CA1168655A - 2-[2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DI-METHYLBENZYL) PHENYL]-2H-BENZOTRIAZOLES ET SUBSTANCES STABLES - Google Patents

2-[2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DI-METHYLBENZYL) PHENYL]-2H-BENZOTRIAZOLES ET SUBSTANCES STABLES

Info

Publication number: CA1168655A
Authority: CA; Canada
Prior art keywords: alkyl; phenol; alpha; hydrogen; formula
Prior art date: 1978-06-26
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

Application number

CA000405938A

Other languages

English (en)

Inventor

Martin Dexter

Roland A. E. Winter

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1978-06-26

Filing date

1982-06-24

Publication date

1984-06-05

1978-06-26 Priority claimed from US05/918,984 external-priority patent/US4226763A/en

1982-06-24 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1982-06-24 Priority to CA000405938A priority Critical patent/CA1168655A/fr

1984-06-05 Application granted granted Critical

1984-06-05 Publication of CA1168655A publication Critical patent/CA1168655A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title description 10
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 30
239000000243 solution Substances 0.000 claims abstract description 30
-1 hydroxyl ions Chemical class 0.000 claims abstract description 25
239000012954 diazonium Substances 0.000 claims abstract description 19
238000000034 method Methods 0.000 claims abstract description 17
230000008569 process Effects 0.000 claims abstract description 14
150000001989 diazonium salts Chemical class 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 13
238000006243 chemical reaction Methods 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 10
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 7
239000007864 aqueous solution Substances 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 7
150000001412 amines Chemical class 0.000 claims abstract description 4
230000003472 neutralizing effect Effects 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
230000002829 reductive effect Effects 0.000 claims description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
VSJRBQDMBFFHMC-UHFFFAOYSA-N 5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound CCC1(C)NC(=O)NC1=O VSJRBQDMBFFHMC-UHFFFAOYSA-N 0.000 claims 2
229910006069 SO3H Inorganic materials 0.000 claims 1
UTLVQENMPIUJSJ-QTARTGBFSA-N dT10 Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 UTLVQENMPIUJSJ-QTARTGBFSA-N 0.000 claims 1
FZZMDWLROBNSRG-UHFFFAOYSA-N n-phenyliminonitramide Chemical compound [O-][N+](=O)N=NC1=CC=CC=C1 FZZMDWLROBNSRG-UHFFFAOYSA-N 0.000 claims 1
DSZOTMKIKJOOPG-UHFFFAOYSA-N (2-nitrophenyl)-phenyldiazene Chemical class [O-][N+](=O)C1=CC=CC=C1N=NC1=CC=CC=C1 DSZOTMKIKJOOPG-UHFFFAOYSA-N 0.000 abstract description 7
229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000005859 coupling reaction Methods 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
150000002989 phenols Chemical class 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000012043 crude product Substances 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
229910052725 zinc Inorganic materials 0.000 description 5
239000011701 zinc Substances 0.000 description 5
KMRSVJOEUGWWBX-UHFFFAOYSA-M 2-nitrobenzenediazonium;chloride Chemical compound [Cl-].[O-][N+](=O)C1=CC=CC=C1[N+]#N KMRSVJOEUGWWBX-UHFFFAOYSA-M 0.000 description 4
PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229960004592 isopropanol Drugs 0.000 description 4
239000002904 solvent Substances 0.000 description 4
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000004611 light stabiliser Substances 0.000 description 3
125000006606 n-butoxy group Chemical group 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
ZZNAYFWAXZJITH-UHFFFAOYSA-N 4-amino-3-nitrobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1[N+]([O-])=O ZZNAYFWAXZJITH-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
239000010408 film Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
DNYCICZKXQGHBJ-UHFFFAOYSA-N 2,4-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(C(C)(C)CC(C)(C)C)=C1 DNYCICZKXQGHBJ-UHFFFAOYSA-N 0.000 description 1
ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 1
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
RLMZELPHRPTNJX-UHFFFAOYSA-N 2,4-dioctylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(CCCCCCCC)=C1 RLMZELPHRPTNJX-UHFFFAOYSA-N 0.000 description 1
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
GTLMTHAWEBRMGI-UHFFFAOYSA-N 2-cyclohexyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C2CCCCC2)=C1 GTLMTHAWEBRMGI-UHFFFAOYSA-N 0.000 description 1
DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 description 1
AYTSDBGAHOKDHJ-UHFFFAOYSA-N 2-nitrobenzenediazonium Chemical class [O-][N+](=O)C1=CC=CC=C1[N+]#N AYTSDBGAHOKDHJ-UHFFFAOYSA-N 0.000 description 1
WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
FSGTULQLEVAYRS-UHFFFAOYSA-N 4,5-dichloro-2-nitroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O FSGTULQLEVAYRS-UHFFFAOYSA-N 0.000 description 1
BBELMWNCSCNWAO-UHFFFAOYSA-N 4-butoxy-2-nitroaniline Chemical compound CCCCOC1=CC=C(N)C([N+]([O-])=O)=C1 BBELMWNCSCNWAO-UHFFFAOYSA-N 0.000 description 1
AJDPAYNGRJNIDB-UHFFFAOYSA-M 4-chloro-2-nitrobenzenediazonium;chloride Chemical compound [Cl-].[O-][N+](=O)C1=CC(Cl)=CC=C1[N+]#N AJDPAYNGRJNIDB-UHFFFAOYSA-M 0.000 description 1
RUQAPQLDPWSAQM-UHFFFAOYSA-N 4-ethyl-2-nitroaniline Chemical compound CCC1=CC=C(N)C([N+]([O-])=O)=C1 RUQAPQLDPWSAQM-UHFFFAOYSA-N 0.000 description 1
BXMIALYGTOMKCD-UHFFFAOYSA-N 4-hydroxy-3-propylbenzoic acid Chemical compound CCCC1=CC(C(O)=O)=CC=C1O BXMIALYGTOMKCD-UHFFFAOYSA-N 0.000 description 1
MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
239000003513 alkali Substances 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
229940064734 aminobenzoate Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
150000001565 benzotriazoles Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000010409 thin film Substances 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000405938A 1978-06-26 1982-06-24 2-[2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DI-METHYLBENZYL) PHENYL]-2H-BENZOTRIAZOLES ET SUBSTANCES STABLES Expired CA1168655A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000405938A CA1168655A (fr)	1978-06-26	1982-06-24	2-[2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DI-METHYLBENZYL) PHENYL]-2H-BENZOTRIAZOLES ET SUBSTANCES STABLES

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US918,984		1978-06-26
US05/918,984 US4226763A (en)	1978-06-26	1978-06-26	2-[2-Hydroxy-3,5-di-(.alpha.,α-dimethylbenzyl)-phenyl]-2H-benzotriazole and stabilized compositions
CA000330477A CA1146948A (fr)	1978-06-26	1979-06-25	2-¬2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DIMETHYLBENZYL) PHENYL\|- 2H-BENZOTRIAZOLES ET COMPOSITIONS STABILISEES
CA000405938A CA1168655A (fr)	1978-06-26	1982-06-24	2-[2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DI-METHYLBENZYL) PHENYL]-2H-BENZOTRIAZOLES ET SUBSTANCES STABLES

Publications (1)

Publication Number	Publication Date
CA1168655A true CA1168655A (fr)	1984-06-05

Family

ID=27166305

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000405938A Expired CA1168655A (fr)	1978-06-26	1982-06-24	2-[2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DI-METHYLBENZYL) PHENYL]-2H-BENZOTRIAZOLES ET SUBSTANCES STABLES

Country Status (1)

Country	Link
CA (1)	CA1168655A (fr)

1982
- 1982-06-24 CA CA000405938A patent/CA1168655A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-06-05	MKEX	Expiry

Publication	Publication Date	Title
US4347180A (en)	1982-08-31	High caustic coupling process for preparing substituted 2-nitro-2'-hydroxyazobenzenes
US4275004A (en)	1981-06-23	High caustic coupling process for preparing substituted 2-nitro-2'-hydroxyazobenzenes
US4041044A (en)	1977-08-09	Process for the production of 2-aryl-2H-benzotriazoles
US6605727B2 (en)	2003-08-12	Processes for the preparation of benzotriazole UV absorbers
US4230867A (en)	1980-10-28	Process for the production of 2-aryl-2H-benzotriazoles
EP0130938B1 (fr)	1989-02-15	Procédé de préparation de 2-arylbenzotriazoles
CA1047500A (fr)	1979-01-30	Synthese industrielle de (hydroxyphenyl-2)-2 benzotriazoles
US4780541A (en)	1988-10-25	Method for preparing 2-phenylbenzotriazoles and 2-phenylbenzotriazole-N-oxides
CA1168655A (fr)	1984-06-05	2-[2-HYDROXY-3,5-DI-(.alpha.,.alpha.-DI-METHYLBENZYL) PHENYL]-2H-BENZOTRIAZOLES ET SUBSTANCES STABLES
JPH0236588B2 (fr)	1990-08-17
US5739348A (en)	1998-04-14	Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process
US4224451A (en)	1980-09-23	Process for the preparation of 2-aryl-2H-benzotriazoles
US4929771A (en)	1990-05-29	Process for the preparation of alkyl-substituted phenols or naphthols
CA1241659A (fr)	1988-09-06	Methode de preparation de 2-phenylbenzotriazole
US4918195A (en)	1990-04-17	Process for preparing triazoles fused with aromatic systems by reaction of o-arylenediamines with nitrites
EP0034836B1 (fr)	1983-07-13	Procédé de préparation de nitroazobenzènes
CA1145745A (fr)	1983-05-03	Methode de preparation de n,n-dimethyl-n- (2-bromo-4-methyl-phenyl)-triazene
US5436256A (en)	1995-07-25	Process for the preparation of arylhydantoins
US4549026A (en)	1985-10-22	Process for the preparation of condensed triazoles
US2981740A (en)	1961-04-25	Certificate of correction
US4354976A (en)	1982-10-19	Process for the preparation of azidobenzal compounds
JP2769178B2 (ja)	1998-06-25	２―フェニルベンゾトリアゾール類の製造法
EP0259530B1 (fr)	1992-04-08	Méthode pour la préparation de 2-phénylbenzotriazoles et de N-oxydes de 2-phénylbenzotriazoles
CA1154777A (fr)	1983-10-04	Methode d'obtention de 2-aryl-2h-benzotriazoles
JPS61218577A (ja)	1986-09-29	２−（２′−ヒドロキシフエニル）ベンゾトリアゾ−ル類の製造方法