GB774010A - Improvements relating to fluorescent stilbyl triazole compounds and to their use - Google Patents
Improvements relating to fluorescent stilbyl triazole compounds and to their useInfo
- Publication number
- GB774010A GB774010A GB29720/54A GB2972054A GB774010A GB 774010 A GB774010 A GB 774010A GB 29720/54 A GB29720/54 A GB 29720/54A GB 2972054 A GB2972054 A GB 2972054A GB 774010 A GB774010 A GB 774010A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulpho
- stilbyl
- prepared
- naphtho
- para
- 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
- -1 triazole compounds Chemical class 0.000 title abstract 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- 239000002253 acid Substances 0.000 abstract 8
- 125000001424 substituent group Chemical group 0.000 abstract 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003277 amino group Chemical group 0.000 abstract 5
- 125000004104 aryloxy group Chemical group 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- 230000008878 coupling Effects 0.000 abstract 4
- 238000010168 coupling process Methods 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 239000005977 Ethylene Substances 0.000 abstract 3
- 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 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- 229910052708 sodium Inorganic materials 0.000 abstract 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical class CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 abstract 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical class NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 abstract 2
- VFPLSXYJYAKZCT-UHFFFAOYSA-N 4-(2-phenylethenyl)aniline Chemical class C1=CC(N)=CC=C1C=CC1=CC=CC=C1 VFPLSXYJYAKZCT-UHFFFAOYSA-N 0.000 abstract 2
- BHOZTFDONSBGCM-UHFFFAOYSA-N 5-nitro-2-(2-phenylethenyl)benzenesulfonyl chloride Chemical compound [N+](=O)([O-])C1=CC(=C(C=C1)C=CC1=CC=CC=C1)S(=O)(=O)Cl BHOZTFDONSBGCM-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 abstract 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 abstract 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 150000003931 anilides Chemical class 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical class CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 2
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical class CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 abstract 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical class CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 abstract 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 abstract 2
- 125000003944 tolyl group Chemical group 0.000 abstract 2
- 150000003852 triazoles Chemical group 0.000 abstract 2
- ZISCOWXWCHUSMH-VOTSOKGWSA-N (E)-4-nitrostilbene Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C\C1=CC=CC=C1 ZISCOWXWCHUSMH-VOTSOKGWSA-N 0.000 abstract 1
- ZISCOWXWCHUSMH-UHFFFAOYSA-N 1-nitro-4-(2-phenylethenyl)benzene Chemical class C1=CC([N+](=O)[O-])=CC=C1C=CC1=CC=CC=C1 ZISCOWXWCHUSMH-UHFFFAOYSA-N 0.000 abstract 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- WPGVQDHXOUAJBW-UHFFFAOYSA-N 2-methyl-5-nitrobenzenesulfonyl chloride Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(Cl)(=O)=O WPGVQDHXOUAJBW-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 238000005282 brightening Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000001746 injection moulding Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- YIQJZVRKGSRPLF-UHFFFAOYSA-N phenyl 5-nitro-2-(2-phenylethenyl)benzenesulfonate Chemical compound C=1C=CC=CC=1OS(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1C=CC1=CC=CC=C1 YIQJZVRKGSRPLF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 235000010265 sodium sulphite Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- GKYQYVQDCHBZJM-UHFFFAOYSA-N stilbene 2H-triazole Chemical class N1N=NC=C1.C1(=CC=CC=C1)C=CC1=CC=CC=C1 GKYQYVQDCHBZJM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Polymers and copolymers of vinyl chloride, vinylidene chloride, acrylonitrile, acrylic esters, styrene and ethylene are brightened or whitened by preferably incorporating in the plasticisers therefor 2-(stilbyl-411)-(4 : 5-benzo- or naphtho-) 1 : 2 : 3-triazoles of formula <FORM:0774010/IV(a)/1> wherein A represents a benzene or naphthalene radical in which two vicinal carbon atoms are bound to nitrogen atoms of the triazole ring, at least one X represents a non-acid dissociating sulphonyl substituent -SO2R, R being an aryl, alkyl, aryloxy, amino or organically substituted amino group, and the other X's represent hydrogen or, with the exception of chromophores, hydroxyl and amino groups, any non-ionogenic substituent, and the aromatic radicals may be further substituted as required except by chromophores, auxochromes and other ionogenic substituents. Specified further substituents are halogens and alkyl, alkoxy, alkylenedioxy, aryloxy, phenyl, acylamino, cyano, carboxylic amide, -SO2R and 4 : 5-benzo- or naphtho-1 : 2 : 3-triazolyl-(2)-groups. Dioctyl phthalate is specified as a plasticiser. Exemplified stilbene-triazoles are phenyl, tolyl, xenyl, para-tert.-butylphenyl, para-tert.-amylphenyl-, para-n-octylphenyl, a -naphthyl and b -naphthyl esters and amides, dimethylamides, ethylamides, n-butylamides, di-n-butylamides, n-octylamides, n-decylamides, n-dodecylamides, n-hexadecylamides, n-octadecylamides, diethanolamides, aminoethylamides, diethylaminoethylamides, cyclohexylamides, dicyclohexylamides, anilides, benzylamides, N-methyl-anilides, (5-phenylsulphone-2-methyl)-anilides, 3-sulphamylamides, 4-sulphamylamides, a -naphthylamides, b -naphthylamides, a -N-ethylnaphthylamides, (41-amyl-diphenylether-2)-amides, morpholides, piperidides and 2-pyridylamides of 211-sulpho-, 2111-sulpho-, 4111-sulpho-, 211 : 51-disulpho-, 211 : 61-disulpho-, 211 : 51 : 7-trisulpho-, 31 - phenoxycarbonyl - 211 - sulpho -, 31 - cyclohexylcarbamoyl - 211 - sulpho -, 31 - ethylcarbamoyl - 211 - sulpho -, 211 - sulpho - 3111 : 4111-dimethoxy -, 211 - sulpho - 2111 : 3111 - dimeth oxy-, 211-sulpho-4111-phenoxy-, 211-sulpho-2111-methoxy-, 211-sulpho-3111-methoxy-, 211 : 2111-disulpho - 4111 - (naphtho - 11 : 21 : 4 : 5 - triazolyl - 2) - and 211 - sulpho - 3111 : 4111 - methylenedioxy - 2 - (stilbyl - 411) - (naphtho - 11 : 21 : 4 : 5) - 1 : 2 : 3 - triazoles and 5 - methoxy - 6 - methyl - 21 - sulpho -, 5 - acetamido - 21 - sulpho -, 5 - benzamido - 21 - sulpho -, 5 - methoxy - 6 - chloro-21-sulpho-and 5:6-dimethoxy-21-sulpho-2 - (stilbyl - 41) - 1:2:3 - benztriazoles; and 211 - methylsulphonyl-, 2111-methylsulphonyl-, 4111-methylsulphonyl-, 2111 - n - butylsulphonyl -, 4111 - n - butylsulphonyl -, 211-(2:4 - dimethylphenyl) - sulphonyl - and 211 - (4 - methylphenyl) - sulphonyl - 2 - (stilbyl - 411) - naphtho11:21:4:5)-1:2:3-triazoles. In examples: (1) sheets are made from a gelatinised mixture of polyvinyl chloride, dioctyl phthalate, di-n-butyldilauryldioxystannate, sodium penta-octyltripolyphosphate and stilbyl-triazole brightening-agent with or without titanium dioxide; (2) a mixture of polystyrene and stilbyl-triazole brightening agent is homogenized to give an injection moulding composition.ALSO:The invention comprises compounds of formula <FORM:0774010/IV(b)/1> wherein A represents a benzene or naphthalene radical in which two vicinal carbon atoms are bound to nitrogen atoms of the triazole ring, at least one X represents a non-acid dissociating sulphonyl substituent -SO2R, R being an aryl, alkyl, aryloxy, amino or organically substituted amino group, and the other X's represent hydrogen or, with the exception of chromophores, hydroxyl and amino groups, any non-ionogenic substituent, and the aromatic radicals may be further substituted as required except by chromophores, auxochromes and other ionogenic substituents. Specified further substituents are halogens and alkyl, alkoxy, alkylenedioxy, aryloxy, phenyl, acylamino, cyano, carboxylic amide, -SO2R and 4 : 5-benzo- or naphtho-1 : 2 : 3-triazolyl-(2)-groups. The compounds are prepared (1) by treating the corresponding sulphonic acids (in which R is OH in the above formula) with phosphorus halides to form the corresponding acid halides, which are then treated with ammonia or organic primary or secondary amines to form sulphonamides, with aromatic hydroxyl compounds or salts thereof to form aryl sulphonates, with aromatic hydrocarbons in presence of Friedel-Crafts catalysts to form aryl sulphones or are reduced to sulphinic acids and aralkylated or alkylated to form aralkyl or alkyl sulphones; (2) by coupling a diazotized 4-aminostilbene compound containing at least one -SO2R substituent in a position ortho or para to the ethylene bridge with a benzene or naphthalene azo component coupling in a position adjacent to an amino substituent, oxidizing the ortho-aminoazo dyestuff so formed with alkali hypochlorite or cupric tetrammine sulphate and eliminating or converting any inadmissible substituent introduced with the azo component. The examples describe the preparation of phenyl, tolyl, xenyl, para - tert. - butylphenyl, para - tert. - amylphenyl, para - n - octylphenyl, a - naphthyl and b -naphthyl esters and amides, ethylamides, dimethylamides, di - n - butylamides, n - butylamides, n-octylamides, n-decylamides, n-hexadecylamides, n - dodecylamides, n - octadecylamides, diethanolamides, aminoethylamides, diethylaminoethylamides, cyclohexylamides, dicyclohexylamides, anilides, benzylamides, N-methyl-anilides, (5-phenylsulphone-2-methyl)-anilides, 3-sulphamylanilides, 4-sulphamylanilides, a -naphthylamides, b -naphthylamides, a -N - ethylnaphthylamides, (41 - amyl - diphenylether - 2) - amides, morpholides, piperidides and 2-pyridylamides of 211-sulpho-, 2111-sulpho-, 4111-sulpho-, 211 : 51-disulpho-, 211 : 61-disulpho-, 211 : 51 : 71 - trisulpho-, 31 - phenoxycarbonyl - 211 - sulpho-, 31 - cyclohexylcarbamoyl - 211 sulpho -, 31 - ethylcarbamoyl - 211 - sulpho -, 211 - sulpho - 3111 : 4111 - dimethoxy-, 211-sulpho-2111 : 3111 - dimethoxy-, 211 - sulpho - 4111 - phenoxy-, 211 - sulpho - 2111 - methoxy -, 211 - sulpho-3111 - methoxy-, 211 : 2111 - disulpho - 4111 - (naphtho - 11 : 21 : 4 : 5 - triazolyl - 2) - and 211 - sulpho - 3111 : 4111 - methylenedioxy - 2 - (stilbyl - 411) - (naphtho - 11 : 21 : 4 : 5) - 1 : 2 : 3 - triazoles and 5 - methoxy - 6 - methyl - 21 - sulpho -, 5 - acetamido - 21 - sulpho -, 5-benzamido - 21 - sulpho -, 5 - methoxy - 6 - chloro - 21 - sulpho - and 5 : 6 - dimethoxy - 21 - sulpho - 2 - (stilbyl-41) - 1 : 2 : 3 - benztriazoles; and 211 - methylsulphonyl -, 2111 - methylsulphonyl -, 4111 - methylsulphonyl -, 2111 - n - butylsulphonyl -, 4111 - n - butylsulphonyl -, 211 - (2 : 4 - dimethylphenyl) - sulphonyl - and 211 - (4 - methylphenyl) - sulphonyl - 2 - (stilbyl - 411) - (naphtho - 11 : 21 : 4 : 5)-1 : 2 : 3-triazoles. Sodium 2 - (stilbyl - 411) - (naphtho - 11 : 21 4 : 5) - 1 : 2 : 3 - triazole - 4111 - sulphonate is prepared by a method similar to (2) above. The following intermediates are prepared by method (1) above : 211-chlorosulphonyl-, 4111 -chlorosulphonyl -, 51 : 211 - di - (chlorosulphonyl)-, 61 : 211 - di - (chlorosulphonyl)-, 3111 : 4111-dimethoxy -211 - chlorosulphonyl -, 2111 : 3111 - dimethoxy - 211 - chlorosulphonyl -, 4111 - phenoxy - 211 - chlorosulphonyl - and 31 - chlorocarbonyl - 211 - chlorosulphonyl - 2 - (stilbyl - 411) - naphtho - 11 : 211 : 4 : 5) - 1 : 2 : 3 - triazoles; and 5 - methoxy - 6 - methyl - 21 - chlorosulphonyl - 2 - (stilbyl - 41) - 1 : 2 : 3 - benztriazole. 4 - Nitro - 2 - chlorosulphonylstilbene and 4 - nitro - 211 - chlorosulphonylstilbene are prepared by treating the corresponding sulphonic acid sodium salts with phosphorus pentachloride. 2 - Phenylsulphamoyl-, 2 - (2 : 4 - dimethylphenyl) - sulphonyl -, 21 - dimethylsulphamoyl-, 21 - cyclohexylsulphamoyl -, 21 - morpholinosulphonyl-, 21 - di - n - butylsulphamoyl-, 21 - phenoxysulphonyl -, 21 - methylsulphonyl - and 41 - methylsulphonyl - 4 - aminostilbenes are prepared by reduction of the corresponding 4-nitrostilbenes. 4 - Nitrostilbene - 21 - sulphinic acid is formed as the sodium salt by treating 4-nitrostilbene-21-sulphonic acid chloride with a solution of sodium sulphite and sodium hydroxide. 2 - Phenylsulphamoyl -, 2 - di - n - butylsulphamoyl- and 21-dimethylsulphamoyl-4-nitrostilbenes are prepared by reacting the corresponding 4-nitrostilbene sulphonyl chlorides with an appropriate amine. 4 - Nitro - 2 - phenoxysulphonylstilbene is prepared by reacting 4-nitro-2-chlorosulphonylstilbene with a mixture of phenol and sodium hydroxide. 4 - Nitro - 21 - methylsulphonylstilbene is prepared by reacting sodium 4-nitrostilbene-21-sulphinate with a mixture of dimethyl sulphate and magnesium oxide. 4 - Nitro - 41 - methylsulphonylstilbene is prepared by condensing para-nitrophenyacetic acid with para - methylsulphonylbenzaldehyde. 3 - Nitro - 6 : 21 : 4 - trimethyl - 1 : 11 - diphenyl sulphone is prepared by condensing 4-nitrotoluene-2-sulphonic acid chloride with metaxylene in presence of ferric chloride. 4 - Nitro - 2 - (2 : 4 - dimethylphenyl) - sulphonyl-stilbene is prepared by condensing 3 - nitro - 6 : 21 : 41 - trimethyl - 1 : 11 - diphenylsulphone with benzaldehyde. Specifications 717,889 and 726,119 are referred to.ALSO:Ortho - aminoazo - stilbene dyestuffs are prepared by coupling diazotized 4 - aminostilbenes containing at least one sulphonic acid or non-acid dissociating sulphonyl substituent - SO2R, R being an aryl, alkyl, aryloxy, amino or organically substituted amino group, in an ortho - or para - position to the ethylene bridge, with azo components coupling adjacent to an amino substituent. Exemplified 4-aminostilbenes are 2 - sulpho -, 21 - sulpho, 41 - sulpho -, 2:21 - disulpho, 2 - phenoxysulphonyl-, 21-phenoxysulphonyl -, 41 - phenoxysulphonyl, 2:21 -
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH774010X | 1953-10-16 |
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| Publication Number | Publication Date |
|---|---|
| GB774010A true GB774010A (en) | 1957-05-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29720/54A Expired GB774010A (en) | 1953-10-16 | 1954-10-15 | Improvements relating to fluorescent stilbyl triazole compounds and to their use |
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| GB (1) | GB774010A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008510785A (en) * | 2004-08-27 | 2008-04-10 | メルク シャープ エンド ドーム リミテッド | Diaryl sulfones as 5-HT2A antagonists |
| CN108132221A (en) * | 2016-12-01 | 2018-06-08 | 中国科学院大连化学物理研究所 | A kind of method of total phenol content in detection water |
-
1954
- 1954-10-15 GB GB29720/54A patent/GB774010A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008510785A (en) * | 2004-08-27 | 2008-04-10 | メルク シャープ エンド ドーム リミテッド | Diaryl sulfones as 5-HT2A antagonists |
| CN108132221A (en) * | 2016-12-01 | 2018-06-08 | 中国科学院大连化学物理研究所 | A kind of method of total phenol content in detection water |
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