DE2112198C2 - 2-(3-Phenyl-7-cumarinyl)-v-triazole, Verfahren zu deren Herstellung und deren Verwendung als optische Aufheller - Google Patents
2-(3-Phenyl-7-cumarinyl)-v-triazole, Verfahren zu deren Herstellung und deren Verwendung als optische AufhellerInfo
- Publication number
- DE2112198C2 DE2112198C2 DE2112198A DE2112198A DE2112198C2 DE 2112198 C2 DE2112198 C2 DE 2112198C2 DE 2112198 A DE2112198 A DE 2112198A DE 2112198 A DE2112198 A DE 2112198A DE 2112198 C2 DE2112198 C2 DE 2112198C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- compound
- carbon atoms
- alkyl
- 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 3-Phenyl-7-coumarinyl Chemical group 0.000 title description 20
- 238000000034 method Methods 0.000 title description 17
- 230000003287 optical effect Effects 0.000 title description 16
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 description 72
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 239000003599 detergent Substances 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000460 chlorine Chemical group 0.000 description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 239000000126 substance Substances 0.000 description 7
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 150000003852 triazoles Chemical group 0.000 description 4
- 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 3
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- 125000004414 alkyl thio group Chemical group 0.000 description 3
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000001231 benzoyloxy group Chemical class C(C1=CC=CC=C1)(=O)O* 0.000 description 2
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- 239000007859 condensation product Substances 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
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- 239000002270 dispersing agent Substances 0.000 description 2
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- 239000000194 fatty acid Substances 0.000 description 2
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- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
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- 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 2
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- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
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- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 description 1
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- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
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- 229940126062 Compound A Drugs 0.000 description 1
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical group CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
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- 241000669298 Pseudaulacaspis pentagona Species 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
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
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- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 1
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- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
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- 238000010422 painting Methods 0.000 description 1
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical class OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH432070A CH540270A (de) | 1970-03-23 | 1970-03-23 | Verfahren zur Herstellung von in 4-Stellung eine abgewandelte Methylgruppe aufweisenden v-Triazolverbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2112198A1 DE2112198A1 (de) | 1971-10-14 |
| DE2112198C2 true DE2112198C2 (de) | 1982-11-25 |
Family
ID=4273880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2112198A Expired DE2112198C2 (de) | 1970-03-23 | 1971-03-13 | 2-(3-Phenyl-7-cumarinyl)-v-triazole, Verfahren zu deren Herstellung und deren Verwendung als optische Aufheller |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3875178A (enExample) |
| AT (1) | AT305280B (enExample) |
| BE (1) | BE764621A (enExample) |
| CA (1) | CA961492A (enExample) |
| CH (1) | CH540270A (enExample) |
| DE (1) | DE2112198C2 (enExample) |
| FR (1) | FR2084987A5 (enExample) |
| GB (1) | GB1307171A (enExample) |
| NL (1) | NL7103834A (enExample) |
| ZA (1) | ZA711758B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0047014B1 (en) * | 1980-09-02 | 1986-01-15 | Asahi Kasei Kogyo Kabushiki Kaisha | Novel thioesters and process for the preparation of the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1794396C2 (de) * | 1966-03-19 | 1975-04-10 | Bayer Ag, 5090 Leverkusen | Aufhellungsmittel |
| CH488730A (de) * | 1967-02-16 | 1970-04-15 | Geigy Ag J R | Verfahren zur Herstellung von v-Triazolyl-cumarinen |
| US3646054A (en) * | 1970-08-28 | 1972-02-29 | Ciba Geigy Corp | Coumarin-v-triazole oxides |
-
1970
- 1970-03-23 CH CH432070A patent/CH540270A/de not_active IP Right Cessation
-
1971
- 1971-03-13 DE DE2112198A patent/DE2112198C2/de not_active Expired
- 1971-03-17 US US125383A patent/US3875178A/en not_active Expired - Lifetime
- 1971-03-17 ZA ZA711758A patent/ZA711758B/xx unknown
- 1971-03-17 CA CA107,976A patent/CA961492A/en not_active Expired
- 1971-03-22 FR FR7109996A patent/FR2084987A5/fr not_active Expired
- 1971-03-22 NL NL7103834A patent/NL7103834A/xx unknown
- 1971-03-22 AT AT243071A patent/AT305280B/de active
- 1971-03-22 BE BE764621A patent/BE764621A/xx unknown
- 1971-04-19 GB GB2495271*A patent/GB1307171A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| US3875178A (en) | 1975-04-01 |
| ZA711758B (en) | 1971-12-29 |
| NL7103834A (enExample) | 1971-09-27 |
| GB1307171A (en) | 1973-02-14 |
| CA961492A (en) | 1975-01-21 |
| AT305280B (de) | 1973-02-26 |
| CH540270A (de) | 1973-08-15 |
| FR2084987A5 (enExample) | 1971-12-17 |
| DE2112198A1 (de) | 1971-10-14 |
| BE764621A (fr) | 1971-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |