DE1670852C3 - 5-Arylotriazolyl-2-styrylbenzotriazole - Google Patents
5-Arylotriazolyl-2-styrylbenzotriazoleInfo
- Publication number
- DE1670852C3 DE1670852C3 DE1670852A DEF0052141A DE1670852C3 DE 1670852 C3 DE1670852 C3 DE 1670852C3 DE 1670852 A DE1670852 A DE 1670852A DE F0052141 A DEF0052141 A DE F0052141A DE 1670852 C3 DE1670852 C3 DE 1670852C3
- Authority
- DE
- Germany
- Prior art keywords
- benzotriazole
- styryl
- amino
- nitro
- triazolyl
- 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 carbalkoxy Chemical group 0.000 description 18
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000001425 triazolyl group Chemical group 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- SOFYFIBKFHFLKU-UHFFFAOYSA-N 2-(2-phenylethenyl)benzotriazol-5-amine Chemical class N1=C2C=C(N)C=CC2=NN1C=CC1=CC=CC=C1 SOFYFIBKFHFLKU-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- RIZYFIIEOHPUDL-UHFFFAOYSA-N 2-(5-nitrobenzotriazol-2-yl)acetic acid Chemical compound [N+](=O)([O-])C1=CC=2C(=NN(N2)CC(=O)O)C=C1 RIZYFIIEOHPUDL-UHFFFAOYSA-N 0.000 description 3
- CUOXAAKIJVGSNH-UHFFFAOYSA-N 4-[2-[2-(aminodiazenyl)phenyl]ethenyl]-2H-benzotriazole Chemical class NN=NC1=C(C=CC2=CC=CC=3NN=NC32)C=CC=C1 CUOXAAKIJVGSNH-UHFFFAOYSA-N 0.000 description 3
- SWGKVHBMCWCGHR-UHFFFAOYSA-N 5-nitro-2-(2-phenylethenyl)benzotriazole Chemical class N1=C2C=C([N+](=O)[O-])C=CC2=NN1C=CC1=CC=CC=C1 SWGKVHBMCWCGHR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- AAEVMKKTMHTITR-UHFFFAOYSA-N 3-butoxy-4-methylaniline Chemical compound CCCCOC1=CC(N)=CC=C1C AAEVMKKTMHTITR-UHFFFAOYSA-N 0.000 description 2
- ONADZNBSLRAJFW-UHFFFAOYSA-N 3-methoxy-4-methylaniline Chemical compound COC1=CC(N)=CC=C1C ONADZNBSLRAJFW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 2
- AOCDQWRMYHJTMY-UHFFFAOYSA-N 5-nitro-2h-benzotriazole Chemical compound C1=C([N+](=O)[O-])C=CC2=NNN=C21 AOCDQWRMYHJTMY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000003935 benzaldehydes Chemical class 0.000 description 2
- 238000005282 brightening Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- GKBPPXZGWXQPEY-UHFFFAOYSA-N 3-dodecoxy-4-methylaniline Chemical compound CCCCCCCCCCCCOC1=CC(N)=CC=C1C GKBPPXZGWXQPEY-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
- PSVPUHBSBYJSMQ-UHFFFAOYSA-N 4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1 PSVPUHBSBYJSMQ-UHFFFAOYSA-N 0.000 description 1
- JEUAWMJVEYFVNJ-UHFFFAOYSA-N 5-Aminoacenaphthene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3N JEUAWMJVEYFVNJ-UHFFFAOYSA-N 0.000 description 1
- MJWDIGUUVRCTFY-UHFFFAOYSA-N 6-methoxynaphthalen-2-amine Chemical compound C1=C(N)C=CC2=CC(OC)=CC=C21 MJWDIGUUVRCTFY-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- DKVLFALBQQNIRZ-UHFFFAOYSA-N CCCCOC1=CC2=NN(C3=CC4=NN(C=CC5=CC=CC=C5)N=C4C=C3)N=C2C=C1C Chemical compound CCCCOC1=CC2=NN(C3=CC4=NN(C=CC5=CC=CC=C5)N=C4C=C3)N=C2C=C1C DKVLFALBQQNIRZ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- BJPRVYBGBYAMLN-UHFFFAOYSA-N NC1=CC=2C(=NN(N2)C=CC2=CC=C(C=C2)C)C=C1 Chemical compound NC1=CC=2C(=NN(N2)C=CC2=CC=C(C=C2)C)C=C1 BJPRVYBGBYAMLN-UHFFFAOYSA-N 0.000 description 1
- JAVAKSSVPGYMOV-UHFFFAOYSA-N NC1=CC=2C(=NN(N2)C=CC2=CC=C(C=C2)OC)C=C1 Chemical compound NC1=CC=2C(=NN(N2)C=CC2=CC=C(C=C2)OC)C=C1 JAVAKSSVPGYMOV-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- XZXAWFISELBNCW-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=2C(=NN(N=2)C=CC2=CC=C(C=C2)C)C=C1 Chemical compound [N+](=O)([O-])C1=CC=2C(=NN(N=2)C=CC2=CC=C(C=C2)C)C=C1 XZXAWFISELBNCW-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- BHYVHYPBRYOMGC-UHFFFAOYSA-N ethyl 4-formylbenzoate Chemical compound CCOC(=O)C1=CC=C(C=O)C=C1 BHYVHYPBRYOMGC-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 230000002087 whitening effect Effects 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/22—Naphthotriazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1670852A DE1670852C3 (de) | 1967-04-17 | 1967-04-17 | 5-Arylotriazolyl-2-styrylbenzotriazole |
| US719722A US3595859A (en) | 1967-04-17 | 1968-04-08 | 5-arylotriazolyl-2-styryl-benzotriazoles |
| GB07332/68A GB1163890A (en) | 1967-04-17 | 1968-04-10 | 5-(Arylotriazolyl-2')-2-styryl-benzotriazoles |
| NL6805333A NL6805333A (en:Method) | 1967-04-17 | 1968-04-16 | |
| CH564868A CH491239A (de) | 1967-04-17 | 1968-04-17 | Verwendung von 5-Arylotriazolyl-2-styryl-benzotriazolen zum optischen Aufhellen von Textilmaterialien aus Kunstfasern |
| AT03737/68A AT284772B (de) | 1967-04-17 | 1968-04-17 | Aufhellungsmittel |
| BE713811D BE713811A (en:Method) | 1967-04-17 | 1968-04-17 | |
| FR1568419D FR1568419A (en:Method) | 1967-04-17 | 1968-04-17 | |
| CH564868D CH564868A4 (en:Method) | 1967-04-17 | 1968-04-17 | |
| CH1440469A CH481929A (de) | 1967-04-17 | 1968-04-17 | Verfahren zur Herstellung von 5-Arylotriazolyl-2-styrylbenzotriazolen und deren Verwendung als optische Aufhellungsmittel für synthetische Materialien, mit Ausnahme der Behandlung von Textilmaterialien in der Textilindustrie |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1670852A DE1670852C3 (de) | 1967-04-17 | 1967-04-17 | 5-Arylotriazolyl-2-styrylbenzotriazole |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1670852A1 DE1670852A1 (de) | 1971-03-25 |
| DE1670852B2 DE1670852B2 (de) | 1977-11-17 |
| DE1670852C3 true DE1670852C3 (de) | 1978-07-06 |
Family
ID=7105207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1670852A Expired DE1670852C3 (de) | 1967-04-17 | 1967-04-17 | 5-Arylotriazolyl-2-styrylbenzotriazole |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3595859A (en:Method) |
| AT (1) | AT284772B (en:Method) |
| BE (1) | BE713811A (en:Method) |
| CH (2) | CH491239A (en:Method) |
| DE (1) | DE1670852C3 (en:Method) |
| FR (1) | FR1568419A (en:Method) |
| GB (1) | GB1163890A (en:Method) |
| NL (1) | NL6805333A (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH587831A5 (en:Method) * | 1973-05-17 | 1977-05-13 | Sandoz Ag | |
| US4070339A (en) * | 1976-08-16 | 1978-01-24 | Eastman Kodak Company | Bichromophoric benzotriazole-styrene ester ultraviolet stabilizers and their use in organic compositions |
| DE3800074A1 (de) * | 1988-01-05 | 1989-07-13 | Helmut Dipl Ing Roehser | Verfahren zur verbesserung weisser, grauer oder geringfuegig eingefaerbter ersatzhaare aus polyester |
| KR102639587B1 (ko) | 2018-01-03 | 2024-02-21 | 에코랍 유에스에이 인코퍼레이티드 | 부식 억제제로서의 벤조트리아졸 유도체 |
-
1967
- 1967-04-17 DE DE1670852A patent/DE1670852C3/de not_active Expired
-
1968
- 1968-04-08 US US719722A patent/US3595859A/en not_active Expired - Lifetime
- 1968-04-10 GB GB07332/68A patent/GB1163890A/en not_active Expired
- 1968-04-16 NL NL6805333A patent/NL6805333A/xx unknown
- 1968-04-17 AT AT03737/68A patent/AT284772B/de not_active IP Right Cessation
- 1968-04-17 CH CH564868A patent/CH491239A/de not_active IP Right Cessation
- 1968-04-17 FR FR1568419D patent/FR1568419A/fr not_active Expired
- 1968-04-17 BE BE713811D patent/BE713811A/xx unknown
- 1968-04-17 CH CH564868D patent/CH564868A4/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH491239A (de) | 1970-02-13 |
| GB1163890A (en) | 1969-09-10 |
| FR1568419A (en:Method) | 1969-05-23 |
| BE713811A (en:Method) | 1968-09-16 |
| NL6805333A (en:Method) | 1968-10-18 |
| CH564868A4 (en:Method) | 1970-02-13 |
| US3595859A (en) | 1971-07-27 |
| AT284772B (de) | 1970-09-25 |
| DE1670852A1 (de) | 1971-03-25 |
| DE1670852B2 (de) | 1977-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |