CH615922A5 - Preparation of bis(triazolyl)stilbene compounds and their use - Google Patents

Preparation of bis(triazolyl)stilbene compounds and their use Download PDF

Info

Publication number: CH615922A5
Authority: CH; Switzerland
Prior art keywords: compounds; formula; groups; alkyl; coom
Prior art date: 1974-08-14

Application number

CH986575A

Other languages

German (de)

English (en)

Inventor

Fritz Fleck

Alec Victor Mercer

Roger Paver

Original Assignee

Sandoz Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-08-14

Filing date

1975-07-29

Publication date

1980-02-29

1975-07-29 Application filed by Sandoz Ag filed Critical Sandoz Ag

1980-02-29 Publication of CH615922A5 publication Critical patent/CH615922A5/de

Links

238000002360 preparation method Methods 0.000 title claims description 8
UIACIUMOCZUZSC-UHFFFAOYSA-N 4-[1,2-diphenyl-2-(2h-triazol-4-yl)ethenyl]-2h-triazole Chemical class C1=NNN=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=NNN=C1 UIACIUMOCZUZSC-UHFFFAOYSA-N 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
230000003287 optical effect Effects 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
239000000758 substrate Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
238000005282 brightening Methods 0.000 claims description 7
150000001768 cations Chemical class 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000000129 anionic group Chemical group 0.000 claims description 5
239000004952 Polyamide Substances 0.000 claims description 4
229920002647 polyamide Polymers 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 3
239000001913 cellulose Substances 0.000 claims description 3
229920002678 cellulose Polymers 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
239000004753 textile Substances 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000003852 triazoles Chemical group 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
-1 Ci-4-alkyl Chemical group 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
239000000243 solution Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000004744 fabric Substances 0.000 description 9
239000011734 sodium Substances 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
239000012265 solid product Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229920003002 synthetic resin Polymers 0.000 description 5
239000000057 synthetic resin Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
239000004677 Nylon Substances 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
229920001778 nylon Polymers 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
239000005695 Ammonium acetate Substances 0.000 description 3
229920001095 Ban-Lon Polymers 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229920002302 Nylon 6,6 Polymers 0.000 description 3
235000019257 ammonium acetate Nutrition 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000004552 water soluble powder Substances 0.000 description 3
229940093475 2-ethoxyethanol Drugs 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
229910006074 SO2NH2 Inorganic materials 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 2
229960002218 sodium chlorite Drugs 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007858 starting material Substances 0.000 description 2
ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
FHTGJZOULSYEOB-UHFFFAOYSA-N 2,6-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC=CC(C(C)CC)=C1O FHTGJZOULSYEOB-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
SIXNZOAVAZCXJE-UHFFFAOYSA-N O.O.[S-][S-].[Na+].[Na+] Chemical compound O.O.[S-][S-].[Na+].[Na+] SIXNZOAVAZCXJE-UHFFFAOYSA-N 0.000 description 1
229920000388 Polyphosphate Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
239000004745 nonwoven fabric Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Compositions Of Macromolecular Compounds (AREA)
Detergent Compositions (AREA)

CH986575A 1974-08-14 1975-07-29 Preparation of bis(triazolyl)stilbene compounds and their use CH615922A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB35746/74A GB1520633A (en)	1974-08-14	1974-08-14	Triazolyl stilbene derivatives

Publications (1)

Publication Number	Publication Date
CH615922A5 true CH615922A5 (en)	1980-02-29

Family

ID=10381119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH986575A CH615922A5 (en)	1974-08-14	1975-07-29	Preparation of bis(triazolyl)stilbene compounds and their use

Country Status (11)

Country	Link
JP (1)	JPS5145124A (fr)
AR (1)	AR208561A1 (fr)
BE (1)	BE832368A (fr)
BR (1)	BR7505164A (fr)
CH (1)	CH615922A5 (fr)
DE (1)	DE2535069A1 (fr)
ES (1)	ES440189A1 (fr)
FR (1)	FR2281929A1 (fr)
GB (1)	GB1520633A (fr)
IT (1)	IT1041832B (fr)
NL (1)	NL7509475A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3041199A1 (de) *	1979-11-14	1981-05-21	Sandoz-Patent-GmbH, 7850 Lörrach	Neue stilbenverbindungen, deren herstellung und verwendung

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH603601A5 (fr) *	1973-05-17	1978-08-31	Sandoz Ag

1974
- 1974-08-14 GB GB35746/74A patent/GB1520633A/en not_active Expired
1975
- 1975-07-29 CH CH986575A patent/CH615922A5/de not_active IP Right Cessation
- 1975-08-06 DE DE19752535069 patent/DE2535069A1/de not_active Withdrawn
- 1975-08-08 NL NL7509475A patent/NL7509475A/xx unknown
- 1975-08-12 FR FR7525030A patent/FR2281929A1/fr active Granted
- 1975-08-12 AR AR259976A patent/AR208561A1/es active
- 1975-08-12 ES ES440189A patent/ES440189A1/es not_active Expired
- 1975-08-12 BE BE159149A patent/BE832368A/fr unknown
- 1975-08-12 JP JP50098009A patent/JPS5145124A/ja active Pending
- 1975-08-13 BR BR7505164*A patent/BR7505164A/pt unknown
- 1975-08-13 IT IT26328/75A patent/IT1041832B/it active

Also Published As

Publication number	Publication date
BE832368A (fr)	1976-02-12
IT1041832B (it)	1980-01-10
FR2281929A1 (fr)	1976-03-12
GB1520633A (en)	1978-08-09
AR208561A1 (es)	1977-02-15
BR7505164A (pt)	1976-08-03
NL7509475A (nl)	1976-02-17
JPS5145124A (en)	1976-04-17
ES440189A1 (es)	1977-06-01
DE2535069A1 (de)	1976-02-26
FR2281929B1 (fr)	1979-05-25

Legal Events

Date	Code	Title	Description
1983-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0038296B1 (fr)	1984-05-09	Composés disazoiques
DE1805371C3 (de)	1979-02-08	Bis-v-triazol-sryrolderivate, Verfahren zu deren Herstellung sowie deren Anwendung als optische Aufheller
DE1923267A1 (de)	1970-11-19	Sulfonsaeuregruppenhaltige optische Aufheller der Bis-styryl-benzolreihe
DE1470242B2 (de)	1977-12-08	7-arenotriazolyl-3-phenyl-cumarine, deren herstellung und verwendung
DE2921641C2 (fr)	1988-03-10
DE2142564C3 (de)	1980-06-19	3- eckige klammer auf 3',4'- dichlor-6' -alkyl-phenyl eckige klammer zu - delta 2-pyrazolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als optische aufheller
DE1105375B (de)	1961-04-27	Optische Aufheller
CH439563A (de)	1967-07-15	Einrichtung zur Steuerung und Überwachung des Zündvorganges an einem Gebläsebrenner
DE2535069A1 (de)	1976-02-26	Organische verbindungen, deren herstellung und verwendung
DE943075C (de)	1956-05-09	Verfahren zur Herstellung von neuen Disazofarbstoffen und deren Metallkomplexverbindungen
DE2524927C3 (de)	1980-11-06	Organische Verbindungen, deren Herstellung und Verwendung
EP0026414B1 (fr)	1985-04-10	Composés monoazoiques solubles dans l'eau, leur préparation et leur utilisation comme colorants pour la teinture et l'impression de matières textiles, ainsi que les amines en soi
DE828986C (de)	1952-01-21	Verfahren zur Herstellung von optischen Aufhellungsmitteln
DE2133159A1 (de)	1973-01-18	Bis-1,2,4-triazolyl(5)-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als optische aufhellungsmittel
US4167626A (en)	1979-09-11	Triazolyl stilbene triazoles
DE2429168A1 (de)	1975-01-16	Pyrazolinverbindungen
DE937822C (de)	1956-01-19	Optische Bleichmittel
DE1802642B2 (de)	1979-07-12	Fluoreszierende 1- (PyrazolinylphenylsulfonyO-piperazine
AT235234B (de)	1964-08-10	Optische Aufhellungsmittel
DE1047163B (de)	1958-12-24	Optische Aufhellungsmittel
DE3041199A1 (de)	1981-05-21	Neue stilbenverbindungen, deren herstellung und verwendung
DE2434162A1 (de)	1975-02-06	Pyrazolinverbindungen
DE1719005C3 (de)	1976-11-04	2-(4'-Carboxystyryl)-benzoxazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als optische Aufheller
DE2129855A1 (de)	1971-12-23	Neue Styrole und ihre Verwendung als optische Aufheller
EP0502820A1 (fr)	1992-09-09	Nouveaux semi-carbazides et leur utilisation pour la stabilisation des fibres polyamides et leurs couleurs