-11-16 |
| JPS5848571B2 (ja) | 1983-10-29 |
| JPS58154727A (ja) | 1983-09-14 |
| CA1066719A (en) | 1979-11-20 |
| JPS5915429A (ja) | 1984-01-26 |
| FR2272988B1 (en, 2012) | 1977-11-18 |
| SU627751A3 (ru) | 1978-10-05 |
| GB1493799A (en) | 1977-11-30 |
| AU7689074A (en) | 1976-07-01 |
| JPS58154726A (ja) | 1983-09-14 |
| JPS60342B2 (ja) | 1985-01-07 |
| FR2272988A1 (en, 2012) | 1975-12-26 |
| IT1031425B (it) | 1979-04-30 |
| JPS50116422A (en, 2012) | 1975-09-11 |
| BE825103A (fr) | 1975-08-04 |
| JPS60343B2 (ja) | 1985-01-07 |
| ZA75680B (en) | 1976-01-28 |
| FR2279792B1 (en, 2012) | 1979-08-03 |
| JPS5946979B2 (ja) | 1984-11-16 |
| JPS58154551A (ja) | 1983-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |